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

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.

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?

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.

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?

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?

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.

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?

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?

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.

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?

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.

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?

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.

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?

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.

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?

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.

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?