Episodes
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Zach Perret is the CEO and Co-Founder of Plaid, a technology platform reshaping financial services. To date, Zach has raised over $734M for Plaid from the likes of NEA, Spark, GV, Coatue and a16z, to name a few. Today, thousands of companies including the largest fintechs, several of the Fortune 500, and many of the largest banks use Plaid. In addition, Zach is also a Co-Founder of Mischief, an early-stage venture fund in San Francisco.
In Today’s Episode with Zach Perret We Discuss:
1. Founder Mode:
Why “Founder Mode” will be the most dangerous blog post written in the last decade for founders? What is most misleading about it?
What are “grinder problems”? Why does Zach believe that grinder problems are the best problems for startups to try and solve?
Why does Zach believe that OKRs are BS and should be removed? What should be used instead?
2. Lessons from Raising $734M for Plaid:
What is the worst advice that VCs give that most founders take?
Why does Zach believe that angel investing is more distracting than helpful for founders to do? What are the pros of investing alongside running a company?
Why does Zach encourage founders to raise money as infrequently as possible? What does this mean for the size and price of rounds Zach thinks we should see occur?
3. The $5BN Exit and the $13.4BN Round:
Why did Zach turn down the $5BN exit to Visa? Was it the right choice?
Does Zach regret raising at such a high price of $13.4BN when the exit did not happen?
Would Zach sell the company today for $13.4BN if offered it?
What did Zach not do that he wish he had done? What did he do that he wishes he had not done?
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David Frankel is the Co-Founder and Managing Partner of Founder Collective, one of the best seed firms of the last decade. David has led rounds in companies such as Suno, Coupang, SeatGeek and PillPack (sold to Amazon for ~$1B). Previously, David was Co-Founder and CEO of Internet Solutions (IS), the largest ISP in Africa, ultimately acquired by NTT Japan. David has been named to the Midas List six times. In 2023, he was #11 and in 2024, he appeared at #15 on the Midas List of the world's best venture capital investors and at #2 on the Midas list of seed investors.
10 Questions With One of the World’s Best Seed Investors:
1. Reserves: Why are reserves the hardest part of venture? What have been David’s biggest lessons in how to do them well?
2. Why does David believe that pro-rata is the original sin of VC?
3. Has DPI died in 2024? Is PE the salvation for the VC exit market and liquidity?
4. Why does David believe LPs are so pissed of with VCs right now? What will change that?
5. When will IPO markets open? Are M&A markets shut? What would cause them to open?
6. How does David reflect on price today? When will he pay up and break his rules?
7. Biggest lessons for David on knowing when is the right time to sell? Why does David believe you should never sell your winners? What has David sold that he regrets most?
8. What companies returned the most to Founder Collective Funds? Uber? Coupang? Airtable? The Trade Desk? What did he learn from those mega hits?
9. What have been David’s biggest losses? How did losing the company change his mindset and approach to investing?
10. What does David believe is the future of venture capital? How can seed funds play in a world of mega multi-stage funds? Who wins? Who loses?
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Eoghan McCabe is the Co-Founder and CEO @ Intercom, one of the largest private software companies in the valley with hundreds of millions in revenue and thousands of customers. To date, Eoghan has raised over $238M from Index, Kleiner Perkins, ICONIQ, GV, Bessemer and more incredible firms. Intercom’s goal is to reinvent customer service with AI agents replacing human agents over the next 10 years.
10 Questions with One of the Largest Private Company CEO’s:
AI Investing: Why will most AI investments not do better than the S&P 500?
Building SaaS Tools with AI: Why is it crazy for companies to follow Klarna and use AI to build their own tools?
Going Public: Why is Bill Gurley wrong that more later stage companies should go public? Why did Intercom shelve plans to go public in 2022?
Early-Stage is F*******: Why is the early-stage venture ecosystem as an asset class f******?
Founder Mode: Why does Eoghan believe all of the best founders are unbalanced? What is the difference between Founder vs Manager mode?
Political Voice: Why did Eoghan decide he had to voice his political opinions now?
The Danger of Harris: Why does Eoghan believe a Harris administration would rob the US of immense freedom, democracy and civil liberty?
Why Vote Trump: Why does Eoghan believe that Trump will regain immense freedom for the sovereign individual?
Freedom of Speech: How does Eoghan determine right vs wrong when freedom of speech leads to harm and injustice?
Middle East and Nuclear War: Why does Eoghan believe that nuclear war is much closer than we think? Will we see the Middle East descend into war?
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Jeff Wang is the Managing Partner of Sequoia Capital Global Equities (SCGE), a public/private crossover investment firm with investments spanning from late-stage private companies to public companies. As Managing Partner, Jeff has primarily focused on public growth technology companies but has also invested $3 billion in private companies including Bytedance, SpaceX, and Stripe. Prior SCGE private investments that have since gone public include Airbnb, Doordash, MongoDB, Nubank, and Snowflake. Before joining SCGE in 2010, Jeff also worked at TPG Capital and Silver Lake Partners where he focused on investments in technology buyouts.
10 Questions with the Leader of Sequoia’s $9BN Global Equities Fund:
1. Crossover Fund Opportunity: Why are crossover funds more attractive today than ever? Have the tourists gone?
2. Public Market Opportunity: Why is the opportunity in the public markets, not the private markets today?
3. IPO Markets: When will IPO markets open? What will cause them to open?
4. Breaking Hedge Fund Rules: What are the biggest ways that Sequoia break the traditional rules of hedge funds?
5. Google: Why does Jeff believe that Google’s cash cow of search is under threat?
6. Meta: Why does Jeff believe Meta will be the biggest competitor to Google?
7. NVIDIA: Why is NVIDIA’s price today reasonable? What is the bull and bear case?
8. China: Is there a recovery for China? How do Sequoia play China in this market?
9. AI in Public Markets: How are Sequoia playing the AI game in the public markets?
10. Investing Lessons: What have been Jeff’s biggest investing lessons from Mike Moritz, Doug Leone and Roelof Botha?
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Eiso Kant is the Co-Founder and CTO of Poolside.ai, building next-generation AI for software engineering. Just last week, Poolside announced their $500M Series B valuing the company at $3BN. Prior to Poolside, Eiso founded Athenian, a data-enabled engineering platform. Before that, he built source{d} - the world’s first company dedicated to applying AI to code and software.
1. Raising $600M to Compete in the AGI Race:
What is Poolside? How does Poolside differentiate from other general-purpose LLMs?
How much of Poolside’s latest raise will be spent on compute?
How does Eiso feel about large corporates being a large part of startup LLM provider’s funding rounds?
Why did Poolside choose to only accept investment from Nvidia?
Is $600M really enough to compete with the mega war chests of other LLMs?
2. The Big Questions in AI:
Will scaling laws continue? Have we reached a stage of diminishing returns in model performance for LLMs?
What is the biggest barrier to the continued improvement in model performance; data, algorithms or compute?
To what extent will Nvidia’s Blackwell chip create a step function improvement in performance?
What will OpenAI’s GPT5 need to have to be a gamechanger once again?
3. Compute, Chips and Cash:
Does Eiso agree with Larry Ellison; “you need $100BN to play the foundation model game”? What does Eiso believe is the minimum entry price?
Will we see the continuing monopoly of Nvidia? How does Eiso expect the compute landscape to evolve?
Why are Amazon and Google best placed when it comes to reducing cost through their own chip manufacturing?
Does Eiso agree with David Cahn @ Sequoia, “you will never train a frontier model on the same data centre twice”?
Can the speed of data centre establishment and development keep up with the speed of foundation model development?
4. WTF Happens to The Model Layer: OpenAI and Anthropic…
Does Eiso agree we are seeing foundation models become commoditised?
What would Eiso do if he were Sam Altman today?
Is $6.6BN really enough for OpenAI to compete against Google, Meta etc…?
OpenAI at $150BN, Anthropic at $40BN and X.ai at $24BN. Which would Eiso choose to buy and why?
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Maria Angelidou is a seasoned product leader, having spent close to a decade at Meta where she was VP of Product and General Manager for some of the largest products such as Facebook Groups (2B+ users), Events, Profile, and Search. Before that, Maria led the Facebook App Monetization team, driving billions of dollars in revenue. Today, Maria is the Chief Product & Technology Officer at Personio, an HR tech company with an ambitious mission to unlock the power of people for SMEs.
In Today's Episode with Maria Angelidou1. How to Hire the Best Product Teams:
What are the three different archetypes for PMs today? What non-obvious traits does Maria look for in new product hires? How does Maria structure the hiring process? What works? What does not? Does Maria do take home assignments? How has her approach changed here? What is Maria's biggest advice to candidates on both compensation and title?2. How the Best Product Teams Do Product Reviews:
What does every team get wrong in how they do product reviews? What are the four different type of product reviews? How often does Maria do a product review? Who is invited? Who sets the agenda? How is it structured? What makes good vs great product reviews?3. Europe vs US: How Product Teams Differ:
What is the single biggest difference when comparing product teams in the US vs EU? Does Maria agree that the work ethic is less in the EU? Which class of employee would Maria say is more entitled? What could Europe do to be more competitive with the US? What was the biggest surprise to Maria on returning to Europe from the US? -
Bret Taylor is CEO and Co-Founder of Sierra, a conversational AI platform for businesses. Previously, he served as Co-CEO of Salesforce. Prior to Salesforce, Bret founded Quip and was CTO of Facebook. He started his career at Google, where he co-created Google Maps. Bret serves on the board of OpenAI.
In Today's Discussion with Bret Taylor:1. The Biggest Misconceptions About AI Today:
Does Bret believe we are in an AI bubble or not? Why does Bret believe it is BS that companies will all use AI to build their own software? What does no one realise about the cost of compute today in a world of AI?2. Foundation Models: The Fastest Depreciating Asset in History?
As a board member of OpenAI, does Bret agree that foundation models are the fastest depreciating asset in history? Will every application be subsumed by foundation models? What will be standalone? How does Bret think about the price dumping we are seeing in the foundation model landscape? Does Bret believe we will continue to see small foundation model companies (Character, Adept, Inflection) be acquired by larger incumbents?3. The Biggest Opportunity in AI Today: The Death of the Phone + Website:
What does Bret believe are the biggest opportunities in the application layer of AI today? Why does Bret put forward the case that we will continue to see the role of the phone reduce in consumer lives? How does AI make that happen? What does Bret mean when he says we are moving from a world of software rules to guardrails? What does AI mean for the future of websites? How does Bret expect consumers to interact with their favourite brands in 10 years?4. Bret Taylor: Ask Me Anything: Zuck, Leadership, Fundraising:
Bret has worked with Zuck, Tobi @ Shopify, Marc Benioff and more, what are his biggest lessons from each of them on great leadership? How did Bret come to choose Peter @ Benchmark to lead his first round? What advice does Bret have to other VCs on how to be a great VC? Bret is on the board of OpenAI, what have been his biggest lessons from OpenAI on what it takes to be a great board member? -
Donald Tang is the Executive Chairman of SHEIN, with oversight of public affairs, business strategy, corporate development, and finance. Donald began his career at Merrill Lynch & Co. He later joined Bear Stearns & Co. Inc. in Los Angeles as Senior Managing Director of Investment Banking. At Bear Sterns, Donald quickly rose to become the Vice Chairman of the firm, as well as Chairman and President of Bear Stearns International Holdings, Chairman and CEO of Bear Stearns Asia, Ltd, and a member of the board of directors at Bear Stearns & Co.
In Today's Episode with Donald Tang We Discuss:1. How SHEIN Became a Global Giant:
As specifically as possible, what did you and the SHEIN team do that enabled you to be one of the fastest-growing companies on the planet? Real-Time Retail: What is this? How is it the core of SHEIN's growth and efficiency? Supply Chain Innovation: How did SHEIN innovate on the supply chain to give them such an advantage over the competition? Price King: How does Donald respond to the statement that SHEIN wins due to price, not quality? Social Media: What social media tactics allowed SHEIN to grow so fast? What did not work? Paid Media: How have SHEIN approached paid marketing? What works? What does not?2. The Big Questions: IPOs, Impact on Climate and Worker Conditions:
IPO: Why does SHEIN want to go public? Is London the right place for the company to go public? Climate: How does Donald respond to the common idea that "SHEIN is bad for the climate" and encourages fast fashion like never before? Tariffs: How does Donald respond to the common question around tariffs and SHEIN benefitting from being under a certain tariff threshold?3. Marriage, Fatherhood and Happiness:
Marriage: What have been Donald's biggest lessons on how to have a successful marriage? Fatherhood: What does being a great father mean to Donald? If he could call himself up the night before his first child was born, what would he advise himself? Happiness: How does Donald think about happiness today? What does everyone get wrong about happiness? -
Jeetu Mahtani was an early member of the HubSpot team. Under his leadership and the sales organization, the business grew its non-US revenue from $3M ARR to close to $1B ARR. After running the International business as the global MD and Sales leader, he then moved to lead the customer success org which expanded to managing 1,500 people in customer success.
In Today's Episode with Jeetu Mahtani We Discuss:1. How to Go International for Startups:
What are Jeetu's biggest lessons from Hubspot on what startups can do to make their international expansion a success? What were the biggest mistakes Hubspot made in their international expansion? How should every team in each new location be structured? What should the ramp time and onboarding process look like or each new team and expansion?2. Scaling Sales from $3M to $1BN in ARR:
What did Hubspot do so well to successfully scale to $1BN in international ARR? What were the biggest mistakes Jeetu made in the expansion of Hubspot's sales teams? What are the first things to break in sales teams? How do you handle them? Why does Jeetu hate discounting? Why does Jeetu not like customer references?3. Scaling Customer Success to 1,500 CS Reps:
When should founders make their first customer success hires? What are the biggest mistakes people make in the scaling of CS teams? Why should customer success be incentivised in the same comp plans that sales teams have? How do the best CS teams work with sales and product teams most effectively?4. Hiring the Best and Ramping Them:
What does Jeetu's hiring process look like for all new sales reps? What are the must ask questions for Jeetu in all candidate interviews? How fast do you know when you have made a mistake with a new hire? What is the secret to effective onboarding? What are the biggest mistakes people make in onboarding?20Sales: Scaling Hubspot from $3M to $1BN in ARR | How to Hire and Ramp Sales Teams | How to Scale Customer Success Successfully | How and When to Go International and Crush It with Jeetu Mahtani
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Eric Vishria is a General Partner @ Benchmark Capital, one of the world's leading venture firms. At Benchmark, Eric has served on over 10 boards including Confluent (CFLT), Amplitude (AMPL), Benchling, Contentful, Cerebras and several other private companies. Prior to joining Benchmark, Eric was the Co‐Founder and CEO of RockMelt, acquired by Yahoo in 2013.
In Today's Episode with Eric Vishria We Discuss:1. How to Make Money Investing in AI Today:
How does Eric think through where value will accrue in the stack between chips, models and applications? Why does Eric believe foundation models are the fastest commoditising asset in history? Why does Eric believe that Nvidia will not be the only game in town in the next 3-5 years?2. How to Invest in AI Application Layer Successfully:
How does Eric analyse between a standalone and deep product vs a product that foundation model will commodities and incorporate into their feature set? How does Eric differentiate between the 10 different players all going after customer service, or sales tools or data analyst products etc? How does Eric analyse the quality of revenue of these AI application layer companies? What does he mean when he describes their revenue as "sugar high"?3. How the Best VC Firm Makes Decisions:
What is the decision-making process for all new deals in Benchmark? As specifically as possible, how does the voting process inside Benchmark work? What deal was the most contentious deal that went through? What did the partnership learn? How has the Benchmark decision-making process changed over 10 years?4. Does AI Break Venture Capital Models:
Does the price of AI deals and size of their rounds break the Benchmark model? Will foundation model companies all be acquired by the larger cloud providers? Unless multiples reflate in the public markets, does venture as an asset class have hope? Why does AI make paying ludicrously high prices potentially rational? -
Dmitry Gurski is the Co-Founder and CEO of Flo Health, the leading women's health app and the first European femtech unicorn. Launched in 2015, Flo Health has grown to over 70 million monthly active users and 5 million paid subscribers. The app is recognized as the #1 recommended tool for period and cycle tracking, and it recently achieved a valuation exceeding $1 billion. Beyond Flo, Dmitry is a partner at Palta, a co-founding company with a portfolio of successful startups including Simple App, MSQRD (acquired by Facebook), AIMatter (acquired by Google), and Wannaby (acquired by Farfetch).
In Today's Episode with Dmitry Gurski We Discuss:1. Why 99% of Startup Advice is BS:
Why does Dmitry believe that speed is not the most important thing? Why does Dmitry believe that competition is actually a good thing? Why does Dmitry believe that craziness not intelligence is the most important trait in founders? Why does Dmitry believe that fundraising is simply a numbers game? What does no one understand about retention that everyone should know?2. From Potato Farms to Billion Dollar Apps:
What a childhood in potato farming taught Dmitry about leadership and technology? How mushroom farming taught Dmitry about diversification and focus? How does Dmitry advise people analyse the hardest moments in their life? Why Dmitry does not believe in talent? What else is there?3. Scaling to Flo's First 1M Users:
What were Dmitry's biggest lessons from two failed prior versions of Flo? What is the secret to success in consumer subscription? How did Flo acquire their first customers? What worked? What did not work? Why does Dmitry not believe in brand and PR?4. Building a $200M Revenue Market Leader:
What have been Dmitry's biggest lessons on monetisation? How does Dmitry think about retaining product simplicity with time? What are the first things to break in the scaling of a company? What did they do with Flo that he wishes they had not done? -
Phil Carter is one of the best growth leaders of the last decade helping world-class companies like Faire, Quizlet, and Ibotta accelerate their growth. Today, Phil is a growth advisor and angel investor who helps Seed - Series C consumer subscription businesses define their growth strategy.
In Today's Episode with Phil Carter We Discuss:The Seven Core Levers to Win at Consumer Subscription:
How to Optimize Subscription Pricing and Packaging:Step:
Single vs multiple subs tiers? Monthly, weekly or annually? How often should it be revisited? Biggest mistakes companies make with pricing and packaging? How to deliver immediate value through new user onboarding?Target Metrics:
Best tactics for delivering value in the shortest amount of time? Biggest mistakes companies make in user onboarding? Thoughts on the very long surveys companies like Noom make people fill out pre getting access to the product? How to boost paid marketing efficiency by investing in desktop web flows?Target Metrics:
Why is now the time to be investing in desktop workflows? What are the most effective and specific tactics to do so? How to optimize paywall visibility and conversion?Target Metrics:
Why is paywall view rate so important? What is good vs bad? What are the most common places to trigger paywall? Thoughts on hard paywall vs consumer value first? Specific tactics to refine paywall design to maximize conversion? Single biggest mistakes companies make when it comes to paywall conversion? How to distinguish and emphasize premium value props?Target Metrics:
What are the most effective ways to do this? Who does it best? Lessons from them? How to leverage motivation tactics (stats, streaks, badges, leaderboards, notifications)?Target Metrics:
What is the most effective? Do we not have notification overload? What used to work but now does not work? Who does this best? Why them? How to leverage strategic discounts and promotions?Target Metrics:
What are the most effective discounting methods used? What are the biggest mistakes companies make when using promos or discounts? Who does it best? What do they do? -
Akshay Kothari is Co-Founder at Notion, one of the fastest-growing companies of the last decade. Akshay has run every function in the company from sales, to marketing to finance and even led their fundraising efforts raising $340M+ from Sequoia, Index and Coatue with the latest round pricing them at $10BN. Before Notion, Akshay was VP Product at Linkedin for 5+ years, leading all of their content efforts. He joined LinkedIn when his previous company, Pulse, was acquired by LinkedIn in 2013.
In Today's Episode with Akshay Kothari We Discuss:1. Founder Mode, Veto Powers and Focus:
Does Akshay agree with "founder mode"? What are the biggest downsides to founder mode that not enough people are discussing? Why does Akshay believe that the single greatest power of a founder is their "veto power"? What is the biggest opportunity that Notion jumped on that they should not have done? What is the biggest opportunity that Notion did not jump on that they should have jumped on?2. Raising $50M @ $2BN Valuation:
Why did Ivan and Akshay decide to do this raise when they did not even need the money? How did the fundraising process for this round go? Why did they choose Coatue and Index? Why did Sequoia say no to this round? With the benefit of hindsight, what does Akshay wish that they had done differently?3. Raising $270M @ $10BN Valuation:
How did Sequoia come back into the frame with this round? Why did they say yes here when they did not before? Why does Akshay believe that of all the investor brands, Sequoia is the most powerful? In what way does having Sequoia as an investor change the trajectory of the company? Is Akshay concerned about how he will be able to scale into the $10BN valuation? How does Akshay address the challenge of bringing new team members in with stock options priced at $10BN? How much of a blocker is that?4. Boards and Social Media are F*******:
How is the way in which boards are constructed broken? How does Akshay believe that boards should be constructed? What roles should founders hire for in their board members? Why is Akshay most concerned about the "Tiktokification of everything"? Why does Akshay believe that social media has never been more concerning? -
Shardul Shah is a Partner at Index Ventures and one of the greatest cyber security investors of the last two decades. Among his many wins, Shardul has led rounds in Datadog, Wiz, Duo Security, Coalition and more. Shardul is also the only Partner investing at Index to have worked in every single Index office from London, to SF, to NYC to Geneva. Prior to Index, Shardul worked with Summit Partners, focusing on healthcare and internet technologies.
In Today's Episode with Shardul Shah We Discuss:1. Investing Lessons from Wiz and Datadog:
Why does Shardul believe that TAM (total addressable market) is BS? Why does Shardul believe that every great deal will be expensive? How does Shardul evaluate when to double down and concentrate capital vs when to let someone else come in and lead a round in an existing company? How does Shardul think about when is the right time to sell a position in a company?2. How the Best VCs Make Decisions:
How does Shardul and Index create an environment of truth-seeking together, that is optimised for the best decision-making to take place? What are the biggest mistakes in how VCs make decisions today? Why does Shardul believe that all first meetings should be 30 mins not 60 mins? Why does Shardul believe it is so much harder to make investment decisions when partnerships are remote? What is better remote?3. The Core Pillars of Venture: Sourcing, Selecting, Securing and Servicing:
Which one does Shardul believe he is best at? What is he worst at? Does Shardul believe with the downturn we have moved into a world of selection and not just winning every new deal? Does Shardul believe that VCs provide any value? What are the biggest misnomers when it comes to "VC value add"?4. Lessons from the Best Investors in the World:
Who is the best board member that Shardul sits on a board with? What has Shardul learned from Gili Raanan and Doug Leone on being a good board member? What have been some of Shardul's biggest investing lessons from Danny Rimer? Why does Shardul hate benchmarks when it comes to investing? -
Mike Hudack is the Co-Founder and CEO of Sling, a peer-to-peer payments app whose vision is to simplify the way the world connects financially. Previously, he held roles at Monzo Bank as Chief Product Officer, Deliveroo as Chief Product and Technology Officer, and Facebook where he led ads product and sharing product.
In Today's Episode with Mike Hudack We Discuss:1. Product: Art vs Science:
What is the true art of product? What makes the great product leaders and PMs? Is simple always better in product? How do you retain product simplicity with time? When should data be used over intuition in product building?2. Lessons from Leading Ads at Facebook:
What are Mike's single biggest product lessons from building the ads product at Facebook? How did a meeting with Mark Zuckerberg discussing a product change, alter how Mike thinks about product today? What makes Zuck so special on product? What are the biggest mistakes that Facebook made when it came to the ads product? What did they not do that he wishes they had done?3. Leading Product at Deliveroo: What I Learned:
What are Mike's biggest takeaways from his time at Deliveroo on how to make consumer products? What did Deliveroo do from a product perspective that worked so well? What did he learn? What were the single biggest product mistakes that Deliveroo made? What did he learn? How fast do you know when a consumer app is working or not working? When do you go against data and follow your intuition?4. Building the Biggest Bank in Britain with Monzo:
What are Mike's biggest lessons on product building from his time at Monzo? What did Monzo not do that he wishes they had done? Why does Mike think the US is crucial for Monzo? How did Monzo change how Mike thinks about competition? What do you do when your competitor, Revolut, is outshipping you at such a speed? -
David Schneider is a General Partner @ Coatue and one of the great operators of the last 20 years. Prior to Coatue, David was instrumental in ServiceNow’s growth to over $100B+ public market value. David led the growth of the company from $100M to $5BN in revenue. Before joining ServiceNow, David held senior positions at Data Domain, the company he joined at $0 in revenue and scaled to $1BN in revenue and an IPO and acquisition.
In Today's Episode with David Schneider We Discuss: ServiceNow: Secrets to Scaling to $5BN in ARR: What are David's biggest lessons from scaling ServiceNow to $5BN ARR? What worked? What did not work? What are the most common reasons companies plateau? How did ServiceNow roll out so many different products so effectively? How did David hire and ramp 180 people in 90 days?2. From OG Operator to Newbie Investor:
What have been the single most challenging elements of making the transition to VC? What advice did David get from the biggest names on entering venture? How long did it take David to do his first deal? What advice does he give other operators entering? How does doing deals in 2024 compare to when David started doing deals in 2021?3. VC Value: Do 90% of VCs Really Damage Companies:
Does David agree that 90% of VCs actually detract value? What does David mean when he says that the worst VCs are "seagull VCs"? What are David's biggest tips to founders on how to get the most out of their board? What is enough ownership for David to really give the time needed to a company?4. Lessons from the Greats: Doug Leone, Bill McDermott, Frank Slootman:
Doug Leone: What has David learned from Doug on what it takes to be a great investor and board member? Frank Slootman: What has David learned from Bill on how to be the best leader of a mega company? Bill McDermott: What has David learned from Frank about decision-making and execution. -
Sean Rad is the Founder and former CEO of Tinder. Sean has made more romantic connections between humans than anyone in history with Tinder having matched 50BN different people. Sean is also the Founder of Rad Fund which has made over 100 investments in companies and funds.
In Today's Episode with Sean Rad We Discuss:1. Lessons Scaling Tinder to the Fastest Consumer Social App:
Starting: How did the idea for Tinder come to Sean in a restaurant in LA? Scaling: What are Sean's biggest lessons for consumer apps scaling to their first 10,000 users? User Acquisition: How did a party change the entire user acquisition strategy for dinner? What did Tinder not do that Sean wishes they had done? What did Tinder do that with the benefit of hindsight, they should not have done?2. Leadership Lessons from Tinder CEOship:
Annual Product Redesign: Why does Sean believe that every consumer company should have a complete redesign of the app every year? What are the benefits? Detachment: How does Sean advise founders when it comes to detaching their happiness from the performance of the company? What works? What does not work? Common Mistakes: What are the most common mistakes that Sean sees early-stage founders make when it comes to leadership?3. Money, Wealth and Creating a Family Office:
How does Sean analyse his own relationship to money? How has it changed over time? At what stage of wealth does Sean believe you have true financial freedom? What is the single best investment Sean has made? What did he learn? What is the worst investment he has made? What did he learn? What have been the single hardest and most surprising elements of creating a family office?4. Love, Death, Marriage:
In what ways does Sean think love has changed with time? How do we deal with the loneliness pandemic? What does Sean believe are the most non-obvious but important secrets to a happy marriage? How does Sean approach and think about his own spirituality today? Why does he not fear death? -
Nick Chirls is the Founder of Asylum Ventures, a new venture firm dedicated to the creative act of building companies; treating founders like artists, not assets. Asylum raised $55 million to invest $1-2 million in early-stage founders practising the art of making startups. Prior to Asylum, Nick co-founded Notation Capital, one of NYC's most successful pre-seed firms.
In Today's Episode with Nick Chirls We Discuss:1. Why Venture Capital is Broken Today:
Why is VC a ponzi scheme today? Why are most VCs sheep and have lost all creativity? Why are most investors today incentivised to get dollars out of the door and not to make great investments? Why are services functions within VC firms total BS? Why do no VCs provide significant enough value to a company that it is needle-moving?2. How to Make Money in VC in 2024:
What are the two ways to make money at seed in 2024? Why do founders in unloved markets care more than those in hot markets? Why will large institutions lose a ton of money investing in the large firms of today? Why does Nick believe VCs should always sell when their founders sell shares?3. Lessons from 3xing a Fund on One Check:
Why does Nick think about not purchasing preferred shares and only buying common shares? Why does Nick believe that investing in competitive markets is stupid? What does Nick believe are the conditions you must accept if you are doing a $5M on $25M seed? -
Zico Colter is a Professor and the Director of the Machine Learning Department at Carnegie Mellon University. His research spans several topics in AI and machine learning, including work in AI safety and robustness, LLM security, the impact of data on models, implicit models, and more. He also serves on the Board of OpenAI, as a Chief Expert for Bosch, and as Chief Technical Advisor to Gray Swan, a startup in the AI safety space.
In Today's Episode with Zico Colter We Discuss:1. Model Performance: What are the Bottlenecks:
Data: To what extent have we leveraged all available data? How can we get more value from the data that we have to improve model performance? Compute: Have we reached a stage of diminishing returns where more data does not lead to an increased level of performance? Algorithms: What are the biggest problems with current algorithms? How will they change in the next 12 months to improve model performance?2. Sam Altman, Sequoia and Frontier Models on Data Centres:
Sam Altman: Does Zico agree with Sam Altman's statement that "compute will be the currency of the future?" Where is he right? Where is he wrong? David Cahn @ Sequoia: Does Zico agree with David's statement; "we will never train a frontier model on the same data centre twice?"3. AI Safety: What People Think They Know But Do Not:
What are people not concerned about today which is a massive concern with AI? What are people concerned about which is not a true concern for the future? Does Zico share Arvind Narayanan's concern, "the biggest danger is not that people will believe what they see, it is that they will not believe what they see"? Why does Zico believe the analogy of AI to nuclear weapons is wrong and inaccurate? -
Scott Gorlick was employee #99 at Uber. Over 6 years, Scott built Uber in Atlanta and helped the company scale from 10 cities to $10B in revenue. Scott is also a prolific angel investor having written early checks into Lime and Standard Cognition to name a few.
In Today's Episode with Scott Gorlick We Discuss:1. The Driver Acquisition Playbook: Scaling to 1M Drivers
How did Uber acquire 1M drivers? What was the playbook? What worked? What did not work? How much of a role did driver-to-driver referral payments have in driver acquisition? What did Lyft do on the driver acquisition side that Uber should have done? What did the retention look like for drivers on a 30, 60 and 90 day period?2. The City Expansion Playbook:
What was the expansion playbook that Uber used for new cities? What worked in ramping demand in a new city? What did not work? How much of a role did promotions and discounting play? Lessons from them? Why did Uber often let Lyft launch in a new market first? What was the benefit of this? How did Scott see the maturation rate change with new markets opening? How fast did each subsequent market reach profitability?3. Travis Kalanick and What Uber Could Have Been:
How would Uber be different today if Travis was still in charge? What are the biggest mistakes that Dara has made with their M&A strategy? What are some of Scott's biggest leadership lessons from working with Travis? How did Travis create such strong followership and cult around him? What were the single biggest management mistakes made by Travis? - Show more
