20VC: Carvana CEO on Buiding a $50B Company, Losing 99% and Coming Back | Ernest Garcia: Inside the Mind of the Most Misunderstood CEO in America

Erik Allebest is the CEO @ Chess.com, the #1 online chess service on the planet with more than 150+ million members and 15+ million games played each day. Erik has scaled the company to over 700 people and $100M+ in revenue with no venture funding. In Today's Episode with Erik Allebest: 1. From Unemployable to $100M+ Revenue Founder: How did Erik make his way into the world of tech and startups? Was his MBA worth it? How does he advise others on whether to get one or not? What does Erik know now that he wishes he had known when he started? 2. Scaling to $100M Revenue with No Venture Funding: Why did no one want to invest in Chess.com in the early days? What did Erik do differently as a result of not raising any venture funding? What would Erik have done if he had money from the start? What are Erik's biggest pieces of advice to founders with funding today? 3. Hard Lessons Scaling to 150M Members: What are 1-2 of Erik's biggest lessons on how to scale users with zero budget? What customer acquisition worked? What did not work? How important was COVID and The Queen's Gambit to memberships and sign-ups? What are the single biggest mistakes Erik sees founders make on customer acquisition today? 4. Parenting, Marriage, Metrics and Money: Why does Erik not care about money or capitalism today? How has Erik's style of parenting changed over the years? What works? What does not? What does Erik believe is the secret to marriage? What have been his biggest lessons? Why does Erik hate metrics? If so, how does he run the business towards goals and output? Public.com Disclosure: Options are not suitable for all investors and carry significant risk.  Certain complex options strategies carry additional risk. Options can be risky and are not suitable for all investors. See the Characteristics and Risks of Standardized Options to learn more. For each options transaction, Public Investing shares 50% of their order flow revenue as a rebate to help reduce your trading costs. This rebate will be displayed as a negative number in the “Additional Fees” column of your Trade Confirmation Statement and will be immediately reflected in the total dollars paid or received for the transaction. Order flow rebates are only issued for options trades and not for transactions involving other assets, including equities. For more information, refer to the Fee Schedule. All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Open to the Public Investing, Inc., member FINRA & SIPC. See public.com/#disclosures-main for more information.

7 Feb 20241h 11min

David Tisch is the Managing Partner of BoxGroup, one of the leading seed-stage investment firms of the last decade having invested in over 500 seed-stage startups, including Plaid, Ro, Ramp, PillPack, Amplitude, Stripe, Warby Parker, Harry’s, Flexport, Classpass, Airtable and more. Terrence Rohan is the Managing Director @ Otherwise Fund, a fund that discretely empowers a network of today's top founders to make multi-stage venture investments. Terrence has invested in the likes of Figma, Hugging Face, Vanta, Notion and Robinhood to name a few. In Today's Seed Investing Special We Discuss: 1. Is Seed Investing Now a Commoditised Asset Class: Why does Dave Tisch believe seed investing will remain the most inefficient market? What does that mean for the future of returns at seed? Why should you always pay up and be price-insensitive at seed rounds? Why does David believe that no one is great at seed investing? Why does David believe that you cannot index the seed market? 2. The Biggest BS Elements of Venture Capital: Signaling: Why does David believe that the theory of signaling is total BS? Why does Terrence disagree and think it is valid and common? Group Decision-Making: Why does Terrence believe that investing decisions should be made solo and groups merely encourage consensus decision-making? Reserves: Why does Terrence believe reserves hurt DPI and are not good? How does David respond given his growth fund? Venture Value Add: Why do David and Terrence think venture value add services platforms are BS and not worth it? 3. The World of LPs: What is the single biggest misalignment between VCs and LPs? What are David and Terrence's biggest pieces of advice for emerging managers today? Should LPs expect depressed returns from venture as the asset class commoditises?

5 Feb 20241h 29min

Will Wu is the CTO @ Match Group, the owner and operator of the largest global portfolio of popular online dating services including Tinder, Match.com, OkCupid, and Hinge to name a few. Prior to Match, Will was VP of Product at Snap Inc. As the 35th employee, Will spearheaded the creation of Snapchat’s “Discover” content platform. He also led the creation and growth of the “Chat” messaging feature, which today is a primary Snapchat engagement driver that connects hundreds of millions of people each day. In Today's Episode with Will Wu We Discuss: 1. The Journey to Snap CPO: How did Evan make his way into the world of product and come to meet Evan Spiegel? What are 1-2 of his biggest takeaways from his time at Snap? What does Will know now that he wishes he had known when he started in product? 2. How to Hire Product Teams: How does Will structure the interview process for new product hires? What are the most telling questions of a candidate's product skills in hiring? What case studies and tests does Will do to assess a candidate? What are 1-2 of Will's biggest hiring mistakes in product? 3. How to Do Product Reviews Effectively: What are Will's biggest lessons on what it takes to do product reviews well? What are the biggest mistakes product leaders make in product reviews? How can teams drive focus in product reviews? What works? What does not? 4. Product: Art or Science? How does Will balance between gut/intuition and data in product decisions? Is simple always better in product design? What is human-centered design? How does it impact how Will approaches product?

2 Feb 202454min

Dave Kellogg is one of the OGs of Saas. Among his many accomplishments, Dave was the CMO of Business Objects where he helped scale the business from $30M to $1BN in revenue. Dave has also been a CEO twice, once scaling the business from $0 to $80M and the other business from $8M to $50M before selling it. Dave is also an advisor to some of the best including GainSight, Logickull, MongoDB, Pigment, Recorded Future, and Tableau. In Today's Episode with Dave Kellogg We Discuss: 1. What are the Metrics That Matter: Why is CAC payback period such a flawed metric? What is CAC ratio? Why is it more effective than understanding payback? Why is gross revenue retention more important than net revenue retention? What are the single biggest mistakes that founders make when using metrics today? 2. How to Build and Scale the Best Sales Teams: Why should founders hire three sales reps at one time? What is the benefit? What are the three different types of sales calls all teams must have? What should all CEOs and Heads of Sales ask of their sales team in forecasting? What is the single biggest mistake most companies make in forecasting? How should a CEO/board member respond to a sales team that lets a deal slip to next quarter? 3. Are CFOs Buying New Tech and How to Win Renewals: Are CFOs open for business? How has the top down sales process changed in the last year? Why is the way that startups think about renewals completely broken? What are the three different types of customer success teams we have today? What is the core role of customer success? How can we incentivise them to sell more? 4. Mastering Product Marketing, Customer Profiles and Crossing the Chasm: How can we use product marketing to increase sales velocity? What is the single biggest risk in product marketing today? What does Dave mean when he says "an ICP starts as an aspiration and becomes a regression?"

31 Jan 20241h 10min

Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company. In Today's Episode with Ryan Akkina We Discuss: 1. From Engineer to LP with MIT: How did Ryan make his way into the world of fund investing as an LP with MIT? Why did he turn down the chance to be a VC early in his career? What does Ryan know now that he wishes he had known when he started at MIT? 2. The Manager Evaluation Process for MIT: What does Ryan look for most when investing in new managers? How important is track record when evaluating a new manager? What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process? 3. How MIT Builds Their Portfolio: How does MIT construct their portfolio from private to public to everything in between? What are the three different types of check sizes that MIT writes when investing in new managers? What are the most common reasons why MIT will not re-up with a manager? What are the single biggest reasons why great managers turn bad? 4. MIT: The Direct Investor: Why does MIT see so much opportunity in direct investing? How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process? How do MIT think about the right number of direct deals to make up their portfolio? How do they approach check sizing on a per-company direct investment? What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset? 5. LP Markets Today and Where We Go From Here: Are LPs open for business today? What type of firms will not struggle? Which will? How does Ryan view liquidity windows today? When will M&A and IPO markets open? What would Ryan most like to change about the world of LPs? Why does Ryan believe the LP incentive structure in terms of compensation is broken?

29 Jan 202457min

Dave Ripley is the CEO @ Kraken, one of the world's largest cryptocurrency exchanges, valued in 2022 at a whopping $10.8BN. Prior to Kraken, Dave was the Co-Founder of Glidera, a market-leading Blockchain technology company that Kraken acquired in 2016. In Today's Episode with Dave Ripley: 1. From Boston Consulting Group to CEO of Kraken: How did Dave first make his way into the world of crypto? What are the single hardest elements of a CEO transition? What does Dave know now that he wishes he had known about CEOship? 2. What is the Usage for Crypto: Other than as a store of value, what application usage does crypto serve? Global payments are fine as is and are improving, why do they need crypto? Global remittance is served by Remote and Deel, why do they need crypto? No applications have been provided well, what really is the use case that makes sense? 3. Should Gensler Be Let Go and The SEC is Wrong: Why is the approach of the SEC completely flawed? Should Gensler be fired for his ineffectiveness? What is the right policy stance and approach to take from here?

26 Jan 202430min

Sean Murray is the CRO @ Greenhouse which is the fourth company Sean has scaled successfully into the enterprise. Sean's prior roles include revenue leadership positions at Saleloft (CRO), Xactly (VP Sales), and CEB, now Gartner (Head of MID Global Sales). In Today's Episode with Sean Murray 1. The Origin Story: Is a Love of Sales Born: How did Sean first fall in love with Sales? What does Sean know now that he wishes he had known when he started his career in sales? What is Sean's biggest advice to a young person entering the sales world today? 2. Sales has Changed; You Need to Change with It: Why do CMOs need to be good sellers and CROs need to be good marketers today? Have we seen the total blending of sales and marketing today? Should we get rid of all sales teams and just have content marketing teams? 3. How to Move into the Enterprise Successfully: What are the three biggest mistakes startups make when scaling into the enterprise? What easy wins can they do early in the sales process to enterprises to get a good start? How important are logos? Does social validity really work in enterprise? How should sales teams use discounting in enterprise sales most effectively? What is the right way for sales leaders and CROs to budget for enterprise? Is there a way to test enterprise without committing the company and a lot of resources? 4. How to Build the Best Sales Team Today: What is the right hiring process for all new sales hires? What are the questions you have to ask in the interviews? What do the case studies entail? What are signals of the best reps? What are the biggest mistakes teams make when hiring new sales reps? What have been Sean's biggest lessons on comp and negotiation with new reps?

24 Jan 20241h 10min

Adam Fisher is a Partner @ Bessemer Venture Partners and one of the most successful investors in Israel over the last two decades with seed investments in Fiverr, Wix, Melio, HiBob and more. Adam has now made over 60 investments and has had an incredible 23 successful exits. Adam has now been in venture for over 27 years having started his career at Jerusalem Venture Partners in 1996. In Today's Episode with Adam Fisher We Discuss: 1. Lessons from 27 Years in Venture Capital: How did Adam first make his way into the world of venture straight out of college? Does Adam agree with Doug Leone that VC has changed from a "boutique, high margin business to a commoditized, low margin industry"? What does Adam know now that he wishes he had known when he started in venture? 2. How to Pick Winners: 23 Exits in 60 Investments: To what extent does Adam think pattern recognition is a good thing? When is it bad? Does Adam prefer to invest in outsider founders approaching a problem with fresh eyes or insider founders who know the problem back to front? Why does Adam believe that "category creation is BS"? Why does Adam not like to invest in big, hugely ambitious markets? Why are smaller markets best? 3. The Deal: Mastering the Art of Negotiation and the Deal: How does Adam reflect on his own relationship to price? When doing an investment, does Adam think about who would do the next round? How important is ownership to Adam? Does he want it all on first check? Why does Adam not like to invest in hot AI rounds? What have been Adam's single biggest investing mistakes? How did it change his approach? 4. Mastering the Art of Portfolio Management: Why does Adam believe that it is impossible to know which of your portfolio will be the breakout winners early on? How does Adam approach reserve allocations with this in mind? How does Adam know when is the right time to sell a position? What does Adam believe was the biggest sin of the zero interest rate environment period?

22 Jan 20241h 11min