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

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 www.20vc.com for more information on the podcast, show notes, resources and more.

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20VC: The Future of TikTok; Is it a Danger to US National Security| Why the "Woke Mind Virus" is a "Post-Modern Religion" and Is it Too Late to Reverse | Why the Education System is Broken | Investing Lessons from Wish, Palantir and Lady Gaga | Joe Lonsda

Joe Lonsdale is the Founder and Managing Partner at 8VC, an early-stage venture capital firm managing over $6 billion in capital. In 2003, he founded Palantir Technologies. Since then, he has founded over a dozen companies, including Addepar, a wealth management platform helping investors manage over $5 trillion, and OpenGov, recently sold for $1.8BN.

In Today?s Episode with Joe Lonsdale We Discuss:

The Making of a Multi-Unicorn Founder:

What was Joe like as a child? How would his parents and teachers have described him? What does Joe know now that he wishes he had known when he started his career? How does Joe view the importance of luck and skill in success?

America?s New Dawn: Navigating Frontiers and Accountability

What did Joe mean by describing America as a ?frontier nation?? How does Joe contrast America?s frontiers with Europe?s social safety nets? How does Joe propose restoring America using the ?scalpel over the sledgehammer? approach? How can America introduce accountability to non-profit institutions? What role do for-profit prisons play?

Woke Mind Virus

Why does Joe consider the Woke Mind Virus a ?Bad Postmodern Religion?? Why does Joe see Elon Musk as a key figure in challenging ?woke minds?? Why does Joe believe the education system is a core problem? What needs to change? Is it too late to reverse the current state of ?woke mind virus??

TikTok, China, Israel:

What does Joe believe is the right solution for TikTok?s ownership? To what extent is TikTok a danger to American national security? What does Joe predict will happen to China from here? What needs to change? How does Joe predict the next 24 months for the conflict in Israel and Gaza?

Investing Lessons: Wish, Palantir and more

What are Joe?s biggest takeaways from the failing of Wish? What did Joe learn from the failed project with Lady Gaga? How does Joe reflect on when is the right time to sell? How does Joe reflect on his own relationship to money?
2024-03-11
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20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy

Brendon Cassidy is one of the OG of enterprise sales of the last decade, having advised the likes of Gong.io, Pipedrive, Showpad. Previously Brendon was first Head of Sales at LinkedIn and VP of Sales at Talkdesk.

In Today's Episode with Brendon Cassidy We Discuss:

1. From Recruiter to Sales OG and Linkedin's First Head of Sales:

How did recruiting prepare Brendon for a career in sales? What impact did the dot-com bubble burst have on his early career? What does Brendon know now that he wishes he had known when he started his career in sales?

2. The Sales Playbook and Hiring The Team:

How does Brendon define the "sales playbook"? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire? 

3. Why Discovery and Outbound Are Broken Today:

Why does Brendon feel discovery is useless in today?s sales process? Why does Brendon believe outbound will move under the marketing function? How does AI change the world of outbound sales? Why will no great sales leaders join a company that doesn?t have an inbound machine?

4. How to Master Onboarding and Increase Sales Performance:

What is the right way to onboard new sales reps? How quickly do you know if a sales rep is not good? What are the signs? What is the right way to measure the effectiveness of sales teams today? What are the biggest mistakes founders make in onboarding sales teams?

2024-03-08
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20VC: 27 Years of Investing Lessons on Picking Founders, Price Discipline, Reserves and Selling Positions | Can Seed Investors Compete with Multi-Stage Venture Firms | Why Returns Will Not Worsen Moving Forward with Peter Wagner, Founder @ Wing

Peter Wagner is a Founding Partner of Wing. Peter has led investments in dozens of early-stage companies including Snowflake, Gong, Pinecone, and many others which have gone on to complete IPO's or successful acquisitions. Prior to founding Wing, Peter spent an incredible 14 years at Accel, starting as an associate in 1996 and scaling to Managing Partner, before leaving to start Wing.

In Today's Episode with Peter Wagner We Discuss:

1. From Associate to Managing Partner to Founding Partner:

How did Peter first make his way into the world of venture as an associate at Accel? How important does Peter believe it is to have early hits in your career as an investor? What is the biggest mistake Peter sees young VCs make today?

2. The Venture Market: What Happens Now:

Does Peter agree with Roger Ehrenberg that venture returns will worsen moving forward? How does Peter answer the question of how large asset management venture firms co-exist in a world of boutique seed players also? Does Peter agree with Doug Leone that "venture has transitioned from a high-margin boutique business to a low-margin, commoditized industry?

3. Investing Lessons from 27 Years and Countless IPOs:

What have been some of Peter's single biggest investing lessons from 27 years in venture? Why is Peter so skeptical of capital-intensive businesses? Will defense and climate startups suffer the same fate as clean tech did in the 2000s? How does Peter reflect on his own relationship to price? When does it matter? When does it not? What have been Peter's biggest lessons on when to sell positions vs when to hold? What has been Peter's biggest miss? How did it impact his mindset?

4. Building a Firm from Nothing:

How was the fundraise process when leaving the Accel machine and raising with Wing? What have been the single hardest elements of building Wing? What did he not expect? What advice does Peter have for someone wanting to start their firm today?

2024-03-06
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20VC: Managing the Largest Sovereign Wealth Fund in the World: $1.55 Trn of Assets & Owning 1.5% of all Listed Companies with Nicolai Tangen, CEO @ Norges Bank Investment Management

Nicolai Tangen is the CEO of Norges Bank Investment Management, the largest sovereign wealth fund in the world with $1.55 Trn in assets, owning on average, 1.5% of every listed company. Tangen was previously Chief Executive Officer and Chief Investment Officer in AKO Capital, which he founded in 2005. Prior to this, Tangen was a partner and senior analyst at Egerton Capital and an equity analyst at Cazenove & Co.

In Today's Episode with Nicolai Tangen We Discuss:

From Religious Town in Norway to Leading the Largest Sovereign Wealth Fund:

What was Nicolai like as a child? How would his parents have described him? Why does Nicolai think that loners have a greater chance/ability to make money? What does Nicolai know now that he wishes he could tell a 20-year-old Nicolai?

The Top 10 Questions:

1. US Tech Firm Concentration: Is Nicolai concerned by the concentration of enterprise value in US tech firms? Have incumbents ever been as strong as they are today?

2. Impact of AI: What does Nicolai believe the impact of AI will be on society and productivity? What is his approach to investing in it moving forward?

3. Bitcoin: Why does Nicolai not want to hold Bitcoin? Why does he not understand it?

4. China: What would need to happen for China to be investable? How will the China situation play out?

5. Europe: Does Nicolai believe Europe is so far behind the US? Why? What can we do to improve?

6. Climate Change: How does Nicolai approach investing in climate? What works? What does not?

7. Sam Altman: Would Nicolai invest in Sam's new $7Trn project? What are some of Nicolai's biggest lessons from the time he has spent with Sam?

8. Investment Psychology: How does Nicolai retain a neutral investor psychology? How does he not get too up when doing well and too low when not doing well?

9. Investing Lessons: What are Nicolai's biggest investment hits and misses? What did he learn from them?

10. The Future: Why is Nicolai so optimistic about the future? What is he concerned about? How will we overcome our greatest challenges?

2024-03-04
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20VC: Are IPO Windows Shut? Has Regulation Killed the M&A Market? M&A OG Frank Quattrone on Lessons from 650 M&A Deals Worth Over $1TRN and Taking Amazon, Cisco and Netscape Public

Frank Quattrone is the Founder and Executive Chairman of Qatalyst and served as its CEO from the Firm?s founding until January 2016. Over more than four decades, Frank and the teams he has led have advised on more than 600 mergers and acquisitions with an aggregate transaction value over $1 trillion and on more than 350 financings that raised over $65 billion for technology companies worldwide. Frank led the IPOs of Amazon.com, Cisco, Intuit, Netscape, among many others. He advised Apple on its $400 MM acquisition of NeXT (which led to Steve Jobs? return to Apple); Concur on its $8.3B sale to SAP; LinkedIn on its $28.1B sale to Microsoft; Qualtrics on its $8B sale to SAP and Twitch on its $1B sale to Amazon.com.

In Today's Episode with Frank Quattrone:

1. Has Regulation Killed M&A:

Why does Frank disagree that regulation has killed M&A? What is the real reason why M&A is so down at present? What would impact would a Trump administration have on the M&A environment? What are some of Frank's biggest lessons from 600 prior transactions over dour decades of what happens when an M&A market shuts down?

2. When Will the IPO Window Re-Open:

Does Frank agree that the IPO window is currently closed for tech companies? How does this IPO window compare to the dot com bust and 2007? What is needed for the IPO window to re-open? What is the timeline that Frank puts on the IPO window opening again?

3. M&A: How Do Companies Get Bought:

What is the process for a company to be bought? What are the single biggest mistakes the seller makes in the process? What do the best buyers and sellers do to get the best price? Does Frank agree with the notion that "companies are bought and not sold"?

4. IPOing Amazing, Selling Linkedin and Qualtrics:

What is the story behind, Frank, Bill Gurley, Jeff Bezos and John Doerr pricing the Amazon IPO? How did Linkedin come to be bought by Microsoft? What did that process look like? How did Frank structure an event to ensure that Ryan @ Qualtrics and Bill McDermot @ SAP would meet and lead to the acquisiiton?

2024-03-01
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20VC: Startups Only Fail When Founders Stop Trying, Why the Two Weeks Following Our IPO Were the Worst of my Life & Why Tieing Your Identity to Your Company is the Most Dangerous Thing and How to Avoid It with Sami Inkinen, Co-Founder & CEO @ Virta Health

Sami Inkinen is the Co-Founder and CEO of Virta Health, the company reversing type 2 diabetes. Before Virta, Sami was the Co-Founder of Trulia, steering the company to a successful IPO and its eventual sale to Zillow Group. Outside of the boardroom, he launched Fat Chance Row, a daring venture to row 2,750 miles across the Pacific, unsupported with his wife, rowing 18 hours straight per day.

In Today's Episode with Sami Inkinen:

1. From Farm in Finland to IPO Founder: Relationship to Money

How did Sami's humble upbringing on a farm in Finland impact his early mindset and ambition? How does Sami analyze his relationship to money today? How has it changed over time? Why was the two weeks following Trulia's IPO the worst two weeks of his life?

2. The Secret to Marriage: Rowing 2,750 Miles Together:

What are some of the biggest lessons on marriage Sami has from spending 45 days rowing the Pacific with only his wife for company? What was their single biggest argument over the 45 days? What did Sami learn from it? Sami worked with his wife, what are the biggest pros and cons of working with your spouse? Would Sami recommend it? What does Sami believe are the core fundamentals that underpin the best marriages?

3. The Secret to Parenting: The Regret of Delegation:

What is Sami's biggest regret when it comes to parenting? How does Sami think about what it means to be a great father today? How has that changed? How did Sami's relationship with his wife change when they had kids?

4. Relationship to Identity:

Why does Sami believe tieing your identity to the company, as a founder, is so dangerous? How does Sami advise on creating multiple personas to prevent this? Why does Sami believe that all the best founders are addicts to some extent?

2024-02-28
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20VC: What it Takes to be Top 1% in Private Equity | Why the Best Companies are Talent Systems | Three Traits Required to Succeed in Private Equity | Marriage, Fatherhood and Sports Team Owner, What it Takes to Do It All, with Justin Ishbia, Founder @ Sho

Justin is the Founder and Managing Partner of one of the nation?s best-performing private equity firms, Shore Capital Partners (?Shore?). Since the firm?s inception in 2009, Shore has grown from 4 to over 140 team members managing over $6 billion in AUM, representing 900+ acquired companies and more than 33,000 employees. Shore is also one of the most active private equity firm in the world by deal volume according to PitchBook while continuing to achieve return profiles that rank Shore among the top 1% of private equity firms. Justin is an avid sports fan/investor and is the Alternate Governor for the Phoenix Suns (NBA), Phoenix Mercury (WNBA) and Nashville SC (MLS). 

In Today's Episode with Justin Ishbia:

1. From Law Student to Founding Shore Capital:

How did seeing Justin's father operate impact how he thinks about building Shore today? What does he know now that he wishes he had known when he started Shore? How important a role does luck play in success? How has his mindset changed on this?

2. How to Make Top 1% PE Returns:

Why does Justin see private equity done well like "using a flashlight in a dark room"? What are the top 3 elements that Justin looks for in all acquisitions they make at Shore? When did Justin think there was an advantage of scale/network effect but was proved wrong? How does Justin think about downside protection and risk mitigation? Why does Justin like to back and invest in first time founders more than any other type?

3. Building World-Class Investing Teams:

Why does Justin believe the best companies are talent systems? How does Justin structure the talent system at Shore to ensure consistent incredible talent? What does Justin believe are the three traits required to win in private equity? What question does Justin ask all potential CEOs he hires for acquired companies? What has Justin learned is the single clearest sign of the top .1% talent?

4. Justin Ishbia: The Family Man and Husband:

What metric does Justin use to track whether he is being a good and present father? Is it possible to be top 1% and have balance with a wife and family? What does "great fatherhood" mean to Justin? How has his thoughts on this changed? How does Justin think about bringing kids up in a world of immense privilege and ensuring they remain ground and ambitious?

2024-02-26
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20Product: The Five Step Process to Hiring the Best Product People, The Four Core Skills the Best PMs Need to Have, The Two Product Documents that Drive World Class Product Teams & Why the Best PMs are Writers with Scott Williamson, Former CPO @ Gitlab

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?

2024-02-21
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20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital

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?

2024-02-19
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20VC: From Selling 75% of Trade Republic for ?600K to Raising $1.3BN at a $5.3BN Valuation, The Biggest Fundraising Lessons Having Raised $1.3BN From the Best in the World; Trade Republic CEO, Christian Hecker and Creandum General Partner Johan Brenner

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?

2024-02-16
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20Growth: How to Master Product-Led-Growth, The Biggest Mistakes Startups Make When Scaling into Enterprise, How to Assess "Bets" in Growth; Which to Take and Which to Not with Gonto, Interim CMO @ Vercel

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?

2024-02-14
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20VC: The Ultimate Guide to Scaling Marketplaces, Why Rule of 40 and EBITDA Optimisation is BS, How Founders & VCs Should Approach Market Sizing and Outcome Scenario Planning and Why Europe is Failing with Vinted CEO, Thomas Plantenga & Alex Taussig

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?

2024-02-12
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20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When to Pay Up vs When to Stay Disciplined, The Biggest Lessons on Price Discipline from 8 of the World's Best Investors

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:

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

2024-02-09
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20VC: The Chess.com Memo: The Most Untold Story in Startups; Scaling to $100M Revenue, 150M Members and 700 People, All with Zero Venture Funding | Erik Allebest, CEO @ Chess.com

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?

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2024-02-07
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20VC: The Biggest Misconceptions & Hardest Truths About Seed Investing Today; Why The Best Founders Don't Need You, Why Uncapped SAFEs Are Good, Why Reserves Are Bad, Why Signalling is BS, Why Price Doesn't Matter with David Tisch & Terrence Rohan

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?

2024-02-05
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20Product: Top Five Product Lessons from Creating Snapchat "Discover" and "Chat", How to Hire the Best Product Talent and Why Case Studies in Interviews are not Helpful & How AI Impacts the Future of Product Design with Will Wu, CTO @ Match Group

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?

2024-02-02
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20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K

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?"

2024-01-31
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20VC: How MIT Selects Venture Managers to Invest in | The Three Categories of Check MIT Writes Into Funds | How MIT Builds Their Venture Fund Portfolio | How MIT Approach Direct Investing | Why Being an LP Has Never Been Harder with Ryan Akkina @ MIT

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?

2024-01-29
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20VC: Are the SEC Overreaching with its Approach to Crypto? Should Gensler Step Down? How do US Elections Impact Crypto Markets? How Did SBF and FTX Impact Crypto Long Term and more with Dave Ripley, CEO @ Kraken

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?

2024-01-26
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20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

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?

2024-01-24
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20VC: Why Small Markets are Better Than Big Markets, The Biggest Delusion of Early Stage VC, Why AI Investing is like a Horserace and Why The Most Ambitious Companies Growing the Fastest are not the Best Investments with Adam Fisher, Partner @ Bessemer

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?

2024-01-22
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20VC: How Duolingo Scaled to 8M TikTok Followers, How to Create Viral Content, Why Most Companies Suck at Content Marketing and How to Change & Why You Should Not Work with Content Agencies with Zaria Parvez, Global Social Media Manager @ Duolingo

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

2024-01-19
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20VC: Palantir CTO on The Broken Incentive Structure of How Governments Buy Defence, The Danger of Defence Spending at Historic Lows, How Elections and Wars Change Government Defence Buying & Why Budgets are Anti-Creative with Shyam Sankar

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?

2024-01-17
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20VC: Hubspot Co-Founder Brian Halligan on Leadership Lessons Scaling Hubspot to a $28BN Market Cap | The Best Series A Investment in Venture History & What Makes Sequoia so Successful?

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?

2024-01-15
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20VC Exclusive: Keith Rabois on Rejoining Khosla Ventures

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?

2024-01-12
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20VC: Did Figma Kill M&A Markets in 2024, The Three Biggest Mistakes Made in Growth Investing, The Three Requirements Companies Need to Go Public in 2024 with Ed Sim and Jamin Ball

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?

2024-01-10
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20VC Crypto Roundtable: How Will US Elections Impact Crypto? Why Will Trump Lean Into Crypto in 2024? Should FTX Investors Have Known About SBF? Will Opensea Ever Be Worth $13BN Again? Will NFTs Come Back with Kyle Samani and Nick Tomaino

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?

2024-01-08
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20VC: Predictions for 2024: What Happens to Early Stage VC Funding, Do a Load of Venture Funds Die, What do LPs Do in 2024, Does Figma Kill the M&A Market, Will IPOs Comeback & What Does a Trump Administration do for Startups with Jason Lemkin @ SaaStr

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?

2024-01-04
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20VC: From a $1.1M Acquisition to $1.4BN in Revenues; The Meteoric Rise of Hoka Running with Deckers CEO, Dave Powers

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?

2023-12-22
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20VC Roundtable: Spotify, Adobe & Linkedin CPOs on How AI Changes The Future of Product, Why AI is Now the Product, How TikTok Changed Product, Why Cost is the Biggest Barrier to LLM Usage & Why Incumbents Can Adopt AI Faster Than Any Prior Innovation Cyc

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?

2023-12-20
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20VC: Why Now is the Best Time to Invest in Emerging Managers, Biggest Mistake Emerging Managers Make When Fundraising & Investing Lessons from Investing $1.5BN Per Year and Being Early Investors in Thrive, a16z and Founders Fund with Peter Lacaillade

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?

2023-12-18
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20VC: Cotopaxi: From Selling $6M of Pool Tables to Scaling $150M in Revenues and Challenging Patagonia, Fundraising Lessons from 100+ Rejections & What Founders Do Not Understand About VC with Davis Smith, Founder @ Cotopaxi

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?

2023-12-15
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20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

Steve Goldberg is the Chief Revenue Officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for $2.3BN. Prior to Salesloft, Steve was Group Vice President of Enterprise at Yext and before that was a Senior VP @ InsideSales.com.

In Today's Episode with Steve Goldberg:

1. Becoming a Sales Leader:

When did Steve first fall in love with sales? Why does Steve believe sales is more psychology than anything else? What can sales reps do to master the psychology of their prospects? What does Steve know now about sales that he wishes he had known in the beginning?

2. How to Close Prospects Faster Than Ever:

How does Steve build relationships with prospects very fast? What questions does he ask? How does Steve know if he is really speaking to a buyer? What are the signals? How does Steve advise sales reps on getting multiple relationships within an account to prevent the potential of losing your champion? How does Steve feel about discounting? When is the right time to do it?

3. How To Do The Best Deal Reviews:

What makes good vs great deal reviews? Who is invited? Who is not? Who sets the agenda? Who is responsible for what? How do deal reviews change throughout the quarter and throughout the year? Is a deal slipping into the next quarter an acceptable excuse for a sales rep to give?

4. How to Ensure Renewals in a World When They are Not Guaranteed:

Have all budgets centralized back to the control of the CFO? Are people right to say that no CFOs are buying new technology today? What is the best way to show to customers the value you provide? Why does Steve believe revenue operations is the most valuable role within an org?

2023-12-13
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20VC: Why Founders Should Take as Many VC Meetings as Possible, Should Founders Meet Associates, How to Get Intros to the Best VCs, How To Extract the Most Value From Your Investors, Why Post IPO Operators Are the Best Angels with Sam Corcos @ Levels

Sam Corcos is the Co-Founder & CEO @ Levels, the company helping you see how food affects your health with data from biosensors like continuous glucose monitors (CGMs). To date, Sam has raised over $89M for Levels from the likes of a16z (Jeff Jordan sits on his board), Founder Collective, Breyer Capital and Shrug Capital to name a few. Prior to Levels, Sam founded two prior companies, CarDash; a Y Combinator company that makes automotive repair and maintenance convenient. Before Cardash, Sam founded, Sightline Maps, an intuitive platform for 3D printing and visualizing topographical maps, marketed primarily towards the U.S. military.

In Today's Episode with Sam Corcos:

1. The Founding Moment:

What was the a-ha moment for Sam with the founding Levels? What were the big mistakes Sam made with prior companies that he did not take with him to Levels? What does Sam know now that he wishes he had known when he started Levels?

2. How to Fundraise Like a Pro:

Why does Sam believe that founders should take as many meetings with VCs as possible? What are the biggest mistakes founders make when meeting investors? Should founders meet with associates in the fundraising process? What does Sam mean when he says, "you have to create theater" when pitching?

3. How to Extract the Most Value from Your Investors:

What have been Sam's biggest lessons on how to put your investors to work? What is the right and most strategic way to ask investors for specific help? How can founders create a competitive environment where VCs are competing to help? Which investors have been the most helpful? Why are post-IPO operators the best angels to have as investors? How has the a16z platform team been such a needle mover?

4. How to Find Your Partner and Master Parenting:

What does Sam mean when he says he had a "one pager" in what he wanted in a partner? What was in the one-pager? How did dates respond? What are the biggest mistakes people make when dating? What is Sam most nervous about on becoming a parent? How does Sam think having a child will impact his marriage?

2023-12-11
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20VC: $18BN Market Cap and $1BN in ARR in 8 Years; Samsara | How to Find Product Market Fit Reliably | How to Create a Multi-Product Company | The Pros and Cons of Serial Entrepreneurship with Sanjit Biswas, Founder & CEO @ Samsara

Sanjit Biswas is the Founder and CEO @ Samsara, allowing businesses that depend on physical operations to harness Internet of Things (IoT) data. Over the last 8 years, Sanjit has scaled Samsara to $1BN in ARR and a public company with tens of thousands of customers. Before Samsara, Sanjit was the CEO and co-founder of Meraki, one of the most successful networking companies of the past decade. Sanjit grew Meraki from his Ph.D. research into a complete enterprise networking portfolio. Meraki's sales doubled every year from inception and in 2012, Cisco acquired Meraki for $1.2 billion. Huge thanks to Doug Leone for some fantastic question suggestions pre this episode.

In Today's Episode With Sanjit Biswas We Discuss:

1. From Founding to $1BN in ARR in 8 Years:

What was the founding a-ha moment for Sanjit with Samsara? Sanjit sold his prior company Meraki for $1.2BN, what worked with Meraki that Sanjit took with him to Samsara? What did not work that he left behind? What does Sanjit know now that he wishes he had known when he started Samsara?

2. The Man Who Found Product Market Fit Time and Time Again:

What is the one single moment that Sanjit believes you know you have product market fit? What are the biggest mistakes founders make when chasing product market fit? How does being a bootstrapped company change how a company approaches chasing PMF?

3. Mastering a Multi-Product Company:

How do you know when it is the right time to launch a second product? Does the second product have to make the first product better? What are the biggest mistakes companies make when going multi-product?

4. The Art of Great CEOship:

Does Sanjit believe that the best CEOs are the best capital allocators? What has been the single best and single worst capital allocation decision in Samsara's journey? What are the biggest mistakes Sanjit has made in leadership? How did he learn and grow from them?

2023-12-08
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20VC: Ramp's Product Playbook: How To Hire Product Teams, How to Run Sprints, How to Increase Product Velocity, When and How to Go Multi-Product with Geoff Charles, VP Product @ Ramp

Geoff Charles is the VP of Product at Ramp, leading the product management, operations, and support teams. Prior to Ramp, Geoff helped spin off Mission Lane and scale credit products to millions of consumers. He started his career advising Fortune 100 financial services companies.

In Today's Episode with Geoff Charles We Discuss:

1. How to Become a Product Leader:

How did Geoff make his way into the world of product? What are the single most important skills for product people to learn early? What are the biggest mistakes that product people make early in their career?

2. When and Who to Hire for the First Product Team:

When is the right time to hire your first product people outside of founding team? Why are the best product teams in the early days professional services teams? What is more important; the person has stage or sector experience, when joining? Should you hire senior product people or junior product people as the first hires?

3. How to Increase Velocity Using Sprints:

How does Geoff and Ramp use two-week sprints to have insane product velocity? How are they structured? How are goals set? Who is included? What makes a good vs a bad sprint? How is accountability tied to sprints? When do two-week sprints no longer become possible? What happens then?

4. Going Multi-Product, Will Incumbents Kill You and Product Re-Usability:

When is the right time to add a second product? What are the biggest mistakes companies make when going multi-product? Why is it unlikely that an incumbent is the one to kill you? What competitor should worry you? What does Geoff mean when he speaks of "product re-usability"? Why is it crucial to velocity?

2023-12-06
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20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Tooey Courtemanche, Jr. is the Founder, CEO, President, and Chairman of the Board of Procore. He founded Procore in 2002 with a mission to connect everyone in construction on a global platform. After 13 years of business, the company had just $9.6M in revenue, 8 years after that they have over $890M in revenue. Under his leadership, Procore has grown to become a leading global provider of construction management software, connecting over 2 million users across 150+ countries. Today Procore trades on the New York Stock Exchange under the ticker PCOR. Huge thanks to Brian @ Bessemer and Will @ Iconiq for some amazing question suggestions today.

In Today's Episode with Tooey Courtemanche:

1. The Founding of a $8.5BN Company:

How did Tooey's wife, Hilary and their house-building lead to the idea for Procore? What does Tooey know now that he wishes he had known when he started? Did Tooey always know he would be a success? What was the moment of most doubt?

2. The 13-Year Journey to $9.6M in Revenue:

Why did it take so long to hit the $10M revenue mark? What changed in 2015? What is Tooey's biggest advice to founders and investors who face market timing risk? Why was Tooey laughed out of VC offices in 2008? What are his biggest pieces of advice to founders raising from VCs today? How does Tooey advise founders on the balance between vision and sticking to a mission vs realising when it is not working and giving up?

3. The Art of Great CEOship:

What advice did Tobi @ Shopify give Tooey on being a great CEO? How did it impact his approach? What are the biggest differences between the reality of being a CEO and the Instagram version? What have been Tooey's biggest lessons on hiring? Why does hiring smart, ambitious but not humble people never work? Why does Tooey believe the idea of "becoming an entrepreneur" to be BS?

4. Parenting, Money and Marriage:

Why does Tooey believe great parenting is like great CEOship? How does one bring up children to be ambitious and humble in a very privileged upbringing? What are the secrets to being there as a husband while also being a rockstar CEO? How does Tooey reflect on his own relationship to money and wealth today?

2023-12-04
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20VC: HelloFresh CEO on Why When You Raise VC You Only Have Two Options, Why Your IPO Price is Irrelevant, Why Timing is So Important in Going Public & Why D2C is Not Dead with Dominik Richter

Dominik Richter is the Founder & CEO @ HelloFresh, one of the largest direct-to-consumer businesses of the last decade and the #1 recipe box delivery service. Fun fact, two of the three biggest cooking facilities in North America are HelloFresh facilities with the third being Disney World Orlando. Dominik has made over 40 angel investments in the EU and the US.

In Today's Episode with Dominik Richter We Discuss:

1. The Founding of One of the Largest D2C Companies:

How did Diminik's dreams of being a footballer translate to founding HelloFresh? What does he know now that he wishes he had known when he started? Why does Dominik respect the brands that large banks have built?

2. To Raise or Not to Raise:

Why does Dominik believe when you raise VC, you either have to sell or go public? What are the single biggest differences between raising in the US vs Europe? What are Dominik's biggest pieces of advice to founders raising today? Why does Dominik believe so many of the D2C companies should not have raised venture funding?

3. The IPO: When, How and Why:

Why did Dominik decide to IPO the business so early? Why does Dominik believe that the first-day trading price is irrelevant? Why does Dominik believe that timing is so important when going public? What are the biggest pros and cons of being public?

4. The Rise and Fall of D2C:

D2C has been crushed lately, why? Is this the end of D2C as a category? Is D2C an investable category for VC? HelloFresh is one of the biggest and $2.5BN market cap? What have been the best and worst resource allocations Dominik has made? Do recessions help or hurt recipe box businesses?

2023-12-01
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20Growth: The Golden Rule to $100M in ARR, Why CAC to LTV is BS Early On, Why Your First Growth Hire Should Be a Former Founder & How Ramp Does 200 Growth Experiments Per Quarter with Guillaume Cabane

Guillaume Cabane is a growth advisor to high-growth SaaS Startups, including Ramp, Spot, Airbyte, G2, Gorgias, Metadata, Madkudu, and others. Guillaume held VP of Growth roles at Drift, Segment, and other successful startups, where he helped them grow from ~50 to 300. Prior, Guillaume spent 6 years at Apple.

In Today's Episode with Guillaume Cabane We Discuss:

1. Entry into Growth:

How did Guillaume make his way into the world of growth? What are 1-2 of his biggest lessons from him time at Segment where he 4x revenue? What does Guillaume know now that he wishes he had known when he entered growth?

2. Enterprise vs SMB & CAC/LTV:

Why does Guillaume think it is harder to go enterprise down than SMB up? What are the biggest mistakes companies make when scaling into enterprise? What are the biggest mistakes startups make with product-led-growth motions? Why does Guillaume believe it is impossible to analyse CAC/LTV in early companies?

3. Activation, Engagement and KPI Setting:

What are the biggest mistakes companies and teams make in activation? What can growth and marketing teams do to guarantee engagement in prospects? Why are all KPIs not tied to revenue BS?

4. Hiring the Growth Team:

What are the core characteristics of great growth hires? How quickly does it become apparent when you have made a bad growth hire? Why do founders make the best profiles when hiring your first growth hire? What are the biggest mistakes Guillaume has made when hiring for growth?

5. Why Growth is Like Venture:

What is the secret to building a great growth portfolio? Why is it impossible to scale to $50M ARR with only one good channel? What is the right way to spread resources across channels? When is the right time to add new channels and diversify?

2023-11-29
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20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?

Keith Rabois is a General Partner @ Founders Fund, one of the world's best venture funds with a portfolio including the likes of Facebook, SpaceX, Anduril, Tesla and many more. For the last 23 years straight, Keith has either invested in or founded a $BN company. Keith is also the Co-Founder and CEO @ Openstore, the company that will buy or run your Shopify business.

Mike Shebat is the Founder and CEO @ Traba, the company providing industrial staffing when and where you need it. To date, Mike has raised $49M with Traba from some of the best including Founders Fund, General Catalyst and Khosla Ventures.

In Today's Episode We Discuss:

1. What it Takes to Build a Great:

Why does Mike expect everyone to work in office 12 hours per day, 4 days per week? At what point does an extra hour of work not lead to more output? What are the expectations in terms of emails, out of office, the weekends? Keith, from the 23 BN companies you have worked with, is this insane work ethic aligned to all of them? Which had it? What did not? What core components of PayPal's work ethic made it so strong? What does Keith mean when he says Linkedin could and should have been 5x bigger?

2. The Hiring Process for the Swat Team:

What does the hiring process look like for this type of work environment? What are the signs that someone is really aligned to it vs faking it for the interview process? What have been Keith's biggest lessons on both compensation and title in the hiring process? Why does Keith believe that culture is like concrete? What are the biggest mistakes he has made on culture and what would he have done differently?

3. First-Time Founders, Innate Entrepreneurs & Europe's Failing:

Does Keith agree the best founders always show signs of early entrepreneurship in their teens? Why does Keith prefer first-time founders to serial entrepreneurs? Why are they better? Why does Keith believe that Europe has not created a $100BN company since 1990?

4. Remote Work, Network Effects and Baseball:

Why does Keith believe being great in venture is like baseball? Why does Keith and Founders Fund not invest in remote teams? How does he explain Gitlab? Why does Keith believe Airbnb has the best network effect he has ever seen?

2023-11-27
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20VC: AI's Biggest Questions: The Commoditisation of LLMs, Open vs Closed: Who Wins, Model Size vs Data Quality, Why Google are Vulnerable and Apple are the Dark Horse

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support.

Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science. 

Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity?s potential.

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC.

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages.

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses.

Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. 

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016.

In Today's Episode We Discuss:

Foundational Models: Analysis

Will foundational models become commoditized? Who are the major players? What are their different strengths? Who will win? Who will lose? How important is the size of the model vs the quality of the data?

2. Open vs Closed:

What are the biggest pros and cons of an open ecosystem for LLMs? Why is it naive to think that open-source LLMs will prevail? What will determine which method wins?

3. An Analysis of the Incumbents:

Why is Google the most vulnerable? What can they do to regain ground? Why is Apple the sleeping giant? How could they win the next wave of AI? What should Amazon do today to compete with Microsoft?

4. The Future: Doom and Gloom?

Why is it ridiculous to assume AI systems want to dominate? Why will AI create a renaissance of creativity and human freedom? What role should regulation play in the advancement and progression of AI?

2023-11-24
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20VC: Why OpenAI Will Become an Infrastructure Play, Why Apple Will Win in an AI World, Why Google is the Most Vulnerable Incumbent, Will LLMs Be Commoditised, Which Startups Are Thin vs Thick Wrappers on Top of LLMs with Jeff Seibert, Founder @ Digits

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Jeff previously served as Twitter's Head of Consumer Product, a position he came to following the acquisition of his prior company, Crashlytics. Today, Crashlytics is the de-facto mobile crash reporting solution for iOS and Android and runs on over 6 Billion monthly active smartphones worldwide.

In Today's Episode with Jeff Seibert We Discuss:

1. The Art of the Pivot:

What are Jeff's biggest pieces of advice to founders pivoting? How do you know when you have enough data to make the decision to pivot? What are the single biggest mistakes founders make when pivoting?

2. AI: Who Wins and Who Loses:

Why does Jeff believe that OpenAI will transition into an infrastructure play? What are the most significant challenges OpenAI will face moving forward? Why does Jeff believe that Apple are best positioned to win in an AI world? Why does Jeff believe that Google are the most vulnerable incumbent? What would Jeff do if he was CEO of Google?

3. LLMs: What Happens Now:

Will we see the commoditization of LLMs? What are the biggest misconceptions people have on training and fine-tuning LLMs? Will we see LLMs increasingly specialise to vertical-specific models or will they remain horizontal? What is the difference between a thick and a thin wrapper when building on top of LLMs?

4. Angel Portfolio in Review:

How many angel checks has Jeff written? How many failed? How many home runs? Does Jeff believe that company valuations are being kept artificially high? How did Jeff make 200x selling through the secondary market for a now failing company? What are Jeff's three biggest pieces of advice for angels today?

2023-11-22
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20VC: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | What Makes Truly Great Leaders and How They Give Feedback | Do VCs Really Add Value; Lessons from Hard Fundraises with Matteo Franceschetti, Co-Founder @ Eight Sleep

Matteo Franceschetti is the Co-Founder and CEO @ Eight Sleep, a company dedicated to fueling human potential through optimal sleep. To date, Matteo has raised over $160M for the business from the likes of Founders Fund, Ryan Petersen, Naval Ravikant, Kevin Hart, AROD and many more.

In Todays Episode with Matteo Franceschetti We Discuss:

1. Why Did Sleep Need "Solving":

Why did Matteo decide he wanted to spend decades of his life-solving sleep? If Matteo has known how hard it was going to be, would he do it again? What does Matteo know now that he wishes he had known at the start of the journey?

2. Hiring the Best Team:

What is Matteo's playbook for hiring? What are the five questions that Matteo asks in every interview? What are big red flags? What are strong signals of great talent? If people have been let go in a RIFF, is that a concern? How does Matteo construct hiring panels? What vote count is enough for an approved hire? What are Matteo's biggest lessons on title and pay a new hire receives? What are some of Matteo's biggest lessons when it comes to firing people?

3. Funding the Business:

What was the hardest round to raise? Why? Are investors justified in their skepticism of hardware? What are the single biggest pieces of advice Matteo would give to founders on raising? How impactful has it been having Keith Rabois and Founders Fund as an investor? Do VCs really add value?

4. Mastering Health, Sleep and Nutrition:

How does your diet impact the quality of sleep you have? How does exercise and the time of exercise impact your sleep? What are some common rules on sleep that are BS and myths? What are some of the most non-obvious truths about getting great sleep?

2023-11-20
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20VC Will Seed Pricing Remain High | Where is the Funding Crunch? | Three Core Elements Required to Raise a Series B/C | Why AI is Like the Lottery Today | Why Now is the Best Time to be Investing in Crypto | Why Investors Do Not Want to Reprice Companies

Rebecca Kaden is a Managing Partner @ Union Square Ventures, one of the leading early-stage firms of the last decade with investments in Twitter, Twilio, Coinbase and many more.

Nicole Quinn is a General Partner @ Lightspeed where she has led investments or sits on the board of Calm, Cameo and LunchClub to name a few.

Eurie Kim is a Managing Partner @ Forerunner Ventures, the leading early-stage consumer fund. Eurie has led investments and sits on the board of Oura, The Farmers Dog, Curology and more.

In Today's Roundtable We Discuss:

1. Seed Rounds:

Is it even possible for traditional seed funds to play in a world of multi-stage funds investing so aggressively at the seed stage? Is seed immune to the macro environment? Will seed pricing remain as high as ever? What advice does the team have for seed founders approaching a Series A? What do they need?

2. Series A:

How is the Series A market looking today? Is there a crunch at the Series A? To what extent are valuations compressed at the Series A? What 3 core elements do companies at the A stage, looking for a Series B next, need to focus on?

3. Series B and Beyond:

Is the real crunch at the Series B? Why are down rounds so much better than structured rounds for companies raising? Will we see a wave of M&A in the next 12 months?

4. Crypto, AI and Hot Takes:

Why is now the best time to be investing in crypto? Why is investing in AI a lottery right now? What is the most controversial thing that each believes today?

2023-11-17
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20VC: How to Survive and Thrive in a World of OpenAI, Are LLMs Being Commoditised, Where Does the Value Lie; Infrastructure or Application Layer, How Apple Could Win in a World of AI, How Amazon Could Threaten OpenAI and Why Google Struggle with Des Trayn

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all Intercom?s R&D efforts, and parts of Intercom?s marketing.

In Today's Episode with Des We Discuss:

1. From Consultancy to Founding a Unicorn:

What was the founding a-ha moment for Des and the team with Intercom? Why does Des believe that most startup advice is BS and outdated in 5 years? What does Des know now that he wishes he had known when he started?

2. LLMs: The World is Not Equal:

What does Des mean when he says the world of LLMs is not equal? How do the different LLMs very in quality, price and speciality? Does Des agree with Alex @ Nabla, "the best companies in the future will work with many LLMs at the same time and switch between them for different things"? To what extent does Des believe LLMs will be commoditised and it will be a race to the bottom? Would Des be a buyer of OpenAI at a $90BN price? Why not?

3. How to Survive in a World of OpenAI:

What two simple questions will determine if Open AI will kill your existing business? What 3 criteria will determine if there is a new business to be built on top of OpenAI? What is the different between a thin layer on top of an LLM and a thick wrapper with real value? Which traditional incumbents are most vulnerable? What should they do in this new world? How long does it take for incumbents to really be impacted?

4. The Titans of Tech: Who Wins:

Why does Des believe that Apple could be a massive winner in the next wave of AI? Why does Des believe that Google have not been impressive and failed to keep pace? Why does Des think OpenAI should be wary of Amazon? What could they do to threaten them? What opportunity does Facebook have here? How could Instagram and Whatsapp win?

5. Startup and Investing 101:

Why does Des believe that every founder should write a blog post per week? Why does Des believe that most B2B marketing sucks? What makes great B2B marketing? What are Des' biggest lessons from the Hopin journey? How has Des' angel investing changed in the last year with the rise of AI?

2023-11-15
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20VC: Flexport's Ryan Petersen: Reflections on Leadership from 13 Years Leading Flexport, Why Velocity not Speed is Most Important in Company Building, How Money Creates Inefficiencies in Scaling, The Future of Trade with China & Why Remote Work is so Cha

Ryan Petersen is Founder & CEO @ Flexport, a leader in global supply chain technology. In 2022, Flexport moved more than $26 billion of merchandise. Over the last 10 years, Ryan has raised close to $2.5BN for the business with the latest valuation pegging the business at $8BN. Prior to starting Flexport, Ryan was the founder and CEO of ImportGenius, a premier provider of transaction data for the global trade industry.

In Today's Episode with Ryan Petersen We Discuss:

1. The Origins of a Generational Defining Leader:

What did Ryan want to be when he was growing up? How did scooters and motorbikes in China lead to the idea for Flexport? What does Ryan know now that he wishes he had known when he started Flexport?

2. Speed and Money: The Secrets To Execution:

Does Ryan believe speed is key to execution? What is the difference between speed and velocity? What advice does Ryan have to founders who raise a lot of money? How should it impact hiring? What are the most common ways founders become inefficient post-fundraising? Why does Ryan look to invest in founders with jaded pasts and a chip on their shoulder?

3. The Art of Resource Allocation:

Are the best CEOs the best resource allocators? What is the single best resource allocation Ryan has made? What did he learn? What is the worst? What did he learn? What have been Ryan's biggest hiring mistakes? How did that change his approach?

4. The Wider World:

Is Ryan long or short on China? Why? Will we see global trade become nationalized? Why? Will we see interest rates raised further? What impact does that have on trade? What has been the impact of war on trade and the shipping industry?

5. Ryan Petersen: The Father and Husband:

How has having kids changed how Ryan approaches leadership and management? How does Ryan juggle 2 young kids and leading a 2,500 person company? How does Ryan retain romance with his wife while also being a full-on CEO of a large co? Does money make you happy? What does it help with? What does it not help with?

2023-11-13
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20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Chris Degnan serves as Snowflake?s Chief Revenue Officer and has been with the company since 2013. Starting as employee #13 and Sales employee #1, Chris built a go-to-market strategy from the ground up, driving sustained high growth and global reach. Under his sales leadership, Snowflake has grown its annual product revenue from $0 to over $1 billion. Prior to Snowflake, Chris served in Sales leadership roles at EMC and Aveksa, and worked in enterprise sales at Informatica and Covalent Technologies (acquired by VMware).

In Today's Episode with Chris Degnen We Discuss:

1. From SDR To World Leading CRO:

How did Chris first make his way into the world of sales? What does he know now that he wishes he had known when he started in sales? What are the single biggest mistakes young sales people make today scaling their careers?

2. The Secret to Hitting Quota in Sales:

Why does Chris believe all reps need to do 8 customer calls per week? How do the best sales reps approach sales prospecting today? Is cold outbound dead? How does Chris advise his teams on cold calls and emails? What are the best reasons reps should say no to customers? Should reps be discounting today? What is an acceptable level?

3. Sales and Product: The Most Important Relationship:

Why does Chris believe sales and product is the most important relationship? What can leaders do to ensure sales and product communicate effectively? How does Chris use sales calls today both with his sales team and with product? What are the single biggest reasons comms between sales and product breaks?

4. Mastering Sales Leadership:

How does Chris approach sales forecasting? What works? What does not work? Does Chris celebrate when quota is hit? How do you find the balance between pushing further and harder but also celebrating the wins? How do the best sales leaders train and develop their talent? What do the worst do?

5. Customer Success is BS: Professional Services for the Win:

Why does Chris believe that customer succeed is BS and you should get rid of it? Why are professional services so much better? How should the org be structured then when removing CS and adding professional services? Who is then responsible for upsell?

2023-11-10
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20VC: From Leading the BBC to Leading Venture Capitalist, The Biggest Similarities and Differences Between the Best Founders and the Best Actors & The Future of Media; Legacy vs New, The Creator Economy, The Rise of TikTok and more with Danny Cohen

Danny Cohen is the President of Access Entertainment, a division of Len Blavatnik's Access Industries. Access Entertainment?s corporate investments include film and television studio A24; Europe?s fastest-growing company Tripledot Studios; creator economy leader Spotter; and a new immersive arts? experience launched in collaboration with David Hockney and Lightroom. Before joining Access, Danny was the Director of BBC Television where he had responsibility for all of the BBC's network channels and the greenlighting and production of the BBC's drama, entertainment, comedy, arts, history, science, educational content and documentary. 

In Today's Episode with Danny Cohen We Discuss:

1. From Leading the BBC to Investing for Len Blavatnik:

How did Danny make his way from leading the BBC to investing for Len @ Access? What was he most nervous about when making the transition to investing? What has been the hardest investing skill to learn?

2. Great Founders are Like Great Actors:

What are the biggest similarities in what makes the best founders and the best actors? How are the best founders different from the best actors? Why does Danny believe the risk that an actor takes is so different to the risk founders take? How does Danny feel both founders and actors can and should be managed?

3. The Future of Media:

What does Danny mean when he says he looks for "eyeballs and attention" when investing? How does legacy media respond to the threat created by social media today? How does AI change the future of content creation and distribution today? How do the strikes in Hollywood impact the future of content supply?

4. Marriage, Children and Loneliness:

Why does Danny believe that loneliness will continue to be the biggest problem we face? What are Danny's biggest pieces of advice from 17 years of happy marriage? Why did Danny decide to not have children? What did that decision-making process look like?

2023-11-08
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20VC: From $4.1BN to $142M Market Cap; Why Public Markets Have Written Allbirds Off, What Allbirds Need to Do to Get Profitable, Why Growth has Slowed and The Bull Case for Allbirds Next Five Years with Joey Zwillinger, Co-Founder @ Allbirds

Joey Zwillinger is the Co-Founder & CEO @ Allbirds, the company behind the world's most comfortable shoe. In Nov 2021, Joey took the company public and the stock soared to an all-time high of $4BN, today the company has a market cap of $137M. Prior to Allbirds, Joey spent six years at biotechnology firm, Terravia, leading its renewable chemical business, developing and selling high-performance algae-based chemicals into various industries such as CPG, personal care, and industrials.

In Today's Episode with Joey Zwillinger We Discuss:

The Founding Moment:

How did Joey's wife's friendship lead to the co-founding of Allbirds? What does Joey know now that he wishes he had known at the founding moment? What does Joey believe he is running away from? What is he running towards?

2. Public Market Performance Review:

Why has Allbirds lost 97% of it's value since going public? What mistakes were made? Why has revenue declined for the first time this year? What strategic investments have Allbirds pulled back on or paused entirely? When will Allbirds be profitable?

3. The Competition:

How do Allbirds compete and catch up with On and Hoka? What strategic mistakes did Allbirds make in COVID that allowed others to take the crown? Was the movement into running and athletics a mistake for Allbirds?

4. Joey Zwillinger: The Leader and Person:

Did Joey take secondaries out during the Allbirds journey? How does Joey reflect on his own relationship to money? How has Joey dealt with the last 12 months personally? How does he manage the stress effectively?

2023-11-06
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20VC Roundtable: Why Early Stage Founders Should Not be Investing, Why Great Founders Have Low EQ, How the Structure of VC Firms Will Change, Will Founder-Led Funds Compete with Sequoia & Is Investing a Team Sport?

Jack Altman is the Founder and CEO @ Lattice, the #1 people management platform, last valued at $3BN. Jack is an investor through his founding of Jack Altman Capital where he has invested in WorkOS, NexHealth, Owner.com, Mercury and more.

Auren Hoffman is the Founder and CEO @ Safegraph, the most accurate database of global points of interest, last valued at $550M. Auren is an investor through his founding of Flex Capital where he has invested in Chime, Checkr, Coinbase, Flexport, Vercel and more.

Jason Lemkin is the Founder and CEO @ SaaStr, the world's largest SaaS community. Jason is an investor through his founding of The SaaStr Fund. In the past, Jason has invested in Pipedrive, Algolia, Salesloft, Front, GreenHouse, Owner.com, Gorgias and more.

In Today's Episode on Founder-Led Funds We Discuss:

Why have we seen the rise of "Founder-led Funds"? Are founder-led funds more empathetic to the founders they invest in? How do founder-led funds source and pick investments in a way that traditional VC does not? Will we see founder-led Funds truly compete against the Sequoias of the world? How does being an operator make you a better investor? How does investing help you be a better founder and operator? How do you communicate your investing practice and firm to your company and team? What are the biggest excitements and concerns LPs have for Founder-led Funds? Will we see the face of venture changing much more broadly and structurally? How do founder-led funds manage both time and company conflicts?

2023-11-03
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