Venture Unlocked: The playbook for venture capital managers

Samir Kaji
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Sep 28, 2021 • 47min

Founders Fund Delian Asparouhov on Miami as a major tech hub, what he thinks as the drivers for innovation now, and the pros of incubating companies like Varda within firms

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today we’re thrilled to bring you my conversation with Delian Asparouhov of Founders Fund, a Silicon Valley and now Miami based firm that has long been known for backing some of the most category defining companies in the world including SpaceX, Palantir, Facebook, AirBnB, and Stripe. While at Founders Fund, Delian also co-founded Varda Space Industries, and previously worked at Khosla Ventures.A message from our sponsor:Pacific Western Bank is a full service commercial bank with over $34 billion in assets. The venture banking team specializes in financial products and services for startups, venture-backed businesses, and their venture capital and private equity investors.The experienced team is committed to the space and dedicated to delivering high-touch, tailored solutions, helping innovators take their business to the next level.In the first half of the year, the venture banking team has booked over $800 million in new loan commitments to help support the community.  No matter the size or stage of your business, you can expect guidance, resources and flexibility, making them the perfect team to support your evolving needs.Turn your vision into reality with PWB. For more information, visit www.pacwest.com/lending-solutions, or follow us on LinkedIn and Twitter.*Equal Housing Lender & FDIC insured*Total assets & loans booked are as of June 30, 2021.In this episode we discuss:01:43 Delian’s journey to becoming an investor05:24 Why he felt VC was a better path for him than operating roles 11:52 Why he chose to go from Khosla Ventures (& now Founders Fund) instead of starting his own firm14:24 The decision to co-found Varda while being a full time investor17:38 How Delian attracted co-founders for Varda.21:31 Why there are a relative lack of investment dollars into areas like space. 25:22 How Founders Fund looks at the risk in investing in areas such as space.28:07 The catalyzing events in tech that will help drive exponential innovation. 31:27 Ingredients Miami has that will help it build a significant presence in tech, and why is talent going there?38:47 The most counterintuitive lesson Delian has learned as an investor40:56 Delian’s prediction for the venture market for the next few years43:47 The legendary investor that has most inspired himMentioned in this episode:Founders FundVarda Space IndustriesKhosla VenturesI’d love to know what you took away from this conversation with Delian. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Transcript:Samir Kaji:Hi, I'm Samir Kaji, host of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. Today, I'm thrilled to bring you my conversation with Delian Asparouhov who's a Principal at Founders Fund. Based in Miami and Silicon Valley, the firm has long been known for backing some of the most category-defining companies in the world, including SpaceX, Palantir, Facebook, Airbnb, and Stripe. While at Founders Fund, Delian also co-founded Varda Space Industries and then previously worked at Khosla Ventures. I had a lot of fun in this week's show as we talked about a number of things, including incubations within larger firms, the arc of where he sees technology, and what's going to drive innovation in the coming years, and why regional hubs like Miami will be major forces and drivers of innovation. Now let's get into the episode to hear all of that and more.Samir Kaji:Today's episode is sponsored by Pacific Western Bank, a full service commercial bank with over 34 billion in assets. The venture banking team of PacWest specializes in financial products and services for both startups and the venture and private equity funds that back them. I've worked with many of their team members over the last few decades, and I can attest with their commitment to bringing a high touch and personalized experience for every startup and fund manager client they have. So whether you're a founder or a fund manager at any stage of development, and you want to find out more, check them out at www.pacwest.com.Samir Kaji:Delian, great to see you, and thanks for joining us.Delian Asparouhov:Thanks so much for having me. Excited to be on today.Samir Kaji:Well, this is going to be a really fun conversation given how multifaceted your background is. And actually going from a waffle boy to becoming an entrepreneur and getting into tech, to now being a full-time investor at Founders Fund. Tell us how you got interested in tech in the first place and what led you to investing.Delian Asparouhov:Yeah, I had always been a computer scientist. My dad studied computer science and statistics and was a software engineer for basically his entire career. And so I think my first website I put up, I think summer between eighth and ninth grade, I had my first paid software gig summer between ninth and 10th grade, and so, the waffle boy experience was actually like, "I can tell where this life is headed and it's unlikely to have a service job in its life unless I intentionally do it now, and I think it's an important skillset to have, because I can't wait of just get paid for just working with your hands."Delian Asparouhov:And so, I actually had a much higher paying job the prior summer, where again, I was a software engineer and then I was like, "I'm gonna be a waffle boy this summer. I'm not going to do any software engineering." I did a some of that and I was like, "This it for me. I'm not a very good waffle boy." I basically quit at the end of the summer to go back to high school, but I think I got fired too. I think they were at their wit's end with me of, I really just like overselling the waffles more so than I like making them.Delian Asparouhov:And so yeah, I basically had this software engineering background, thought that I was headed into the world of academia. I really liked software robotic space, and so the plan was, both of my parents are PhD academic types, my mom's a professor, my dad's basically a professor, and so I was like, "Okay, my path in life is going to be academic robotic space." That points me towards undergrad at MIT, grad school at Caltech and then basically working at JPL/NASA on robotic space missions.Delian Asparouhov:And basically in freshman year at MIT, I had a couple of chance encounters with the most maybe influential, being with this guy, Bilal Zuberi, who's actually now a partner at Lux Capital, basically met me on I think fourth or fifth day of undergrad, and just introduced me to the world of venture capital startups, just like a potentially alternative path that had a much near term and faster path, should we say, impact on the world.Delian Asparouhov:And so I got hooked on that. I started going to these weekly dinners at MIT. They were these entrepreneurship dinners hosted and funded by the entrepreneurship center. And then just very quickly got obsessed, started reading about all these things, reading Hacker News, and had this idea stuck in my head where I was like, "Man, Jack Dorsey, he seems like he's the best entrepreneur right now. I got to figure out how to go work for him." And so that basically spring of my freshman year, I hustled my way into getting a summer internship with Square.Delian Asparouhov:And so moved out to Silicon valley in whatever, late May of 2012, fell in love over the course of that summer, had a really awesome experience in the summer of 2012 working for Square. I think I interviewed when the company was a 100, 120 people. By the time I joined, it was 150 and then by the time I left, it was 300. So, I remember when I left the Android engineering team at the end of the summer, one of the other engineers was like, "Oh, f**k, you're an intern? You're not a full-time really? You've been here longer than the rest of us." And I was like, "Yeah, but I'm actually just an intern and I guess I'm going to head back to school/head back to school with the intention of figuring how to drop out and get back here as soon as possible." Because I was like Square is awesome, but I'm young enough that, the risk reward curve, I should probably go start my own thing rather than working at a bigger company.Delian Asparouhov:And so I was lucky enough to be roommates with a guy who was friends with a Thiel Fellow and I learned about that program, applied, and then managed to make it out full-time to Silicon Valley in May of 2013. So yeah, thank you Bilal for teaching me about startups and eventually leading me out to Silicon Valley.Samir Kaji:It's a really interesting story. You think about 2013. You drop out of MIT to pursue being a startup entrepreneur, which comes with a lot of risks. And then ultimately you did that for four years and then took on a jump eventually with Keith Rabois at Khosla Ventures. And I always think about, as you go through your career, you're always making decisions that have opportunity costs. Why did you decide to go into venture versus staying within the operating role, either running a startup or actually working for a startup in some of the spaces that you really enjoyed?Delian Asparouhov:Yeah, so the original role at Khosla Ventures was actually due to me wanting to actually start another startup. I had this idea around cybersecurity insurance that I've been towing around with Keith for a while, and didn't feel like I had the right founding team yet to pull the trigger, but I really did want to figure start working on it. I had actually been having dinner with Keith talking about this, but then also happened to be talking about a friend that had dropped out of Harvard, but had gone back and finished school, and was graduating that was looking for what his first gig was going to be.Delian Asparouhov:And Keith was like, "Hey, I really like your friend, maybe I should hire him as my chief of staff." And so we talked about what the chief of staff role would entail, how it would work, et cetera. And I remember calling my friend literally right after that dinner and being like, "Hey, Keith wants to me to pitch you on this role." I literally got halfway through the pitch and had this set of an aha moment where I was like, "Oh f**k, I think I want to do this. And then I'm going to work on the cybersecurity insurance idea on the side while doing it."Delian Asparouhov:And so literally I was doing this call outside Keith's house after this dinner, and I knocked on his door after I was done with the call. And he's like, "What the f**k are you still doing here? We finished dinner like an hour ago." And I was like, "I've been outside on this call, but by the way, I think I just want the job. What do you think about me being your chief of staff? And then I'm going to work on this cybersecurity insurance idea and just use Khosla Ventures and this role as the platform to find these potential ideal co-founders, and in parallel, just learn a lot from you."Delian Asparouhov:And he was like, "That sounds great." We came to an agreement that I would do it for at least minimum of a year. So even if I did find the exact team, I would still keep doing the chief of staff role for at least a year since he was going to have to train me up on it. And I was like, "Great, I'm happy to do it for a year, and then I'll go back and operate this company."Delian Asparouhov:About, let's say six or seven months in, I had a couple of different realizations that hit me all at once that convinced me that I should potentially take the idea of staying in venture capital for the longer term actually made sense. Because nowadays I think people think like venture is cool, blah, blah, blah, but how? When I was growing up in Silicon Valley, 2014, '15 and '16, venture capital is where you went to retire. Nobody cool was doing venture capital. All the cool people were starting companies. And I think that's still honestly mostly the case.Delian Asparouhov:But I had a sudden realization that hit me about six months in where two things, the first was that my personality and skillsets were much more likely to make me a highly effective venture capitalist than they were to make me a highly effective founding CEO. I am super ADD. I'm super intellectually curious. I like to speak my mind even when it's relatively controversial and out there takes, and I don't particularly love managing other people's emotion ends or acting as a therapist. All those things are huge cons to be a founder, right? The ideal founders are monomaniacal, very perfect in their storytelling and are careful not to step over any bounds, are very good at being a therapist and managing people underneath them, and if anything, dislike contact switching.Delian Asparouhov:I realized, I was like, "Huh, these things are all huge cons to the founder, and yet they're all huge pros as an investor, right?" The best investors are intellectually curious and context switching and don't necessarily need to manage people. And so I'd always given other friends the advice of, when considering various career paths, you should generally likely lean into your strengths rather than try to mitigate your weaknesses, because by leaning into your strengths, you're much more likely to be top 1% and top 0.1 top 0.01% of the people in that particular category.Delian Asparouhov:And so I was like, "I think if I really, really worked hard, I could make be a top 10 or top 5% CEO," but it would take like a lot of work. Or I could do the thing that clearly comes much more naturally to my skillset and personality and just do that. And I can probably work less "hard," and I'll actually be top 0.1 or 0.01%. And then I had this sudden aha moment where I can't describe to you, up until then I'd had this obsessive, since that day with Bilal and then reading about Silicon Valley, I was like, "Oh, okay. To be one of the greats, you have to be a founding CEO." And so like, "I'm going to be a CEO. I'm going to be a CEO." And it was literally obsessive in my mind. And every day I was like, "In some ways, I don't care about the idea, I don't care what I'm working on, but I have to be the CEO."Delian Asparouhov:And then it was just this first crack where I was like, "Hmm, seems like I can be one of the greats and have a really great impact on the world without necessarily being a CEO. And then who knows maybe one day I'll figure how to do the job half, half and co-found something again one day," which eventually does happen four years later. And so yeah, maybe a month, six or seven or so, realized that.Delian Asparouhov:And then the second thing was, I actually happened to basically stumble across and source an aerospace company that Khosla Ventures ended up investing into at roughly month six or seven. And so the second aha moment that I had was, I'd always really wanted to work in aerospace, but the only models that I had for how to do that were either you went and worked at SpaceX as an engineer, which I had friends that did that, and I didn't really love the day to day life of just being an engineer. And then I had the second type of model, which was the Chamath, Elon, et cetera, which is basically, "You got to get rich in normal tech and then you get to go do space tech."Delian Asparouhov:And so I was like, "Okay, I'm going to do path two. I'm going to try and get rich in normal tech, and then I'm going to go do space tech." And then instead, all of a sudden option three opened itself up to me where it was like, "Whoa, I get to do aerospace today as a broke 22-year-old, by basically 23-year-old, I think, by finding these companies that are really great space companies and then convincing investment firms to invest in them, and then I really actually get exposure to the world of the commercial space industry and operating within that."Delian Asparouhov:And so I had those two aha and I was like, "Oh s**t, I got to lean into this hard. And I'm going to show that I'm a very good normal investor, but I'm going to make sure that on the side I'm constantly building up this space expertise." And so very intentionally I started going to space conferences and meeting every space CEO, and thinking about what ideas would I want to fund? What opportunities were there out there? I started very proactively with my friends that were SpaceX engineers grabbing dinner with them and being like, "let me know anytime that you're interested in leaving and wanting to start a company. I want to work on something with you." And so those early bets were obviously what eventually led to what I'm working on today.Samir Kaji:Going back in a second, you were at Khosla making the determination that being a VC is probably better aligned with your skillset. You still have to do the normal tech, you have this affinity for space, and I think that goes back a long time, well before even being part of the tech world. But there's a couple options that people have when they're thinking about being an investor and starting off in the early days. In today's world, that means either joining a firm, like you ultimately went from Khosla to Founders with Keith, or actually start your own firm where you get a taste of actually running a company, but in the context of an investment firm. Why did you decide to go to Founders versus just start your own tech or space tech type of firm?Delian Asparouhov:I do think that fundamentally venture investing is an apprenticeship-based industry where I think it's far easier to learn from other really great people than try to re-engineer from scratch. And then honestly, most things in life are easiest learned being in apprenticeship. And that was incredibly clear to me if I looked at, let's say peers that started around the same timeframe that I did in venture four and a quarter years ago, those that had very type mentorships and apprenticeship opportunities, have definitely far outperformed the ones that were out on an island and expected to learn and operate entirely on their own.Delian Asparouhov:Founding a firm can make a lot more sense once you've had that apprenticeship experience. I think early on in a career, it's not like it's impossible to succeed that way, but you're really in it for the grind. And in some ways I would much prefer to spend ideally the majority or 99% of my time doing the things that I really love and things that I'm good at. I think I'm pretty good at, for having been a former founder, I'm pretty good at advising other founders, finding very interesting ideas to invest in, figuring out how to convince those founders to take our capital, those things I'm quite good at and enjoy doing.Delian Asparouhov:Do I love pitching to limited partners to invest into a fund? Not particularly, and so this was a have to. Yeah, maybe it constrains the upside or maybe you don't get as much ownership, et cetera, but I find that I didn't really want to apply my "entrepreneurial independent energies" towards actually making an investment firm. I was much more interested in, and this is definitely an explicit part of the conversation when I joined Founders Fund, I was interested in, at some point, incubating something and applying the entrepreneurial spirit towards that.Delian Asparouhov:And so yeah, I think there are plenty of investment firms in the world. Are you really going to create the next greatest hot new thing? Maybe. But I think that isn't bringing that much innovation and interesting things to the world versus applying that same entrepreneurial energy to company building. To me, it's much more exciting. But obviously, I've had friends and peers that have done phenomenally well taking this purely independent approach, but this wasn't something that I was super interested in.Samir Kaji:So given all that, let's talk about your work at Founders Fund. And one of the things that struck me as unique was, you starting a company or at least co-founding a company in Varda while you are a full-time investor. And we're starting to see those type of models emerge, and certainly in the past we've seen things like EIR models, incubations with firms like Sutter Hill and then now studio models. But maybe you can walk us through a little bit about how does that work for you? And within Founders Fund, what does it actually mean to co-found a company while you're a full-time investor?Delian Asparouhov:Yeah, there's definitely a couple different models, most of which I'm typically not very interested in. Let's call the first most common just being the EIR model. Typically, for sure there's some success with EIR models, but I don't typically love them because they tend to create a relatively artificial constraint on, you come in basically without an idea and the firm tells you, "you've got to start something within a year, either we'll fund it at the end of the year or you're out of here at the end of the year." And so it creates this artificial time constraint that I don't think is the healthiest way to start a company. I think you should start a company when you have an idea that's really itching at you and you just can't get out of your head, and need to build as opposed to try to force yourself into a company. And so I don't necessarily love the EIR model.Delian Asparouhov:The second model, which I'd call venture studio model, people that only focus on incubations. And so maybe the best example of this being Sutter Hill Ventures. They basically only do incubations. Snowflake obviously being their best example, but they have many more coming down the pipe that are quite, quite good. And that model not necessarily mean anything to me because it's only incubations typically. And those do tend to have more success, but you do need to do a lot of them. And so you can't spend as much time on any individual one. And so it feels like in some ways, you have all the downs of investing, your time is very split amongst all your companies. And yes, you're more involved at each individual one and you help kick it off the round, but there's no one that you can feel true, true ownership over. But without all the upsides investing, I can invest in any company and whatever any founding team builds. So, I wasn't super interested in the venture studio model.Delian Asparouhov:And then third model being the relatively unique model that so far, at least I think only, let's say Founders Fund and a very small handful of others have truly succeeded at and scale at, which is, you still keep investing in a variety of different external companies at an aggressive pace, but then you choose one, and exactly basically one company, to really focus as your external incubation. And so you get that real sense of ownership, control something that you're truly proud of, but while not being constrained to only investing in the ideas that you come up with, but being able to invest in, I do really like the process of, a founder comes and pitches me on something that maybe a lot of other investors think is crazy, wouldn't succeed unless we funded it, and then getting to fund those companies, those are in some ways the most emotionally rewarding investments, because you're getting to enable somebody else's dream.Delian Asparouhov:And that doesn't always happen right. For sure a lot of the companies that we fund, a million other people would have also may be funded, but there's this occasional exceptions where we're truly out on an island in comparison to all the other venture investors. That's kind of the model that Founders Fund takes, and so it's like, I'm definitely not starting any other incubations anytime soon, but I really like that model, both getting to aggressively invest at a top-tier level while also running one and exactly one incubation, which we've done with, first Trae Stephens doing Anduril and Peter back in 2004 doing Palantir.Samir Kaji:So you started Varda at I think it was mid last year, so 2020, and I think this was a few months before you ultimately recruited Will over to become CEO, and I know Will came over from SpaceX, but are there any challenges in terms of when you do start a company and incubate it to actually bring in talent when the person that you're bringing in wasn't part of the co-founding team?Delian Asparouhov:Yeah, I do think this is the trickiest part of incubations. And what I'd say is, the idea and the potential for Varda wasn't real until after I decided on Will and the founding team. It definitely felt like Will was there basically since day one, because there was just no way it was going to happen without Will. And then by the way, he has a lot of, this is not, unlike the venture studio model where they really do take a lot of the company up front, they get it up to a significant level and then they sometimes will recruit CEO, this was very different.Delian Asparouhov:And I'd say Anduril and Palantir were similar to this where it's just like their incubations didn't exist until after we had found the founding team. And so that was most of the focus was, I've been thinking about the idea that Varda's working on micro gravity factories or micro gravity manufacturing for almost a decade. I've been pondering it for quite some time, studying all the companies that were working on it. Earlier in 2020, I actually considered a variety of companies that were working on it as investments from Founders Fund, and for a variety of reasons, decided they weren't a fit. And so in late July or early August of last year, I was like, "Okay, well, I've got some time right now where we're not investing a ton, let me think about what would the ideal archetype for founding team be, and let's go and try and find those and convince them."Delian Asparouhov:And so I basically articulated and listed a set of things that basically Will Bruey perfectly has, which is I wanted somebody from the Dragon Project with entrepreneurial experience and ideally had done annual investing on the side. So I'm not teaching them about fundraising and safes all from scratch. And then ideally a chief scientist that has done micro gravity manufacturing before.Delian Asparouhov:And so, the early days of the idea, weren't like, for sure there's some amount of, I was starting to do really early exploration of business model and customers and things like that, but it was super light. 95% of my focus was, I need to find this co-founding team that makes it feel real such that, this is sort of day one. And yeah, I think it was like third week of August, I'd need to double check the Varda Twitter, but somewhere around third week of August or maybe first week of September, the three co-founders myself, Will and Daniel had dinner down in, I think Manhattan Beach or something like that in LA. And that was day one. And then I was like, "Okay, I think we're doing this. Let's start to go through the motions of, let's talk about equity splits and let's start to work on the pitch deck and things like that. And it took a couple more months until we were really ready to go out and fundraise.Delian Asparouhov:But yeah, it's definitely not like, I was working on it for months and months and months, and had all these things, and I recruited in Will, and it was artificially he was coming in to run something that wasn't really his idea. It was more like, "Yo Will, here's an idea that I've been towing for awhile, I think you would be a really great CEO for it. And then I think it's in your best interest to have it be in incubation with me rather than doing it on your own. Because this is a capital intense idea and I can just help speed this up, where on your own," I'm sure he would have been able to like raise a seed, and then an A blah, blah, "But I can help you skip a couple of steps. And then by the way, the net dilution impact is going to be roughly equivalent," where rather than selling a bunch of the equity to a bunch of external investors over the course of several rounds, just give me some equity and then we'll just skip basically to a nine million dollar seed." Basically a series A.Samir Kaji:Right. Okay, so that makes a ton of sense. And you look at the space and pun intended, I guess, that you ultimately started this company, and what we've seen at least, at least in my view, we've seen a lot of investors focus on traditional technologies, many of which are just incremental in nature. And you talked about Bilal being at Lux Capital, and Lux does a lot of stuff that I'd consider true moonshots that are looking at hard technical problems that are in things like, whether it's bio, space or other, why are we not seeing more funding going into companies that are within spaces like the space sector? Is it because there's not enough entrepreneurs that are looking to solve those problems, or is it something unique about the capital requirements for the companies that get VCs not comfortable with it?Delian Asparouhov:Yeah, a couple different subpoints within here. The first I'd say is, I actually do think if you study it across biotech, aerospace, et cetera, the number of venture dollars going to these ecosystems is actually increasing quite a bit. Could it be increasing even faster? Potentially. So I do think it's actually headed in a positive direction. On, let's say second point, what is the limiting factor here? I think one of the things that is actually counterintuitive, and I spun this out into a pithy tweet. And this is somebody else's idea so I apologize that I'm not crediting them here. But the idea that I heard at a dinner party that I really enjoyed that stuck with me is that, the best social media app founders are actually PhDs in mathematics and the best deep tech founders are actually party promoters.Delian Asparouhov:And it sounds like a little bit pithy, but the reason being that, social apps, they don't need any marketing. What they need is deep mathematics around how do you architect these viral loops and behaviors such that people will actually use it and cross to create a viral growth. You don't actually need a marketer. And then for deep tech things, the limiting reagent almost always actually being, can you convince investors that this could potentially return their capital over the course of much longer timeframes than what's simply necessary? And so what you actually need is the best storytellers.Delian Asparouhov:And so the other way that, Peter at least has drilled this into our heads at Founders Fund is that, the bar for ability to fundraise, actually for deep tech counterintuitively needs to be even higher than for traditional tech, because you're not going to be able to raise on metrics or customers or things like that, you're going to raise off of technical progress in a story. And so, you need to be able to tell that quite, quite well.Delian Asparouhov:In terms of big shot or big swing companies like Varda getting founded, the limiting reagent there, I would say is people like me, technical enough that you know where to take a big swing. I had been thinking about micro gravity manufacturing for a decade, but then once I started really digging into it, I realized like, "I've been thinking about it lightly for a decade." It is very different to be thinking it to now a year and having worked on the company on it, lordy lordy, did I not know what I was getting myself into. It is a very different beast than what I expected. But that's part of it. It's like, I'm technical enough to now figure out how to navigate all of the challenges that have come through this, and technical enough to figure out that, Will's a very good CEO for this. Am I a very good space engineer? No, but I'm technical enough to assess who is a good space engineer and who isn't, and Will is definitely a very good space engineer.Delian Asparouhov:And so the combination of that plus concise, succinct, and let's say compelling storytelling, that's probably the limiting reagent to starting companies this, because the limiting factor for starting a company like this is convincing investors to fund it, right? There are a variety of people that have thought, "I'm not the first person to think about space manufacturing. I can list a 100 or a 1,000 researchers that have thought about this. Hell, even people that have tried to go out and raise from the venture capital ecosystem before that have thought about this idea." But none of them were able to articulate it in a simple and compelling way that got investors on board, and this is a particular idea that it's like, it's tough to bootstrap this one. It requires capital markets to fund for the first couple years so you get over the hump of the R&D and unit economics curve.Samir Kaji:What type of DNA then do you need from an investing standpoint? Because we talk about Founders Fund trying even from the very beginning investing in companies that, and I think Fund One had a lot of capital in one single company that obviously now has done extremely well, but it was a big risk. And taking big swings or things that you think investors would do, but the counterintuitive lessons is, or people are actually doing risk mitigation, and so when they look at these actors, that involves because it could be three, four, or five years before there's something, and it could take hundreds of millions of dollars in certain cases. What type of DNA as an investor, do you need to get comfortable with those type of investments? How do you guys talk about it within Founders Fund?Delian Asparouhov:Yeah, I do think similar to what you're actually looking for in the founders in the companies, you do need the same thing as an investor. Take, Josh Wolfe, probably one of the best deep tech investors right now, he is an incredible storyteller. He's both technical enough to actually understand what is the background across both the biotech, space, hardware, et cetera, companies he's investing, but then most importantly, he can also help translate that story to the future investors. Because a lot of what you need to do in deep tech is convince future investors to also invest in it while the unit economics, et cetera, don't pencil out. And people need to be able to trust your judgment so that in the future, let's say, hedge funds are like, "Oh yes, Josh Wolfe of Lux is very good at choosing great deep tech companies. Therefore, if we fund this, it is likely to turn out well."Delian Asparouhov:And so there is that recursive positive signaling that takes some time to build up. But I think the necessary components of that are in deep tech investor signaling in some ways matters even more so than normal tech. If you're a killer growth SaaS company, nobody cares what your cap table is, anybody will invest. In deep tech, people definitely want Lux, Founders Fund, et cetera on the cap table, feeling comfortable that, "okay, these people have clearly assessed this, know that this is a viable technology, legitimate team," et cetera, and feel much more comfortable then investing more capital later on.Delian Asparouhov:And so yeah, I think similarly it's definitely a very limited set of people in the venture capital ecosystem that are technical enough to actually understand the underlying technologies. Because you also can't look like a buffoon and accidentally keep funding Theranoses where it's like, the technology clearly it doesn't work, or ultrasound wireless power. We can argue, is it a great company? Is it a great investment? Was it the right approach? At the end of the day, that is a fundamental law of physics that is quite difficult to overcome. Energy loss from ultrasound, speakers shooting towards one area in air, R3 is difficult to deal with. And you need to be able to assess that and not just fall for just great storytelling as well.Samir Kaji:It's exciting for me personally, to see some of these companies that are attacking really big issues, whether it be healthcare, or things like space, or climate. But as you look at history within tech and life sciences, there's usually been catalyzing events that have either been platforms or things that have really driven waves of innovation. That could be the internet, it could be things like AWS that made building a software company much cheaper. Within the type of companies that you're looking at, which often are a little bit different than your traditional enterprise software company, are there any catalyzing events or platforms that you believe will drive the next generation of innovation within that space?Delian Asparouhov:Yeah, I think just as AWS created the infrastructure that allowed for digital innovation to happen very quickly, I think you're seeing the same thing happening in physical innovation. The pithy one liner that I like to give is, in the 2010s returns were largely defined by the world of bits, and then in 2020s, the returns will largely defined by the world of atoms. And the reason being that just as AWS allowed us to control bits very cheaply and precisely and much more easily with outsourced companies, the same thing is happening with the world of atoms, whether it's in biotech, you can remotely run an experiment now without actually having to open your own wet lab to outsource metal 3D printing, where if you want a very complex metal park, you no longer need to build a manufacturing facility in house.Delian Asparouhov:Outsource analysis, design, et cetera, everything that you need to, let's take Varda as an example. A decade ago, Varda would have had to be 1,000 to 3,000 person company that raised on the order of two or three billion dollars, maybe at minimum, to actually get over the line and come to fruition. Instead, today, I can buy a rocket off the shelf from SpaceX, Rocket Lab, Relativity, on down. I can buy a satellite off the shelf from Blue Canyon, Tyvak, Rocket Lab, tons of companies that now offer that off the shelf and let alone all the other components, the radios, the batteries, the solar panels.Delian Asparouhov:And so, I think what has changed a lot in the world of atoms is, in order to have significant influence in the world of atoms, you no longer need to have nearly as many of the core competencies entirely in house, just as it happened in the world of bits, right? Uber no longer needed to have expertise in building data centers. The same thing is happening in the world of atoms across a multitude of industries. And so, I think it's a really exciting time. Is it going to be as clear like a single platform like AWS? I don't think so as much. There might be one for biotech and one for aerospace and one for materials manufacturing and things like that. But I think it would be much more interesting area where there's a lot more alpha over the next decade is definitely from this world atoms.Samir Kaji:This continues that trend of reducing the amount of friction and cost of starting companies within whatever sector. And we've seen that even in things like semiconductor. I remember, in the 2000s, how much time and cost it took to get a chip to tape out, and now you look at it's a completely different world. It's really interesting to think about where that goes.Samir Kaji:The other thing that I always think about is, the world has also changed from a regional standpoint. I remember 10, 15 years ago, Silicon Valley was the only place where you would start a company. And over the years, it changed to Silicon Valley to global places like Israel, within the US places like New York and LA, and now we're seeing more regional hubs be created. You're sitting in one right now in Miami, which I think you're going to be the mayor of Miami pretty soon.Samir Kaji:But tell us a little bit about why places like Miami? For example, when Keith moved from San Francisco to Miami, he could have gone to a place that was already built out a little bit more like Austin or somewhere else that had similar tax benefits. He decided Miami, you decided Miami, you spent a lot of time there. Tell us what's unique about Miami, what ingredients do you need to have in a regional hub for it to be durable?Delian Asparouhov:Yeah, the reason that I got excited about moving to San Francisco originally was, that was where I thought the really exciting ambitious misfits were, and that was why I wanted to go work for Jack Dorsey. That guy was f*****g weird. He's still f*****g weird, but he clearly was going to do some really great things and I wanted to make sure that I was along for that ride. And unfortunately, just as at the time when I was deciding when to move, South Bay felt like this fossil embedded inside of amber and frozen in time, it felt like the same thing happened to San Francisco over the course of the roughly decade that I was there. The city's local politics and liberalism was completely unwilling to grow, expand, build new buildings. And that simple fundamental constraint caused it to freeze into an amber like state, because unfortunately startups grow exponentially.Delian Asparouhov:And so as they expanded and as they competed they took up more and more of the commercial office space, more and more of the residential space for their employees to live in. And so at some point, it started to break at the seams where in 2012 as a college dropout, I could definitely afford to live in San Francisco. In 2019, '20, '21 in San Francisco, no way. The rent prices got totally insane. And so the reason that we decided Miami over anywhere else was, Austin feels like its starting to have those exact same problems. And it's extremely politically a homogeneous city. They're already starting to see signs of breakage and unwillingness to build. I fear that it's where San Francisco was in 2015 and '16, and it's also just not an international metropolis.Delian Asparouhov:The thing that I think has been really missing in the United States is, if you look at other countries, let's say like Japan, Hong Kong, Singapore, they all have capitals that are these just equatorial, international, true metropolises that have also been very pro-growth and very pro-tech and that's what allows them to thrive. And we haven't had that in the United States. New York, yes, very international and a metropolis, not very pro-tech, not super pro-growth. San Francisco, yes, extreme tech, but again, not an international metropolis.Delian Asparouhov:If you talk to people that have lived in Dubai or London or Hong Kong, they're interest in moving to San Francisco, quite limited. Versus it felt like Miami have this opportunity to one, be a very high quality of life, low cost of living, low taxes, but then two, also evolve over time into this, ideally, my goal is, I think we can make Miami the largest tech ecosystem, not only in the United States, but the entire world within a decade. Because it turns out exponential curves grow quite quickly and when the city doesn't try to artificially dampen those exponential curves, that can be quite attractive. And so I love that Miami has more cranes per block, per a three block radius here than all of San Francisco combined.Delian Asparouhov:And in terms of the ingredients that you need in some ways, Miami is just getting such a crazy kick-start. If you look at ecosystems like New York and Austin, it started off with like a onesie, twosie, one founder, maybe one investor, et cetera. And so you had to grow entirely organically and very slowly, versus here, you're just getting this sudden rush of incredible investors like Dan Sundheim, and Keith Rabois, Antonio Gracias from Valor, these are all three completely different architects.Delian Asparouhov:Antonio on the board of Tesla and SpaceX, one of the best deep tech investors over time. Keith, one of the best FinTech investors and broadly generalist investors of all time. Dan Sundheim, one of the best crossover hedge funds of all time. All completely different genres of investing, but all focused on technology. And what it allows is that Miami gets this jumpstart where maybe in New York it took a decade to go from scratch to having five, six, seven IPOs of multi-billion dollar companies. I think Miami can do it much more quickly because you're getting this jumpstart on day one. And the Keith's and the Antonio's and the Dan Sundheim's of the world are much more able to both import entire companies, but the top executive talent, the engineers, et cetera, that you need. And then it's a much heavier draw.Delian Asparouhov:And so if you look at that both where the exponential curve is starting, but then also the exponential rate of that curve, Miami's in a very great spot. Is it going to happen overnight? No, but I wouldn't be surprised that a decade from now, if you're looking at tech IPOs, the amount that Miami's producing is on the order of, or equivalent to San Francisco. Maybe it's not quite the majority because things will be so distributed, and then within 15 years Miami actually being the largest ecosystem, not only in the world, but in the United States as well.Samir Kaji:Yeah, and it's a pretty ambitious vision. And you think about some of the regions that have done well, and it's really a combination in my mind of culture and particularly a government that supports a pro-tech type of environment. The second is, there's local capital that is funding startups. And the third, there is talent. You spoke about the first two a little bit, but tell us a little bit about talent. Why is talent going to places like Miami? And where are we in the curve within the Miami ecosystem for founders?Delian Asparouhov:I don't have a perfect statistical data set, let's say on this, but we recently funded a Miami-based born and raised company series A. It's actually going to be announced tomorrow morning at 11:00 AM. So by the time it gets published this will probably be live, so I'll just say it, the company's called Lula, it's an insured tech company. 17 million dollar round co-led by Founders Fund and Khosla Ventures.Delian Asparouhov:A year and a half ago, no way could this company get the attention of Silicon Valley VCs and say that they're going to be building the company in Miami, and no way could it attract top tier talent to move there. Since COVID, and since this whole Francis Suarez thing, a 100% flipped. They're pulling directors of engineering from Twitch and from Google and et cetera, really great companies from ecosystems like San Francisco, Seattle, New York, that previously these candidates would have never considered Miami, but now are going through the exact same trade off that the rest of us are going through, which is like, "I paid a lot of money for my rent and a lot of money in my taxes, and I don't know if I get much benefit, and this Miami thing seem pretty damn interesting." And so, their ability to import raw local talent, raw talent from abroad has significantly improved due to all of these, let's say high-level changes and then investors now being here.Delian Asparouhov:And again, is this going to happen overnight? No, but I'm really excited for the metric that I've been watching is, I'd probably say that, today there's probably three Founders Fund portfolio companies that have more than 10 employees in Miami. I'd say by the end of the year, I think that number will be closer to 10 companies. A year from today, I think that number will be close to 20, 25. And that's where I get really excited because a lot of the top-tier founders, if you look at in San Francisco, they come from employees of other venture backed companies.Delian Asparouhov:And so right now, is there a thriving ecosystem of lots of lots of founders that are like "born and raised Miami?" Not yet, but as these companies start to scale and as these local talents are to work at these companies, see how these venture back companies operate, they will be the pool of the future talent that I'm really looking forward to funding in Miami. And so I think we'll have a much richer and deeper pool, let's say, two years from today as the OpenStore's, the Lulu's, et cetera of the world really starting to scale up.Samir Kaji:Yeah, and without a doubt, the growth rate has been tremendous. And I know Twitter is not a necessarily a very great proxy always for reality, but even the folks that I know that have gone there even for a week or so have seen the energy Miami has. And it is going to be exciting to see how it grows. So I want to end a little bit with our heat check segment where I ask you three questions. I'm going to switch one up actually. But the first question I have for you is, now you've been investing for a few years, what's the most counterintuitive lesson you've learned about being an investor?Delian Asparouhov:Maybe it sounds like somewhat I tried, one of the things that I feel like Keith taught me that's really nailed into my head is, when considering any investment, the first question that should be on your mind or one of the primary ones is, why am I the right investor for this company? From afar, I would've thought like, "Oh, there's clearly like hot assets and your job as an investor is to just invest in the hottest assets or the things that are most likely to generate the most returns. And that's what you should focus on."Delian Asparouhov:And I feel like it actually flipped it on its head and has been a very useful favorite for me where, it might a somewhat similar outcome of, yes, you're still generating the greatest returns, but the way to just generate the greatest returns isn't to start with, how do I generate the greatest returns? The question asked is what is my differentiated advantage approach and why am I the right investor for this particular company? And that is much more likely to lead you to the best possible returns. Otherwise you'll revert towards the mean of what everyone else is doing. And then it turns out the mean in venture capital is not quite good, not very good.Delian Asparouhov:And so, I guess that's one of those counterintuitive things is that, rather than analyzing why is this company a great company to invest in? It's actually more like analyze yourself and why are you a great investor that this company should want to have on the cap table? And then if you don't have a good answer for that question, it's not clear that you necessarily should be investing.Samir Kaji:Yeah, and I think the other side of the coin there, if you are aligning yourself to the type of companies and entrepreneurs that best fit you, you're also going to provide a better experience for those founders in helping them build their companies. And over the long term, all that really matters from a branded reputation standpoint is, what are you actually doing with founders and what did they say about you? And so, totally get that.Samir Kaji:You're always pretty open out there ether in terms of your opinions and what your vision of the future is, thinking about bold predictions. And if we love look at past 2021, we are in, I would say, an insane environment right now with so much capital flowing around, valuations have obviously gone way up there, exit values of companies are also way up there, what's your bold prediction for 2022?Delian Asparouhov:I think the train is only going to continue on. If you have this ecosystem where companies are figuring out how to allocate capital productively and actually generate incredible innovations, maybe an artificial government version of this being the Warp Speed Program, basically enabling like mRNA technologies to exist, the macro capital environment is effectively doing the same thing where we're just willing to throw far more capital at problems that previously felt impossible. And it's fine if a series of them fail. If you take the Tiger approach of, "Let's throw a hundred million at every single Silicon Valley company," it's like, two or three years ago people would've critiqued that approach and be like, "Actually that doesn't work."You know SoftBank’s returns actually don't look that bad now that you've got DoorDash and a couple of other companies going public. And I think that's endemic of the ecosystem as a whole, which is like, I think it will only continue where the number of net new venture capital firms, the number of unicorns being produced, the number of really core innovations that are progressing is only going to continue to accelerate.Delian Asparouhov:I think humans are just really bad at predicting and understanding exponential curves. I've been watching the space industry now for a decade and I think because of that, I can understand the exponential curve that space has been on, and is perfectly tracking towards, when I started paying attention to it in 2012, this exponential pace that leads me to say statements that other people say is particularly crazy, but it's like, "I believe that 2030, we will not only 100, but 100s of people living in low earth orbit and operating there for not just research reasons, but there for actual commercial reasons being up there." And I'm sure people that are more sophisticated in the world of either Bio materials, et cetera, can also make just as wild predictions about these other areas.Delian Asparouhov:And so that's maybe obviously a further out prediction, but it is the best time to be starting deep tech companies, especially if you have a clear swing and story to tell. And I think it's only going to get better and better and better, and that the pace of innovation is only going to continue to increase. And so when people complain about is progress slowing down or speeding up? I'm definitely on the side of, I love your progress, studies institute, but progress is definitely speeding up.Samir Kaji:And it ties to everything you've been talking about how we've reduced the cost of infrastructure to allow these things to happen. And so it sounds like your prediction in 2022, the train continues to go. We continue to see funding at a high level, we continue to see these outcomes, but we also see these companies that will build multi, multi-billion dollar outcomes that are focused on things that are really hard, things like space.Samir Kaji:And I don't want to be presumptive in this last question, but you've worked with a lot of different investors, both at Founders and Khosla and probably even before that as an entrepreneur. But is there an investor out there that particularly inspires you, that you study and you believe has the type of framework that best resonates with you? Who is that and what is it about them that really resonates with you?Delian Asparouhov:Yeah, I obviously work with a variety of investors and there's a ton of things that inspire me about all of them. But if there were one investor that could point to of, this is the archetype that I would like to aim for and what I really aspire to in my career, it probably is actually Vinod Khosla. I think he does an incredible job of being extremely deep across so many different types of technologies, everything from semiconductors, to biotechnology, to space, all these different types of things, and is willing to invest in the very early stages and back up the truck into companies. Hell, take a look at QuantumScape. Khosla just funded that company, I think originally like 2011 or something like that, and they've continually backed the truck over the course of a decade now leading to this spec.Delian Asparouhov:I think there are very few investors that have that level of conviction in these types of deep technology companies that can also marry it with both a philanthropic side and a sort of story telling side, that I think Vinod is actually quite good at. And so yeah, I definitely admire his breath and I think I've done a great job of learning a lot about material science, about fiber optics, about space, about home construction. And I've got some core areas of expertise that I feel like I'm at the tip of the field of, and I hope to be able to expand that over time. And I think that definitely takes decades of reading various research papers, but it's impressive. Vinod literally wakes up every day and he's got like, whatever five nature articles on his desk every day that he chows through and make sure to stay up to speed. And I aspire to be able to do that as well.Samir Kaji:Do you agree with his statement that 90% of VCs actually destroy value?Delian Asparouhov:I don't know if it's quite that extreme, but definitely, most are not super helpful. The one code of his that I really believe in the most and think about all the time is, "The team you build is the company you build." And so, definitely, take that to heart across both with the investments that I consider, a lot of the time, it's mostly just analyzing the broader team more so than studying the strategy or the metrics. And then similarly with Varda, we probably spend in our exec team meetings, 80 or 90% of the time just talking about recruiting, team building, who are we bringing on? That's almost where we put all of our efforts.Samir Kaji:Well, this has been a lot of fun, man. I really appreciate you being on, look forward to seeing you in person, and again, congrats on getting Varda off the ground and doing all the great stuff you're doing at Founders.Delian Asparouhov:Sweet. Well, thanks so much for having me on.Samir Kaji:Thanks so much for listening to another episode of Venture Unlocked. We really hope you enjoyed our conversation with Delian. To learn more about him and Founders Fund, be sure to get at ventureunlocked.substack.com for detailed notes on the show and my ongoing commentary about the world of venture capital. Venture Unlocked is also available on iTunes or Spotify for download. And while you're there, please leave us a rating and a review as it really helps us out, and hit the subscribe button in order to get each and every Venture Unlocked episode as soon as it's released.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Sep 21, 2021 • 50min

Banana Capital's Turner Novak on his unconventional path in breaking into VC, being a successful stage agnostic investor, and leveraging social platforms to build advantages

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.We’re thrilled to bring you my conversation with Turner Novak, founder of Banana Capital. While fairly new to venture, Turner continually brings some of the most interesting perspectives about technology, and is one of best venture follows on social media.  Turner has an incredible backstory on how he broke into VC, and ultimately within a few years was able to found Banana Capital in January 2021, with $9.99M in commitments, including several institutional investors. Prior to having his own fund, he was General Partner at Gelt VC and also interned at a pre-seed firm Afore Capital. We talked with Turner about the value of social media in VC, how he thinks that successful investing can be stage agnostic, and his views on where the public and private markets are today, and where they may go in the future. A message from our sponsor:Pacific Western Bank is a full service commercial bank with over $34 billion in assets. The venture banking team specializes in financial products and services for startups, venture-backed businesses, and their venture capital and private equity investors.The experienced team is committed to the space and dedicated to delivering high-touch, tailored solutions, helping innovators take their business to the next level.In the first half of the year, the venture banking team has booked over $800 million in new loan commitments to help support the community. No matter the size or stage of your business, you can expect guidance, resources and flexibility, making them the perfect team to support your evolving needs.Turn your vision into reality with PWB. For more information, visit www.pacwest.com/lending-solutions, or follow us on LinkedIn and Twitter.*Equal Housing Lender & FDIC insured*Total assets & loans booked are as of June 30, 2021.In this episode we discuss:02:00 Turner’s journey into Venture Capital03:21 Getting his first internship in VC at Afore Capital07:43 The early days as an investor and his first investments11:25 How he built a strong deal flow channel despite being so new. 13:37 Choosing to raise his fund without a 506c provision and going the traditional way despite a huge social following. 15:42 The impetus behind raising $9.99M18:55 Turner’s scaling plan22:04 The role of speed in the capital environments today25:26 Using social media to amplify his strategy and brand30:51 How he strikes the right balance on social media to ensure he’s productively adding to the brand, but while staying authentic. 34:28 Turner’s investment criteria and how he evaluates deals and companies38:06 What he believes the markets will look like in the next 2-3 years43:18 The most counterintuitive thing he’s learned as an investor45:10 The lesson he’s learned from an investing miss46:51 The investor that most inspires himMentioned in this episodeBanana CapitalGelt VCAfore CapitalI’d love to know what you took away from this conversation with Turner. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Transcript:Samir Kaji:Hi, I'm Samir Kaji, host of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. Today, we're thrilled to bring you my conversation with Turner Novak, Founder of Banana Capital. While fairly new at venture, Turner continually brings some of the most interesting perspectives about technology and venture and also happens to be one of the best follows in social media.Samir Kaji:He's also got a great backstory on how he broke into this sea and ultimately within a few years was able to found Banana Capital in January 2021 with 9.99 million amendments, including several institutions participating. Before starting his own fund, he was a general partner at Gelt VC and also had interned at pre-seed from Afore Capital.Samir Kaji:We covered a lot of ground at this podcast, including the value of social media in VC, how he thinks being stage agnostic can be a successful strategy and his views on the public and private markets and where we're headed. Now, let's get into the episode to hear all of that and more.Samir Kaji:Today's episode is sponsored by Pacific Western Bank, a full-service commercial bank with over 34 billion in assets. The venture banking team at PacWest specializes in financial products and services for both startups and the venture and private equity funds that back them. I've worked with many of their team members over the last few decades. And I can attest to their commitment to bringing a high touch and personalized experience for every startup and fund manager client they have.Samir Kaji:So, whether you're a founder or a fund manager at any stage of development, and you want to find out more, check them out at www.pacwest.com.Samir Kaji:Hey, Turner, it's great to see you, man. Thanks for being on the show.Turner Novak:Hey. Awesome, thanks for having me.Samir Kaji:This will be a lot of fun given your backstory, which is really unique, and then all the great content that you put on Twitter and TikTok regarding venture and tech in general. But let's get back to how you got into this, why you became interested in being an investor. And then ultimately, how did you actually break in when you didn't have the traditional Silicon Valley networks that a lot of people that get into venture do.Turner Novak:The first time I really got interested in venture and knew it was possible to do it from Michigan, was I read a post from Blake Robbins at Ludlow saying, I forget the title, it was how I became a VC from Michigan. And it was always something I thought was fascinating because there's intersection of all these different things I wanted to do when I grew up and what I was interested in.Turner Novak:But yeah, I live in Michigan. I kind of thought I might have moved to a big city at some point, but ended up getting married right after school, met my girlfriend, now my partner during school. So, we never moved away.Turner Novak:And yeah, so I remember reading Blake's post was like, "Oh, cool. So, it's possible." And that was really the first thing that kind of got me. I mean, I had joined the investment club in college and was the president of the club for a couple of years.Turner Novak:And I just loved investing. And I was mostly investing in venture style things in the public markets anyways, kind of knew that's what I was going to do. But I never actually thought it was possible until that moment when I first read that.Samir Kaji:Yes. So, you read the post that inspires you. You're like, I think I can do venture from a place like Michigan. But it still requires you to find a landing spot, have somebody believe in you in the early days. And I know you interned at Afore, how did you go about actually getting in front of folks like that to even intern or even ultimately get a job?Turner Novak:Here's a long process. Initially, it started, I had just started tweeting, essentially. I'd use Twitter for, I don't know, a decade for fantasy football. I think that was initially what I use it for a lot. And I just noticed that it seems like a lot of people are on Twitter talking about this stuff. It's a way to kind of share your thoughts, build a brand, a kind of funny word to say but showing how you're thinking about things. And I kind of just slowly started to meet people that way.Turner Novak:And initially, I just kind of picked a niche or certain things to talk about with the end goal of eventually making the jump into VC. So, I kind of started, I think the first couple months I was on Twitter, all I talked about was Snapchat and just how I thought it was coming back. I mean, the consensus at the time was this is the next Myspace. And I was very firmly just thought that was just wrong. And if I just put my thoughts out there eventually over time. It might take a while, but I'd kind of show how I was thinking about things.Turner Novak:And then started tweeting a lot about TikTok when it first launched, just same thing. It was kind of crazy at the time, but I was just like, I mean, it's the best product I've ever used. I think this is going to be the most valuable company in the world one day. And again, crazy things to say, but that's what you have to do to be a good investor.Turner Novak:And then probably one of my big, I guess, the smarter things that I did that kind of accelerated things was I made this fantasy VC portfolio. So, it's fantasy football combined with investing. I had a fake million dollars, picked some startups, fake invested. Honestly, I had no idea how these companies were doing in most cases. It was going on Google, Reddit, Product Hunt, listening to a couple of the founders who go on a podcast.Turner Novak:And there's a 30, a 15-minute conversation, it was kind of like you talk to them, they talk about the business. Maybe they'd share some metrics and how they were doing. But it was basically just, essentially, what's the business model? Does it make sense? Does this seem like a good venture bet, to kind of hack together this fake portfolio.Turner Novak:And one of the founders actually found it and threw it up on his Twitter. And he had 100,000 followers at the time, and was just like, this is the best analysis my company I've ever seen. And I was like, "Whoa, did not expect that. That's pretty cool."Samir Kaji:What year was that? That was around what, 2018?Turner Novak:Yeah. It was the summer of 2018. I kind of just used that type of stuff over. It was like a two-year period, maybe a little under two years. But just DMing people pretty strategically, trying to line up meetings, San Francisco. And if enough people said, yes, I'd actually book a flight, take time off work to go.Turner Novak:And it was a very long process, probably had about five interviews all at once. We're kind of associate principal type roles moving to San Francisco and Afore was looking for someone to help out part time as an intern. But they're open to someone working remotely. And that was kind of insane a couple years ago. That was off the table at every firm. They weren't even open to discussing that because there's all these great candidates in San Francisco.Turner Novak:And so, I ended up taking that job. And it was interesting, because I remember having conversation with Anamitra, my old boss, and I told him, I'm just going to quit my job and I'll work for you full time. But you can treat me like I'm an intern. And it actually took me a couple days to convince him. I was just like, "Don't worry, I will drive for Uber. I'll do whatever I need to do to just make money."Turner Novak:And what I ended up doing was I couldn't afford my mortgage. So, we just sold the house we were living in. And then I had a rental property, too, that I bought. It was like a couple of years prior, my mom had got some money from her divorce. And I used that and my tax return or tax refund as a down payment on a rental, and then she lived with me. So, she prepaid me 12 months of rent and lived with me in this house. So, I had a ton of equity in the house. And I sold it also and then we used that to live off of for a while. So, that was the initial kind of how it happened.Samir Kaji:That's a great story and certainly epitomizes some of the sacrifices you made to get into venture. And I'm curious in terms of when you started actually putting money in the ground between the constructing that fantasy portfolio and then pre-Banana Capital, which we'll of course talk about later. What was that process like and what were the early days of your investment career?Turner Novak:It was a lot of fun. It was interesting story. So, I had met Keith Wasserman, my partner at Gelt, a couple of years prior on Twitter. He'd been following me. We'd met up a couple times when I had flown out to LA to interview, meet with people.Turner Novak:And he was dead set convinced on I was going to be a good VC. We were going to raise this venture fund from his real estate investors. And then I was going to invest the fund split everything three ways. And he kind of convinced me that ... He was more for this than I was, that I was going to team up with them, and we were going to do this fund.Turner Novak:So, kind of how it went, I joined, no, October 1st of 2019, we started investing their personal balance sheet and kind of built a deck around the portfolio companies that I had invested in. And our first close was set for March 31st of 2020, which, if you remember what it was like then, it was pretty crazy. It made it a little bit difficult to get everybody across the finish line.Turner Novak:It also the dynamics of running a $1.5 billion AUM real estate fund and then a $5 million was what we're shooting for venture fund, they were really focused on the real estate business. And I was trying to raise this fund that I honestly had no idea what I was doing to be completely honest with everybody listening, never raised a fund before. I thought I might do this in 10 years.Turner Novak:So, I was basically just forced to go try to fundraise and a lot of people I was talking to, they were saying like, "I would love to invest in your fund, but this doesn't really make sense. If you ever do your own thing, maybe we can talk about it." And so, when you talk about what it was like investing it, I remember looking March, I think I have a couple founders on a waitlist. Three things I've committed to, doing the first close at the end of the month, and I can send you the money.Turner Novak:And then, we don't exactly have a first close. There's a little bit of money that came in, but there's a global pandemic. The economy is essentially like the stock market is collapsing. These founders need money and even over the course of the summer, it was basically like, I'm in to give you the money. I just need eight weeks to raise it. And I've got a couple people that actually need it more than you. And I was basically raising 100K, I've wired to a founder, raised 50K, wired to a founder. It really affected the kind of companies that I was investing in.Turner Novak:And I basically just had a really, really good relationship with the founder. I mean, it's basically founders that didn't need my money at the end of the day. I was coming in at the tail end of an $8 million round or something or couple million dollar round and I wasn't making the difference.Samir Kaji:As you're doing that, you're right, trying to close during the beginning of the pandemic, you'd spent a lot of time looking at the public markets and March 18th, I think was a low point where we saw the markets really dipped to I think the Dow was something like 18,000. And everyone was really nervous. I mean, if you talk to VCs, everyone's thinking about triage, think about their existing portfolios. LPs, it completely stopped. But here you are, getting a new close, you started investing.Samir Kaji:But you were still pretty early. You did an internship at Afore, now you're investing out of a fairly small fund. Why were founders allowing you in into these, it seems like these rounds were oversubscribed? How much of it was related to the fact that you had been putting your thoughts out there? And I do want to get into this creator economy and what we're seeing right now is so many funds that are 10 million or under raising in different ways than the past. But tell us a little bit about what really helped you get into those deals in the early days?Turner Novak:It was usually people that I had an existing relationship with who, I remember one founder specifically said, "I could raise money from anyone, but I wanted to have you just because I know what you've done over the last couple years. And I just I want to work with Turner, not logo of some big fund." So, that was genuinely what it was. A couple of them are my fantasy companies, fantasy portfolios that I was following on to, quote unquote, like for real.Turner Novak:And typically those I had a good relationship. They were just pumped that, holy cow, some dude from the internet is excited about our company and they wanted to have me in. That's typically kind of how and why they're having me. And I mean, maybe I had interesting things to say or share. And then even as a writing publicly about certain things for a while, I mean, people start to see how you think and maybe you kind of have a track record where maybe people want to be a part of your track record, per se, is taking an early bet on them. So, that's mostly what it was.Turner Novak:And then other times, it wasn't like hot competitive rounds. It was just, I was just someone on the list of a couple other people they're raising money from and maybe they didn't even fill around, that kind of the thing. That's typically more with my style is I really don't try to do these hot rounds, I just think the lower the valuation, the better. You got to go earlier rather than later.Samir Kaji:So, you're doing this and then ultimately do decide to launch your own firm, which you raised. And I think it was 9.99 million for the first fund. What we've seen, of course, with things like rolling funds and AngelList is this new generation of investor that is raising in one or two ways. They raise typical, which is raise a small fund, you do it as a private placement.Samir Kaji:And then there's this new method that is actually been around for a while, the 506(c), which is you can go on and solicit. You decided not to go that route, which for me, it was a little surprising because you do have this major Twitter presence. And a lot of the folks that have large Twitter followings really weaponize it by getting in front of a lot of people through a public fundraise. Why did you decide to go the route you did and what are the pros and cons?Turner Novak:Yeah. I think for me, I am trying to get an institutional capital base as fast as possible. And so, a lot of conversations I had with institutional investors, there's a lot of questions around it. And me, I was an LP. I worked in endowment for three and a half years. I was also looking at maybe what the incentives look like for someone investing that fund. And it was a little bit different than I'm going to build an institutional investment firm.Turner Novak:They really feel like an evolution of scope programs. To me, that's how I think about them. I mean, I know so many people that instead of being a scout for a big fund, you launch a rolling fund. And you're essentially a scout for 10 or 20 firms then instead of just one. I probably could have done it and it may have made my life easier. But over the long term, I mean, I think it's important to have a more permanent institutional capital base. That's honestly what I'm going for.Turner Novak:So, I've just been trying to build those relationships and had a couple of those people in my fund. And I think just showing that I'm trying to do it a little bit more institutional from day one and just sets the messaging right. And so, that was really the main reason.Turner Novak:I also honestly didn't want to take oxygen away from other people who probably needed it. I didn't have to do it. So, I didn't want to take away from anybody else who actually maybe doing five or six, even actually really benefited down. I was lucky enough that just kind of all the people I've met over the last couple years, I didn't have to do it publicly.Samir Kaji:You look at that first funded, I was thinking about fund sizing, and there's a lot of discussion that, hey, $10 million and other funds are really interesting for a number of reasons, because your low friction checks to those founders. And generally speaking, it's easier to get in at 50,000 or 100,000 than it is at 1, 2 or 3 million. Was there anything intentional about why you raised 9.99? Because based on what you just said, it sounds like you had plenty of interest that you probably could have gone above that. Why effectively cap it at 9.99?Turner Novak:I knew that I was going to have more than 99 LPs just based on ... It was a lot of friends, people that were interested with smaller checks. I think the smallest check I took was $1,000, just from a founder that I back to a year prior. So, I had a bunch of founder, like seven founders that I've invested in the past, who gave me like, very immaterial amounts of money, but it's good signal. Also, friends who work at tech companies, maybe they're like a PM at Snapchat. They know all the people leaving Snap starting companies. Those people are writing me million-dollar checks.Turner Novak:And I knew that I would get way past that 99 LP threshold just based on how I was constructing it. I ended up having some institutional investors that came in at the end, who wrote really weird small checks to make it work, some of the smallest checks they'd ever written. And I wasn't planning on that. But it was nice to just get them on board. I got a couple commitments to the next fund kind of a thing, which it was awesome to just kind of already start building towards that.Turner Novak:Again, also, I didn't want to go out and raise a massive fund, because I think the different dynamics investing a $10 million fund and a 50 or $100 million fund, and those two numbers were both thrown out, and I just started thinking, no way, that's insane to think that I should go and do that right away.Turner Novak:So, they'll happen eventually. And I've been working on kind of synthetically through SPVs. You write a 200K check from the fund, but you put in a million dollars total, or you put in 500K total to just start showing that the economics on this fund, it still totally makes sense. But your kind of almost training and getting everything ready for when you do the next one.Turner Novak:I mean, it's just like, a VC will tell the founder, just start doing the things before you need to like, yeah, I think about the same way. What's my product? What's my distribution? I'm investing, my distributions, like founders taking my money, essentially, or how they know about me. So, I kind of think about it in the same way. So, as a founder of a company, I'm just a founder of an investment firm.Samir Kaji:Right. No, and I agree. A lot of times I do say that if you're raising a first time fund and you're starting a firm, you're basically an entrepreneur. You're writing checks versus writing code. But ultimately, you have to build. You have to build your brand and you have to execute, and you have a product that you deliver to founders and your LPs. So, what I heard is 10 million allowed you to take more than 100 because I think you're going to go up to 250 LPs if you wanted to under $10 million.Samir Kaji:The other thing though is a lot of people don't stay at that 10 million and under. And they level up to something bigger, 20, 30, 40 million in a fund two or maybe even a fund three. And oftentimes what happens is the investment model is dramatically different because you're writing bigger checks. Oftentimes, that means the value you had to provide these founders is more than just, hey, I want to get in, here's 50 or 100K.Samir Kaji:How do you think about scaling yourself up in terms of the product you're providing these founders as you invariably will grow your base given that you have institutional LPs, who I know want to see bigger funds in the future?Turner Novak:I think the most value investor can provide to a founder is just by default, just giving them money, having conviction and just not bugging them, getting out of the way, not ruining anything, 90% of it I really think. I think the best founders don't actually need help 99% of the time.Turner Novak:I think that's the biggest thing is just you basically find things that you have really high conviction in or you have a thesis in. And it's not about doing a ton of due diligence, dragging people along. It's just like I already know that this is what I want to invest in because I've just spent so much time thinking about it talk to or looked at so many companies, or going super fast.Turner Novak:I mean, this past weekend, I just made my biggest first initial check ever. I spent the entire weekend doing a bunch of research, wrote my model for it, actually sent it to the founder to read and show him my thoughts and everything. I just accelerated everything, just went super quickly. I mean, I think you have to be super fast.Turner Novak:Being through a bunch of portfolio companies raising a bunch of follow on rounds, the people that aren't moving fast and are just dragging their feet and don't have conviction, they're missing out. So, there's other dynamic of moving fast, it's easier to mess up. But I think you do have to just have a ton of conviction and you have to go fast.Turner Novak:And that's really the best thing you can give founders. And you can maybe have a couple things. I mean, I've helped founders, I'm sure you want to talk about this later. But with memes and marketing strategy, and just every VC, you can help with fundraising, you can help with recruiting. But for me, I really don't do anything unique that another VC can't do.Turner Novak:So, I never really pitched this value add because I just think it's kind of silly at the end of the day, if for me, it's just like, I really want to invest. Here's why. Here's the money. I can wire it to the next day. I'm ready to go. I don't care who else is investing.Turner Novak:And typically, for the founders I'm investing in, that's what they need the most. And yeah, I'm really not trying to sneak in any rounds and prove why I'm worth it. It's just I don't think that's the way I want to invest. So, it works for me so far.Samir Kaji:And what point does that actually matter? This conventional wisdom, and if you talk to LPs just say, all right, Turner you're going up from whatever your fund is, now you're writing bigger checks. I think that in order to win in a competitive market because there's so many seed funds out there, you have to have some kind of superpower. Something that you're providing these founders that's tangible that they're saying, hey, I want him on my cap table because of X, could be customer introductions, can be this.Samir Kaji:And everyone plays that up. In those VC, LP meetings, VCs always talk about that. It sounds like you say at the earliest stages, it's really over index on things like high conviction speed, kind of get out of the way and provide the capital that they need. But is that something that scales up if you're raising 100 or $200 million fund, and now writing 2 to $3 million checks, do you still think that would be your philosophy or do you think that at that point, yeah, you need to start to drive different type of value propositions?Turner Novak:In theory, yes. You probably should. But again, I really don't think the best founders really care. They just want people to give them money. I can't tell you how many times the founder, like yeah, the two-month fundraising process, and how many times we just take, wow, somebody just made me an offer after our first meeting, I'm just going to take it. That happens so much more than what is publicly discussed.Turner Novak:So, I'm really at the end of the day, I think it is just having conviction and speed. And we saw it with SoftBank, who maybe they had some good ideas. And now we're seeing it with all these crossover funds that are coming into private markets.Turner Novak:These are very solid investors. People put up 30 to 50% IRRs over long periods of time. I mean, I think even the big ones that we all know about, I mean, they're just sub 30% IRR. I mean, better than most VCs at the end of the day. These people are good investors, they come in prepared. I mean, they come in with prebuilt models and assumptions on these companies and ask them three questions. And then, they know if they're going to invest or not.Turner Novak:So, I think at the end of the day, yeah, it kind of is defensible in some senses. And I think there's also founders that do maybe want some help. But I've also seen too some founders actually get disenfranchised from that help. They're just like, I took this deal because there's all this value promised and it wasn't actually there. So, I'm never doing that again. And I think that's just becoming more and more prevalent. And part of that is a function of the capital markets and where we're at. And that could very easily change.Turner Novak:So, I don't have very hard set in stone rules on it right now. I think, for me, I am working on building out more sustainable distribution value add maybe in that sense and maybe it's more related to memes or helping get the word out about what you're doing. But I don't really think that's my, to my value.Turner Novak:I mean, I think my differentiation in an LP's eyes is that everything I'm doing is something they've never really seen or invested in before. So, that's typically why people are investing right now. And I have some ideas on longer term defensibility in the model, but still playing around a lot of stuff.Samir Kaji:You have a lot of latitude in terms of what you invest in when it comes to stage regions, valuations and all those things. And I think there is a unique model that I think it's really interesting, especially where you are right now. The other thing I was going to bring up is social media and the creator economy, which obviously, over the last 5 to 10 years has exploded.Samir Kaji:I remember you used to tweet about really serious things and you still do every now and then with some deep analysis, but at the same time, over the last couple of years, you've really created a brand around things like memes both on Twitter and TikTok.Samir Kaji:What a lot of people often ask me is that when people do that and they're building these big brands, how does it actually help the investing model? Is it a sourcing thing? Is it winning? Is it a combination of the both? How do you cut through the noise invariably that you get? I'm sure you have plenty of DMs on your Twitter of founders. Because I think it was very intentional, very strategic, in many ways, but tell us why did you start switching your style and what that's meant for you from an investor standpoint?Turner Novak:Like I mentioned earlier, I think about it as I'm a company, I'm a startup. Every VC will tell the startup founders, you're fighting against incumbents that have distribution. They have a bunch of existing things they do. You probably won't beat them head on. What kind of product can you build that's differentiated, and hopefully, over the long term differentiated where you also become an incumbent over time. I mean, that's ultimately what VCs are investing in.Turner Novak:So, that's really how I thought about it as an investor. It's like, "Okay, I'm competing against incumbent venture firms. There's thousands of them. A lot of them do the same thing." I basically just said, "How can I literally do the opposite and do things that are unique to what I'm kind of doing and building and just essentially build an investment firm or brand like VCs that are almost just completely the opposite of what everyone else is doing?"Turner Novak:And you don't quite inverse everything, but you do pick apart certain things that maybe you think, oh, I literally just do the opposite, this is actually better in this case. So, I'll just do that. And since you kind of find whitespace.Turner Novak:So, initially, it was more serious content. It was just trying to show how I was thinking about things, building a track record. And I think that worked over time. I kind of think of the content piece as there's all these different people that you're trying to hit. You want founders of companies of people who want to build $100 billion businesses, you want them coming to you and talking to you.Turner Novak:You all seen both the angel investors who might had some deal flow. You might think about the VCs who also might have some deal flow might want to follow on. You all think about the public market investors who are coming earlier, also, don't want them shorting your company when it goes public. You want them bringing the price up and supporting you in the public markets. And I mean, there's also LPs. You want to attract capital from LPs.Turner Novak:So, I kind of thought about what kind of stuff that I put out there. And it was really the more serious stuff. It was typically deep dives on companies that people weren't really talking about at the time, like Snap, ByteDance. Pinduoduo was a big one. That also really kind of overlap with my thesis as an investor. I'm doing mostly consumer stuff, which there's not as many people doing that. So, pitching into an LP and giving you a little bit of a different exposure.Turner Novak:And it was over time, I had started ghost tweeting for meme accounts on the tech Twitter and there's every tweet would do insanely well. And so, I got to a point where I was like, man, I should just start doing this for my own account because I'm leaving some stuff on the table.Turner Novak:It was risky, for sure, in the same sense, as a big established venture firm thinking we're going to start posting a bunch of crazy stuff online, instead of these serious blog posts about how to run a sales process. How to hire a board member or how to cold email us or make a pitch deck? You have something that no one else is doing. There's some VCs that kind of do it. I was just like screw it, entire thing.Turner Novak:And the more I was thinking about it, at the end of the day, the reason that venture firms do that stuff, it's just a top of funnel brand awareness, it's pretty insane how much top of funnel you get when you just constantly have things that you're doing, blowing up the founder group chats, making everybody laugh.Turner Novak:When you talk about inbound, so much stuff on some strain of hey, raising around, they don't really know very many VCs, don't like following them, but I really want to reach out to you because I think you get it and want to chat or around coming together, here's the people they're investing. I just wanted to talk to you before we close it out because I value your opinion want to have you on board.Turner Novak:It's so many times founders that are they're like Indonesia or something. And I asked him like, "How did you know to reach out to me?" He's like, "I saw your TikToks." Or, "My one friend, he loves your stuff. He thinks you're hilarious. So, I just wanted to talk to you." I'm not raising any money right now. But it's a lot of that kind of stuff.Turner Novak:And so, it was really dialing it back. I was just thinking about what products do I need to build to allow founders and LPs to give me money and take my money at the end of day. It was just building something different that I think will generate really good returns over the long term. And that was fun, too. That was another thing is I think too many people take themselves too seriously. I don't think you have to take yourself 100% serious. And you can dial it back just a little bit. So, that's another thing I kind of want to do.Samir Kaji:Yeah. I'll tell you, the content is great and it's memorable. And for a lot of founders, ultimately, they sort of feel like they know you before ever meeting you, and they kind of know your personality. And people do want to work with people they like. I do think that in today's world, especially in the early days, I've always seen this, the founder or the partner brand will far exceed the actual firm brand. And it's really about who am I working with.Samir Kaji:So, I think you've done a phenomenal job. But conventional wisdom, as you talk to these LPs, especially the institutional ones, they have their own boxes that they like to fill in. They talk about differentiation that if you're too differentiated, and everything's inverse, inverse, inverse, they get a little nervous, too. It is a high risk sort of maneuver in terms of some stuff you put out. How do you balance that and how did you get the institutional to be excited about such a different way of doing things?Turner Novak:I guess that it's working so far. That's probably, I guess, the short answer I mean, essentially, I'm trying to do a bottoms up crossover fund. So, I look at all these public market, hedge funds, creeping early and earlier. They're doing like Series B, Series A. I think it's really hard to be a good pre-seed and seed and even Series A investor.Turner Novak:So, my internship at Afore was a pre-seed. The Gelt Fund was mostly pre-seed and seed with a little bit of A. Banana is mostly pre-seed to seed with a little bit of B and C. And I've always been talking about public markets. I mean, I have a ton of theses out there of companies where if I would have invested, it would have looked really good. So, I'm kind of building the public markets component. And essentially, it's going to be a bottoms up crossover fund. I can be the first jack. I can write 200K in the company. I can do 2 million Series C, a 100 million in the public markets, different funds, obviously.Turner Novak:But essentially, you're just like these crossover funds, but you have the DNA to source and be the very first one in. And you're able to follow up over time. You can come in for the first time at the D, like you're super nimble. And it takes a little bit more consumer, but you can invest any sector stage, check size, geography. There's good founders building things everywhere. And my whole, I guess, the DNA of Banana has all been on the internet and not going on existing networks that already exist. And I'm building a bunch of those now.Turner Novak:But I just had to think about what were my advantages as an investor and just lean into those. And kind of walking LPs through it, showing them how it's working. I mean, I have a bunch of case studies of invested in the seed, was able to follow up all the way to it becoming a unicorn and potentially can keep investing over time when you just have a couple case studies of that. And it's even inbound, like the founder came to me and wanted to take my money.Turner Novak:So, just being able to kind of show those, it's been a fairly easy sell. I mean, I haven't got a whole lot 100% committed yet because obviously, it's a small fund. And it was more of a maybe like, let's just get to know each other. I also treated it as, no, I think a lot of emerging managers, they'll raise the fund and then they'll go invest it for a year or two. And then, they'll be like, oh, s**t have to fundraise again. And then they get back into it.Turner Novak:I probably have like one LP call a week, just staying up to date with people, I think know what I'm doing. I mean, it's just like, if you're a VC investing in companies, it's great to get to know these founders. And then, over the course of six months, you're like, "Wow, okay, let's just do this Series B right now. We don't have to really do a whole process, let's just do it, because we've gotten to know each other." So, it's kind of the same strategy, I guess, with LPs. And it's just I also love talking to people who like investing. It's just fun to hear what's going on. So, that's kind of been the strategy.Samir Kaji:Yeah. And speaking of inverse thinking, because one of the things that a lot of people say is, okay, venture or tech investing really has three categories. You have growth and crossover. You have lifecycle investors who put most of their capital the funds in A and B, and then you have the seed category. And they're pretty bifurcated because a lot of people say the muscles that you need to have or in skills really from a seed to a growth is completely different. But you're doing everything.Samir Kaji:What's your view on that? And are there things that are just really similar from an analysis standpoint that you sort of look at and say, "Well, it's really not that. You can actually invest across the stack and be successful within a sole GP or within one person looking at all those type of deals?"Turner Novak:Yeah. I think as an investor, it's ultimately especially like a tech investor it's is this a platform that has really high returns on invested capital probably the most granular way to put it. Will this have a competitive advantage, now at scale? So, I think that just thinking about it that way, it's basically every startup investment that I make, it's could this be a publicly traded company? A lot of different ways to answer that question, but then in terms of public market, it's really just if they triple quadruple revenue, how much of that is just incremental cash flow? And do you have a different view than other people?Turner Novak:I mean, I think that's really what you have to do to be a good investor is you have to have a different view on things, different opinion, maybe you have to be early, you have to be right over time. But you just have to see it before other people. And that's ultimately how you make money as an investor at the end of the day.Turner Novak:So, there's a lot of similarities or differences. I mean, to be a good public market investor, you listen to a lot of earnings calls, you're making fairly robust spreadsheets. And it's almost unnecessary, but it is important to sort of do that versus, I mean, some of the startups I invest in, I don't make a spreadsheet for invest. There's almost no need to. It's more about, can they build a product? What are they charging for it?Turner Novak:Okay, in theory, they could do a billion revenue, maybe. But that doesn't even matter at this point because nobody's a customer yet. The bigger question is just like, can they hire a team? Can they convince someone to sell it? How are they going to grow it? Can they grow really quickly? A lot of those kinds of questions. So, there's a lot of similarities. I think you also have some advantages, too. Like one of the companies I'm investing in, there's a bunch of publicly traded comps that are massive businesses, and these guys have a way better model, but I think they've unlocked.Turner Novak:And so, if you understand the publicly traded model, you're like, "Holy cow, if this actually works, this is going to be insane." And no other VC is thinking about it that way. They're just like, what's the TAM? What's the LTV, the CAC? All that comes up. Where do you go to school? So, it's a totally different way of kind of thinking about it, if you can kind of blend the two.Samir Kaji:Yeah. I agree with that. And since you have a lot of views that are not consensus, I want to maybe zoom out for a second and look at the market as a whole, particularly since you've spent so much time thinking about both private and public markets. It seems today that if anyone has invested in technology over the last 5 or 10 years, they've probably done pretty well as a function of this massive economic expansion coupled with the size and scale of these technology companies.Samir Kaji:And today, there's 750 unicorns, companies worth over a billion, which at one point in time, it was really rare for a company to hit a billion-dollar valuation in the private markets. I'm curious in how you look at the world today, because there are two views right now. One is everything's vastly overvalued as a function of the massive supply of capital out there chasing yields and it just can't continue.Samir Kaji:And then there's the other school of thought that, yeah, while valuations are perhaps ahead of themselves across the entire board, a lot of these companies eventually will grow to a point where some of these valuations will look like a bargain one day. And the scope of what a successful exit is, is going to be redefined forever. Where do you sit on the spectrum and what's your view of what the next two to three years might look like?Turner Novak:Yeah. I mean, I think we've probably had a lot of multiple expansion that people are painting on revenue, cash flow, users or height, however, you want to think about the thing you're paying on multiple on. I don't expect a lot of multiple expansion in the future, maybe even some contraction. I mean, I think it's just about finding businesses that are growing really fast that are actually economical. That's totally what I tried to do.Turner Novak:And if you company growing 100% month over month, if they can truly sustain that, I don't want to say the valuation doesn't matter, but it almost doesn't. It might seem high but then a year later, it might seem like, wow, we paid half of this month's revenue. It was the valuation that we paid.Turner Novak:So, it's really just about finding good businesses. And I do tend to skew away from things that are extremely insane. If it's a category, that's a thesis in the slide of another VCs LP deck, I'm probably not investing in it. That's kind of, I guess, how I think about it.Turner Novak:Basically, you just want to find those things before they become super hyped up. Invest in a company that's growing 20% month over month, but is going to be growing 100% in a year because of new products, new hires, changes in the market, timing, stuff like that, that's kind of more how I think about it. And then, I get a little more comfortable investing in those kind of hyper growth companies because you've been there and maybe you understand that a little bit better.Turner Novak:And I do think we're going to see the public and private markets just continuing to blend. I mean, essentially, it's the illiquidity premium that's in the private markets is kind of going away. And that's ultimately why all these funds are moving in. They're just like, why are we paying 40 times revenue and we could pay 20 in private or 30. And then that's where all the VCs get upset because they're throwing everything out whack in the public market investors like, wow, we're going to get 30% IRR, what a steal.Turner Novak:And so, I think that will keep happening. I think it's getting easier and easier to raise a small fund. I mean, as more capital if you just look at, if you're an LP doing analysis, you have a billion-dollar portfolio, you have to distribute some, you've got all your buckets, equities projecting 5% returns, real estate projecting whatever, fixed income projecting 5% returns, shoot, we got to earn 7% a year, where are we going to get the extra 20%. No, it's in venture capital, because historically, it's done it.Turner Novak:So, it just makes sense to put a bunch of money. And so, there's just going to be more money coming in from the top until LPs decide they don't want to do that anymore. And that flows down to the bottom where someone like me can pretty easily raise money from other downstream investors who essentially just want deal flow.Turner Novak:I mean a lot of these smaller farms are essentially scale funds for someone, whether it's a hedge fund and LP that wants to do direct another VC firm, GPs these funds, maybe friends or companies who want to invest in the SPVs when there's breakouts. That's ultimately what all these small funds are doing at the end of the day. So, I just think it's getting easier and easier to access that capital.Turner Novak:So, to your earlier kind of question of, yeah, just make sense. It's kind of fragmenting and I think networks are getting ripped apart, where it's more and more on the internet. We're seeing you can make a venture back business in Georgia, like in Russia, or in Tanzania and Africa. Instead of just San Francisco and maybe the San Francisco on that's a trillion dollar outcome. But maybe in Peru, it's like, yeah, it's like a $10 billion company. It's still an awesome outcome depending on the economics of who's doing it, who's investing.Turner Novak:So, yeah, I think is just going to keep opening up. But I do worry about a wipeout in terms of March 2020 happening again, markets not recovering, which is why I've been kind of really thinking a lot about institutional LP base. I just think it's really important to have those long-term partners. I want to be long-term partners to founders, to my investors. So, I think that's important to kind of get to and that's what LPs want to.Samir Kaji:Yeah. It's hard to make a case that there's never going to be some level of a recessionary environment, it's just cycles. Historically, it never lasted forever. This has been one of the longest economic expansion. So, you start to feel it. Although I will say, a lot of us are thinking back in 2015, we're like, okay, there's a bubble now. Now, 2016 is going to be a bad year. And then 2017, '18, '19. And of course, if you and I ran this conversation in March with like here it is, it's going to be a couple lean years, and that didn't happen.Samir Kaji:So, it's going to be an exciting time to see tech, obviously, and where innovations, it's a long-term effort that is not going to stop. And it's just a matter of how do you future proof yourself? We saw people that were really successful venture funds, not be able to raise in '08, '09, because they didn't have the right type of LPs.Samir Kaji:So, it certainly makes sense to get some of those institutions. I want to end with our heat check and I have three questions that I feel like the first one, we've kind of talked about a lot of this stuff, but what's the most counterintuitive thing you've learned as an investor in the time you've invested in startups?Turner Novak:I would say the most counterintuitive thing, if you look at some of the biggest outcomes, breakout companies, they weren't necessarily always backed by who you think of is the best VCs, which the narrative is that those are the best funds, and they are really good. But you can also build a great business if you don't raise capital from one of these brand name funds.Turner Novak:Eventually, the numbers will speak for themselves, and investors will back and support it. And if it's really good, I mean, you can build a 50 billion, $100 billion business and there's been so many cases of someone's struggled to raise a seed round a bunch of angels or it was maybe led by a fund that was not thought of as one of these tier one great firms. But eventually those other firms did fall one come in.Turner Novak:And so, I think we kind of get away from that a little bit too much. Everyone thinks you have to raise money from whatever the top funds. I don't think it's necessarily 100% true. They're good investors and they'll invest in really good companies. But don't let it dissuade you if you're a founder and you struggled to raise capital from certain names, certain brands.Samir Kaji:Yeah, especially in today's world where there's so many different options. I have seen some of the best companies in the world. If you look at their cap table particularly early on, they're not the traditional tier ones. And so, there's another guest in our shed that said the same thing. I know it's been early and you probably haven't missed on too many deals and probably don't have a big anti portfolio.Samir Kaji:But is there a deal that you missed on that you look back in the last couple of years and like, okay, well, I missed it, but not necessarily like that you just missed it. But did you learn something from that experience that you took away and will help you if this type of situation comes up again, what company was that and what did you learn from it?Turner Novak:I would say I'm not going to say the name of the company. But there's a company that was probably the biggest beneficiary of COVID, like startup, that I remember someone mentioned it to me in DM back in late 2019. I was like, oh, it looks cool. I just never really looked it up. And I remembered it when I was like, "Oh, wow, I probably should have at least tried to talk to the founder." I guess that's the big miss.Turner Novak:I mean, I think one of my other misses has been not sizing positions and doubling down into the winners fast enough or aggressively enough. And I mean, I think part of it's just a function of, it's been kind of, I've had weird capital situations.Turner Novak:And again, that's partially why I'm trying to get to a really permanent institutional LP base, where I look at hypothetically what it could have looked like because the cases where founders like, what do you want to invest in the next round? You can invest whatever you want. And I do like 100K check in to 2 million, but I probably would have liked to do.Turner Novak:So, that's been another really big lesson and almost a miss honestly. It's just not doubling down on the company with a lot of conviction. And almost thinking I needed to get more shots on goal to just kind of prove that I could do it. But I think now I'm at a point where I really just need to start all the best practices that all these seasoned VCs tell me about. I'm like, wow, I need to actually start doing that now.Samir Kaji:Well, speaking about seasoned VCs, is there an investor out there that you particularly aspire toward that inspires you? If so, who is it and what about them that resonates with you?Turner Novak:I would say Bill Gurley probably kind of a maybe that's a cop out answer. But I liked the way he publicly talks about what he's thinking about. And I just think he's very good investor. I mean, that's what I want to be. I want to be someone who people say, "Oh, Turner, yeah, he's a really good investor. He's like one of the best." And that's ultimately what I kind of aspire to.Turner Novak:So, probably the answer, that there's a lot of other people I like different things or what they do or different philosophies they have. Maybe I've never even met them before and maybe how I disagree with a lot of other things that they say or do. And I like, yeah, person is a pretty good investor, there's a lot of things you can learn from how they think.Turner Novak:So, yeah. And that's one of things I love about investing is, I mean, you can learn just as much. As a VC, you can learn just as much from other VCs as you can from public market investors, fixed income investors, real estate investors, all these different asset classes. You can really learn a lot from.Turner Novak:And whether it's just how to think about investing in your portfolio, but also thinking about, I mean, especially now, one of the big themes a lot of VCs are chasing is unlocking liquidity in different asset classes. It's like the stocks and people that specialize in similar asset classes and learn how they think about it. So, learning from other people is one of the things I like the most fun investing. So, there's a lot out there.Samir Kaji:When I do read a lot of stuff and I talked to a lot of guests on the show, I don't agree at first, with everything people say, and then you started thinking about and you apply your own beliefs on what makes sense and what doesn't, but it does make you think. And VC is this continuous learning game where you're always confronting your own biases and challenge your own assumptions. And I think people like Bill, Bill was a public analyst before he was a VC. And he's never been afraid of actually speaking against some of the craziness that happens where a lot of people buy into the hype factory.Samir Kaji:And so, I'm not surprised that you mentioned the name. There are people across many different asset categories I also look at that are just super interesting. This has been great, man. I have really enjoyed the conversation. Congrats on getting the first fund. Look forward to seeing both more memes, but also the growth of Banana Capital over the next few years.Turner Novak:Yeah. Well, thank you. Thanks for having me.Samir Kaji:Thanks so much for listening to another episode of Venture Unlocked. We really hope you enjoyed our conversation with Turner. To learn more about him and Banana Capital, be sure to go to ventureunlocked.substack.com for detailed notes in the show, as well as my ongoing commentary about the world of venture cap.Samir Kaji:Venture Unlocked is also available on iTunes or Spotify for download. And while you're there, please leave us a rating and a review as it really helps us out. And hit that subscribe button in order to get each and every Venture Unlocked episode as soon as it's released.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Sep 14, 2021 • 43min

Primary Venture Partners Jason Shuman on integrating partners into an established partnership, KPI's on measuring value to founders, and views on portfolio construction.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today, I’m excited to bring you my conversation with Jason Shuman, a partner at NY based Primary Venture Partners. The firm leads seed rounds for companies in NY and has previously invested in companies such as Jet, Mirror, and Latch. The firm recently raised two funds totaling $200MM. Prior to joining Primary, he spent time as Chief Of Staff for GLG founder Mark Gerson, was an associate at Corigin Venture, and founded and ran a company called Category Five from 2011-2015. We chatted with Jason about the importance of culture in building lasting teams, KPI’s for delivering founder success from their internal portfolio services team, and how he views both NY and the entire venture market today. A message from our sponsor:Pacific Western Bank is a full service commercial bank with over $34 billion in assets. The venture banking team specializes in financial products and services for startups, venture-backed businesses, and their venture capital and private equity investors.The experienced team is committed to the space and dedicated to delivering high-touch, tailored solutions, helping innovators take their business to the next level.In the first half of the year, the venture banking team has booked over $800 million in new loan commitments to help support the community.  No matter the size or stage of your business, you can expect guidance, resources and flexibility, making them the perfect team to support your evolving needs.Turn your vision into reality with PWB. For more information, visit www.pacwest.com/lending-solutions, or follow us on LinkedIn and Twitter.*Equal Housing Lender & FDIC insured*Total assets & loans booked are as of June 30, 2021.In this episode we discuss:01:44 Jason’s journey into the startup world04:37 What he learned in working with GLG founder Mark Gerson07:05 The decision to join Primary versus starting his own firm11:42 How Primary was able to seamlessly integrate him into the partnership14:37 Jason’s advice to someone who is joining a successful venture firm17:42 Why being selective and keeping a smaller portfolio is important to Primary21:23 Primary’s philosophy on building a team 24:31 The KPIs Primary uses to assess whether they are delivering value to founders27:21 Why Primary has decided to remain geo-focused on New York instead of expand 29:41 How Jason views speed versus diligence when investing in today’s marketplace33:41 Thoughts on the seed market in 202137:15 The most counterintuitive lesson he’s learned as an investor38:03 The investment miss that he’s learned from39:54 The investor that inspires himMentioned in this episodePrimary PartnersI’d love to know what you took away from this conversation with Jason. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Transcript:Samir Kaji:I am Samir Kaji, your host of Venture Unlocked, the podcast that takes a behind the scenes of the business of venture capital. On this week's episode, I'm thrilled to bring you my conversation with Jason Shuman, a Partner with New York based Primary Venture Partners. The firm leads seed rounds for companies in New York, and previously invested in companies such as Jet, Mirror and Latch. Earlier this year, the company raised two funds totaling $200 million. Before joining Primary in 2018, he spent time as Chief of Staff for GLG founder Mark Gerson, was an Associate at Corigin Ventures and founded and ran a company called Category Five from 2011 to 2015. I found Jason to be really thoughtful and we had a great conversation on things like finding alignment when you join a firm, the tangible KPIs they use to measure success and what type of value they're providing founders and his view of New York and the market as a whole. Now let's get into the episode to hear all of that and more.Samir Kaji:Jason, it's so great to have you on the show and thanks for joining us.Jason Shuman:Thanks for having me, man. Appreciate it.Samir Kaji:Let's go back a little bit. I know you're now investing out of fund three, but what led you into becoming a venture investor and getting interested in startups?Jason Shuman:Yeah, so I'm from Boston originally and I grew up in a family of entrepreneurs. My dad was running his own company, my aunts and uncles, my cousins, it felt like everybody was running their own thing. So I became obsessed with startups when I was pretty young, like literally in middle school, I was writing business plans for mobile payments on flip phones. And in high school I went to work at this identity theft protection company that was run by my aunt and uncle. And they had a former VC from SoftBank working over there at the time and I just learned a ton from them about A/B testing and customer acquisition and LTV. And I just became a total nerd around startups more broadly, which ended up taking me down to the University of Miami for college, where I studied entrepreneurship and marketing and launched my first company, which was direct-to-consumer footwear company back in 2011.Jason Shuman:It was good timing, but pretty bad execution if I could say so myself. So when you can't operate, go ahead and invest, is sometimes that I joke about, but literally about a year out of school we had gotten the thing around profitability, but co-founder breakups, cashflow issues with that company, I just decided to wind it down. I couldn't imagine myself really doing it for the next 10 years. And sitting there as a 23 year old in Boston at the time at home, I was like, "What do I want to do next?" And I didn't have the confidence to start a new company and I didn't know if I really wanted to go operate at a friend's company, but this thing called venture capital became super interesting. Really at the beginning, it was for four reasons. The first one was I could learn about different industries nonstop and I'm a huge nerd and so doing that was great.Jason Shuman:Number two, is I wanted to be able to fundraise easier and number three was really that I could meet a better team for the next time around. And you only know an A-player when you've seen it. And I felt like the VC would put me at the forefront of meeting some of the best operators really in the world. And lastly, venture really aligns with my why in life. And I'm sure we'll get more into this, but the idea of being able to go help others, give them the confidence, the skill set, the tools, the relationships to live a more successful fulfilling life, venture really aligns with that. So I drove for Uber at night and sourced deals during the day for free and eventually found myself getting a 90 day trial offer from the guys over at Corigin Ventures to be their first hire and the rest has been history.Samir Kaji:So you started at Corigin which at the time was the venture arm of the parent company. Ultimately did that for a while and worked then I think with Mark Gerson of GLG. You and I have talked about that offline. That was an interesting experience where you got exposure to a lot of different things. It wasn't just traditional venture. Tell us a little bit about the experience with Mark.Jason Shuman:Mark Gerson's an incredible guy. He did an incredible job building GLG to the behemoth that it is. I would say the quiet behemoth that it is actually in New York City being a billion dollar plus market place business. But he's also an incredible philanthropist and he has his hands in so many buckets. So when I came over there to really get the family office stood up, I was doing a slew of different activities. One, was venture capital investing, the second was we were working on incubating companies. The next was LP investing. We had some philanthropic efforts that I was involved in, in Israel and Africa. And then the last thing that I was supposed to be doing was spinning up a mentor network between ultrahigh net worths and pro athletes.Jason Shuman:So one of the first people that actually we onboarded was a guy by the name of Kevin Beacham who has gone above and beyond all expectations that I ever had in terms of his investing career now, and really become like a brother to me in many ways. But about six months into that gig, I actually got pulled into a portfolio company of Mark's to operate again. So at that point I was doing both operating, raising some capital for the company and also investing in startups. So it was a heck of a time and it really made me have a lot of empathy for founders, even more because of the fact that during my first startup, I didn't raise venture. But during that one, I was a big part of the process and going out and fundraising.Samir Kaji:It's such a unique experience to be able to run so many different things from investing directly in early stage startups to doing LP investments, to working with debt funds. And you probably learned a lot of how the investment world works and the fact that there are so many ways you can make money and there's so many ways to capitalize companies. At a certain point, you probably were deciding like, "What do I do with my life and on a go-forward basis?" And where you spend your time. You ultimately went to Primary Ventures. And my presumption is that there were a lot of things that you've learned during your time with Mark that really shaped your view on the type of firm you wanted to join. Walk us through exactly the decision model you had of "I'm going to join Primary, not another firm, not start my own." What was that like and take us inside your head at that point.Jason Shuman:Yeah. So I need to give credit to Ash Egan. He had actually just launched his own fund Acrylic, which is in the crypto space, but Ash and I were having a conversation when I kind of hit this point that I knew I wanted to move on. I knew I wanted to go back into venture full time. And I went through this exercise that was like, "what do I want out of my next gig and what do I want to optimize for?" And I went down to my notebook and I wrote down the different types of funds that fundamentally existed at seed. And on one side of the spectrum, you have these funds that are like, "Spray and pray, come over here, hustle your butt off, go and network nonstop, but write 250K checks and 30, 40 companies a year."Jason Shuman:And you're networking mainly with VCs because at the end of the day, that's where you're probably going to get a lot of your deal flow from. On the other side of the spectrum, I was like, "do I want to go to a multi-stage fund? These guys are starting to come down the stack and they're starting to get some seed practice going and do I want to start that for them?" Because I've always considered myself relatively entrepreneurial. But then in the middle of the spectrum was the absolute sweet spot and what I love. And honestly, life is too short for you to do something that isn't what you love. And that sweet spot for me was high conviction, hands-on investing at the seed stage and that meant leading deals, and it meant leading very few deals a year.Jason Shuman:And so when I drew each one of those buckets, I wrote the firms down below each one of those buckets that I knew, or that I had worked with. And in one day I had sent out about 35 emails to folks saying, "Hey, so-and-so, I've really enjoyed getting to know you. I'm thinking about my next move would love to have a conversation." Now that weekend, I got a phone call from Luke Schoenfelder at Latch. And he said to me, "Hey man, I think you really need to talk to Ben and Brad. They just announced their second fund, $100 million from an investment strategy perspective. You guys are super aligned and they're just great humans." And so I met up with Ben at Le Pain Quotidien on Broadway and 21st that morning and what was supposed to be like a 30 minute meeting turned into two hours.Jason Shuman:And what I realized was that from a strategy perspective, we were literally the most aligned that you could get. I mean, fundamentally we believe that at the earliest stages, there's many ways to make money, but startups are hard and founders deserve better. So if we're focused and we're pushing them to be focused, we need to be even more focused. So it's like we're New York only, we're seed only. We only lead and we're trying to bring a tank to a knife fight. Like we invest more in our portfolio impact team than anybody else. And when I was looking at funds in full transparency, there was a few that I was at the offer stage with.Jason Shuman:And some that were even giving me offers to make more money or have a better title from day one. But when you have two firms that have the exact same AUM and one firm has a team of 13 people, and out of that more than half are on portfolio impact. And the other firm is only a couple of GPs and a platform person. I said to myself, "which side of history do I want to be on?" And ultimately I am where I am today.Samir Kaji:Looking back then you sort of go through this decision model, which sounds very thoughtful, right? You've kind of forced rank what you cared about. You had this view that Primary in itself, and the partners were just incredibly aligned with the way you thought about it. But going into a new firm, especially a firm that's already established, you a couple partners with Ben and Brad that had worked together for a long time. And a lot of firms have struggled with integrating new senior investment professionals having a seat at the table and having a culture. How did you yourself think about those intangibles when joining? What has Primary done right to be able to integrate new people in a way that provides really long-term viability and the right culture?Jason Shuman:Ben and Brad get a ton of credit for this. I think it starts with trust. When they go out to find new people to bring on the team, the interview process is not just about getting to know you as a person, but it's getting to the place where they feel like they can really trust you. If I can give a piece of advice to young investors that are going into a firm with an established partnership, it's really that the skill of, "getting a deal done," is really about trying to help build consensus. And if you can't build consensus, it's about articulating your framework from an investment evaluation perspective and getting people to see your point of view and your perspective. At the end of the day, we have an investment framework internally where we write down a list of got to believe in any investment and it's like, if you believe in X, Y, and Z, then we should be doing this investment. And the thing is in a diligence process, maybe two out of the three gotta believes you can diligence and check that box and say, "that's obvious. Let's just say that's completely obvious." But the third one is the one that gets debated the most. And at the end you never know, one person could be right and the other person could be wrong, but this is the type of business where we're arguing about things that nobody really fundamentally knows the answer today.Jason Shuman:And so if you're working with people whose point of view you trust, and you think they're really smart and they worked their butt off and have learned through years of experience, then you're going to give them the leash. And to my credit, I think to Ben and Brad is that they've given me the leash to really go out and try to get deals done and to win the trust of entrepreneurs and to work super closely with them. I hope that I've proven them right in giving me that trust and I hope that continues.Samir Kaji:It's also a challenge on the other side of the coin. If you're entering into an established partnership to have, in some ways, the confidence to be able to have a voice at the table, imposter syndrome, I think, is a very real thing for a number of people. In fact, I would say the most, the majority of people in the industry have some level of imposter syndrome, regardless of how successful they've become. It's even tougher the longer a partnership has been around, the longer those people have worked together. What advice would you impart to somebody that's joining a successful firm with an established partnership in overcoming some of those things that relates to imposter syndrome and just integrating with a new set of family members?Jason Shuman:I think it requires two things. One, the education piece that I just brought up, I think is really important. Angus Davis at Foundation, I think did an incredible job at bringing his partnership up to speed on the challenger bank space. And he was able to essentially just show them the deep dive in the work that he put into really figuring out everything and anything he could about the space and showing them the framework that he had. And by being able to do that, he was able to build trust and I think their conviction in him. In terms of how to completely remove "imposter syndrome," I think imposter syndrome is one of those things that most seed stage investors can have it, but it probably is going to end up lasting your entire career.Jason Shuman:And the reason being is that when you look back on your best investments, good luck trying to connect all of the dots aside from the fact that the people were really, really good and the timing was really, really great and the market was really, really big. If I can get this one piece of advice across it's, you're being paid for your opinion. Ryan Freedman said that to me super early on when I was at Corigin and said, "I'm paying you for your opinion." And that was on day 15 of my job sitting in an office and I really didn't know anything. And ever since then, I've started to just continue to think and reframe imposter syndrome where it's like, "You know what, everybody's an impostor," because most people, especially at seed, yes, there is skill.Jason Shuman:And yes, you're putting yourself in the position to succeed and you're meeting the right founders and you're getting into the right circles. But if you look back at all of these investment theses or the investment memos on certain deals that worked out, maybe 50% of it's right. Maybe 80% of it's right. So you just don't know. And I think the more that you can get comfortable with the unknown, which I know we all like to control as much as possible because most of us are type A, but the unknown is real. So imposter syndrome will either continue to persist or you should believe it's fake.Samir Kaji:And it's probably something that all of us have to get comfortable with to a certain degree and understand why we're in a certain position to be able to provide those types of opinions, knowing that we're going to be wrong a lot and that's just the nature of the business. Speaking of the business itself, you mentioned something that I found really interesting, and I like it, which is bringing a tank to a knife fight. I would say the world has evolved so dramatically over the last 15 months or so that you could probably pack in multiple lifetimes. The game of venture has changed with so many different firms, company formations, valuations, and it feels like we're entering an environment where funds have to sort of adjust how they approach winning deals. You've taken at Primary, fewer companies per portfolio indexing heavily on a team that helps these entrepreneurs. Tell us why that matters so much today.Jason Shuman:Founders are getting married to venture firms for the next 10 years, right? If they're successful. And at the earliest stages, there are many things that a founder at the seed stage cannot afford. They're not going to be able to go out and hire a Chief People Officer who has scaled the company from 20 to 500 people. They're not going to be able to hire the Chief Revenue Officer from a company that's scaled to $200 million of ARR. They're not going to be able to hire the CFO from a company that got acquired for $400 million. These things just aren't resources that they can get on their own, but they are resources that we as Primary have and will continue to invest in and bring full-time onto our team so we can provide those resources to the companies that we're trying to work with.Jason Shuman:So when we meet with founders not only are we introducing them to Rebecca Price who came over from Capsule and Enigma, or Cassie Young, who came over from Sailthru and CM Group, but we're introducing them to the other three people on our market development team who are going out and helping you as sales and go to market and the two other recruiters and community people, and the person on the marketing side of things that can really help them think about things in a way that they probably wouldn't be able to, without the resources that we're providing them with.Jason Shuman:The other thing I will say is that as a young partner at a fund, who's trying to win deals, having these people by your side, who by the way, are 100 times better at the things that they do than I am. And I don't care which fund you go to who the partner is, unless they've done that job, specifically that job, not the CEO done that one job, they're not going to be better than their old CRO most likely in scaling up the function. So by applying these people from a value add perspective, it makes it easier for me to win deals. And then at the same time we fundamentally believe it's great to bring on board what's called board partners who are folks that can come into the boardroom alongside people like myself to provide that other support in the boardroom.Jason Shuman:And those are people like Scott Norton, who started Sir Kensington or Jason Harinstein, who is the CFO over at Flatiron Health. These are people that are going in alongside us and trying to provide even more pointed feedback because not only have they seen the earliest stages, but they've seen the latest stages and have been in the weeds and more recently. So if there's anything we can do to help a founder get 10X the value out of us and not just us as a one single person team that's exactly what we're going to optimize for.Samir Kaji:There's something embedded in there that speaks to being a service provider versus just a pure investment firm. And I've always said that as an investor you're selling a commodity, which is capital in markets that are like the ones today where founders have so many different options, you have to actually provide something above and beyond that consistently. And it has to actually be meaningful to founders. And I want to get into this a little bit more because there's a lot of skepticism because a lot of venture funds say, "We add value beyond the investment." You've built a team around certain capacities that drive value to these founders. The first question I have around that is, how did you think about which pain points you wanted to solve for in recruiting that team that you built? And you mentioned some of those, but tell us a little bit about what went into that team build.Jason Shuman:I can't take any credit for it because it happened long before me, but fundamentally from a framework perspective we asked ourselves the question of, "what are the resources that seed stage founders wish that they could have, but they can't afford today?" And that's how we came up with recruiting. So on the recruiting side, we save our companies nearly $3 million a year in recruiting fees. And time to placement is like 50% of time to placement for companies who are trying to hire on their own. I mean, you think about that and you think about a CEO's job and maybe 20, 25% of their time at the seed stage is going on LinkedIn and cold messaging people. And it's like, the unlock of time is incredible and speed with these companies is absolutely imperative. It's like a number one priority when we think about what makes a great founder.Jason Shuman:And if you can't get butts in seats in 45 days, and it takes 75, that's a huge gap. And so we can bring recruiters in to support you. And by the way, because we only focus on New York, we've built this massive database of 1,000s of people who we've also back channeled. So we're not sending you people that we don't know at all. We're sending you high quality candidates with higher conversion rates, with higher success rates. And by being able to do that, we feel better about the opportunity for you to succeed or the probability for you to succeed. And it's the same thing on the go-to-market side with relationships. So we can make all sorts of introductions there. We can coach a lot of your executive team on that side, we can coach the junior team on that side. And then on the finance side, I think a lot of seed stage investors don't love diving into the weeds on the financial modeling and projection side and the cohort analyses, and really cutting up all the data, so we've brought on folks that love doing that and have done it at a scale that a seed stage CFO just wouldn't.Jason Shuman:And most of these companies don't have CFOs. So we really try to package our companies from a financial perspective too, by the time that they go and get to an Andreessen or a Sequoia or a Bessemer or a GGV, they're like, "wow, this is the cleanest data room, the cleanest financial model I've ever seen." And the amount of times that I think I've heard that from my friends at those firms is I can count on by more than two hands and I haven't even been there that long.Samir Kaji:This is a question that was actually posed to me by another manager who's scaling and their AUM now allows them to start to hire a operations team that helps founders with a whole host of things, similar to what you guys are doing. The question though, that they posed was, "how should I think about KPIs?" And another firm that had chimed in and said, "well we actually look at founder NPS scores. So we do these founders surveys and we ultimately look to test, what is the overall benefit we're providing? How much value are we really driving and NPS is a great way to do it because it shows tactical." Are there certain KPIs that you guys use to really assess the quality of performance of this team that you've built?Jason Shuman:Giving you all of our secret sauce right now. Yeah, we have inputs and outputs on the portfolio impact side and really credit Cassie and Rebecca who have implemented an incredibly powerful system there. So on the people's side, there are KPIs around dollars saved, but there are some other KPIs that regard or surround smaller projects for instance. On the market development side, there are KPIs around the actual pipeline and the actual sales that they generate for the portfolio companies. And then what kind of sits on top of everything is in our CRM we track basically all the interactions between, or projects that we have with ourselves and our portfolio companies. And those are broken out into high, medium and low intensity. And there are KPIs around high intensity projects, medium intensity projects, low intensity projects.Jason Shuman:And then at the end of the year, really, I think it's actually twice a year, we do a founder CSAT or NPS score depending on how they are different. I mean, we do a CSAT, we didn't find that NPS was that helpful although we do ask the question, but the CSAT is an important, which is the customer satisfaction score. And that is basically getting input on every single person on the team and every single team. And then we now can overlay that data on the interaction side of things to figure out, "well, founders that have high intensity interactions are the happiest, but you know what actually low intensity ones are pretty happy too because of X, Y, and Z reasons and interactions with this team."Samir Kaji:That makes total sense. And it's very clear that what you guys actually built is working based on everything I've heard in the market. So congratulations on building such a great group. Going to the investment side for a second. You talked about this earlier, Primary's New York focus. So focusing on companies that are only New York, you're not looking at other geographies. And a lot of people have had the view that being single geo focused if it's not Silicon Valley is hard because how many massive companies are going to be built. And if you're going to provide those 3 to 5X returns fund after fund, you kind of have to be an every single great company that is in these smaller geos. Now New York part of me is like, it's not really a small geo, but at the same time, I think you understand just directionally the things that you probably have heard during your LP pitches. Tell us a little bit about why geo focus, what does it actually mean to win a single geography?Jason Shuman:New York is an incredible city that yes, 10 years ago, if we wanted to have this conversation, I would agree with you. But 2015, when Primary was started, Ben and Brad had a key insight. And I think they've been spot on. I mean, if you fundamentally believe that there will be 5, 10, 15 unicorns a year coming out of New York City, then you want to be an LP in Primary because we're going to go out and we're going to hunt down those companies and we're going to get into them. And even if we're only in half of them, our returns are still going to be extremely strong. And that's why I think from a focus perspective, it's incredibly powerful because it unlocks so much more on the portfolio impact side of things and kind of creates a network effect within our own city.Jason Shuman:And there's a reason why Andreessen just hired David Haber here in New York. And there's a reason why Lightspeed just announced that they have an office here in New York. And most of the seed funds are sending people out here. And most of the SF funds are sending people out here. So this city is going to get more and more and more competitive. Series A funds are coming in at faster paces than I've ever seen before. But if we can continue to own seed with focus, I feel like we're putting ourselves in a good position to succeed.Samir Kaji:So speaking about New York and you're right, New York is a massive market that's evolved so dramatically in the last decade. However, today it's more competitive, right? You see downstream investors coming and doing seed. You see more money flowing into the ecosystem. And in today's world, a lot of founders are indexing heavily toward investors that can work with speed. You you're writing big checks. You're not doing 250, you're doing $3 million checks, which means you have to have diligence, you have to have conviction, not only in the founder, but the business model. How do you manage speed versus diligence in today's world, such that you're not missing on the best opportunities because you can't move quickly enough?Jason Shuman:We're really doing it in two ways. And I want to give credit to Mark Gerson who taught me about sense of urgency and really having a sense of urgency with everything that you do, if you want it prioritize it. So when it comes to a diligence process, if I'm meeting with the founder and we like the deal, or we like the founder before the meeting's over, I'm literally going to open up my calendar and I'm going to schedule a meeting with that person for the next day. And we've now brought on an investment team of... Let's see, six people, five, six people since the beginning of last year to help us speed up the diligence process.Jason Shuman:And so folks like Lia Zhang who came over from Stripes Group or Tobias Citron who has been here last couple years as an intern and Paige from Insight and Sam from Nomad Health and Kai. They're here essentially not only to just source deals, but to create these deal pod structures that help us take a deal from day one, come up with the list of got to believes that we need to diligence, go out, track down the answers to those questions. "What does the market look like?" Have those customer calls, back channel the founder. And then once you've really gone through that process, which by having three people on a deal, instead of one, you're able to do it a lot quicker. And we're going to meet with that founder three times over the course of six days.Jason Shuman:And that helps us really start to get to know them. Now I do think this is a period of time that I'd say a lot of mistakes will be made by many other firms, and maybe there will be some made by us as well, because you sometimes just don't know what you're missing. Maybe not even in terms of the market, but the person. And it sucks because I don't want this to be transactional, I want this to be as genuine as possible. And I want to be able to go have dinner with you and get to know you a lot more. And so we're trying to make sure that we're checking all of the boxes that we were checking before, but in a little bit more of a condensed timeline and that's worked out pretty well for us.Jason Shuman:But that said I've talked to multi-stage firms that have led some of the seed deals that we've looked at and I'm like, "well, did you look into X and Y?" And they're like, "nope," because it's like, "why do they need to? This is a tiny check for us." So we really pushed founders to work with seed firms, whether they work with us or not, that are at least doing the work. The other thing though, that we've been doing is going earlier and earlier. Tobias and Brian here launched the New York City Founder Fellowship, which is our version of an equity free, fee free version of YC or kind of like an On Deck. And we've had some incredible talent coming in. And now we're getting to know them at the earliest stages. We're getting to see how the sausage is made, how the idea evolves, how they learn, the speed of learning, and then we can make bets on them even earlier. And it's the same thing on the pre-seed side of things, where we're getting to work with people that we really enjoy working with and we've gotten to know over the years.Samir Kaji:And that's a great framework in terms of how to manage all these different variables that are in play right now, which leads me into a more global question to you. So when you started investing, it was at a time where prices were low and actually it's coincided with a time where as those companies have matured, we're in a great capital market. Liquidity, the exit environments are great. So if you look at the performance of funds that were 2008 to 2015, amazing performance. It's not uncommon to see 5 to 10X seed funds, right? I mean, we've just seen so many of them. What do you think about the market today, right?Samir Kaji:The old adage is always, "buy low, sell high." Are we in a place where innovation just is in an area where it's just rapidly evolving and growing so quickly that even if you're buying higher relative to fundamentals that in spite six, seven years, you'll still be able to sell higher, or do you view this as, "yeah, valuations are high and the best companies will continue to do it, but there is going to be some deterioration and maybe some carnage that happens if there is a downturn in let's say a couple of years now that we are going on 12 or 13 years in a bull run?"Jason Shuman:I think we're at a period of time where the pace of innovation is shifting at such a rapid rate, that there really will be these massive companies that generate these really strong returns. Now that's not every company and that's not every market and not every company in every market has real moats and should be traded like a tech company. But there are many markets that are going to have a new champion crowned that can generate a significant amount of enterprise value and returns for LPs and ourselves. Looking broadly at the ecosystem today, and this is anecdotally from a Primary and a New York perspective, we have more high quality founders that have seen scaling from 10 to 100 or 1,000 now than we ever had before because the New York ecosystem is really starting to mature. Secondly, you're getting better ideas than you've ever had before, and why is that?Jason Shuman:I think one, there's been a shift and a why now in a lot of these industries, but also because there's a democratization of access to information on the internet today. And you think about the amount of healthcare companies that are getting started, that we see that are incredible. People are leaving Oscar and RO and Cedar and starting companies that have really strong moats and great tailwinds and massive markets and you back them. And then what's crazy is not only is this speed of innovation changing, but it's the speed at which these companies can scale. I mean, we have a company in our portfolio, that'll go from like zero last year when they just like pivoted to over 50 this year.Jason Shuman:And it's like, "whoa, that's recurring revenue." It's an incredibly powerful thing. And so, yeah, I mean, are people overpaying? Maybe, definitely in some deals they certainly are, but there are certainly a lot of other companies out there that will live into it but it is buyer beware and its founder beware because when you do end up taking on money at a ridiculously high evaluation and you don't actually have product market fit growing into that might give you a little bit of digestion.Samir Kaji:I think that is such an important point. And I've always talked to founders about that. "Don't take too much money at too high a valuation until you're ready." Now, yes there's money out there and you don't want to under capitalize yourself in this market, but it is founder and buyer beware for sure. I also agree with the point that the pace of innovation today is at breakneck speed and you can look no further than the vaccine roll out using RNA technology with Pfizer and Moderna, so the world has shifted. I'm personally very excited to see what the next couple of decades look like. I try to disassociate that with the financial aspect. It's too hard to know and I've been long around long enough to know that I'm not smart enough nor do I think many people are smart enough to actually project what the financial markets are going to look like for the next five years, let alone the next year.Samir Kaji:So let's go to our last segment, which is our heat check. I'm going to ask you three questions, rapid fire, the first being, what is the most counterintuitive lesson you've learned as a venture investor?Jason Shuman:People, I would say founder first, and I do agree, but you put a good founder in a bad market, the market will keep its reputation and the founder won't. So you need to make sure that you back a founder that will recognize when they're in a bad market and they'll move over to a different one.Samir Kaji:And we do see that quite often and having that awareness. Well, let's talk about founders and you've invested in companies like Latch at the early stages. You probably have spent enough time looking at companies where you're going to miss companies too. Looking back in your career, is there a company that you look back on that you missed that's turned out to be a great company, and you've learned a particular specific lesson from? If so, tell us who the company is or if you're comfortable with and what you actually learned from that miss?Jason Shuman:My entire portfolio has a good size to it, but I'll use LeafLink as the example here. Ryan Smith actually has become a great friend. And I was at Corigin Ventures at the time when we looked at Leaflink. And I remember asking a lot of questions about, "well, what's your engagement like? And your this and that on these features and are people really using it?" And he wasn't really tracking that much of the data in the early days. There wasn't the foundation laid and he had sold the company before. And I remember thinking, "how good is this guy?" And at the same time I knew his market timing was really good. And I knew he was really, really thoughtful, really thoughtful and learned super-fast and had done it before.Jason Shuman:But at the end of the day there is some extenuating circumstances that made it so we didn't win the deal. And then I ended up leaving Corigin but if there's a lesson that I learned there, it was definitely stay in touch with founders as much as possible that you really believe in. And then also there's a lot of things that founders just don't have the time for in the early days. And if they have a bias for action and they know how to sell, and they know how to build product tracking when you're like two people in a closet is not necessarily something that needs to happen.Samir Kaji:Playing the long game and keeping mind share is a really good lesson to learn for anybody. My final question, just because you have mentioned guys like Mark and Ryan and Brad and Ben, but is there an investor out there that particularly inspires you given the way they think about things? If so, who is that and what about them?Jason Shuman:My answer, I don't know if you're going to accept it is Bill Campbell. Bill Campbell was the executive coach to folks like Steve jobs and Eric Schmidt, the guys over at Google. And long-term, I really do see myself getting into the executive coaching world. My mom's a therapist, my dad's an entrepreneur and I feel like the best investors really are generous with their time and help not only the company at the company level and the metrics level and are thinking about strategy, but they are helping the psychology of the founder and they care deeply about all of the employees within the organization.Jason Shuman:And I'll tell you really quickly having back the guys at Latch and then Ben at the stock exchange when they were going public the other day, seeing the employees that were there since day one, it gave me the chills. It was awesome and I was so overcome with gratitude that I walked up to all of them that I remembered and I was giving them hugs and just saying, "thank you." And Bill Campbell is the type of person that more investors should really admire and try to be like.Samir Kaji:A lot of people who don't know Bill, just because he is a Silicon Valley legend and obviously coached some of the best founders, entrepreneurs and VCs. I don't think he started his career in tech until he's in his early 40s coming off as being a football coach, right? And there's a great book out there on bill that's called Trillion Dollar Coach, which is a great read. So I definitely will accept the answer because privately, a lot of people have told me the impact Bill has had on them. Jason, this has been a lot of fun. Congratulations on being promoted to Partner as part of fund three, excited for what you guys are doing in New York and look forward to... I'm going to continue to track the story.Jason Shuman:Thanks man. Appreciate you having me.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Sep 7, 2021 • 46min

Broadhaven Ventures' Michael Sidgmore on democratization of venture capital, why Alts are the future of private portfolios, and the role of wealth management firms.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today we’re thrilled to bring you a very unique conversation with Michael Sidgmore, Co-Founder of Broadhaven Ventures and host of the Alt Goes mainstream podcast. Broadhaven Ventures is fintech focused and has invested in several platforms that make alternatives more accessible including, Republic, Party Round, iCapital, Alt, and of course our startup Allocate. Additionally, Michael was an early employee at iCapital (currently valued at $4B), which enabled private wealth managers to offer top alternatives to their clients. Michael is also a Venture Partner at Goodwater Capital, one of the top global consumer focused venture capital platforms in the world with over $2 Billion of assets under management. We covered the broad topics of retail influence within alternatives, the future democratization of venture capital, and why a larger supply of LPs is coming. A message from our sponsor:Pacific Western Bank is a full service commercial bank with over $34 billion in assets. The venture banking team specializes in financial products and services for startups, venture-backed businesses, and their venture capital and private equity investors.The experienced team is committed to the space and dedicated to delivering high-touch, tailored solutions, helping innovators take their business to the next level.In the first half of the year, the venture banking team has booked over $800 million in new loan commitments to help support the community.  No matter the size or stage of your business, you can expect guidance, resources and flexibility, making them the perfect team to support your evolving needs.Turn your vision into reality with PWB. For more information, visit www.pacwest.com/lending-solutions, or follow us on LinkedIn and Twitter.*Equal Housing Lender & FDIC insured*Total assets & loans booked are as of June 30, 2021.In this episode we discuss:01:06 Why Michael got into investing08:02 The world of alternatives12:55 How the demand for alternatives assets has changed over the years18:31 Navigating the challenges for people to access alternatives24:19 The long term progression of alternative investments29:29 Important thematic trends in the next generation of investors34:09 What adding value to investments means to Broadhaven37:52 Balancing the relationship between founders and VCs41:43 Successfully scaling for valueMentioned in this episodeBroadhaven VenturesI’d love to know what you took away from this conversation with Michael. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Aug 31, 2021 • 50min

Act One Ventures Silton and Guerrero on the Diversity Rider initiative, building meaningful partnerships, and operating experience has been key to their model

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today’s episode is with Michael Silton and Alejandro Guerrero of Act One Ventures, a Los-Angeles based firm that invests in pre-seed and seed-stage .Before becoming Managing Director of Act One, Michael was Executive Director of the UCLA VC Fund for three and half years. He was also CEO & Founder of RainMaker Systems(to which he took public) and co-founder of UniDirect Corp. Prior to being General Partner at Act One, Alejandro was Volunteer Associate at UCLA Ventures from 2013-2016,  Co-Founder & CEO of Uniq Apps and Co-Founder & President of the Live Entertainment Network.We chatted with them about their unique partnership, how they tangibly drive real diversity into cap tables, and how they navigate in today’s white-hot market. A message from our sponsorAnduin is revolutionizing fund management with streamlined fund operations, digitized fund subscriptions, and real-time status updates. Traditional, paper-based subscriptions are costly, tedious and error-prone, with up to 80% of submitted documents being incorrect and considered not in good order.Fund managers lack real-time visibility, facing manual processes, endless back-and-forth and a mountain of emails, documents and spreadsheets.Anduin’s investor onboarding workflow improves the investor experience, bringing clarity, guidance, and efficiency to fund subscriptions which drastically reduces error rates.The Anduin platform allows GPs to perform fund operations simply and efficiently with improved data accuracy, freeing up time so they can focus on what they do best... investing.For more information, or to arrange a demo, visit fundsub.io/ventureunlockedIn this episode we discuss:02:15 How the team got into investing05:22 Why Michael started an independent firm, after so many years as an operator13:10 Key lessons learned from raising their first fund15:11 Staying positive when fundraising is going slow22:53 The Act One Ventures investment model26:34 Why learning from failures is a superpower29:18 How their unique differences as a partnership drive value to founders38:35 The Diversity Rider; What it means and why is it critical for the future of underrepresented GPs and founders. Mentioned in this episodeAct One VenturesI’d love to know what you took away from this conversation with Michael and Alejandro. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Aug 24, 2021 • 47min

From Norwest to starting Roble Ventures, Sergio Monsalve on equity and diversity in tech, adapting from large VC to a small, solo-GP, and investing in heated markets.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today’s episode is with Sergio Monsalve, founding partner of Roble Ventures, a seed firm based in Silicon Valley that invests in solutions that help human progress. Their portfolio includes Kahoot, Mosaic, and Dragonboat, among others. Prior to Roble, Sergio spent 14 years at one of the longest standing VC firms in the world, Norwest Venture Partners, where he led investments in companies such as Udemy and Adaptive Insights. Before he started his investing career, he held various roles in high-growth technology companies like eBay and Portal Software. He currently teaches at his alma mater, Stanford, on education and entrepreneurship. We chatted with Sergio about equity and diversity in the VC world, adapting to a smaller GP model after so much time at a large partnership, and how he thinks about investing in human enablement technologies. A message from our sponsorAnduin is revolutionizing fund management with streamlined fund operations, digitized fund subscriptions, and real-time status updates. Traditional, paper-based subscriptions are costly, tedious and error-prone, with up to 80% of submitted documents being incorrect and considered not in good order.Fund managers lack real-time visibility, facing manual processes, endless back-and-forth and a mountain of emails, documents and spreadsheets.Anduin’s investor onboarding workflow improves the investor experience, bringing clarity, guidance, and efficiency to fund subscriptions which drastically reduces error rates.The Anduin platform allows GPs to perform fund operations simply and efficiently with improved data accuracy, freeing up time so they can focus on what they do best... investing.For more information, or to arrange a demo, visit fundsub.io/ventureunlockedIn this episode we discuss:02:19 Why Sergio decided to get into venture and the unique challenges he faced 04:47 Sergio’s departure from a large shop in Norwest to starting Roble07:45 Transitioning from a partnership-driven ethos to being a single operator10:23 The meaning of ‘human-enablement’ investing13:27 Post-pandemic predictions16:46 Why you must bring diversity on a team20:31 Diversifying the decision making process and identifying implicit bias24:44 Investing in highly competitive markets with discipline 28:19 Sergio’s parameters for investing32:01 Capitalizing founders in the appropriate way in today’s market36:19 What did Roble Ventures look to accomplish in the early days39:58 The most counterintuitive thing Sergio ever learnt41:27 Dominant trends coming up in venture43:22 Investors he is inspired byMentioned in this episodeRoble VenturesI’d love to know what you took away from this conversation with Sergio. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Aug 17, 2021 • 51min

Haystack's Semil Shah on building the firm from the ground up, portfolio models, and the state of VC today

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today’s episode is with Semil Shah, founder and general partner at Haystack, a pre-seed and seed-stage supporting outlier founders. Haystack’s portfolio includes DoorDash, Instacart, HashiCorp, Figma, Applied Intuition and many more.Semil is also Venture Partner at Lightspeed Venture Partners, and in 2017, was selected to the Midas Brink List.  He previously was a venture partner at both GGV Capital and Bullpen Capital.We covered topics like the challenges Semil faced when trying to get into VC, how he’s evolved his approach over the years and his current and future view of the industry. A message from our sponsorAnduin is revolutionizing fund management with streamlined fund operations, digitized fund subscriptions, and real-time status updates. Traditional, paper-based subscriptions are costly, tedious and error-prone, with up to 80% of submitted documents being incorrect and considered not in good order.Fund managers lack real-time visibility, facing manual processes, endless back-and-forth and a mountain of emails, documents and spreadsheets.Anduin’s investor onboarding workflow improves the investor experience, bringing clarity, guidance, and efficiency to fund subscriptions which drastically reduces error rates.The Anduin platform allows GPs to perform fund operations simply and efficiently with improved data accuracy, freeing up time so they can focus on what they do best... investing.For more information, or to arrange a demo, visit fundsub.io/ventureunlockedIn this episode we discuss:02:26 Semil’s path into VC and some of the challenges06:00 Initiating relationships with LPs12:54 Scaling as a venture firm16:15 Semil’s portfolio construction methodology20:30 Were there any transferable elements from LSVP and GGV to running a seed fund?23:21 Semil’s take on differentiation31:06 Do LPs push venture firms to be too big?33:25 Redefining venture scale outcomes40:08 What it means to be disciplined41:15 Semil’s view of the venture landscape today43:50 The most counterintuitive lesson he’s learned being a VC46:07 Underrated characteristics of successful VCsMentioned in this episodeHaystack VenturesI’d love to know what you took away from this conversation with Semil. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Aug 10, 2021 • 46min

137 Ventures Justin Fishner-Wolfson on why ownership is an overvalued heuristic, building lasting teams, and the current state of secondary markets.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today we’re thrilled to bring you my conversation with Justin Fishner-Wolfson, co-founder and managing partner of 137 Ventures, a growth-stage venture firm that provides customized liquidity solutions to founders, investors, and early employees of high-growth private technology companies. With a total AUM of $1.5B, 137 Ventures has backed some of the most impactful companies of the past decade, including Wish, Flexport, SpaceX, Uber, and Airbnb. Prior to launching 137 ventures in 2010, Justin worked on the investment team at Founders Fund. A message from our sponsorAnduin is revolutionizing fund management with streamlined fund operations, digitized fund subscriptions, and real-time status updates. Traditional, paper-based subscriptions are costly, tedious and error-prone, with up to 80% of submitted documents being incorrect and considered not in good order.Fund managers lack real-time visibility, facing manual processes, endless back-and-forth and a mountain of emails, documents and spreadsheets.Anduin’s investor onboarding workflow improves the investor experience, bringing clarity, guidance, and efficiency to fund subscriptions which drastically reduces error rates.The Anduin platform allows GPs to perform fund operations simply and efficiently with improved data accuracy, freeing up time so they can focus on what they do best... investing.For more information, or to arrange a demo, visit fundsub.io/ventureunlockedIn this episode we discuss:02:10 Justin’s journey into venture capital03:36 Learnings from Founders Fund05:52 Differentiating yourself in tangible ways07:45 How Justin thinks about the sales process10:34 Fund sizing14:59 Liquidity solutions for the future17:42 How efficient are the secondary markets right now?20:40 Justin’s philosophy on risk26:00 The considerations of check size and ownership requirements28:53 What are the toughest things to get right in building a firm?31:01 Avoiding talent atrophy and ensuring generational succession32:56 The hardest lesson learned in building a firm39:47 The most counterintuitive lesson Justin learned in investing42:19 Learnings from misses43:47 Justin’s inspirationsMentioned in this episode137 VenturesI’d love to know what you took away from this conversation with Justin. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Aug 3, 2021 • 46min

Jeff Morris, Jr. on finding your own fund/market fit, having like Lightspeed and Sequoia as LPs, and the ever-changing dynamic between entrepreneurs and VCs

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Today’s episode is with Jeff Morris, Jr., founder of Chapter One Ventures, an early stage product fund that has invested in Cameo, Pipe, Alt, and Roam. After a significant track record as an angel investor (including investing in Lyft) he started Chapter One in 2019 that featured tier one investors such as Lightspeed and Sequoia as LPs. Jeff was previously the VP of Product at Tinder, spearheading popular features like Boost and Tinder Gold. He graduated with an MBA from UCLA’s School of Management and is a frequent speaker on monetization, product, and growth.We chat about finding your product market fit as an investor; thinking about scaling yourself, and the ever-changing relationship between entrepreneurs and VCs. A message from our sponsorAnduin is revolutionizing fund management with streamlined fund operations, digitized fund subscriptions, and real-time status updates. Traditional, paper-based subscriptions are costly, tedious and error-prone, with up to 80% of submitted documents being incorrect and considered not in good order.Fund managers lack real-time visibility, facing manual processes, endless back-and-forth and a mountain of emails, documents and spreadsheets.Anduin’s investor onboarding workflow improves the investor experience, bringing clarity, guidance, and efficiency to fund subscriptions which drastically reduces error rates.The Anduin platform allows GPs to perform fund operations simply and efficiently with improved data accuracy, freeing up time so they can focus on what they do best... investing.For more information, or to arrange a demo, visit fundsub.io/ventureunlockedIn this episode we discuss:02:11 Jeff’s journey into investing05:43 Jeff’s learnings as an angel investor to being a scout to starting a firm08:38 The main differences between being an angel investor and a full-time venture capitalist11:13 Adjusting to doing venture full time13:51 How Jeff evolved along each step of the way in his investing career16:22 How he constructed his LP base, and him taking on capital from Tier 1 VC’s17:58 How Jeff thought about fund sizing and what he learnt from his first fundraising22:14 Why bring a Chief of Staff onto a VC firm24:47 The debate between optimizing for # of companies vs. ownership27:27 Learnings from Sequoia about investing and entrepreneurship30:23 Jeff’s decision-making model34:39 The future of the VC 37:17 The pros and cons of having a brand on Twitter/ social media39:52 The most counterintuitive lesson Jeff has learned41:20 Lessons learned from companies that he missed43:26 Inspirations in the VC worldMentioned in this episode:Chapter One VenturesI’d love to know what you took away from this conversation with Jeff. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com
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Jul 27, 2021 • 46min

Miriam Rivera on going from angel to running a firm, driving real change in diversity in tech, and how traditional heuristics should be challenged in VC.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape. Our guest today is Miriam Rivera, managing director and CEO of Ulu Ventures, an early seed stage venture fund in Silicon Valley focused on IT startups. Currently Ulu Ventures has an AUM of >$200MM and the team has invested in companies such as Palantir, BetterUp, SoFi, Guild, and Span [For full disclosure, Ulu Ventures is also an investor in my startup, Allocate).Prior to Ulu, Miriam was deputy general counsel at Google, which she joined in 2001 as the second attorney.  She graduated from Stanford University, where she earned the AB, AM and JD/MBA degrees. Miriam is the co-founder, former co-president and on the board of Stanford Angels & Entrepreneurs, an open source network of Stanford alumni investors and entrepreneurs.Listen to our conversation to hear Miriam’s thoughts on moving from angel investing to starting a firm, being a husband and wife team, the reasons behind Ulu’s large portfolio strategy, and why diversity is so important to her.  A message from our sponsorStandish is the largest provider of fund administration services to Venture Capital funds globally. Currently, we serve approximately 750 Venture Capital funds and have more than $150 billion in committed capital under administration.  Standish has been designed by experienced Chief Financial Officers with a deep understanding of the service needs of both finance departments and General Partners at every stage of the product life cycle.  Standish can handle all of the needs of finance department so General Partners can focus on investing.Standish is an employee owned company.https://www.standishmanagement.com/In this episode we discuss:02:05 Miriam’s journey into the investment side03:23 Why they started Ulu and raised outside capital05:22 The challenges of starting a fund as a wife-husband duo 08:14 Navigating their working relationship 11:33 Their unique view on what portfolio construction should be14:06 What the stats say on returns16:53 Trade-offs between size of portfolio and ownership20:20 Strategies for venture investing at the seed-stage23:14 Ulu’s unique decision making framework29:15 Benefits of investing in diverse teams31:58 Changes that can be made in the LP/VC ecosystem35:06 LPs with diverse managers38:18 The social vs. financial impetus in making investments in diverse managers/ partners40:39 Miriam’s most counterintuitive learning as an investor42:00 Companies Ulu missed out on43:36 Inspirations in the VC worldMentioned in this episodeUlu VenturesI’d love to know what you took away from this conversation with Miriam. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

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