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

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











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Now displaying: 2024
Apr 15, 2024

Sam Altman is the CEO @ OpenAI, the company on a mission is to ensure that artificial general intelligence benefits all of humanity. OpenAI is one of the fastest-scaling companies in history with a valuation of $90BN and $2BN+ in revenue. Prior to OpenAI, Sam was the President and CEO @ Y Combinator and made angel investments in the likes of Airbnb, Stripe, Reddit, Pinterest, Asana and more.

Brad Lightcap is the COO @ OpenAI and the man responsible for the incredible scaling of sales, GTM, partnerships and business to today being over $2BN in revenue. Before OpenAI, Brad was an investor at Y Combinator, where he met Sam and before that led finance and operations initiatives at Dropbox.

In Today's Episode with Sam Altman and Brad Lightcap We Discuss:

1. The Partnership: The Most Powerful Double Act in Tech:

  • How did 25 people rejecting OpenAI's CFO positions 6 years ago, lead to Brad joining OpenAI before Sam even did? What did he see that the world did not?
  • What does Brad think is Sam's biggest superpower that the world does not know? What does Sam think it Brad's biggest superpower that the world does not now?
  • How do decisions get made between Brad and Sam? How do they decide what to delegate vs what not to? What is the most recent disagreement they had? How did they resolve it?

2. The Next 12 Months for OpenAI: Bottlenecks, Compute and Commoditisation:

  • What are the core bottlenecks facing OpenAI in the next 12 months?
  • How does Sam believe we solve the fundamental problem of compute?
  • What is the single biggest barrier to the quality of models improving?
  • What is the end state for the model landscape? Will models become commoditised?

3. OpenAI: The Fastest Scaling Company in History:

  • What has been the secret to how OpenAI has scaled to $2BN in revenue in 24 months?
  • Why does Sam believe that he is "not a great operator"? What drives this thinking?
  • What have been the first things to break in the scaling of OpenAI?
  • What do Brad and Sam know now about the scaling that they wish they had known at the start?
  • Why does OpenAI lean towards hiring more experienced people in the team?

4. How to Invest and Operate in a World of OpenAI:

  • What single question can founders ask that will reveal if they will be steamrolled by OpenAI?
  • Does Sam believe huge numbers of companies will be steamrolled by OpenAI?
  • For investors, is there money to be made investing in the application layer of AI today?
  • What question should all businesses be asking about how to adopt and use AI in their business?

5. Sam Altman: AMA:

  • What have been the single biggest lessons Sam has learned from the founders he has invested in?
  • Which founders has he learned the most from? What did he learn from each?
  • What is Sam most concerned about in the world today? Why what?
  • What unexpected traits or characteristics does Sam most look for in the founders he invests in?
  • Why does Sam say that he is not happy but he is grateful?



Apr 12, 2024

Sam Blond is the former CRO at Brex, where he led the company from near $0-$400M in ARR and a $12.5B valuation. Before Brex, Sam was VP of Sales at Zenefits, where he led the company from $0-$70M ARR in 2 years and a $4.5B valuation. Sam joined Founders Fund as a Partner in 2022 and recently left to focus more on operating.

In Today's Episode with Sam Blond We Discuss:

1. Lessons From Scaling Brex to $400M ARR & Zenefits to $70M ARR:

  • What are the secrets that very few people know, that led to the success of Brex and Zenefits?
  • What was the single worst sales investment Brex made? What was the best?
  • What are Sam's biggest tips to people picking the rocketship they will join?

2. Who, What and When to Hire:

  • When is the right time to hire your first sales rep?
  • Should the founder be the one to create the sales playbook?
  • What is the right profile for the first sales hire?
  • Does it matter if the new hire has domain experience?
  • Why does Sam always advocate to hire through network and not recruiters?

3. How to Hire the Best Sales Reps:

  • What are the questions Sam always asks in interviews with sales hires?
  • Does Sam do case studies with candidates? What is he looking for?
  • What are the biggest green and red flags a candidate can show in an interview process?
  • What are the biggest mistakes founders make when hiring sales teams?

4. How to Have the Best Performing Sales Team:

  • What are the three ways to measure the success of a rep in the first 30-60 days?
  • Why does Sam believe most startups are doing outbound wrong? What should they change?
  • Why does Sam believe demand gen is the bottleneck for all companies?
  • What can be done to solve the demand gen challenge?
  • How does outbound change in a world of AI?

Apr 10, 2024

Kevin Ryan is one of the leading serial entrepreneurs and investors in New York. Previously he co-founded MongoDB, Business Insider, Gilt Groupe, Zola, Nomad Health, Pearl Health, and was the CEO of DoubleClick (Acquired by Google for $3.1B). Today, Kevin is the founder and CEO of AlleyCorp, a venture capital firm that incubates and invests in transformative companies in healthcare, diversified tech, robotics, and impact. Just yesterday, Alleycorp announced their $250M fund, their first ever external capital. 

In Today’s Episode with Kevin Ryan We Discuss:

  1. Early Signs of Entrepreneurship

  • How did Kevin’s early life shape his career? How would his parents and teachers describe him?

  • Does Kevin agree that successful entrepreneurs always show signs early?

  • What does Kevin think about luck vs. skill? Why does Kevin think that most things are out of your control as an entrepreneur?

  1. Lessons from Founding 10+ Companies Worth $27BN

  • Does Kevin agree the best CEOs are also the best fundraisers?

  • What were Kevin’s biggest lessons from scaling DoubleClick from 20 to 2000 employees?

  • What was Kevin’s a-ha moment behind Business Insider? What was the reason behind its success?

  • Why does Kevin believe the best founders are always in unfamiliar fields?

  1. Incubating World’s Best Companies

  • How does Kevin allocate resources between incubations vs. investments?

  • What are the biggest commonalities between successful companies at AlleyCorp?

  • Is Kevin a market-led or people-led investor?

  • What does Kevin think is the most important element in achieving product-market fit?

  • What was Kevin’s biggest miss on selecting founders? What were his takeaways?

  1. Current State of Venture

  • Why does Kevin believe venture is more competitive now than ever before?

  • What does Kevin know now that wish he’d known when he started investing?

  • Does Kevin agree rich investors make better investors?

  • Why does Kevin not care about ownership?

  • Does Kevin agree with Doug Leone that venture has transitioned from a high boutique margin industry to a low margin commoditised industry?

  • Does Kevin agree with Peter Fenton that price is a mental trap?


Apr 8, 2024

Basti Lehmann is the co-founder and former CEO of Postmates, the on-demand delivery service that raised over $900M from the likes of Tiger Global, Founders Fund, Spark Capital and Andreesen Horowitz. Following Uber’s $2.65BN acquisition in 2020, Basti founded TipTop, a platform for fast tech sales which Marc Andreesen led the $20M seed round for.

In Today’s Episode with Basti Lehmann We Discuss:

  1. From US Immigrant to Billion Dollar Founder

  • How did Basti start his career hacking AT&T?

  • How did early hardships shape Basti’s work ethic?

  • What were Basti’s biggest challenges building Postmates?

  1. Lessons from Raising $900M

  • How did Basti raise $20M from Marc Andreesen?

  • How does Basti select which VCs to work with?

  • Why does Basti think 99% of VCs are sheep?

  • Why does Basti think great VCs add no value?

  • Why does Basti think having to educate investors is a massive red flag?

  1. Selling Postmates for $2.65BN

  • Why did Basti sell Postmates to Uber? How did the acquisition happen?

  • Was there anything Basti would have done differently?

  • What does Basti think makes Dara Khosrowshahi a great CEO?

  • What is Basti’s biggest advice to founders on acquisitions?

  1. Future of AI: Startups or Incumbents?

  • What does Basti think is the biggest challenge of LLMs today?

  • Why does Basti think inference computing will be the future of AI?

  • Why does Basti think incumbents can be replaced?

  • Why does Basti think the biggest companies are being born today?


Apr 5, 2024

Mario Schlosser is the Co-Founder and Chief Technology Officer at Oscar Health. The public company that went public with a market cap of $7.1BN. Following a tumultuous time in the markets, their stock price dropped 94%. Today, the company has rebounded and has a market cap of $3.2BN with an astonishing $5.8BN of revenues. Before co-founding Oscar, Mario also co-founded the largest social gaming company in Latin America.

In Today's Episode with Mario Schlosser We Discuss:

1. From German Middle-Class to Public Company Founder:

  • How did Mario make his way into the world of tech and come to co-found Oscar with Josh Kushner?
  • Does Mario agree with Jensen Huang that "we should all have lower expectations"?
  • What does Mario know now that he wishes he had known when he started Oscar?

2. Why Did Oscar Tank 94% in the Public Markets:

  • What was the core reason why Oscar tanked 94% in the markets?
  • What would Mario have done differently knowing all he knows now about public markets?
  • Does Mario regret going public? What are the biggest pros and cons?

3. The Mental Challenge of a 94% Market Cap Decline:

  • How did Mario mentally deal with the company being down 94%?
  • What does he say to himself in the truly hard times?
  • How did Mario use his co-founder, a coach and his family, to get through the really bad times?
  • What are Mario's experiences like with anti-depressants? What worked? What did not?

4. Firing Yourself as CEO:

  • Why did Mario decide to step aside as CEO? What was the decision-making process?
  • On reflection, does Mario think he was a good CEO? Where was he good? Where was he bad?
  • What are the biggest management pieces of advice that Mario thinks are BS?

Apr 3, 2024

Trae Stephens is a Partner at Founders Fund, one of the world's leading funds where he has worked with some of the best and backed the likes of Palmer Luckey with Oculus and Ryan Peterson @ Flexport since the very early days. Trae is also Co-founder and Executive Chairman of Anduril Industries, a defense technology company focused on autonomous systems, and Co-founder of Sol, a next-generation wearable e-reader. Previously, Trae was an early employee at Palantir Technologies, where he was also an integral part of the product team, leading the design and strategy for new product offerings.

In Today's Episode with Trae Stephens We Discuss:

1. From Hustling into Georgetown to Peter Thiel Ushering You into VC:

  • What is Trae's story of how he got into Georgetown University, despite being rejected the first time?
  • How did Trae make his way into the world of VC? How did Peter Thiel recruit him to Founders Fund?
  • What advice did Brian Singerman give Trae in his first week in VC? Why is it so important?

2. How the Best Venture Firm in the World Invests:

  • Decision-Making Process: Why do Founders Fund not have partner meetings? What is the investment decision-making process? Why does more process lead to mediocre outcomes?
  • Competitive Deals: Why does Trae believe the most competitive deals are always the worst? What do Founders Fund do to specifically avoid the "herd mentality"?
  • Upside Maximisation: Why does no one at Founders Fund care about "downside protection"? How do the team approach scenario planning and upside maximisation?

3. Do VCs Really Add Value:

  • Why does Trae think putting VCs on a board for "value add" is total BS?
  • Are there any cases in which Trae believes the VC can really move the needle for a company?
  • Why does Trae believe venture would be better if it were just operator investors?
  • Why does Trae believe platform approaches to VC value add is BS?

4. The Future of VC: Who and How to Win:

  • How did being an operator at the same time as investing, make Trae a better investor?
  • Why does Trae believe that vertical investing is BS and generalised is better?
  • How does Trae favour; market, product and people? Will Trae back a founder when he hates the idea?
  • What have been Trae's biggest lessons from his biggest hits and biggest misses in 10 years?

Mar 29, 2024

Billy Hult is Chief Executive Officer of Tradeweb Markets (Nasdaq: TW), as Billy puts it, they are the "electronic interface that connects Citadel and Goldman". They are also one of the most under the radar but incredible businesses of the last 20 years. Through no glitz acquisitions or specific moments, TradeWeb has compounded organic growth for the last 27 years to today, with a market cap of $22BN.

In Today's Episode with Billy Hult:

1. From Betting Shop Worker to Public Company CEO:

  • How would Billy's teachers and parents have described the young Billy?
  • Why does Billy think it is so important to have a hard first job when growing up?
  • What does Billy know now that he wishes he had known when he started?

2. What it Takes to be a World-Leading CEO:

  • How does Billy define the role of the CEO? What are the core tenets?
  • What has been the single hardest element of CEOship to learn?
  • Does Billy care about being liked? How does that impact his management style?
  • Why does Billy think it is so important for CEOs to make "big bets"? What have been his biggest?

3. Hiring World-Class Teams in 2024:

  • What have been some of Billy's biggest hiring mistakes? What did he learn from them?
  • How does Billy weigh IQ vs EQ and hustle? Which wins? Why?
  • Does Billy think this generation of millennials is too soft?
  • What are the single biggest lessons Billy has on when to delegate vs when to retain control?

4. Money, Power and Family:

  • How does Billy approach his relationship to money today? How has it changed over time?
  • Fame, power or money, rank them from 1-3. How does Billy rank them?
  • How does Billy describe his own style of parenting? How has it changed over time?

Mar 27, 2024

Chris Dixon is a General Partner at Andreessen Horowitz, one of the leading venture firms of the last decade with investments in Oculus (acquired by Facebook), Coinbase, and many more. Chris also founded and leads a16z crypto, a division of the firm that he has grown from $300 million in 2018 to more than $7 billion of committed capital. Due to his many successes, Chris was named #1 on the Forbes Midas List in 2022.

In Today’s Episode with Chris Dixon We Discuss:

  1. From Founder to Leading GP in Venture:

  • How did Chris make his way into the world of venture and startups?
  • When did he realize investing was his calling?
  • How did Chris Dixon come to co-found Founder Collective with Dave Frankel and Eric Paley?

  1. Lessons from 12 years Investing:

  • What are Chris’ biggest lessons from working with Marc Andreesen and Ben Horowitz?
  • Does Chris agree with Doug Leone, “venture has transitioned from a boutique high margin business to a low margin commoditised industry”?
  • What are the two ways to win in venture? 
  • Does Chris agree the best founders don’t need their VCs?
  • What is Chris’ biggest investing miss? How did it impact his mindset?

  1. Are Incumbents Too Big To Be Replaced:

  • What is the biggest problem with open-source internet today?
  • Does Chris think incumbents can be replaced?
  • Why does Chris think AI will strengthen incumbents?
  • Does Chris think OpenAI should be open-sourced?

  1. Biggest Challenges in Crypto:

  • What is the biggest misconception of crypto today?
  • Does Chris think speculation is bad for crypto?
  • What would Chris most like to change in the world of crypto?
  • How does Chris think Trump will affect crypto?

Mar 25, 2024

David Clark is the CIO of Vencap, one of the leading fund of funds in the venture landscape. David has been at Vencap for 32 years and has been an LP his entire career.

In Today's Episode with David Clark We Discuss:

1. From Unemployed Student in Love to Leading LP:

  • How did a girlfriend lead to David taking his first steps into the world of fund investing?
  • What does David know now about fund investing that he wishes he had known when he started?

2. Is Being an LP Harder than Ever Before:

  • Does David agree with Doug Leone, "venture has transitioned from a boutique high margin business to a low margin commoditised industry"?
  • Does David agree with Ryan Akinna @ MIT, "it is harder than ever to be an LP"?
  • Does David think that venture returns will worsen in the coming years?
  • Has the denominator effect for LPs gone? Do LPs have liquidity today?

3. What Makes the Best Performing Funds:

  • What are the single biggest commonalities in managers that did a 3x net DPI fund?
  • Of managers with a 3x net fund, how many had a single company return the fund?
  • How do the best firms do generational transition?
  • How do the best firms take cash off the table and sell part or all of their position?

4. Five Things LPs Hate In Potential VC Investments:

  • What are the two most common reasons David will turn down a manager?
  • How does David feel about the varying fee and carry levels?
  • How does David feel about the compression of deployment times of funds?
  • How does David feel about managers increasing fund size so significantly on every cycle?

5. Fund Sizes, Exits and Concentrating Returns:

  • Why does David believe exit sizes will increase and fund sizes could be even larger?
  • Why does David think that despite the above, the concentration of returns will be even smaller?
  • Is David concerned by the IPO window being largely shut and the increased regulation on M&A?

Mar 22, 2024

Bryan Johnson is the founder of Blueprint, the man is at war with death and is mastering longevity. Bryan is on a mission aimed at enhancing human intelligence and being respected by people in the 25th century. Before starting Blueprint, Bryan also founded Braintree (acquired by PayPal for $800M) and OS Fund – a $100M venture capital fund investing in genomics, synthetic biology, and complex systems.

In Today’s Episode with Bryan Johnson We Discuss:

  1. The Philosophy of Don’t Die

  • What does Bryan think is the biggest existential threat to humankind?

  • Why does Bryan believe humans are unfit to manage their own affairs?

  • Why does Bryan care about being liked by the 25th century?

  • Does Bryan think society is ready to adapt to immortality?

  1. How to Process New Ideas

  • What 3 questions does Bryan ask to test new ideas?

  • How does Bryan combat against his own biases?

  • How does Bryan adapt to change? What has been his most painful experience?

  • Why does Bryan think religion is humanity’s most durable technology?

  1. The Most Measured Human in the World

  • What did Bryan learn about himself as the most measured human in the world?

  • How does Bryan use algorithms to take care of himself?

  • What has been Bryan’s most expensive test?

  • How did Bryan use data to rejuvenate his sexual function?

  • How will tech & AI play a role in human longevity?

  1. Health & Parenting Advice

  • How does Bryan raise his children? 

  • How does Bryan get perfect sleep every night? What are his tips?

  • What is Bryan’s advice to people who think it’s too late to start becoming healthy?

  • What health advice does Bryan think is BS?


Mar 20, 2024

Jean-Michel Lemieux is one of the OGs of engineering and product having been the CTO at Shopify and the VP Engineering at Atlassian. Jean-Michel helped grow both Shopify and Atlassian from single-product to multi-product companies and led the building of their platforms. 

In Today’s Episode with Jean-Michel Lemieux We Discuss:

  1. From band class to Shopify CTO

  • How did Jean-Michel make his way into the world of product?

  • What were Jean-Michel’s biggest lessons from his time at Atlassian & Shopify?

  • How are Shopify & Atlassian the same? How are they different?

  • Why does Jean-Michel think Shopify could have been 10x bigger?

  1. Building the Perfect Product

  • How does Atlassian & Shopify build movements instead of product?

  • What does Jean-Michel know now that he wishes he had known before he joined Atlassian & Shopify?

  • How does Jean-Michel balance between shipping speed vs. quality?

  • Why does JM think scrums and TDDs are BS? How did his last year at Shopify change his approach in product development?

  • What is a time horizon friction? And how does it impact teams?

  1. How to Lead a Product Team:

  • What is micro alignment, and why does Jean-Michel think it is so important?

  • What 3 types of decisions every team makes?

  • What does Jean-Michel think are the most common reasons teams become average? How does he prevent it?

  • What do Jean-Michel think are the most common mistakes CEOs make today?

  1. Hiring the Best Product Team:

  • How does Jean-Michel structure the interview process for new product hires?

  • What signals does Jean-Michel look out for when hiring? Why does he believe experience does not matter?

  • What are Jean-Michel’s biggest hiring mistakes? What were his lessons?

  • What are 2 of the most common mistakes founders make when hiring a product team?


Mar 18, 2024

Gili Raanan is the Founder of Cyberstarts and one of the most successful seed investors ever. In his 19 company portfolio, Gili has invested in a decacorn (Wiz), seven unicorns and had three others acquired. Prior to Cyberstarts, Gili spent over 15 years as a General Partner @ Sequoia Capital investing in some of the world's best cyber security companies.

In Today's Episode with Gili Raanan We Discuss:

1. From Founder to World's Best Seed Investor:

  • How did Gili make the move into the world of venture with Sequoia?
  • How did Mike Moritz and Doug Leone recruit him? What was that process like?
  • What are 1-2 of Gili's biggest takeaways from working with Doug and Mike?

2. How to Find and Pick the Best Founders:

  • What did Mike Moritz teach Gili about getting to know founders?
  • Why does Gili look for the pain in the eyes of the founder? What questions does he ask?
  • What are the most common signals of truly exceptional founders, having backed 7 unicorns?
  • Why does Gili believe that both market and product is BS? Why are the founders all that matters?
  • Why does Gili believe that the founder does not have to be a domain expert in a market to create a massive company in that market?

3. What it Takes to be the Best Seed Investor:

  • Why does Gili believe that the best seed investors do not have theses?
  • How important does Gili feel the brand of the VC firm is? What were his biggest lessons on brand from spending 15 years as a General Partner @ Sequoia?
  • Why does Gili believe that the best investors are never happy? When you are happy, you lose.

4. 2021 is Back: Pricing, Uprounds and more

  • Why does Gili believe that the best companies are always expensive and will always be expensive at every round?
  • Why does Gili believe that 2021 pricing and funding is back?
  • Is this a good thing? How does Gili advise founders on how much to raise and what valuation to set with investors?
  • What does Gili believe are the single biggest sins from the zero interest rate environment?

Mar 15, 2024

Luca Ferrari is Co-Founder and CEO of Bending Spoons, one of the most incredible but untold success stories in startups. Luca has scaled Bending Spoons to 100M monthly active users, $380M in sales in 2023 and aiming to reach $500M in EBITDA by the end of 2026. The company’s products include Evernote, Meetup, Remini, and Splice and their products have now been downloaded more than 500M times.

In Today’s Episode with Luca Ferrari We Discuss:

  1. From McKinsey Associate to $2BN Founder

  • What was Luca like as a child? How would his parents have described him?
  • Why did Luca share his McKinsey salary with his co-founders?
  • What were Luca’s biggest lessons from his failed startup?

  1. Bootstrapping Bending Spoons 

  • Why did Luca decide to bootstrap Bending Spoons?
  • What does Luca think about the EU vs. US startup environment?
  • Why did Luca kill a $7M project? What were his lessons?
  • How did Luca pick his investors?

  1. How to Find the Best Talent

  • What are the 3 key traits Luca looks for when picking the best talent?
  • Why does Luca think traditional interview strategies do not work?
  • What tests does Luca conduct for each candidate?
  • What were Luca’s biggest hiring mistakes?

  1. Mastering Acquisition & Growth

  • How does Luca determine which products to acquire? How does he identify signals?
  • How does Luca approach pricing assets? How does he win every bid?
  • What are Luca’s biggest lessons from acquiring Evernote?
  • What key lessons on risk management does Luca wish he’d known 10 years ago?
  • What are Luca’s biggest challenges on user acquisition?

Mar 13, 2024

Chandra Narayanan is one of the growth and analytics OGs having spent 7 years at Facebook leading analytics for the Facebook App and for Instagram. After Facebook, Chandra became Chief Data Scientist @ Sequoia Capital, helping Sequoia, find, select and help the best entrepreneurs in the world. Today, Chandra is the Founder & CEO @ Sundial, building products to help builders make meaningful use of data to fulfill *their* mission.

In Today's Episode with Chandra Narayanan

1. From Working on the Weather to Leading Analytics at Facebook:

  • How did Chandra make his way from analyzing weather patterns to leading analytics for Facebook?
  • What does Chandra know now that he wishes he had known when he started his career in growth?
  • How did one piece of advice from his manager at Paypal change Chandra's mind forever on "quitting" and when to "quit"?

2. Growth and Analytics 101:

  • What does growth mean to Chandra? What is it? What is it not?
  • When is the right time to hire a growth team/person?
  • What is the right profile for the first growth hires?

3. How to Hire the Best Growth Teams in the World:

  • What are the must-ask questions when hiring for growth?
  • How does Chandra use case studies to determine the quality of a candidate?
  • What does Chandra believe are the four main reasons people go to work?
  • What are the three different types of execs in tech? How do you know when you need each one?

4. Lessons from Leading Analytics at Facebook and Sequoia:

  • What are 1-2 of Chandra's biggest takeaways from leading analytics at Facebook?
  • What does Chandra believe are the two core skills needed to do analytics well?
  • How can you easily test if someone is good at analytics?
  • How did being Chief Data Scientist @ Sequoia change Chandra's perspective on growth?

Mar 11, 2024

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?
Mar 8, 2024

Brendon Cassidy is one of the OG of enterprise sales of the last decade, having advised the likes of, 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?

Mar 6, 2024

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?

Mar 4, 2024

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?

Mar 1, 2024

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, 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

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?

Feb 28, 2024

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?

Feb 26, 2024

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?

Feb 21, 2024

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

In Today's Episode with Scott Williamson We Discuss: 

1. From Sales to Product Leader:

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

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

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

3. Hiring the Best Product People:

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

4. The Best Product Teams are the Best Writers:

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

Feb 19, 2024

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

In Today's Episode with Roger Ehrenberg We Discuss:

1. The Commoditisation of Venture and Worsening Returns:

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

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

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

3. Where Does the Liquidity Come From:

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

4. When to Sell and When to Hold:

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

5. Relationship to Money:

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

6. The Secrets to Parenthood and Marriage:

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

Feb 16, 2024

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

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

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

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

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

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

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

3. Scaling into Europe's Next Decacorn:

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

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

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

Feb 14, 2024

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

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

1. From No Idea to Growth Leader:

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

2. Growth: What, When and Who:

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

3. Mastering PLG and Enterprise:

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

4. Data vs Intuition: Art vs Science:

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

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