The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified

On this special segment of The Full Ratchet, the following Investors are featured: Michael Cardamone Jenny Rooke Scott Dorsey Each investor highlights a situation where they decided not to invest, why they passed, and how it played out. To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

John Vrionis of Unusual Ventures joins Nick to discuss The DNA of Startup Success. In this episode, we cover: Backstory/path to venture. Talk about your experience at Lightspeed and your decision to leave. Where/when did you first meet Jyoti Bansal, the founder, AppDynamics? What's unusual about what you do? 'Unusual Academy' and 'Get Ahead Platform' -- what are they and what's the difference? You’ve spoken about your team at Unusual being focused on redesign the early-stage VC market and giving founders a distinct advantage. What about your approach gives founders a distinct advantage? You've spoken about founder focus on "How it works" vs. "Why it matters" -- what's the disconnect you've observed with early-stage founders? You've covered your own experience of learning through suffering -- is that also a quality/characteristic you look for in founders? Arrogance vs. Humility -- have you invested in founders displaying these traits? What's been your experience? 3 must-haves that you look for in a new investment? If there's one common theme in failed investments -- what is it? Is there anything unusual about your approach to sourcing? If so, what is it? What are some best practices for founders when picking a VC? Over the past year or so the percentage of total VC dollars invested in early-stage deals fell to the lowest levels the industry has seen in five years. Why do you think this is the case? You've talked a lot about the seed funding gap and challenges to get to Series A. I'd love to get your thoughts on what's required to raise an A? Do you focus on product-market-fit prior to the A round -- if so, how do you define it? What's the problem with Sovereign Wealth in Silicon Valley? Do you have specific examples of unintended consequences or challenges with certain types of LPs behind a VC fund? Re. founders -- You've said that "the biggest mistake you can make is taking an investment from a mega-fund" Why? How has the early-stage venture landscape shifted from previous years? What do you expect to see in the future? To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

On this special segment of The Full Ratchet, the following Investors are featured: Jeff Clavier Bradley Tusk Scott Kupor Each investor discusses a portfolio company that did not survive and why it was that they failed. To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

Courtney Reum of M13 joins Nick to discuss Creating Unfair Advantages, Surviving Founder Burnout and Driving Successful Exits. In this episode, we cover: Backstory/path to venture Tell us about your experience being an investor at Goldman Sachs and working with brands like Procter & Gamble, Under Armour and Vitamin water. What are some takeaways you got from that experience that influence you today?  You and your brother founded VEEV Spirits which became the first line of organic ready-to-drink cocktails. VEEV received the Technomic Fast 50 Award and was named an Inc. Magazine 500 Fastest-Growing Companies in the U.S. What are some key factors that helped you establish such a successful brand? Tips for founders? Tell us about the approach you used to raise capital for Veev? Tell us the story behind founding M13. What was your vision for the firm early on?  What is your current focus/thesis at M13? Tell us about your “repeatable playbook” approach.  You took some big risks investing early in companies like Lyft, Ring, and Slack, which of course has paid off. Can you share with us some key points as to why you invested and how you were able to get conviction so early on?   I want to switch gears and talk a bit about your book that you and your brother, Carter, wrote “Shortcut Your Startup.” The book is focused on separating yourself from the pack and flipping traditional startup advice on its head to provide an empowering toolkit for founders. Can you dive into that toolkit and a brief summary of the book?  The benefits and biggest challenges to working with your brother? One of the topics in the book I thought was interesting was “obsessively take advantage of your unfair advantages” tell us about what this means and how founders can implement it.  Another topic I want to ask you about was “Success doesn’t equate to a successful exit” - What does lead to a successful exit and how do you gauge that you're on the right track?  You also talk about “getting into the trenches” and “knowing if you're a speedboat or a sailboat” in the book. Can you give us some insight on these topics and why they’re important?  From your experience, what do you think contributes most to founder burnout and how do you avoid it?  What advice would you give CEOs or other C-suite executives to keep employee morale high and help their employees thrive?  What are some of the biggest challenges you’ve faced as a founder and that you commonly see founders face today? You have a passion for startups that are thinking about what consumers don't even know they want -- maybe for 10-20 years. Yet, in the future can't imagine living without. How do you vet a startup investment with such nascent consumer demand? To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

On this special segment of The Full Ratchet, the following Investors are featured: David Horowitz Jim Kim Ash Rust Each investor describes the most unusual situation or pitch that they've encountered as an investor. To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

Oren Klaff of Intersection Capital joins Nick to discuss Flip The Script & Perfect Your Pitch. In this episode, we cover: Backstory/path to finance What led to the founding of Intersection? What's your mandate and focus at Intersection? Tell us about the Velocity product. Your bestselling book Pitch Anything, provides a detailed methodology on effectively presenting, persuading and winning a deal during the pitch. Can you go over some key takeaways from the book for listeners? In the book you talk about the "S.T.R.O.N.G Method.” Can you briefly summarize the most important components of this approach and give some examples on how it works?  Your newest book "Flip the Script: Getting People to Think your Idea is Their Idea" is about to launch on August 13th.. why'd you write the book? I liked the title of your first chapter... Inception.  Many will remember the blockbuster movie.  What's the "We are evolved distrust information from the outside world"... how does this impact the approach? Is there a framework of structure that folks should follow to successfully flip the script? What's the biggest mistake folks make when trying to sell? Whats' the most practical, simple, pragmatic advice you can give... let's say a founder trying to raise venture capital... that they can take away from this convo and implement immediately. Do you have a set of questions and structure for every sales discussion going in or do understand the concepts and then treat every conversation organically? Any tips on getting the meetings w/ prospects?  Let's say someone has optimized their close rate... do you have tips on securing more qualified meetings? If you write another book... what topic is next?   To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

On this special segment of The Full Ratchet, the following Investors are featured: Adeyemi Ajao Roy Bahat Cheryl Cheng Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach. To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

John Gannon of Going VC interviews Nick to discuss The Story Behind TFR & New Stack Ventures. In this episode, we cover: How did you get Brad Feld on early on? How did you stay true to your vision when you were getting asked early on by entrepreneurs to feature them on the podcast? (you mentioned this in episode 10, w/Brad Feld) If you were starting TFR again, in 2019, what would you do differently? Why the podcast format vs blogging vs. ... ? When did you know that the podcast was "working" ... bringing deal flow or whatever you thought was a strong signal that things were clicking for your audience? What surprised you once the podcast got "big"? Anything unexpected on the positive or negative side? How did the podcast tie into your recent fundraising process? Where did it help, and did it hurt or cause any issues, too? How did the podcast tie into your recent fundraising process? Where did it help, and did it hurt or cause any issues, too? Do you measure deal flow that is podcast related, and how much of your deal flow is it? How many completed investments came from the TFR community? I have heard from multiple Angel List employees re: Angel List syndicates that it's very hard to get people to back a deal unless the deal has a lead like Sequoia or KPCB or another top firm attached to it. Has that been true for your syndications? If no, why? What benefits did you see by using Angel List syndicates platform so early on? For those thinking of starting up a syndicate now, how has the game changed? How do you find and vet interns for your fund? Or how do they find you? Are there any processes at your fund that you think work REALLY well, and what are they? How do you execute them? Since we're both Dads: Other than having less time now that you have a child, have there been new tactics you've applied to the podcast, the firm, etc to help you get more leverage at work and free up time for home life? To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

Michael Cardamone of Acceleprise joins Nick to discuss SaaS Acceleration, Sales Savvy Founders & the Rise of Tech-Enabled Services. In this episode, we cover: What is Aaron Levie like to work for? Backstory and path to Acceleprise When you started Acceleprise a lot of folks told you not to -- the world doesn't need another accelerator. Why did you proceed? Why an Accelerator and not a traditional VC fund? Check size then and now? The biggest criticism of accelerators that I'm hearing from investors is that accelerators admit companies that need a lot of help and can't figure things out on their own -- and those are not the companies that one wants to invest in. What's your response to these folks? You've mentioned your interest in working w/ founders that have a "willingness to sell." How specifically do you develop the sell-skills of founders that are willing but green w/regards to sales. What are some the best demand-gen techniques that you use? Talk to us about how you think through pricing models and strategies at early-stage SaaS businesses. ACV initial vs. expansion rev opportunity Lemkin.. TAM... initial traction in SOM/Beachhead niche market is most important. Any company that gets traction here can find a $1B market. Agree, disagree? We talk a lot, on this show, about either why SF is the best place to build a company or why any place but SF is the best place to build a company. You've done both -- Objectively, can you break down the biggest advantages to building in the valley vs. the advantages to building outside? Let's talk a bit about pedigree -- most investors have simple heuristics here. If the founder didn't study at a Stanford/Ivy level institution... pass. If the founder didn't work for a FAANG tech company or fast-growing private tech company... pass. At New Stack, we like to say we're in the business of exceptions (deals that have all the right ingredients for success -- except these optics of provenance). Michael, where do you stand on pedigree and how do you define it? What percentage of the companies in the cohort to you invest in at completion? In terms of measuring success -- what key metric do you measure that you're most proud of? Over the past few years, what trends or major changes have you seen with regards to SaaS that founders and investors should be aware of? Tech-enabled services - a real trend or not? Venture fundable? There has been some recent issues in the Tech space with employee options -- what have you witnessed and what would you like to see change?   To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

On this special segment of The Full Ratchet, the following Investors are featured: Scott Dorsey Aydin Senkut Cyan Banister Each investor discusses sectors, drivers and/or trends that may have significant impact in the future and are potentially positioned for outsized-returns. To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.