Culture is the core of every company, but keeping it consistent isn’t always easy, especially in an increasingly remote-first world. On this episode of The Modern CFO, Tim Brown shares how Dakota prioritizes culture-building and why CFOs should think about the more permanent changes brought on by the pandemic.Show LinksCheck out DakotaConnect with Tim Brown on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInKey Takeaways5:54 – The pandemic caused a shift in business practices for sales professionalsTravel and in-person meetings halted during the pandemic, which meant investment sales professionals had to find other means to connect quickly.“When the pandemic hit, all that changed. Travel was essentially halted for quite a period of time. People were not taking in-person meetings. The vast majority of people were not working in offices, and it just required a very quick, fundamental shift in terms of how you could continue to be effective in that role. I think our team adapted really well, the industry adapted really well–as did a lot of industries. You can't meet live, you meet over Zoom, you meet over some of these other means where you cannot be in the same location, but still have effective discussions. Certainly, it's an adjustment. If you've spent your entire career on the road, and then all of a sudden you're not able to do that, that’s a pretty significant adjustment. I think the software side of our business actually gave us a little bit of a tailwind. Dakota Marketplace was a means that could help bridge that gap between what investment sales professionals were used to, to what the current situation was.”8:07 – Lead with culture during the hiring processIt can be challenging to maintain a consistent culture, especially through periods of growth. Transparency into the important parts of your company culture during the hiring process helps build a strong, well-aligned team.“Culture has always been very important at Dakota. When I joined about four years ago, there were roughly 10 people, many of whom had been at the firm for quite some time. It was very evident from day one what that culture was. As our business has started to grow, we doubled the size of the team in the last 18-24 months. So, coinciding with the pandemic, it's been very important for us to not only formalize or write down, for lack of a better term, what those cultural components are (as opposed to just people understanding what they are), but to lead with [the cultural components] during the hiring process. I think each firm will have a slightly different culture. For the most part, no culture is better than another. I think it's knowing yourself as a human being. It's knowing who you are, knowing who you are as a company, knowing what attributes are important to everyone at that company, and that really helps you identify people who fit well and have similar outlooks of the world, and are likely to be great teammates.”9:48 – Emphasize what’s important to your companyRecognize which components of your culture are most important to the company. That way, potential hires know what to expect from your business.“I do a lot of the initial interviews of candidates that we're meeting with. Inevitably, culture is one of the first things that’s brought up. It's one of the things that we like to emphasize. ‘These are the things that are important to us.’ It's just really recognizing what are those components of your culture that are important that you want people to come in and sort of add to and build on. Like I said, for us, it's really led to a greater degree of success in bringing on new teammates. One of the challenges a lot of companies are facing is retaining talent, and it's really helped us retain employees as well. Because we're doing a better job, upfront, of laying out what's important to us and our culture, people are self-selecting into that.”11:05 – Be a true business partner to your team and CEOCFOs are no longer just experts in finance. Today, the modern CFO is the strategic confidant to their CEOs and a driver of sustained culture to the rest of their teams.“For most companies, gone are the days where the CFO is just the expert in the finance organization. I think those are table stakes for any CFO. I think that a modern CFO is really that true business partner of the CEO and the management team in helping to lead a lot of different components of the organization, not necessarily just the finance component. Certainly, culture is a key component of it. A lot of larger organizations will have separate HR departments, but at smaller organizations like Dakota, that CFO will wear multiple hats and the HR recruiting aspect is a big part of that.”14:33 – Pinpoint where your investors’ incentives and your company’s culture intersect“A family office of a very wealthy family that may have made money under a certain industry, et cetera, may have a very different perspective in terms of what's important to them than a foundation that's geared towards a specific purpose and is utilizing their investment portfolio to help drive income or other value creation that they can then flow through the foundation towards their purpose. So, each one is going to certainly have different things, but I think there's a component of that, of macro long-term trends, ESG being one of them. Then any given day, week, month, year, there's going to be more components that are pressing for that time. Not that those other things aren't pressing, but what I mean by that is in an environment where we sit today, where everyone's looking to the Fed to raise interest rates, and how people look at their portfolios or what the mix of those portfolios are is ever-changing.”16:10 – By investment sales professionals. for investment sales professionalsIf you want to add value for potential customers, find the tools that will help them be more successful.“Our target customer for all of the products and services we create is an investment salesperson–A person who wakes up every day to raise money for the investment strategies that they represent. Dakota has a number of people at the firm, including our founder, who have been in that industry their entire lives. I think we have a very good perspective as to what types of tools and services can help that person be more successful in their job. One of the things that's exciting to me about Dakota is that we're never short of ideas of other things that we could do, or other ways that we could help our customers grow their careers. So what's exciting to me one year, three years, five years out is just looking at our product pipeline, seeing what's coming, and knowing that there's a bounty of ideas that will come after those that will continue to help us continue to add value and drive value for our customers.”17:39 – Give your ideas a shotEven if you don’t have all the details of your idea worked out, give it a shot. Failing fast is better than not trying at all.“Not everything has to be a fully-baked idea before you're going to try it. If you have an idea and you have the basics down, give it a shot! What's t...

Jared Shaw didn’t take the traditional path to the financial world. When his classmates were starting prestigious internships, he joined the military and gained valuable leadership skills. Today, Jared is focused on solving problems: specifically, solving the distribution problem in the world of cryptocurrency.As the Head Of Finance at Gemini, Jared is deeply embedded in the frontier of crypto and digital assets. Gemini’s goal is simple yet ambitious: create a platform so secure and accessible that everyone will feel comfortable adopting it, no matter their age or background.On this episode of The Modern CFO, Jared explains how he fell down the crypto rabbit hole, what’s so different about Gemini’s approach, and why every company needs a digital asset strategy.Show LinksCheck out GeminiConnect with Jared Shaw on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInKey Takeaways2:57 - Jared’s path to cryptoWhen Jared joined Ernst and Young’s San Francisco Bay Area consulting division, he began to encounter startups who were disrupting the traditional financial services industry.“I was helping financial services firms stay out of trouble. Banks, broker-dealers, insurance asset managers were all coming out of the financial crisis. Everyone was dealing with regulatory pressure, and so there was a lot of work helping them stay out of trouble. I started doing that in the San Francisco Bay Area, and shortly thereafter in the 2014-2015 timeframe FinTech really started to emerge. And being in the Bay Area, I was geographically fortunate to be able to focus on that sector and help EY build out its FinTech practice and approach. That was tremendous. Being able to just run around Silicon Valley and meet with all these great emerging startups that were really trying to disrupt the traditional financial services industry. And that's what got me first thinking about how can I work in a financial career, but maybe a little bit differently than the traditional path? And then that largely turned into cryptocurrency emerging in 2017. And in 2018, I did a large consulting engagement for a couple of crypto firms. And then, as everyone who gets involved in crypto, I fell down the rabbit hole and knew this is what I wanted to do with my career.”8:00 - Learn to navigate ups and downsWhether you work in a new environment like the crypto space, a startup, or a large company, you need to be prepared to ride the wave of disruptive technology.“We've grown 2x in our headcount over the last year. And with that, we're still all wearing many hats. And so the day-to-day is just all over the place. What I think that means is an ability to be able to handle a volatile changing environment. Certainly working in cryptocurrency, all of the things happening in digital assets somewhat dulls one’s senses to massive amounts of change, or things being really great one quarter and not so good the next quarter. I think an ability to be able to navigate through those ups and downs is something that we learned really, really well at Gemini and in the crypto industry more broadly. And so having that mindset of focusing on being consistent, of looking towards the future in a measured way. Being able to stomach the ups and downs in the short term is something that's critical for anyone within a startup environment. And probably I would suspect important for someone who is the CFO of a large company or operating a large company, because innovative, disruptive technologies are only going to impact those industries more and more.”10:10 - Taming the wild west of cryptoGemini’s founders, the Winklevoss twins, are focused on a path that will make crypto accessible to and trusted by a mass audience.“The genesis of the company was very focused on Cameron and Tyler Winklevoss, our co-founders’, early experience investing in Bitcoin. Which was as they would put it the wild west, very uncertain, unsecure. Large hacks like Mt. Gox historically made the experience really difficult for the average person. Their vision was trying to make this experience much more approachable for the average consumer. That first started out with the institutions, obviously building weapons-grade security and safety of an environment for buying, selling, storing cryptocurrency. That is the core. And Cameron and Tyler had the vision that ultimately there needs to be regulation, there needs to be rules around this. Because that will bring broader mass adoption. It really focuses on security and trust, and that's something that Gemini has built its brand around, and we will continue to build a brand around.”13:10 - Solving crypto’s distribution problemThe next frontier of crypto is taking it beyond the hands of users who are digitally native and placing it in the hands of older generations.“I think cryptocurrency has a distribution problem. It is very accessible to individuals who are digital natives, who understand having value stored on the internet and who have grown up that way. But there is a vast amount of individuals and wealth out there that are not digital native, and individuals who hear about cryptocurrency but have never had the desire or trust that a digital native person has. So perfect example, you mentioned Andrew before we started that your dad was an RIA wealth manager. I'm sure your dad has a number of customers that ask him all the time ‘What about Bitcoin? What about Ether? Or my child tells me I should buy some Dogecoin.’ Your dad's customers are going to do whatever he tells them. They're not going to go outside for a Gemini account or some other platform and get involved in cryptocurrency. And so that distribution of being able to get folks like your dad’s customers into cryptocurrency is what we think is really the next frontier.”14:37 - The genius of a crypto credit cardGemini’s newest project is a credit card with crypto rewards, where users can instantly select tokens to collect.“Everyone swipes a credit card. And if we can attach the experience of cryptocurrency to something that you do every day, that is a fascinating new entry point for individuals. Even if someone did sign up for a Gemini account, they still didn't have to think about, okay, which token do I want to buy? And now do I buy it today or do I buy it tomorrow? There's a lot of nervousness around that. But if you're just collecting or being awarded cryptocurrency every time you swipe a credit card, that's fantastic. The great thing about the card is it's instant. So you earn up to 3% on purchases. You can pick any of the tokens we offer on our platform. And once you swipe, the next minute that crypto hits your account and it's available for you. You don't have to wait for the end of the month for your statement period, or whatever. It's yours. So you really get a chance to interact with it right away, which is we think is a really compelling offer.”20:50 - Don’t chase shiny objectsGemini’s staying power comes from the fact that they are laser-focused on their vision of secure, accessible cryptocurrency.“Gemini is very fortunate in the sense that we have founders who have a very long-term vision, and have invested in this sector not only person...

In 2012, Woodie Neiss was a CFO and entrepreneur who was seeking to change the rules of the investment game. When President Obama signed his crowdfunding bill later that year, it opened a whole new world for individuals to participate in the private capital markets. Today, the crowdfunding industry has surpassed $1 billion in funding and takes place almost entirely online.Woodie continues to empower entrepreneurs through his latest venture, GUARDD, where he automates the process of ensuring audited financials with the goal of creating a more liquid environment for private company founders and shareholders. He is a vanguard of empowering founders throughout the lifecycle of their businesses from fundraising to exit.On this episode of The Modern CFO, Woodie shares how he architected the roadmap of Regulation Crowdfunding (Reg CF), what is so powerful about crowdfunding, and why one-size regulation does not fit all.Show LinksCheck out GUARDDConnect with Sherwood (Woodie) Neiss on LinkedIn or TwitterCheck out Nth RoundConnect with Andrew Seski on LinkedInKey Takeaways2:30 - Tackle outdated investing lawsIn his early days as an entrepreneur, Woodie was frustrated by the inability to tap into individuals as investors, like his large customer base.“I had started a company with my brother-in-law called Flavor RX. We flavored medicine for children so they’re more compliant. The coolest thing about our company was a mother got her kid to take her medicine by going into the pharmacy and asking pharmacists to flavor it. The kid took the medicine and she's like, ‘Oh my God, you just saved me countless hours of struggling.’ I would get a phone call the next day: ‘How do I invest in your business?’ I thought, well, you can't because we can only raise money from accredited investors. When my lawyers told me this, I knew this was a complete missed opportunity. I have hundreds of mothers calling me saying, ‘How can I become an investor in your business?’ They can be a marketing agent for my company. Why can't I take money from them? These laws were written 80 years ago to protect retail investors, and you have to live by them. I thought was stupid.”3:53 - How the crowdfunding bill was signedWoodie and two friends from business school ultimately drafted a new framework for Reg CF. President Obama signed it into the Jumpstart Our Business Startups (JOBS) Act in 2012.“We wrote this eight bullet-point framework for investment crowdfunding. We went to the SEC, they said it was cute. Then they said, You should head over to that building with the white dome on it.’ I kid you not. Naively enough, we just walked over there, because we had a few days in Washington. We started knocking on the doors of both Republicans and Democrats. People were shocked that entrepreneurs were there, so they listened.”6:04 - Connecting retail investors to the private capital marketsToday, crowdfunding doesn’t just live on websites—it’s been used on social media as well. Woodie never anticipated the breadth and reach of his bill, which he sees as bringing positive transparency to the investment space.“The industry launched in May 2016. Just this past month it surpassed $1 billion in funding. When we put this together, I was thinking, ‘Wouldn't it be great to use a website to be able to allow people that have a customer list, or their own friends and family, to invest in their business the same way that a campaign on Kickstarter or Indiegogo can?’ To see people using Twitter, Instagram, YouTube Live as the outreach, the public solicitation, I think is awesome. It really connects the people to the entrepreneur in a way that a website just doesn't do by itself. I think the advances in technology are really benefiting the industry because it ties you closer to the people that are raising capital. I think that's all good, too, because I think it brings this level of transparency that you otherwise don't have in the private capital markets.”8:43 - Deciding which constraints would minimize retail investor riskOne major fear was that crowdfunding would end up like gambling, leading some investors to lose everything. That’s why Woodie and his team wrote in limits based on annual income.“Any accredited investor can risk everything that they have in one company. Do they? No. They're smart enough to diversify their assets. Now, when we built this framework we were concerned that people might be risking more than they can afford to lose. This is the only segment in the private capital markets where investors are capped on how much exposure they can have. We built into the framework, based on net income, or annual salary I should say, as an individual investor, how much you make or how much you have saved thresholds as to how much you can invest. That doesn't exist anywhere else. People will tell us that’s pedantic, but quite frankly that was an investor protection mechanism we put in there. So, the investors that are saying, ‘I think it's too risky for certain investors to put in there,’ my response to that is well, there are caps and limits on how much people can risk.”11:11 - Tap into the power of the crowdSome assumed crowdfunding would operate only within the San Francisco and New York venture communities. That hasn’t been the case.“The deals are the same deals that are being seen in the Bay Area and New York City, with the same investors. What we've seen is the evolution of this industry, where instead of those people saying, ‘You know what? You shouldn't go to crowdfunding.’ They're saying, ‘Well, we should use crowdfunding and we should syndicate our deals to the crowd because the crowd brings something that we don't bring.’ We can bring deep pockets, but they can bring marketing power because they've got a vested interest in the outcome of the business. They can bring connections. They can bring their own brainpower to how we can help scale this business. VCs are great for that Rolodex of people that they might be able to connect you to, but the reality is you can get so much more out of a crowd.”12:44 - Make transformative moves at the right timeWoodie credits the success of the crowdfunding initiative to timing. His team pitched the idea to Capitol Hill on the back of the recession when political leaders were hungry for job creation.“We were in the right place at the right time. In 2008, we had a recession. Washington was looking for solutions. We went and showed up in 2010 with this [pitch]. People were looking for an answer to the question, ‘How do we create jobs in local communities?’ The whole point of investment-based crowdfunding is you are, essentially, helping people that have great ideas all over the country create businesses that hire people. The government can't do that on a macro level and so they need to look at innovative solutions like this that can actually solve what they need to solve at the most basic zip code level. That's what we delivered to them. That's why we were able to build support for this.”16:34 - One size regulation does not fit all...

With an abundance of capital chasing a limited number of opportunities, one unique entry point for investors is in secondary direct investments. Secondary opportunities consist of buying shares in private, pre-IPO companies directly from employees and investors versus the traditional route of participating in the next round of fundraising.Andrea Walne is at the center of this world at Manhattan Venture Partners (MVP), where 80% of their investments are in late-stage companies by buying secondary investments. Andrea and her team are focused on tapping into the value that already exists. Formerly a founder of Forge Global, Andrea has worked with over 100 late-stage private companies and has facilitated over $10 billion worth of transactions. On this episode of The Modern CFO, Andrea shares insights on this growing market segment in VC, its evolving landscape, and the opportunity for liquidity it presents.Show LinksCheck out Manhattan Venture PartnersConnect with Andrea Walne on LinkedIn or TwitterCheck out Nth RoundConnect with Andrew Seski on LinkedInKey Takeaways3:20 - Build a secondary positionInstead of fighting to issue a term sheet and compete with late-stage investors, MVP uses its network of relationships to enter a business at the ground level.“We're on our fourth fund right now. With our strategy, it allows us, strategically, to pinpoint how we want to enter a business that we're interested in. When I say enter a business, we're not fighting to issue a term sheet and compete against other late-stage investors to lead a round of funding. What we are doing is generally considered “friendly” to many of our counterparts in the late-stage venture community, because we are figuring out a price point and identifying, by way of our network, (who all knows the partners of our firm really well by way of our experience); We find our way in with a certain price point and we're able to dollar cost average and choose that building of a position by way of the secondary. So, it's pretty awesome. It allows us to choose what valuations make the most sense for us.”6:33 - The changing environment of common stockCommon stock used to be considered a risky business. Today, it’s easier to assess if a company—and therefore its common stock—is valuable early on.“I've never seen a world where a company can raise a round of funding and be a mid-stage or late-stage company. I do say mid-stage, because I think it's important. A company will raise a round. It's typically oversubscribed—most companies are raising oversubscribed rounds. There's a ton of capital flowing in and immediately after the round is raised, we're working with issuers and their shareholders who believe that their stock is immediately worth a premium to that round, immediately after the round is closed. Precedent will tell you that, historically, you could see that common stock, which is issued to the employees of a private company, versus the preferred stock, which is issued to the investors when they invest, the common stock is usually priced at a discount, because there's inherent risk associated with common stock. God forbid there's ever a bankruptcy in a private company, the common stock gets paid back last after all the preferred stock and any debt. So, there's inherent risk associated with common stock. If you go back three to five years, 20-25% discounts for common stock were normal relative to the latest round of preferred financing. For the environment to change so rapidly is absolutely fascinating for us.”10:03 - The danger of taxing unrealized gainsCongress has floated different options for taxing wealthy figures, like Jeff Bezos. The problem is the potential for harmful trickle-down effects that could negatively impact budding entrepreneurs and their early employees.“Something that seems like it comes up in Congress quite often is just taxing unrealized gains. That alone is constantly brought up and constantly talked about at both the gains-perspective and then deeper on a carried-interest perspective, which is obviously gains earned by way of the profits to venture capitalists and those that are investment managers. Overall, what I will tell you is that the resounding theme across all of these proposed changes and contemplations is that clearly Congress is looking at the folks like Jeff Bezos, Elon Musk, Mark Zuckerberg, and the upper echelon of the tech community as being the only population that really matters. The more that Congress can better target them and tax them for their wealth, which was in my mind earned wealth, quite well-earned wealth, is something that I feel is so shocking, because I don't think Congress realizes how that permeates down to those who are really the rank and file working at tech companies. Employees these days are given stock options at private companies. That doesn't mean that they own the shares outright. A stock option simply means they have the right to exercise, AKA pay a cost, to then own common stock shares in a private company. For there to be a concept of taxing unrealized gains when there hasn't been any form of a sale, where there's any gain to be had or money in the bank, it's just constantly shocking to me that that's even a consideration. It's something I worry about..”15:44 - Successful startups are impossible to ignoreMany startups today are coming out of the gate with incredible growth and high value.“As much as we all love working with institutional folks, school endowments, pension funds, fund of funds and the like, there's a bit more of a disconnect when you're working with an institution that has a bit more of a regimented strategy as it relates to their venture asset allocation. The passion comes from the family offices and so, when we speak to our LPs, we see that they're all seeing startups more and more and more in the news. What I think has really shifted in the last five or six years has been that you're now seeing startups with bigger market caps than any company listed on the Nasdaq or New York Stock Exchange. So, it's impossible to ignore these startups, because they're bigger by way of market cap and size and growth than most listed businesses. That shift means that startups are in the news every single day. There's a new $10 billion minted company every single day, which is shocking to hear. It used to be that seeing a billion-dollar valuation four years ago was fascinating.”21:41 - The impact of media exposureWith large private companies doing so well, they also get a huge amount of media coverage. That means that determining facts about their financial profile is easier than ever.“The biggest private companies these days are actually getting more exposure in the media than most public companies are, which is really fascinating. It's because they're just so big, they're so innovative, they're breaking rules, and they're making change. With all of that, they are getting more media exposure. With media exposure comes people who are covering them and digging into the company's analytics, digging into the company's financing history, revenues, and growth. There's a lot more of a spotlight on that and late-stage private companies these days than there ever was. Coupled with the concept of vast transparency, compa...

Jeremy Baksht has a rich history in finance, from banking at J.P. Morgan to several entrepreneurial ventures. His specialty is data and FinTech, and his newest company is DataFrame Ventures. Over the years, Jeremy has learned that he has a good eye for investing and generating LP interest in his niche. In this episode, he talks about the importance of generating interest, curating a funnel, and deciding what type of CFO you want to be in today's ever-changing environment.Show LinksCheck out DataFrame VenturesConnect with Jeremy Baksht on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInKey Takeaways2:53 - Invest in high-margin, repeatable businessesEarly in his career at J.P. Morgan, Jeremy saw companies getting out of investments in businesses with poor margins.“You typically want to be in that high-margin, repeatable business and get out of the clunkier businesses. So every time I talked to these businesses, they all wanted to know, what do you see in IoT? What do you see in sensors? What are you seeing in clean-tech? And even though I hadn't been an investor personally at any stage in this formation, I kept coming back to tech and data, SaaS. These are all changing the world, they are the highest multiple companies. Whether they're B2B or B2C, you have to get into these businesses. Coming up with ideas is hard, but seeing what was happening in capital markets in the early 2010s, some colleagues and I from Citi joined up with one of their former colleagues and we created a private markets exchange.”6:15 - The value of automationWhen Jeremy set out as an entrepreneur, the best advice he received from CEO Peter Williams was to look for ways to streamline clunky processes.“The first step was automating a process. When you see a process that has very repeatable patterns yet involves a ton of people, it doesn't often make sense to have all those people involved. Whether you're a real estate broker or private placements broker, you're just thinking about if you could map all the funnels of the 20 things you need to know, maybe some offering documents, and put all the investors or interested parties in one place, and then, hopefully, they can transact in a more automated way. So, I think step one was recognizing there was no leap of faith there. You have all these people and an expensive, clunky process. Can you automate that? That really spoke to me.”8:40 - Get people to show upWhen you deal in marketplaces, you need to generate interest and demand. That’s what led Jeremy to focus on access to Series A and B companies early on.“All marketplaces are massively 'chicken and egg,' and you need to time very carefully which curated product do you have. How do you stoke the initial deals? Whether your eBay finding a beanie baby or Craigslist with San Francisco apartments, you have to have some reason for people to show up. So for us, at first we started to do LPs assets in hedge funds. We realized that was a fun market, but one that wasn't that liquid. People aren't necessarily looking for those unless there's a big secondary discount. What we did try to do was more company stuff, where people are excited about a Series A or a Series B, and they can't get access. This was really early. I know it's very common now, but that was our thesis 8-9 years ago.”11:57 - Create a curated funnelWhen he founded DataFrame Ventures, growing trust with LPs quickly led to more time sources deals and less time needed to promote them.“Two partners and I stood up DataFrame Ventures at the end of last year. We've done 17 deals, a few million in capital deployed. It was almost by happy accident. We would find something we found interesting in a data-oriented company. We'd put it up to our LP group. The first few deals took a lot of stoking the well, and calling people, and actually acting as agents in a way like, ‘Hey, we put this deal up. Are you excited about it?’ But by the fourth or fifth deal, we kept finding as you layer on LPs, they understand your thesis. As you build up trust, deals are moving faster and faster and faster. We spend almost all of our time finding interesting deals and zero time promoting them. Because they don't really require a promotion if you have a really curated funnel.”12:55 - Being a unicorn is overratedJeremy recognizes that some people will achieve unicorn exits, and some won’t. But there’s nothing wrong with a successful multi-million dollar exit, either.“Starting a fund is no different than starting a company. It's a little less focused on some crazy unique idea. It's more putting your ideas onto paper and actually framing those and wrangling LPs and getting people excited about you. So I think the rest of my life, I will probably mostly be an investor. I find that to be really fun. And then look, between us, I've started or been a part of some really interesting companies. I don't know that I'm a next-level founder. You try it a few times, and if you don't have a unicorn exit, you know, society tells you you haven't succeeded. I see a lot of my friends and more people in the industry accepting a 50 to multiple hundred million-dollar exit. As long as you're really helping and influencing people or building a unique product or something interesting and remunerating your LPs, you've done really well. As we've talked about, 95%, or whatever the number is, of companies in the seed stage don't get to the Series A stage. You don't always get to win. So having an exit 10-million plus, as long as you didn't raise 10 million, is probably a good thing for everybody involved.”18:58 - You need trust, a platform, and distributionWhen working on Qineqt, Jeremy started a conversation with Bloomberg to see if they would be interested in a partnership. He ended up starting a job with Bloomberg and working in the pioneer days of their enterprise data portal.“I kept coming around to, 'Wow, there are lots of different data sources. Nobody knows how to find them. There are very few people that can pay for and use them. How do you wrap all this into a bow and package it?' I thought it was using the data structures and being more technical. But what I realized was after a year of trying to make that business go, it was you need trust and you need a big platform and you need distribution. I was talking to Bloomberg and a few others about acquiring the company or somehow working with us. I ended up being lucky enough to join Bloomberg, and spend about three years there with the enterprise data access portal and putting a lot of unique data sets in there. It was the beginnings of what is now a pretty large all-data practice, but it was early for Bloomberg. One of the industry telltale signs is if you're putting a unique product into one place and thousands of people can access, is it really unique anymore? And I think the answer really is, I guess not. In a way, we call it all external data, not alternative data now because you're putting unique things in one place and maybe some of the alpha bleeds out on a one-to-one basis. But at the end of the day, everybody's got the ingredients and they cook together.”23:32 - There are many types of CFOsFrom big companies to small ...

Invest in people. Easy, right? While more money than ever is being deployed around the world into new ventures, Oslene Carrington is leveraging her own entrepreneurial experience to ensure entrepreneurs in Guyana and the Caribbean have access to financing as well. Oslene is not one to wait around for change to occur. She decided she would create her own community of angel investors. By expertly explaining the risks of financing innovation abroad, especially at the angel stage, some of that risk is mitigated by tapping an angel network with first-hand experience within these unique cultures and landscapes. With the Caribbean Diaspora Angel Investor Network Trust and !nnovate Guyana, Oslene is accelerating the trends of access and democratization of private markets with a veteran approach. Show LinksCheck out !nnovate GuyanaCheck out The Caribbean Diaspora Angel Investor NetworkFollow !nnovate Guyana on LinkedIn or TwitterConnect with Oslene Carrington on LinkedInCheck out Nth RoundConnect with Andrew Seski on LinkedInKey Takeaways3:45 - Fostering and funding great ideas from homeOslene traveled home to Guyana and witnessed some innovative business presentations. When she realized those great ideas would need greater support to develop, she started a program to award capital to the most viable ones.“I happened to be at home in Guyana at one point visiting five years ago and was at the university there where I have friends and saw some really amazing things happening in terms of innovation. Like a lot of universities, they have these annual presentations of student research conferences...I had experienced doing startup programs and finding funding for them, and commercial relationships with the private sector and with the academic environment and so on and so forth. And so it just clicked for me very easily to create something. And so what was born from that is something called the Guyana Innovation Prize, which is like an MIT prize or any of these other university-based prizes where I go find money. I find capital. Either initially as donations, we started out and in many ways still are a philanthropic endeavor, and find capital and match those up with great ideas. And so annually, we have a competition and the funding is awarded to the best commercializable ideas.”5:53 - The angel of the CaribbeanOslene’s second major venture was founding the Caribbean Diaspora Angel Investor Network (CDAIN), an angel investor network that takes the concept of funding great ideas in the Caribbean further, this time backed by corporate sponsors and government grants.“That brought me to my second business idea, which is the Caribbean Diaspora Angel Investor Network, or CDAIN. Because, you know, again, we would find the funding. We have corporate sponsors now, you know a USA government grant. But [the] point is, now we're able to take these ideas and go to the next stage. So you can sort of say that the initial support is pre-seed. And that what we then do is, you know, you can sort of categorize pre-seed and stages. Maybe there's a pre-seed A, and a pre-seed B round, or whatever you want to call it. I mean, we can pretty much make up anything we want in this space, because it is still pretty much angel. And so now through the network, we're able to bring those products along further and get them ready for [an investment], or actually get them invested.”9:55 - Invest in solutions aimed at solving big problemsIn Oslene’s eyes, community members are best positioned to know exactly what they need. Investing in ideas that meet fundamental needs feels much less risky than other investing endeavors.“The idea of a community coming together to find opportunities that we're all familiar with, or that we can connect to in some way, because it's either from places that we know, or it's addressing problems that we know happens, quote-unquote, back home, that's kind of how it all came together. To your question about risk, I mean, we don't see these things as risky. Because we know what the challenges are. We know what the needs are...It's amazing what people consider risky. Like I would never put my money, for example, in penny stocks. I would never put my money in yet another IoT solution when most people in America and in the world are not living in quote-unquote smart homes. Like I would never do that. And I'm not saying that stuff isn’t smart, I'm not saying that it's bad investing to do that. I'm just saying there are so many other problems in the world that are fundamental. And there are a lot of smart people in other places that have solutions for these problems. And if the capital met up with that, there'd be a lot of very, very wealthy people. And it's the basis of that, that I said, well, why not us? Why couldn't it be us? Who we're not only pooling our money to solve the problems, but potentially experiencing a wealth boom.”12:23 - Solving for the southern hemisphereSeven billion people live in the southern hemisphere, where primary concerns revolve around agriculture more than tech. Problem-solving in one agricultural area, for example, has immediate potential to expand to other, similar areas.“I know about my particular area of the world and the sector, which happens to be ag-tech, agro-processing, and ag science. Right. Because the part of the world we're talking about is heavily agricultural. But so are a lot of other places in the world. And so we feel like we're not just solving for a country or a few countries in this region. We're talking about any place in the world that's heavily agricultural and tropical. Well, guess what? That's the vast majority of the world, right? Southeast Asia, Southern Africa, the Caribbean. The Southern half of the world is as populated as the Northern part of the world, and the Southern part of the world is tropical. So we're talking about half of the 7 billion people in the world and solving for them. So this isn't risky. We're not talking about is somebody going to buy this IoT solution versus this other one, is somebody gonna buy this electric car versus the other one? That is real risk. Solving for problems that affect billions of people is not risk.”14:33 - Establishing trust outweighs the dataWhen a community already knows what needs to be done, they don’t immediately worry about what the data says. Building trust and the narrative becomes the focal point.“The risk aversion is a different kind. It has to do with trust. And it's not about data. So, you know, how do you bring data to the picture to establish a level of trust? So the fact is, if I say to you, Andrew, I've got this great offering, this great opportunity. Probably because you don't know the region or the area, you're probably going to look at all the numbers. Probably try to do some additional research outside of what I share with you to see whether what I say is in fact the truth, or if I've missed anything, or if there's more, assuming you're interested. When we're talking to people who already know what the problems are, now it's well, I want to be sure that I'm not going to ...

Realized returns on investments for venture capital funds used to happen within three to seven years. Now, the biggest companies are extending funds to 15+ years—and investors are getting impatient. This could dampen venture capital as an asset class, but not if Aman Verjee can help it. On this episode of The Modern CFO, Aman discusses how Practical Venture Capital is creating a secondary market from VC funds, how faster liquidity will keep VC relevant, and how his experiences at PayPal, eBay, and 500 Startups resonate with modern CFOs.Show LinksCheck out Practical Venture CapitalFollow Practical Venture Capital on LinkedIn or TwitterConnect with Aman Verjee on LinkedIn or TwitterConnect with Andrew Seski on LinkedInKey Takeaways02:59 - A new application to a new asset classPractical Venture Capital (PVC) focuses on venture capital secondary, buying LP and GP interests in early-stage venture funds, and direct secondary in breakout portfolio companies.“It's not a new idea, but it's a new application to a new asset class. I think in venture, there wasn't a need for secondary markets, even up to 2005, 2008, 2010. I was at PayPal early. I joined in 2001. That company went public in four years, from founding all the way to the IPO. Yahoo, Amazon, and eBay were all four- to five-year exits. So, there was not a terribly long time to get your money back. The biggest IPOs, now, in the venture community are: Airbnb, which took 15 years and counting to get their liquidity. Palantir was 17 years and counting. All the biggest companies now are taking much, much longer to get their money back. So, there's much more demand on the investor side for that kind of liquidity, around year 8, year 10, year 12, and year 15. That's a fairly new phenomenon, taking place over the last 10 years. That's what we’re capitalizing on.”20:49 - Three functions of the modern CFOAccording to Aman, the modern CFO has an accounting function, a treasury function, and a data analytics function.“There's the traditional [function], or the accounting function, which is really about understanding and applying accounting principles, backward-looking, making sure stuff gets done, operational, and that communications infrastructure is running well. That is one job. And it's a big one. That's the digital controller function. And that's always been part and parcel with the finance function and will never go away. There's increasingly another aspect around treasury and managing cash and making sure, especially in global businesses, that all the functions are adequately capitalized, and you've got the right liquid resources where you need them. That's a big problem in venture and venture-backed companies. They never have enough liquid cash. There's a lot of paper valuations. There's a lot of investors locked up for 5, 10, 15 years, so that's a big challenge. Then, I think the third part is just the business facing [functions]. How do you help a team make good decisions, and how do you use data and use analytics in order to inform those decisions?”24:19 - Communicate data across the organizationMost departments deal with data, but CFOs have to be able to communicate it to every department clearly and accurately.“You have to be able to communicate to all those [department] heads and the entire team about what matters. To be able to store data and make it a single source of truth. That's often a problem in big companies. Like it or not, finance is always going to be seen as an objective repository of the information that then gets to make it into boards. That's how you pay bonuses. If your data is wrong, that's a terrible consequence for the whole organization. If the head of marketing is using imperfect data or some of the analytics isn't perfect, even if it's off by 1%, they'll make mistakes, but it's probably not the end of the world. It doesn't endanger the business in most cases. Product engineers take shortcuts and make quick data-driven assumptions. Finance has got to be right. You have to be able to double click and understand some of the flaws and how data is being kept, how it's been used. You have to be facile with statistics and be able to communicate all these concepts across different teams. That's really the challenge of the CFO job.”29:43 - The need for a secondary marketAs COO of @500 Startups, Aman had a unique vantage point to observe the shifts taking place in the venture community, as well as the developing needs of LPs. “What we recognized a few years ago was that as these funds are getting longer and longer with no liquidity back to LPs, there’s this pent up demand from sellers who've been in a great fund for 8 years, 10 years, 12 years, but haven't gotten their money back. The fund is maybe up 6x, 7x, 9x on paper, but family offices may want to rebalance their portfolio. They have cash flow needs, they have liquidity problems and so they want to be able to sell. No one's doing it in that market right now. There's no market for venture secondary right now. We are literally buying great portfolios at a 30% discount to fair value and there's no bidder. We are the only bidder who says I'll take that portfolio of nine great companies and a lot of other companies you may have never heard of but we like, and I'll pay you 30% less than the fair value. The challenge in this space is they're all private companies, so you don't have a lot of information about the companies, but that's where Dave and I excel. We've been investing in private companies and figuring out how to diligence and source intel about them for years now.”33:53 - Venture capital as an asset class won’t reach its full potential without meeting investor needs.Private companies are extending their funds to longer and longer timeframes, but LPs want their money sooner. If this keeps happening, VC may stop being an in-demand asset class.“I'm just going to extend the fund. We're now in year 17. Please read the fine print in your LP agreement. I can extend the fund as long as I want to and, when I have money, I’ll give it to you. Those early LPs are looking for liquidity and may want to take some money off the table for good reasons. That just doesn't happen in VC today. If that continues, VC as an asset class will just be an afterthought. It won’t ever be as big as private equity, or as big as it should be because it's not solving the key problems. So, I'm hoping that PVC can help solve the problem and really help the whole asset class, too.”35:39 - Modern CFOs serve as the custodian of their CEOs long-term vision.The CEO-CFO relationship is most productive when both address their strengths and weaknesses in sharing the vision of the company and grounding that vision with current financials.   “You have to take your cues off your CEO, because it is a team sport. In many of my cases, I've had CEOs who were very strong in product and marketing. They would kind of amp stuff up. They would tell a story where there's always a happy ending and there's a h...

The heyday of Main Street is over. The spotlight now shines on Digital Street. Curt Sigfstead has been long drawn to the power of entrepreneurs and the opportunity they present to transform the world. After leading the prominent West Coast technology investing division at JP Morgan, Curt joined Clearco. Clearco is at the forefront of digital growth, where they are busy building out the capital infrastructure for the internet in the realm of embedded finance. Working with digital founders, software platforms, and financial institutions, Clearco is helping to revolutionize how founders raise capital.Show LinksFollow Clearco on LinkedIn or TwitterConnect with Curt Sigfstead on LinkedIn or TwitterConnect with Andrew Seski on LinkedInKey Takeaways1:44 - Providing capital based on dataDigitally-founded businesses often don’t have the traditional assets required to raise capital. By providing capital based on more diverse factors, Clearco is serving a new, data-driven market.“It means that we can, in a very innovative way, provide capital, provide advice, provide benchmarking, provide a means by which entrepreneurs can improve their business with capital by using data. That's an important core of our business; our ability to leverage third-party data sources to create a modern finance platform that can serve these digital founders. As you were getting to Andrew, [Clearco is] serving what is a global transition from Main Street to Digital Street. And as more and more businesses are founded, at least initially, online--as businesses become less and less geographically constrained--they don't have the aspects that typical financing institutions like banks or credit unions are looking for. They don't have collateral. They don't have inventory. They don't have the assets. But they do have a lot of data. And their data is very revealing with respect to how the business is performing, what the opportunity is for that business. So, what we found is this vast, global underserved market.”3:32 - Helping entrepreneurs retain ownershipAs a rule of thumb, entrepreneurs don’t want to give up equity. Clearco gets that, helping businesses get off the ground by focusing on repeatable processes.“So we're part of a spectrum. We're not in the business of competing with venture capital or with seed investors or with friends and family. We're in the business of being a complementary pool of capital for entrepreneurs to leverage as they grow their businesses. And in any business, there are aspects that are repeatable. So, you have an understanding of how the business is actually going to perform based on data, historical data, and how you might project that--like your return on ad spend, or how much inventory you need relative to your sales growth. There are other aspects of your business that are not repeatable. It's innovation that you may have underway. It's actually kicking off a very early-stage business."4:19 - Creating repeatable actions to grow your businessClearco understands what entrepreneurs need--helping them control their destiny through repeatable aspects of the business.“Where Clearco comes in is in those aspects of the business that are repeatable. Our perspective--and what we found product market fit with--is the fact that entrepreneurs don't want to give up equity in their company, and therefore ownership, for aspects of their business that are effectively repeatable. It's, ‘okay, I know if I put a dollar here, I will get $3 in revenue. Why should I give up equity for that?’...As businesses grow, ownership is important for entrepreneurs. It's part of the economic puzzle. And so if we can help them control their destiny, if we can help them access lower-cost capital effectively, and maintain ownership, then we think we’re doing our job.”7:06 - The three benchmarks of successCurt says that success comes down to three things: a bulletproof process, strong performance, and a solid market backdrop.“For me, there are really three aspects to a successful process and this is obviously something I learned over many years helping companies to access the market. Which is: 1) you have to have a bulletproof process. You've got to start with a large funnel. You've got to work that funnel and you're eventually going to have a number of investors who come out the bottom of who are committed to funding the company at terms that are acceptable to the board and to the founders of the company. 2) You've got to have performance. Investors really want to understand, at least at the Series C level, how $1 of investment turns into $5-10 of return. It has to be a very repeatable process, i.e., in the Series C you're not introducing new operational risks, you're introducing scaling risk. There's product market fit. Your business works. It's got a huge TAM and really, it's about scaling the company...3) You've got to have a solid market backdrop. None of this happens in isolation. Investors are influenced every day by what happens in the capital markets and what's going on with their investments, as well as how other businesses in their portfolios are growing.”9:39 - A conservative-aggressive approachIt might sound like an oxymoron, but Curt says that the best forecast is optimistic while also building out realistic benchmarks based on market share.“My job was to ensure that our forecast was bulletproof. It was highly conservative, yet aggressive. What do I mean by that? Our job is to express the business in the most optimistic way that we can as a company. That's why we're here. We've got a big opportunity, but at the same time, building in aspects to the forecast that are not leaps of faith. I.e., for us, the size of our marketplace: If there are 10 to 12 trillion of GMV globally, which is cited in a bunch of market forecasts, then trillions of dollars, tens of trillions of dollars - us saying that we can get to 20, 40 billion, 100 billion of GMV, well, that's pretty conservative. We don't have to get a lot of market share. Those are the types of aspects to set the context of your forecast conservatively relative to a lot of external metrics. I think these are important aspects to getting investors to buy into your forecast. [The second factor] is based on your existing business, and so we were very, very focused on that. [The third factor is] you want to make sure that as you go through the funding process, you're meeting and beating your numbers.”11:41 - How to analyze and present dataUse the data you have to prepare. Then, keep investors in an honest feedback loop where you consistently provide contextual updates.“If you fail to prepare, you're preparing to fail. It's kind of like that old adage. We spent a lot of time on that. Then, the second piece of it is obviously thinking about the second and third-order diligence that's going to support that. For us, it’s beating up the metrics. It's analyzing the data. It's focusing on, ‘okay, so what are the cohorts doing? How do ...

Looking for a long-term view of what it means to be a good CFO? Brian Hughes is a retired partner of KPMG and an experienced advisor to public VC- and PE-backed portfolio companies.His perspective spans an entire career of public and private market transactions, overseeing multiple market cycles--like the dot-com bubble and the 2008 recession--and becoming acquainted with the needs of companies through different life cycles. He is uniquely positioned to deliver a holistic picture of our current environment and provide advice to financial leaders.On this episode of The Modern CFO, Brian advises CFOs to plan ahead--not just for internal organization, but for future macroeconomic shifts. As he sees it, a modern CFO needs to ensure the financial plumbing of an organization is not just working, but safeguarded for what lies ahead.Show LinksConnect with Brian Hughes on LinkedIn or TwitterConnect with Andrew Seski on LinkedInKey Takeaways5:09 - Understand the CFO roleIn Brian’s view, the most important job of the CFO is being a great partner to the CEO. The second job is to be strategic, collaborative, and adaptable.“Number one, you know, I think if you're a CFO in a company you've got to understand what your role is. And there's a lot of different things, but I think being the CEO's trusted business partner is probably by far one of the most important things that you can do as a CFO. And you need to really establish that on day one because that's the individual that's helping set strategy and direction. At the same time, I think you also, as an individual, you need to be aware of sort of what your strengths and your weaknesses are, which will dictate the type of CFO you're going to be...I also think that today's CFO needs to be more strategic in their thinking. It used to be that you were the numbers guy and you put together the financial statements. Now it's really how do you make the numbers come alive and really tell the story of the company in terms of their operations, the metrics and the KPIs. And also, it used to be you thought about the CFO just within the financial function. I think it's also extremely important now for the CFO to really get outside of their swim lane and really become more cross-functionally across the organization, supporting all the different functions that help a company operate.”7:28 - Gain the trust of investors and stakeholdersA good CFO isn’t just savvy internally. They have the confidence and ability to communicate with external partners, such as investors and board members.“The other part of a CFO is again it's multi-faceted. And you obviously need to not only have the trust and insight of the people in the company, but also the key investors and stakeholders outside the company. Because the CFO and the CEO tend to be the folks that are interfacing the most with investors and board members. And therefore that requires a unique set of skills as well in terms of understanding sort of what their needs and wants are, and presenting that in a way in which they can understand it. And then, of course, I think you need to also be somebody who can fix things that get broken quickly, right? That happens in organizations, whether it be through acquisitions or divestitures. But you need to make sure that you're able to act quickly to address issues that need attention on a real-time basis.”10:57 - The “going public” craze: then and nowBrian contrasted today’s SPAC boom with the bubble of the dot-com era. In the early 2000s, many unprepared companies went public. Today, companies are generally well-established.“I think there was the euphoria, if you will, around the dot-com boom that created a unique opportunity for companies to go public, but unfortunately they shouldn't have been public. And then I'll compare and contrast that today, where I think we'll talk more about this later, but the SPAC boom is very different than sort of the dot-com boom, in that the companies that are even going public through SPACs today are fairly mature, well-established, later stage either venture-backed or private equity companies that have a business model, have a management team, typically are generating revenues...Some may not be generating profits, but it's a very different feel and type of company going public today than it was back in 2000.”12:31 - The two worlds of the pandemicThe pandemic starkly impacted some industries and helped others. Going forward, Brian believes those temporary inequalities will begin to normalize on both sides.“Today feels very, very different in that even though we've had the pandemic, it's really been certain industries impacted. You know, travel, leisure, hospitality, restaurants. And if you look at the other industries, they have really benefited greatly by the pandemic and people being at home. So it's a story of two worlds. And now that we're coming out of the pandemic and people are now able to go back to stores and restaurants without masks, I think that, again, those industries will come back, obviously laggers we've seen them now perform pretty well in the markets. And so I think we're on a trajectory of all the industries returning to normal. And some correcting, rightfully so, because they benefited abnormally just from the pandemic...The key is that on either side, you, as a CFO, were reacting one way or another, and you were called into action very quickly.”16:51 - The rise of the IPO marketAvailable capital is fueling growth opportunities for both public and private companies. Brian believes that the SPAC model will only increase in popularity.“We've also seen the IPO markets open up rather dramatically last year into this year, and all through three different ways, direct listings, a regular IPO, or a SPAC transaction. And so, in SPACs, just recently, there's been a lot of them that have occurred in the last year; recently have slowed down because of a matter that the SEC raised about certain accounting for warrants that had issued in connection with these initial IPOs, that of course caused some people to slow down and they've had to refile their 10Ks. So although it's slowed down temporarily, I think it is probably here to stay. And in fact, we're also seeing overseas the European community now begin to adopt the SPAC as a bible for a way in which to go public in the European Union. So long story short, whether it be public or private, there's a real significant availability of capital that's driving either 1) helping companies that are earlier stage grow while they're private or 2) help those later stage private companies come public.”23:28 - Be prepared for the unexpectedWhen you have talented teams and proven processes in place, you are better equipped to handle any curveballs that are sent your way.“The CFO needs to be prepared always for the unexpected, right, as I like to call it. And what that means is you better make sure your house is in order if you're going to have something unexpected occur. And so that's why, initially when I talked about some of the things I did at the beginning around, you know, being the trusted partner, being strategic, having elite teams, having the right processes, people and systems in place. If you don't have all those things...

What do Microsoft and a dental care marketplace have in common? Plenty, if you look at it from the inside-out. Dave Monahan, CEO of Kleer, got his entrepreneurial training at Microsoft, where he learned how to focus on solutions, build transparency, and innovate faster. Today, Dave is building a pandemic-proof culture at Kleer, a dental care marketplace aiming to replace inefficient insurance plans. In this episode of The Modern CFO podcast, Dave and host Andrew Seski talk about the benefits of transparency, where to look for product data, and how Kleer survived COVID-19.Show LinksCheck out KleerFollow Kleer on LinkedIn or TwitterConnect with Dave Monahan on LinkedInConnect with Andrew Seski on LinkedInKey Takeaways4:22 - Microsoft-made entrepreneurIn his first year at Microsoft, Dave learned from CEO Steve Ballmer how to stay solution-focused.“The person running that area asked me to present the first 10 minutes of the presentation... when I was done, [Steve’s] first words to me were, ‘I hated that presentation.’ I’m in front of Steve and his leadership team and all the leaders of the group I just joined. And so he goes, ‘let me tell you why.’ And he said, ‘you presented a number of problems. You did not give me any solutions.’ I think I was 29 or so at this point. And then that one for me was, all right. I will never ever do that again. If I'm going to go into a presentation anytime and anywhere, and I am ever going to present any kind of issue or problem, I will not only have the solution, but I'll have the data to back it up.”6:44 - A model of transparencyMicrosoft’s open-access information model encouraged responsibility and encouraged healthy risk-taking.“Transparency was critical to Microsoft's success. They shared everything. It was the first time I'd been in an organization where you could get information about anything within the company. It was very open. Like these presentations we would do - there was, I can't remember the exact number, maybe 30 or 40 subsidiaries in Microsoft - at the time I could go get ahold of all their presentations and look at all their data and the company would post results on a weekly basis. And you can dig in and take a look at it in as much detail as you wanted. With that transparency though, they're their team's responsibility. So they assumed, ‘okay, if you have all that information, I'm mobilizing you to do things and take risks.’”7:35 - If you gotta fail, do it with dataMicrosoft’s corporate culture encouraged rapid experimentation backed by smart data to keep innovation moving.“The second culture piece that came from Microsoft for me, that I instill in every company I'm at is to try things, you know, always try moving forward. It's okay to fail. I know this is sort of a common term now, but back then it was sort of new for me: good news travels fast, bad news travels faster. Something doesn't work, try things, experiment, it doesn't work, kill it fast. It’s really important to try, but also kill when needed. And so that was our thing - just bringing that sort of culture of experimentation to the company that I'm with. And then the other piece of both of those items needs support from a data infrastructure standpoint. You don't want paralysis by analysis, but you want data and information to support where you're going and the decisions you're making.”9:25 - The Kleer revolutionDave’s company, Kleer, is a dental practice marketplace connecting patients, dentists, and affordable care.“So it's a bit of a parlor game, dental insurance, and it ends up costing the dental practice a lot of money, and patients and employers a lot of money...we decided the dental space needed was an open marketplace where dentists and patients can connect directly without a middleman in the way. We created a platform that enables dental practices to design care plans for the patients. And these care plans can be different because one practice might be tailored towards older patients, but others would be tailored towards younger patients. And then the patients pay a subscription to dental practice. A simple subscription could be twenty-five dollars a month, $30 a month, and they get pretty much everything that's in insurance. You get your exams, your cleanings, your x-rays, and then you get discounts off of other treatments. But it costs about 30 or 40%, less than dental insurance. And it also has like, no, there's only no tax. There's no deductibles, there's no waiting periods, all that stuff's going away because we've gotten rid of that middleman. There's no reason for that middleman to be in the way. And once you get rid of that middleman, get rid of all the wasted inefficiency.”17:37- Here’s to the milestonesAs the company grows, the Kleer team builds camaraderie and motivation with a culture of celebration.“A big part of how we run Kleer - or any company I'm in - is it's not me making all the decisions. It's me asking others to sort of step in and take responsibility for certain things. And so one person on my team is in charge of making sure we are celebrating and taking a break,  making sure everybody is having fun and enjoying themselves. So what he's put in place is once a quarter, we actually go off-site. Now, obviously, the pandemic has caused an issue with this, but prior to the pandemic - and we're going to start it up again as soon as everything's back to normal - is once a quarter, we go out and do something and it can be all kinds of different things from bowling to ax throwing to make sure that's part of our culture is that we're willing to relax and enjoy each other and see each other on a personal side. We find the milestones in the company that really matter, and we celebrate those.”21:20 - How transparency beat COVID-19How do you save a start-up in a pandemic? Reinforce your transparent culture to rally your team - and extend the courtesy to customers, too.“So we reflected on that when COVID hit and decided this was a chance to actually rally the company. And to position that as a major challenge, where everybody's going to learn through the challenge, but we're going to have to sacrifice to get through it. So we basically rallied the team around, ‘Hey guys, we're going to get through this, it's going to be some pain along the way, but we're going to come out relatively stronger than any of our competition. So on the other side of this thing, we'll be in a better position than we were prior to it.’ We just basically got feedback from everybody in the company and we had open sessions and everybody was willing to sacrifice. We ended up cutting salaries drastically. We ended up negotiating ahead, my COO went out and negotiated with our vendors to get lots of concessions from a cost standpoint…we actually implemented a thing for our dental practices where they could suspend their subscription. So if a patient was paying a subscription, we enabled dental practices to suspend the subscription until the pandemic passes.  Then they can come back into the office. The net was the goodwill we created.”27:09 - DIY transparency cultureWant an open culture? Stop worrying and allow access to key info - your employees and ...