The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to for more information on the podcast, show notes, resources and more.
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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch











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Feb 21, 2024

Scott Williamson was most recently Chief Product Officer for GitLab, where he led a team of 65 in Product Management, Product Operations, Growth, Pricing, and Corporate Development functions.  Before GitLab, Scott was VP of Product for SendGrid for over six years, where helped lead the company to a successful IPO and $3B acquisition by Twilio. 

In Today's Episode with Scott Williamson We Discuss: 

1. From Sales to Product Leader:

  • Why does Scott believe sales is a great starting point for product people?
  • To what extent does an MBA help someone wanting to pursue a career in product management?
  • What does Scott know now that he wishes he had known when he started his career in product?

2. What, Who, When: How to Build a Product Team:

  • Is product management art or science? What is the ratio?
  • What are the four core roles of a product manager today?
  • When is the right time to hire your first PM?
  • What is the ideal profile for this first PM hire?
  • What are the single biggest mistakes founders make when hiring PMs?

3. Hiring the Best Product People:

  • What does Scott's hiring process look like for all new product hires?
  • How does Scott test for systematic thinking and problem-solving ability?
  • What questions does Scott always ask in interviews?
  • What are the best case studies to use to test a candidate's skill set?
  • How important is it for the candidate to have domain expertise in your product category?

4. The Best Product Teams are the Best Writers:

  • What are the two different types of documents that product teams must use?
  • How do you know when to use a one-pager vs a six-pager?
  • How does the discussion and planning cycle for the different documents differ?
  • How important is it for PMs to be great writers also?

Feb 19, 2024

Roger Ehrenberg is a legend of the venture industry as the Founder of IA Ventures, among the most successful seed-stage venture firms of this generation, having seeded companies including Datadog (NASDAQ: DDOG), Digital Ocean (NYSE: DOCN), The Trade Desk (NASDAQ: TTD) and Wise (LSE: WISE.L). Today Roger is the Founder and Managing Partner of Eberg Capital, a pioneer in bridging the gap among sports franchises, sports betting, media and entertainment. Roger’s current sports investments include stakes in the Miami Marlins, Real Salt Lake, Alpine Racing, Betr, Commonwealth, Kero Sports, Simplebet, SlamBall, Smarkets and WagerWire.

In Today's Episode with Roger Ehrenberg We Discuss:

1. The Commoditisation of Venture and Worsening Returns:

  • Why does Roger disagree with Doug Leone that "we have moved from a boutique high margin business to a commoditised low margin industry"?
  • Why does Roger believe we will see consistently worsening returns in venture?
  • Is this influx of LP capital cyclical or is it here to stay?

2. The New LPs and The Broken Existing LP World:

  • Why does Roger think the existing incentive structure for LPs is totally broken?
  • Who are the most important new LPs entering the venture market?
  • How do sovereigns and pension funds entering venture change the industry?
  • Which players have capitalised on this new LP class best?

3. Where Does the Liquidity Come From:

  • With the closed IPO window and lack of M&A, where will liquidity come from in the next 24 months?
  • Would a Trump administration open M&A markets? Does Roger agree M&A markets are shut down?
  • When does Roger believe IPO markets will open again? Will Databricks and Stripe go out in 2024?
  • If Roger were to run a continuity fund strategy, how would he structure it? What would he do?

4. When to Sell and When to Hold:

  • How does Roger advise managers on when to sell vs when to hold?
  • How important is it for a new firm to have a company go public in the first five years?
  • What are Roger's biggest lessons from selling The Trade Desk at a $2.5BN valuation?
  • How does Roger think about managers thinking they should manage the public book of their portfolio for their LPs? What are the pros and cons?

5. Relationship to Money:

  • Do rich investors make better investors? How does investing when you have a lot of cash already change your mindset around investing and exiting?
  • How does Roger analyse his relationship to money today?
  • What have been the single biggest needle movers in his wealth journey? How did it feel when he made a $6M bonus?

6. The Secrets to Parenthood and Marriage:

  • What does it mean to be a great father for Roger?
  • How does Roger think about bringing his children up with the same level of hunger and ambition, despite being brought up with such wealth?
  • What are Roger's two biggest lessons on the secret to a great marriage?

Feb 16, 2024

Christian Hecker is the Founder and CEO of Trade Republic, the company making it easy and inexpensive for everyone with a smartphone to invest. To date, Christian has raised over $1.3BN for the company from the likes of Sequoia, Founders Fund, Accel and Creandum to name a few. Previously, Christian worked in Bank of America Merrill Lynch’s Investment Banking department.

Johan Brenner is a General Partner at Creandum. Johan has led Creandum’s investments in iZettle (acquired by PayPal for $2.2bn in 2018), Trade Republic, Klarna, Pleo, Neo4J, Vivino and more. Johan was previously a repeat entrepreneur, founding one of the first online brokers in Europe in 1997 (sold to E*TRADE in the US), then JobLine (sold to Monster), Bookatable (Michelin) and Tradera (Ebay).

In Today's Episode with Christian Hecker and Johan Brenner We Discuss:

1. Selling 75% of Trade Republic for €600,000:

  • How did Christian come to sell 75% of Trade Republic for €600K?
  • How did Johan and Creandum solve this challenge when they invested?
  • What are some of Christian's biggest pieces of advice on cap table construction?

2. Raising $1.3BN From the Best Investors in the World:

  • What are Christian's biggest fundraising lessons from raising $1.3BN from the best in the world?
  • How did Doug Leone and Sequoia come to lead Trade Republic's round? What was the meeting with Doug like? What questions did he ask? How did it go?
  • How important of a skill does Johan believe being a great fundraiser is for founders?

3. Scaling into Europe's Next Decacorn:

  • What are the single biggest issues that arise when scaling so fast? What breaks first?
  • Does CAC increase with time or decrease?
  • Why did Christian decide to stop paid marketing on Google and Facebook and stop spending $100M+ there overnight?
  • Why is Christian so bullish on influencer marketing? What works? What does not work?

4. Europe: A Hub for Innovation or a Retirement Home:

  • Does Christian believe that young people in Europe work hard enough?
  • What are the biggest challenges to scaling teams in Europe?
  • Why does Johan believe the biggest challenge in Europe is the lack of exit markets?
  • What can Europe do to improve and increase our chances of being successful?

Feb 14, 2024

Martin Gontovnikas, a.k.a Gonto, is a software engineer at heart who moved to the “dark side” to focus on Marketing. With this career transition, he found a way to combine his 2 passions by applying his “engineering thinking” model to Marketing. He is now a B2B SaaS Advisor to Vercel and Airbyte among others and Co-Founder & GP of Hypergrowth Partners. Previously, he was SVP of Marketing and Growth at Auth0.

In Today's Episode with Martin Gontovnikas (Gonto) We Discuss:

1. From No Idea to Growth Leader:

  • How Gonto made his way into the world of growth when it was not a thing?
  • What does Gonto know now that he wishes he had known when he entered the world of growth?
  • Why does Gonto believe product and marketing is more important than sales and marketing?

2. Growth: What, When and Who:

  • What is growth? What is it not? What do people misunderstand most with growth?
  • When is the right time to hire your first growth person?
  • What is the right profile for the right first growth hire? Junior? Senior?

3. Mastering PLG and Enterprise:

  • What are the single biggest mistakes startups make when scaling into enterprise?
  • Why does Gonto believe that all PLG companies should start with 6-8 design partners?
  • Is it possible to do enterprise and PLG at the same time?
  • How does one provide enough value in a PLG motion to convert enterprise buyers?

4. Data vs Intuition: Art vs Science:

  • Is growth more art or science?
  • Why does Gonto believe qualitative data is more important than quantitative?
  • How does Gonto think about psychology when selling and marketing? What do so few startups? understand about the psychology of their customers?
  • How does Gonto approach messaging and what is truly great product marketing?

Feb 12, 2024

Thomas Plantenga is the CEO @ Vinted, one of the fastest-growing marketplaces in the world with a valuation of $4.5BN. Prior to becoming CEO, Thomas worked with a range of organisations including Bookaboat, OLX, Sellit/Wallapop and FJLabs.

Alex Taussig is a General Partner @ Lightspeed and co-leads the fund's Consumer investment team. Alex's portfolio includes the likes of All Day Kitchens, Archive Resale, Daily Harvest, Faire, Found, Frubana, Keychain, Kikoff, Vinted, YaySay, and Zola.

In Today's Episode with Thomas Plantenga and Alex Taussig We Discuss:

1. The CEO Who Did Not Want to be CEO:

  • How did Thomas come to be CEO @ Vinted? Why did he not want the job at first?
  • What does Thomas know now that he wishes he had known when he started?

2. The Mechanics of the Fastest Growing Marketplace:

  • What is the single most important metric for Vinted?
  • How does Vinted determine what market to open next? What do they look for?
  • How does Vinted think about depth vs breadth in each country?
  • What is the AOV today? How does it vary by country?
  • How long does it take for each country to be cash flow positive?

3. The Biggest BS in Startups: Rule of 40 and EBITDA:

  • Why does Thomas think VC's obsession with "Rule of 40" is BS?
  • Why does Thomas believe EBITDA optimization is BS and useless?
  • What are the hardest elements of scaling a marketplace that no one knows?

4. The Bull, Bear and Investor Approach to Vinted:

  • Alex, what was Lightspeed's pre and post-mortem when investing in Vinted?
  • How does Lightspeed analyze TAM and market sizing when investing?
  • What was Lightspeed's single biggest concern when investing in Vinted?

5. Europe: A Hub of Innovation or a Retirement Home:

  • Does Thomas believe that European young people have a worse work ethic than those in the US?
  • Is Thomas concerned by the state of regulation hampering innovation in Europe?
  • What can be done to improve work ethic and the state of regulation today?
  • Why is Alex and Lightspeed more bullish than ever on Europe today?

Feb 9, 2024

Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.

Marcelo Claure is the Founder & CEO of Claure Group, a multi-billion-dollar global investment firm. He is the Executive Chairman and Managing Partner of Bicycle Capital, a $500M Latin America-focused growth equity fund, and was appointed Chairman in Latin America of SHEIN, the global #1 on-demand fashion company in the world. Claure was also the CEO of SoftBank Group International where he launched SoftBank’s $8B Latin America Funds, and had direct oversight for SoftBank’s operating companies. 

Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel. 

Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets.

Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees.

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world. 

In Today's Episode on Price Sensitivity We Discuss:

  1. Doug Leone: Why the attitude of "deploy, deploy, deploy will get so many in trouble"?
  2. Marcelo Claure: How to know when price matters and when it does not?
  3. Geoff Lewis: What is the right framework to assess price at an early stage?
  4. David Tisch: How does the importance of price change vis a vis company vs portfolio?
  5. Orlando Bravo: What have been Thoma Bravo's biggest lessons on price?
  6. Cyan Banister: Why does Cyan believe there will be a reckoning?

Feb 7, 2024

Erik Allebest is the CEO @, 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 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? Disclosure:

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Feb 5, 2024

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?

Feb 2, 2024

Will Wu is the CTO @ Match Group, the owner and operator of the largest global portfolio of popular online dating services including Tinder,, 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?

Jan 31, 2024

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?"

Jan 29, 2024

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?

Jan 26, 2024

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?

Jan 24, 2024

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?

Jan 22, 2024

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?

Jan 19, 2024

Zaria Parvez is Duolingo’s Senior Global Social Media Manager where she is famed for scaling Duolingo's TikTok from 50K followers in September 2021 to 8M followers today. The Duolingo TikTok has 143 viral videos (view counts of 1M or higher) due to Zaria’s creativity. What started as a test-and-learn initiative has become Duolingo's most successful social buzz and word-of-mouth initiative to date – all because of Zaria's insights, instincts, and expertise.

In Today's Episode with Zaria Parvez:

1. From College Student to TikTok Star:

  • How did Zaria make her way into the world of social media and Duolingo?
  • When did Zaria realize the power of TikTok? What did she do as a first step?
  • What does Zaria know now about growing on TikTok that she wishes she'd known when she started?

2. How to Create a Viral Video:

  • What have been Zaria's biggest lessons in what it takes to create a viral video?
  • What does Zaria mean when she says the best content is "medicine to candy"?
  • What does the ideation process look like for new content ideas?
  • How much budget should be set aside for new content?
  • What does Zaria mean when she says Duolingo's TikTok needs to view like a "sitcom"?

3. How to Tie Success in Content Back to Hard Dollars:

  • How is "success" in content measured at Duolingo?
  • How fast does Zaria know if a video is a hit or not? What is the right cadence to post?
  • How should companies determine whether content is ultimately successful or not?
  • What is the single metric that Zaria is focused on today?

4. How to Build the Best Content Team:

  • Why should companies not work with content agencies if they want the best results?
  • Why does Zaria believe you have to hire troublemakers if you want success in content?
  • What are the single biggest mistakes companies make w

Jan 17, 2024

Shyam Sankar is Chief Technology Officer and Executive Vice President of Palantir Technologies in addition to the Chairman of Ginkgo Bioworks. Shyam holds a B.S. in Electrical and Computer Engineering from Cornell University and a M.S. in Management Science and Engineering from Stanford University.

In Today's Episode with Shyam Sankar:

1. Journey to the Top of Defence:

  • How did Shyam make his way into the world of startups and get a role with Kevin Hartz at Xoom?
  • How did seeing Shyam's parents lose everything impact his mindset and drive?
  • What does Shyam know now that he wishes he had known when he started his career?

2. How the World's Governments Buy Defence:

  • What is the playbook for selling defence to different governments?
  • Why is the way that governments purchase and procure so broken?
  • If Shyam were head of the DOD, what would he change?
  • Why does the DOD "need to pick winners"?
  • Which governments are the best to work with? Which are the worst?

3. A World In Conflict: What Changes:

  • How does conflict change the buying process and urgency for governments?
  • How do elections change the buying cadence and process for different governments?
  • Looking forward to 2024, how does Shyam predict the state of different global conflicts?

4. Hiring 101: You Have To Hire Artists:

  • What have been Shyam's single biggest lessons on what it takes to hire the best of the best?
  • Why does Shyam believe that hiring great people is like talent management in Hollywood?
  • Why does Shyam believe talent should be "shielded from budgets"?
  • What have been some of Shyam's biggest hiring mistakes? How did he learn from them?

Jan 15, 2024

Brian Halligan is the Co-Founder and Executive Chairperson of HubSpot. Brian led the business as CEO for 15 years from Day 1 to a $30BN public company with 7,000 employees. Among Brian numerous achievements, Brian is famed for coining the term "inbound marketing", he is a globally recognised author, he is also an incredible teacher having developed MIT’s popular Scaling Entrepreneurial Ventures class. In addition to all of this, he is also the Co-Founder of Propeller Ventures, a $100 million climate tech venture fund, specializing in ocean innovation investments.

In Today's Episode with Brian Halligan We Discuss:

1. The Makings of a Generational Defining Entrepreneur:

  • How did the first job as a paperboy lead to the founding of a $30BN company?
  • How does Brian analyse the importance of luck vs skill in success?
  • What is Brian running from? What is he running towards?

2. How to Be the Best Leader from 15 Years as CEO:

  • What are Brian's biggest lessons in leadership from Elon Musk and Jensen Huang?
  • How has Brian's leadership style changed over time?
  • Why is the way leaders prioritise what they do today completely broken?
  • How can leaders use quarterly goals to prioritise most effectively?
  • Does Brian believe people are born CEOs? Are MBAs worth it for CEOs?

3. How to Build the Best Team:

  • What is the #1 failure condition of teams today?
  • Why does Brian believe most of your employees are mercenaries and not missionaries? Is that ok?
  • Why do recovery plans never work? Once lost, can trust in teams be regained?
  • Are people destined for certain stages of company growth?
  • Why does culture always break when teams hit 100 people?

4. The Best Deal in VC History:

  • Why did Hubspot sell 47% of the company to General Catalyst in their Series A?
  • How did Sequoia come to lead their Series D?
  • How much of a needle mover is it for companies and founders to have Sequoia invest?
  • Why did Brian sell secondary to Sequoia in the Series D? Is it the most costly mistake he has made?

Jan 12, 2024

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Just last week, Keith announced he would be rejoining Khosla from Founders Fund, where he spent an immensely successful 5 years as a General Partner. Prior to Founders Fund, Keith started his career at Khosla where he spent 6 years and led investments in DoorDash, Opendoor, Webflow and more.

In Today's Episode with Keith Rabois We Discuss:

1. The Decision to Rejoin Khosla Ventures:

  • Why did Keith decide to rejoin Khosla Ventures from Founders Fund?
  • What did Keith miss most that Khosla did, that Founders Fund did not?
  • How did Delian take the news?

2. Comparing Two Great Firms: Founders Fund vs Khosla Ventures:

  • Investing Style: How does Keith compare the investing styles when analyzing FF and KV?
  • Price Discipline: Which firm is more price-disciplined? Does price discipline even matter?
  • What are the single biggest mistakes Keith has made on price? How did it change how he invests?
  • Founder Type: What sort of founder would choose KV? What founder would choose FF?
  • How did the depth & quality of investment decision-making compare between KV and FF?

3. What It Takes To Win in Venture in 2024:

  • Liquidity: What have been Keith's biggest lessons on when is the right time to sell positions?
  • Capital Planning: What have been Keith's biggest lessons on the most effective use of reserves?
  • Why does Keith believe if you do not lose some deals as an investor, you are not competing for the right companies?
  • Khosla Ventures recently raised $3BN. How important is the ability to support companies across their lifetime in 2024 vs stage specific?

4. Where is The Best Place to Invest:

  • Why does Keith think seed is the best place to be investing today?
  • Why despite the better risk/reward profile, does Keith think Series A is not the best place to invest?
  • Does Keith believe we will see the return of growth investing in 2024?
  • What does Keith predict for the M&A market in 2024? Did Figma kill all activity?
  • When will the IPO windows open again? Why would Stripe go out this year?

5. Keith Rabois: AMA:

  • Why did Keith not want to start his own fund? Will he ever?
  • What have been Keith's biggest lessons from working with Vinod Khosla and Peter Thiel?
  • What were Keith's biggest lessons from Roelof Botha on what it takes to be an effective board member?
  • How does Keith think about bitcoin in 2024?

Jan 10, 2024

Jamin Ball is a Partner @ Altimeter Capital where he sits on the board of Airbyte, Clickhouse, dbt Labs, Prisma, Tabular. Jamin has also led investments in Deel, MotherDuck, Personio and Starburst. Prior to Altimeter, Jamin spent 5 years at Redpoint where he led investments in Workato, Monte Carlo, Cityblock Health, Root Insurance.

Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman.

In Today's Episode We Discuss:

1. How to Invest Successfully in 2024:

  • What are the three biggest mistakes growth investors can make in 2024?
  • Why should founders not start a platform company?
  • What were Jamin and Ed's biggest mistakes from the ZIRP era?
  • How does Jamin justify paying an $8BN price for Hopin? What were his lessons?

2. The M&A Markets in 2024:

  • Did Figma kill the M&A markets for 2024? What should we expect in M&A?
  • Why will private companies buying private companies be a massive segment in 2024?
  • What are Ed and Jamin's biggest tips to founders considering selling their company in 2024?

3. When Will IPOs Come Back:

  • What will be the catalyst to the opening of the IPO markets?
  • Will Stripe and Databricks go public in 2024? What others should we expect?
  • What are the three requirements for a company to go public in 2024?

4. Firesales: Investors Need Cashback:

  • Why does Ed believe now is the time in the cycle where late-stage investors want cash back to distribute back to their LPs or to recycle?
  • What should we expect to see in terms of acqui-hires and firesales?
  • What are the different incentives when comparing founders vs early stage VCs vs late stage VCs when it comes to acquisitions?

Jan 8, 2024

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M and the firm now has over $1B in assets under management. Nick is famed for being one of the first investors in OpenSea.

Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few.

In Today's Episode We Discuss:

1. Moving Away from a Shitcoin Casino:

  • What will it take for crypto to move away from being shitcoin casino?
  • Why does Nick believe that "crypto has been a free for all and greed got the better of people"?
  • Why does Nick believe that crypto shilling will reduce the amount of violence in the world?

2. FTX: The Biggest Ponzi Scheme in Plain sight:

  • How does Kyle reflect on SBF and FTX today? Should he have known it was a fraud?
  • How did Nick see so far ahead of time that SBF was not genuine?
  • What are the most striking lessons when comparing Coinbase's Superbowl advert to FTX's?

3. Where Politics and Crypto Collide:

  • SBF was one of the largest donors to Biden, what does this say about the rise of "crony capitalism"?
  • What candidates running in the election will be best for crypto?
  • Why will Trump win the election and be the first President to rule from a prison cell?
  • Why is the strategy pursued by Gensler and the SEC so flawed?

4. The Great NFT Comeback, The Crypto IPO Season:

  • What will be the next crypto company to IPO? When?
  • When will NFTs come back? What will cause this?
  • Will Opensea ever be worth $13BN again? What is their future?

Jan 4, 2024

Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. The discussion today is broken into two segments:

2023: A Year in Review:

  • Breakout company
  • Best early-stage fund
  • Best late-stage fund
  • Most surprising event
  • Founder of the Year

2024: Predictions: What is to Come:

  • Does the IPO window open?
  • Do Stripe, Databricks, and more go public?
  • What happens to early-stage venture markets?
  • Does the growth stage come roaring back?
  • What happens to the M&A market?
  • How does Trump change the startup ecosystem?
  • Will a generation of young VCs be washed out the system?
  • Will a ton of venture firms shut down?

Dec 22, 2023

Dave Powers serves as President and CEO of Deckers Brands, a global footwear and apparel company where he focuses on the company’s five high-performing brands: UGG®, Teva®, Sanuk®, HOKA One One® and Koolaburra®. Prior to Deckers, he held executive leadership roles at Converse and Timberland, where he led worldwide retail merchandising, marketing, visual and store design as well as the creation of a sustainable line of footwear and apparel.

In Today's Episode with Dave Powers:

1. The Unlikely CEO of a Global Footwear Company:

  • How did Dave make his way into the world of consumer and fashion from the ground up?
  • Why did Dave never think he was the type of person to be a CEO?
  • What does Dave know now that he wishes he had known when he started his career?

2. From $1.1M Acquisition to $1.4BN Revenues: The Hoka Story:

  • Why did Deckers acquire Hoka for $1.1M? What did they see in this, at the time, futuristic running shoe that no one else saw?
  • Was the growth of Hoka linear or were there needle-moving moments that propelled the brand?
  • What did they do so right that led to their success?
  • What would Dave have done differently in the Hoka journey if he had his time again?

3. From $14.7BN Acquisition to Oprah's Favourite: The UGG Journey:

  • How much of a needle mover was it for UGG when Oprah added it to her list of favourite items?
  • Why did UGG go through a tough period? What did they do wrong?
  • What does it take to resurrect a brand? How can they bring UGG back to life and make it cool?

4. From Abercrombie to LVMH: An Analysis of the Industry:

  • How does Dave analyse the rise and fall of Abercrombie and Hollister? Where did it go wrong?
  • What does Dave believe LVMH are the best in the world at? What does he learn from them?
  • How important is it for consumer companies to have a hero product?
  • How can consumer companies scale to mass markets without losing their core audience?

Dec 20, 2023

Gustav Söderström is the Co-President, CPO & CTO at Spotify. Gustav has been instrumental in taking Spotify from a 30-person operation in Sweden when he joined to being the global leader of the space.

Scott Belsky is Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. 

Tomer Cohen is the Chief Product Officer @ Linkedin where he is responsible for setting and executing the global product strategy at LinkedIn.

In Today's Episode on How AI Changes The Future of Product and Design We Discuss:

1. Why AI Is Now the Product that UI Serves:

  • Why does Gustav believe that AI is now the product?
  • How has the importance of UI changed with the rise of AI?
  • How did TikTok change the product paradigm over the last few years?

2. What Matters More Models or Data:

  • What is more important the size of the model or the amount of data a company has?
  • Will companies use many models at the same time?
  • Why will companies using many models at once create a huge opportunity for startups?
  • Will every company have their own model? What will be the decision-making framework of whether to have your own model or leverage another?
  • How does the rise of AI change how companies approach data acquisition, collection and cleaning?

3. The Workforce Needs to Change with AI:

  • How do product leaders and teams need to change in an AI-first world?
  • What do designers need to do to stay up to date in an AI-first world?
  • What does it mean to be good at prompting? How can people get good at prompting?
  • Why will AI kill companies that charge by the hour?
  • Why will seat pricing die in a world of AI? What will be the business model for AI?

4. Incumbents vs Startups: Who Wins:

  • Do incumbents win in a world of AI or do startups?
  • Why is AI primed for incumbents to win and move fast in a way they could not in prior technology cycles?
  • What are the biggest hurdles and challenges incumbents have to face that startups do not?
  • What are the biggest barriers that startups have to win in a world of AI that incumbents do not have?

Dec 18, 2023

Peter Lacaillade is a Managing Director @ SCS Financial Services where he leads its private investment program where he oversees the firm’s activities in private equity, opportunistic credit and private real assets. Peter has been an early backer of Thrive, Founders Fund, a16z, Greenoaks and 20VC. Before SCS, Peter was an Associate at HarbourVest Partners in its Secondary Group where he analyzed venture capital, growth equity and buyout investments.

In Today's Episode with Peter Lacaillade We Discuss:

1. Becoming One of the Great LPs in Venture:

  • How did Peter make his way into the world of fund investing as an LP?
  • What does Peter know now that he wishes he had known when he started as an LP?
  • Why does Peter believe now is the best time to be investing in newer, emerging managers?

2. How to Pick the Best Venture Managers:

  • What are the commonalities in the best VCs Peter has invested in?
  • How important is track record for Peter when evaluating managers?
  • What mistakes has Peter made when it comes to manager selection? What did he learn?
  • How do the best managers build relationships with their LPs?

3. Building a Portfolio That Can 5x:

  • In a venture fund portfolio, what is the distribution between those that outperform, perform as planned and then underperform?
  • How does Peter invest in both large franchises and emerging managers with a barbell approach? How much in established franchises and how much in emerging managers?
  • Are managers actively marking down their portfolios in the last 18 months? Who has been the best at this and who has been the worst? How much should portfolios be marked down?
  • How does Peter evaluate the compression of deployment timelines we saw in the last 18 months?

4. A Breakdown of the LP Landscape:

  • Family Offices: What are the biggest dangers of having family offices as LPs? Why do multi-family offices tend to be better?
  • Endowments: Are they really as stable as people think they are? What separates a good vs great endowment? Who stands out?
  • Fund of Funds: Why does Peter think fund of funds deserve more credit? How should managers think about working with FoFs most effectively?
  • What is the right level of concentration managers should have between these different LP profiles?
  • What are the biggest mistakes emerging managers make when approaching LPs?

Dec 15, 2023

Davis Smith is the Founder and Chairman of Cotopaxi, an outdoor brand with a humanitarian mission. The company has assisted over 4 million people living in poverty. The company has been profitable for the last 4 years and is expected to do $160M in revenue in 2023, up from $55M just two years before. In April 2023, Davis resigned after 10 years as CEO to lead a mission for his church in Brazil for three years. Davis is an EY Entrepreneur of the Year and was recognized as Utah’s Businessperson of the Year in 2022. He is an adventurer who has floated the Amazon on a self-made raft, kayaked from Cuba to Florida, and explored North Korea.

In Today's Episode with Davis Smith We Discuss:

1. From Selling $6M Worth of Pool Tables to the Amazon of Brazil to Founding Cotopaxi:

  • How did Davis scale a pool table business to $6M in revenue?
  • What were Davis' biggest takeaways from building the Amazon of Brazil, raising millions in VC funding and the business failing?
  • How did depression and 36 hours on a sofa lead to the a-ha moment for Cotopaxi?

2. The Billion Dollar Company, Rejected by 100 Investors:

  • How was the early fundraising journey for Davis with Cotopaxi? Why did so many investors say no?
  • What was the best VC meeting he has ever had? Why do women understand Cotopaxi better?
  • What does Davis believe are the biggest misalignments between VCs and Founders?
  • Why does Davis believe we need a new type of financial product to fund long term projects?
  • What are the biggest elements of fundraising that Davis believes founders do not understand?

3. Scaling Cotopaxi to $150M in Revenue:

  • What are Davis' biggest lessons on what works and what does not from scaling Cotopaxi to $150M in revenue?
  • Why did Davis not lay anyone off but decide everyone should take a pay cut instead? How did that go down?
  • Why does letting people leave work earlier lead to better talent wanting to join your company?
  • Why does Davis believe that you absolutely can build a huge business with balance in your life?

4. Life, Parenting, Marriage:

  • Why does Davis believe that so many entrepreneurs chase the wrong thing? What do they chase? What should they be chasing instead?
  • How does Davis analyze his relationship to money today? Does it make you happy?
  • What does great parenting mean to Davis? How has that changed over time?
  • How does marriage change when comparing pre-kids and post-kids?
  • Was Davis nervous about becoming a father for the first time at the age of 24?

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