Sarah Tavel is a General Partner @ Benchmark, one of the most successful and renowned venture firms in the world. At Benchmark, Sarah has led rounds in Chainalysis, Hipcamp, Medely, Rekki, Glide, Cambly and more. Prior to Benchmark, Sarah was a Partner at Greylock Partners. Before Greylock, Sarah was the first 30 employees at Pinterest. Sarah joined Pinterest in 2012 after co-leading the Series A investment while at Bessemer Venture Partners.

In Today's Episode with Sarah Tavel We Discuss:

1. Becoming a GP at The Most Renowned Firm in Venture:

• How did the process of Sarah joining Benchmark start? How did it progress? What was it that convinced her to leave Greylock and join Benchmark?
• What does Sarah believe makes Peter Fenton the world-class investor that he is?
• What does Sarah know now that she wishes she had known when she started in venture?

2. Foundation Models: Is it All Going to Zero:

• Will foundation models be commoditised?
• Will 99% of the funding going to foundation models go to 0?
• How does Sarah view the future of open vs closed source?
• Why does Sarah believe that all frontier models of the future will be closed-source?
• Why does the business model of foundation models remind Sarah of the food delivery business?

3. Application Layer: Where $BN Companies Will Be Built:

• Why does Sarah believe that sustainable value-creating companies will be in the application layer?
• How does Sarah determine between a wrapper on top of ChatGPT and true product value?
• Are enterprises opening real budgets for AI today or are we still in experimental budgets?
• How does Sarah think about how AI companies differentiate when there are so many in the same space of customer service, sales team support etc etc?
• Why does Sarah believe that it is rational to pay more for these companies when investing in them?
• What does Sarah mean when she says the future is "selling the work and not the tools"?

4. Inside Benchmark: How the Best Do Venture:

• What is the one rule that Benchmark is willing to break when doing a deal?
• Why do Benchmark aim to be the best recruitment firm in the world?
• Why do Benchmark not agree with the concept of reserves?
• In a case where Benchmark have lost, why did they lose? How did they change their approach?

Eric Glyman is the Co-Founder and CEO of Ramp, America's fastest growing corporate card and finance automation platform. Under Eric’s leadership, Ramp has raised more than $1 billion in financing, with a valuation of $8.1 billion. Prior to Ramp, Eric co-founded Paribus, a price-tracking app to help consumers save money (acquired by Capital One). Ramp recently raised another $150 million series D round co-led by Founders Fund and Khosla ventures, with a post-money valuation of $7.65 billion.

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. Prior to Khosla Ventures, Keith was General Partner at Founders Fund, where he led investments for Ramp, Trade Republic, and Aven. 

In Today’s Episode with Eric Glyman and Keith Rabois We Discuss:

1. Behind Ramp’s Partnership with Founders Fund & Khosla Ventures

• How did the first Founders Fund deal come to be? How was the first meeting?

• What does Keith mean when he says Ramp has the “secret sauce” to be successful?

• What are 1-2 things Keith thinks Eric is world-class at? What are 1-2 things Eric thinks Keith is world-class at?

• How did the latest Khosla deal come to happen?

2. Ramp: The Fastest Executing Company on the Planet.

• How is Eric so good at executing at Ramp? What is his biggest advice to founders on speed of execution?

• What are Eric’s biggest challenges in the next 12 months at Ramp?

• Why does Keith believe momentum is crucial for early stage startups? What are some easy ways founders can build momentum?

• How does Eric think AI will accelerate Ramp and the world of finance?

3. Leadership Lessons From the Best Founders 

• What are Keith’s biggest lessons from Brian Chesky @ Airbnb?

• What did Keith learn from Jack Dorsey @ Square about leadership?

• What does Eric think founders today should build? What should they not build?

• What did Eric learn from Keith on how founders should measure time & progress?

4. Hiring & Team Management

• How did Ramp build a solid talent team? What did they do differently?

• Does Keith & Eric believe it is better to hire externally or promote internally? What is the right balance?

• Does Keith agree founders should hire & get out the way or micromanage?

• How many direct reports does Keith think is enough?

Mark Suster is a General Partner @ Upfront Ventures, one of LA's leading early-stage venture firms. Prior to leading Upfront, Mark was a serial entrepreneur having founded two software companies, selling both with the last selling to Salesforce.com. Mark is also a prolific writer and one of his favourite pieces, Lines Not Dots is one for the ages.

In Today's Episode With Mark Suster We Discuss:

1. From Serial Entrepreneur to Leading VC:

• How Mark made his way into the world of venture having sold two prior companies?
• What does Mark know now that he wishes he had known when he started in venture?
• What advice does Mark give to all young investors starting their career today?

2. How to Raise a Fund:

• What are Mark's single biggest lessons from 15 years of fundraising for funds?
• Should managers look to institutions or friends and family first?
• Are LPs sheep? Do institutions anchoring funds lead to many others jumping in?
• What is the right amount to do a first close on? What is the right way to message the first close?
• What are the single biggest mistakes Mark sees managers make when raising?

3. Exit Environments are F******: What Now:

• Why are IPOs not the liquidity events that everyone thinks they are?
• When does Mark believe IPO windows will open again?
• How does Mark evaluate the M&A landscape today?
• With little M&A and IPO activity, why does Mark believe private equity will step into their shoes?
• With the change to private equity being the buyer, what does that mean for the sale price of the assets? What does that mean for the future of venture returns?

4. Trump, The Woke Left and The World Around Us:

• Is Mark concerned about the potential of Trump winning the election?
• Would Mark rather a Biden administration as the alternative?
• Why is Mark so worried by the woke left?
• Does Mark always believe there has been this deep-seated anti-semitism in the US education system? What can be done to remove this from our education system?

Arthur Mensch is the Co-Founder and CEO of Mistral AI. Since its inception in May 2023, Mistral has raised over $520M in funding from investors like Andreeseen Horowitz, General Catalyst, Lightspeed Venture Partners, and Microsoft with a current valuation of $2 billion. Before founding Mistral, Arthur was a research scientist at DeepMind, one of the leading AI institutions in the world.

In Today’s Episode with Arthur Mensch We Discuss:

1. From Models to Team Building: Arthur’s Greatest Lessons at DeepMind

• What were Arthur’s biggest lessons from his time at DeepMind?

• How did DeepMind shape how Arthur built Mistral?

• Why does Arthur believe smaller teams are better for AI?

• Why did Arthur decide to leave DeepMind and start Mistral?

2. Scaling Mistral to $2 Billion Valuation Within a Year

• What made Mistral 7B so successful? What did Arthur learn from the model release?

• What are the biggest barriers at Mistral today?

• How does Arthur balance the sales and research teams at Mistral?

• What does Arthur know now that he wishes he had known when he started Mistral?

3. How to Win in AI: Open Source, Cost, & Adoption

• Why did Arthur open-source some models? Why did he close some?

• How quickly will the cost of compute go down? Why does Arthur believe marginal costs will not go to zero?

• How will open-sourcing LLMs affect the marginal cost?

• Does Arthur think open source is ready for enterprise adoption?

• What questions should enterprises be asking about AI adoption today?

• What are the biggest challenges to AI adoption today?

4. The Future of LLMs

• What does Arthur think are the largest bottlenecks of model quality today?

• Does Arthur think future models will be more generalized or vertical-focused?

• What does Arthur think about the future of commoditization in models?

• Why is Arthur optimistic about the profitability of the application layer of AI?

• How should models differentiate themselves today?

Adam Gross is one of the masters of product-led growth (PLG). Most recently, Adam was Vimeo's interim CEO. Before Vimeo, Adam was CEO of Heroku, which he joined after selling his startup, Cloudconnect in 2013. Additionally, Adam has held executive leadership roles at Salesforce and Dropbox, and has been an active angel investor & advisor to companies, including Buildkite, Cribl, and Tailscale.

In Today’s Episode with Adam Gross We Discuss:

1. PLG Tactics from Dropbox, Heroku and Salesforce:

• What were Adam’s biggest takeaways from his time at Salesforce? How did it shape his growth mindset?

• What did Adam learn about customer acquisition at Dropbox?

• What would Adam most like to change about growth today?

2. Product-Led Growth: The Fundamentals:

• What is growth? What is it not? What do founders get wrong about growth?

• Why does Adam think PLG is not for everybody?

• What do most great PLG businesses have in common?

• How are value propositions segmented in PLG? How can startups transition from individual to enterprise clients?

• Why does Adam think startups doing paid acquisition sub $100M aren’t actually PLG?

3. The Secrets to Optimizing Growth Channels:

• What are the most common reasons fast-growing companies plateau?

• How does Adam advise founders on diversifying channels?

• What are the biggest mistakes founders make when scaling into enterprise?

• How should startups do effective product marketing in horizontal products?

• What is emotive & strategic marketing? How should startups balance both?

4. How Angel Investing Changes How You View Companies:

• What are Adam’s top 3 pieces of advice for founders?

• What does Adam mean when he says you are either hiring a poet or a librarian?

• What are the biggest mistakes founders make when hiring?

• What was Adam’s biggest investment miss? What did he learn from it?

Rujul Zaparde is the Co-Founder and CEO of Zip, the world’s leading Intake-to-Pay solution, adopted by leading enterprises and startups including Snowflake, Canva, Airtable, Webflow, and others. In 2023, Zip raised $100 million in a Series C round, valuing the company at $1.5 billion. Before founding Zip, Rujul was a Visiting Partner at Y Combinator and a product manager at Airbnb.

In Today’s Episode with Rujul Zaparde We Discuss:

1. From Airbnb PM to $1.5BN Founder

• How did Rujul’s first company fail? What were his lessons?

• What did Rujul learn from his time at Airbnb?

• How did Rujul come to co-found Zip? What was the aha moment?

• What did Rujul wish he’d known when he started Zip?

2. Standing Out in a Hyper-Competitive Market

• Why did Rujul pick such a competitive market? How did they stand out?

• Does Rujul think founders should focus on pain points or platform solutions on day one?

• What is Rujul’s advice to founders who are in the discovery process?

• Does Rujul agree with Trae Stephens @ Founders Fund that serial entrepreneurs doing B2B enterprise SaaS are wasting their talent?

3. The Biggest Lessons Scaling Zip to $1.5BN Valuation

• Which key moment caused Zip to accelerate?

• Why does Rujul think speed is the most important element in startups?

• Why does Rujul not believe in design partners?

• Why does Rujul believe repeatability is the most important thing when pitching?

• Does Rujul think AI will destroy outbound sales?

4. How to Hire & Manage Teams

• What was Rujul’s “rude awakening” building a sales team?

• What was Rujul’s biggest hiring mistake? What did he learn from it?

• How does Rujul decide where to focus his attention and resources?

• Why does Rujul believe younger managers are more creative?

Daniel Dines is the Co-Founder @ UiPath, one of the most incredible journeys in startups. For 10 years, UiPath was a bootstrapped company that scaled to just $500K in revenue. Then it all changed, product market fit became obvious and the rest is history. The company went on to raise funding from Sequoia, Accel, Kleiner Perkins and more. Today, the company is worth over $10BN, listed on the NASDAQ and does $1BN+ in revenue.

In Today's Episode with Daniel Dines We Discuss:

1. From a Dollar a Day to Romania's Richest Man:

• How would Daniel's parents and teachers have described the young Daniel?
• How did Daniel first learn to code? Why was his first programming job on $300 per month the best?
• How did Daniel learn English by playing bridge with his friends?
• What was the a-ha moment for Daniel with UiPath?

2. Becoming a Billionaire: The Mental Journey:

• What does Daniel mean when he says everyone is a prisoner of their own mind?
• How does Daniel reflect on his own relationship to money?
• How did having absolutely nothing impact Daniel's relationship to risk?
• Why does Daniel think that he does not really experience or feel happiness?

3. 10 Years to $500K ARR: The Miracle Bootstrapping Journey:

• After 10 years, UiPath had just $500K in ARR, what was the one single moment that changed everything in 2014?
• How did raising the seed round change everything for Daniel? How did it change his approach to operating?
• What was the impact of having Sequoia invest? Does it change the game? Why did Daniel say no to them the first time they tried for the Series B?

4. Journey to a $10BN Public Company: The Crucible Moments:

• How did the company almost go bust when it spent $400M against a plan of $150M in 2021?
• What is the single proudest moment Daniel has of the 19 year journey with UiPath?
• What have been Daniel's biggest management lessons in scaling UiPath to $1BN in ARR?
• Knowing all that Daniel does today, what would he have done differently about the UiPath journey?

Girish Mathrubootham is the founder and CEO of Freshworks, India’s first SaaS company to list on NASDAQ. Today, Freshworks has over $596M in ARR with a $5.27BN market cap, with investors like Accel Partners, Sequoia Capital, Tiger Global Management, and CapitalG. Girish is also a founding member of SaaSBOOMi, Asia’s largest community of founders and product builders, and has invested in over 60 startups. On top of that, Girish is also the Founder of Together Fund, a $150M fund focusing on Indian B2B companies going global from day 1.

In Today’s Episode with Girish Mathrubootham We Discuss:

1. From Online Forum to the Founding of a $5BN Company:

• How did a horrible customer service experience prompt Girish to start Freshworks? What was the aha moment?

• What were Girish’s biggest challenges founding Freshwork in 2010?

• How was building the first product? What worked? What didn’t work?

2. Biggest Lessons on Product, Pricing and People Scaling to $5.2BN:

• Why does Girish believe Indian companies have to win globally before winning India?

• What were Girish’s biggest mistakes scaling Freshworks? What were his lessons?

• Why does Girish believe starting high and going down never works in software?

• When does Girish think is the best time to build the second product?

• How did Freshworks lose against Slack? What did he learn from the experience?

3. The Biggest Lessons to Becoming the Best Leader:

• How has Girish’s leadership style changed over time?

• What were Girish’s biggest hiring mistakes?

• What was Girish’s biggest challenge in building culture during COVID?

• What is one piece of advice Girish believes every CEO should follow?

4. How India Will Become a Global Player in Tech, AI and Football:

• Why does Girish believe now is the time for India tech?

• What are the most common misconceptions of India tech?

• What traits does Girish look for in founders he invests in?

• What was Girish’s biggest investment mistake? What did he learn from it?

Vickie Peng is a Product Partner at Sequoia and the co-creator of Arc, their company-building immersion programme for pre-seed and seed stage founders. Prior to Sequoia, Vickie was a product manager at Polyvore (acquired by Yahoo for $200M) and Instagram, where she grew SMB advertising from $200M to $1BN.

In Today’s Episode with Vickie Peng We Discuss:

1. Lessons from 15 Years in Product

• How did Vickie make her way into the world of product?

• How did Vickie turn a small side business into a massive revenue machine at TrialPay?

• How did Vickie scale Instagram SMB ads to $1BN? What were her takeaways?

• What was Vickie’s business model at Polyvore that eventually led to the $200M acquisition by Yahoo?

2. Lessons from Scaling 100+ Companies in Sequoia

• What does Vickie believe are the biggest mistakes early stage founders make when telling stories?

• Which 2 components does Vickie believe every great product mission should include?

• How should pre-product-market fit founders set their north star metric?

3. Perfecting Product Strategy

• What was Vickie’s biggest product mistake? What were her lessons?

• Why does Vickie think the best product people build less product?

• What is Vickie’s advice to product leaders starting their first day on the job?

• What are the most common mistakes founders make when hiring product teams?

4. Product-Market Fit Masterclass

• Why does Vickie believe product-market fit is a journey not a destination?

• What are the biggest reasons founders fail to get product-market fit?

• What are the 3 types of product-market fit?

• How does Vickie advise founders to differentiate themselves in competitive markets?

• What is Vickie’s framework for competing against incumbents?

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?

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?

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?

2. 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?

3. 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?

4. 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?

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?

2. 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?

3. 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?

4. 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.

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?

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?

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?

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?

2. 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?

3. 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?

4. 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.

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?

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?

2. 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?

3. 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?

4. 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?

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?

2. 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?

3. 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?

4. 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?

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?

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?

2. 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?

3. 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?

4. 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?

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?

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?

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?