The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch

Scott Galloway is a Professor of Marketing at NYU Stern, where he's taught for over two decades. He's the founder of several successful companies, including L2 (acquired by Gartner for over $150M), Red Envelope, and Prophet. He's a New York Times bestselling author of four books on business and tech, and co-hosts the award-winning Pivot podcast. Galloway also serves on the boards of The New York Times Company and Panera, and his public talks have been viewed tens of millions of times globally. In Today's Episode We Discuss: 02:00 – How to Win in a New Economy of AI 06:00 – Should We Break Up Big Tech? 08:00 – Why Young People Have a Right to Be Angry? 11:00 – Why the Tax Code Is Rigged Against the Young 13:00 – Tax Changes That Would Make Young People Rich Again 17:00 – The Tinder Effect: Why Men Are Angry 20:00 – The Loneliness Epidemic in Men 23:00 – Remote Work & The Case for Alcohol 26:00 – Why Richer Families are Happier Families 30:00 – The Truth About Kids and Career 34:00 – Are Billionaires Happy? 38:00 – Becoming a Better Son, Father, Partner 46:00 – Behind the Persona: Who Scott Galloway Really Is    

AGENDA: 00:00 – $400B in AI CapEx: Rational Investment or Madness? 05:00 – Figma's IPO: Rule of 80, $1.5B in cash, 40% margins. Unreal. 08:00 – Adobe Screwed the Deal—Should They Have Just Bought Canva? 16:00 – Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off? 21:30 – How Index Is Returning $3.5B on 2 Deals 24:00 – Melio's $2.5B Exit: Insane Growth… So Why Did They Sell?! 35:00 – Massive Penthouses and the Death of Focus: AI Founders Beware 39:00 – Chime, Anthropic, Menlo & The Art of Selling LPs the Future 41:00 – Couchbase Acquired: PE Buyers Are Back… Or Are They? 44:00 – Why No One's Buying These 9-Figure SaaS Zombies 48:00 – If You Didn't Grow from AI By June 30, You're Already Dead 53:00 – Superhuman vs The AI-Natives: Who Wins the Replatforming War? 54:30 – Oracle's $30B AI Deal: Larry Did It Before You Even Started 56:00 – Scale Is Dead. Long Live Surge. The AI Data War Gets Bloody. 01:01:00 – Asana CEO Move & the Great Founder Exodus of 2025 01:06:00 – Will Cluely's Founder Be a Billionaire by 2029? Place Your Bets      

Philipp Freise is Co-Head of European Private Equity at KKR, where he manages the largest private fund in Europe with $8BN in the latest fund. Philip has led KKR's investments in FGS Global, Superstruct, Axel Springer SE, BMG Rights Management, Fotolia, GetYourGuide, GfK SE, Leonine, Mediawan SAS, Scout24 Switzerland and Trainline. Previously, Philip worked at McKinsey & Company in and co-founded Berlin-based VC firm Venturepark, Europe's first pan-European incubator. Agenda: 00:00 – "We Lost $500M in Turkey. Here's Why We'll Never Do It Again." 01:40 – Inside Europe's Biggest PE Fund: $8B of Pure Firepower 03:55 – The $100M Dot-Com Failure That Changed My Career 06:45 – Why Picking the Wrong VC Will Destroy Your Company 10:20 – KKR's $500M COVID Gamble: Genius or Insane? 12:35 – Why We Ignored the Market & Deployed 40% of Our Fund 15:55 – KKR's Ruthless Portfolio Discipline: Love Doesn't Matter 17:10 – Do Power Laws Apply in PE? Freise Destroys the Myth 18:45 – The Truth About Capital Intensity in the Age of AI 20:10 – Can AI Kill the PE Model? Here's What Philipp Says 26:00 – The Secret to Great Investment Decisions at KKR 32:40 – Why There's a $3T Liquidity Time Bomb in Venture 34:25 – The Death of IPOs? How KKR Exits Without Going Public 40:05 – Will KKR Europe Hit $20B? Freise's Bold Prediction 43:45 – Helsing, Space, and Defense: The New Age of DeepTech Bets 45:30 – Tariffs, China, and the Future of the German Car Empire 47:00 – Freise vs. Bitcoin: Will USD Still Rule in 10 Years? 48:15 – 4 Global Shocks Happening Right Now That You Need to Know 51:30 – KKR Missed Spotify AND Alibaba?! The Painful Stories 53:00 – Do Andreessen & General Catalyst Scare KKR? Freise Responds 54:30 – The One Metric That Will Define KKR's Next Decade  

Kim Graves is GM, Americas at Notion, where she oversees all Sales and Customer Success efforts across the region. She brings extensive experience in building and scaling high-performing sales organizations, most notably at Slack where she helped grow revenue from $6M to over $1.5B. In addition to her operational role, Kim serves as a founding partner at 20SALES, a GTM-focused VC firm, where she advises early-stage companies on scaling revenue and optimizing sales processes. Agenda: 07:00 – The Secret to Winning a Discount Conversation 09:30 – Notion's Wild New Sales Method: Mindsets Over Stages 12:00 – Why Great Sellers Never Talk Product Too Soon 14:00 – How Slack Avoided the Biggest PLG Trap of All 17:00 – The Fatal Mistake Founders Make Layering Sales on PLG 20:00 – The “Renaissance Reps” That Build Billion-Dollar Motions 23:00 – How to Spot True Grit in a Sales Hire (Without Asking Directly) 26:00 – The Case Study Test That Filters Out Bullshitters 30:00 – The Real Reason Most Reps Fail Onboarding 33:00 – Should Reps Own Their Own Pipeline? Kim's Take Is Clear 36:00 – Why Cold Calling Works in 2025 (And Nobody Does It) 39:00 – The Sales Team Audit: The REKS Framework That Changes Everything 43:00 – How to Avoid Hiring the Wrong Rep Under Pressure 45:00 – When Sales Feels Second Class: PLG vs Enterprise Tension 47:00 – The One Thing Reps Still Do That AI Will Obliterate 50:00 – AI Sales Tools: Why Every Startup Is Failing to Get It Right 53:00 – Will We Have More or Fewer Reps in 5 Years?  56:00 – Enterprises Are Scared of AI – Here's How You Break In Anyway 59:00 – Kim's Secret for Getting Past Gatekeepers and Fake Champions 1:09:00 – Kim's Hardest Phase at Slack and How She Survived It  

Agenda: 04:21 - The Meta Acquisition Bombshell: Nat Friedman & Daniel Gross Join Facebook?! 06:00 - Facebook's $100 Billion Gamble: Can Zuck Buy the Future? 09:27 - The “Magic Room” Theory: Why Only Insiders Get Billion-Dollar Paydays 11:27 - Is Loyalty Dead in Silicon Valley? The Great Talent Exodus 16:00 - Harvey's $5 Billion Valuation: Genius or Bubble? 19:00 - The AI Gold Rush: Can Software Really Eat Human Labor? 22:00 - The B2B Unicorn Dilemma: Are There Enough $100B Companies? 25:00 - IPO Mania: Why Navan, Canva, and Circle Are Shaking Up the Markets 29:00 - Meme Stocks & Market Madness: The Circle Rollercoaster 32:00 - Canva's Billion-Dollar Question: Why Stay Private? 36:00 - Larry Ellison's Power Play: How to Buy Back Your Own Empire 39:00 - The Sales Tech Revolution: Why “Cheating” Tools Are the Next Big Thing 42:00 - Slack Lockdown: Is B2B Software About to Get Ugly? 45:00 - The Ultimate Quickfire: Will Trump Launch a Smartphone? Will the US Seize AI?    

Johannes Reck is the Founder and CEO of GetYourGuide, the $2BN company that started with a holiday to China and nothing to do. For the first two years, GetYourGuide received only 5 bookings. Today the platform does 33,000 per day and is worth $2BN. They have raised from some of the best, including an amazing story with Masa Son and Softbank.  In Today's Episode We Discuss: 01:45 – “I Regret Our Series A — Too Much Dilution” 03:50 – US vs Europe: Why European Founders Are Tougher 06:10 – “Germany Spends €100B on Pensions, €7B on VC – It's Insane” 08:40 – Why Europe Fails to Build $10B Startups 10:25 – 90% of Our Team in Berlin Aren't German. Here's Why. 12:20 – Recruiting Netflix's Head of Growth Nearly Killed Me 16:20 – “We Had 5 Bookings in 2 Years. 3 Were My Mum.” 18:00 – “I Asked My Parents to Remortgage Their House for a Pivot” 21:15 – The Vatican Tour That Changed Everything 23:30 – Why VCs Rejected GetYourGuide 100+ Times 28:30 – The $14M Series A That Nearly Killed the Company 31:00 – “I Hired All the Wrong People – Then Laid Off 30%” 36:30 – The $450M SoftBank Deal... Then COVID Hit 40:00 – “We Went to $0 in Revenue in 3 Weeks” 42:10 – The Sequoia Tree Mindset: Grow Through Fire 49:30 – What SoftBank's Masa Son Was Really Like in Person 52:00 – How He Thinks About Secondary, Wealth, and Not Losing His Soul 55:30 – “My Worst Hires Came from Listening to VCs Too Much” 58:30 – Angel Investing in Trade Republic and TravelPerk: My Lessons 01:01:00 – Do You Have to Work 7 Days a Week to Win?  

Cem Kansu is the Chief Product Officer at Duolingo, where he leads product strategy for over 90 million monthly active learners. Since joining Duolingo, Cem has played a pivotal role in driving record user engagement, revenue growth, and product innovation, including the launch of Duolingo Math and the wildly successful Duolingo Music. Under his leadership, the company has consistently ranked as the #1 education app globally.  In Today's Episode We Discuss: 04:12 – Cem's Origin Story: From Google Ads to Saving Duolingo's Business 06:45 – “Mini CEO” Myth: Why PMs Need to Ditch the Ego 08:55 – The Truth About Design Speed and Pixel Perfection 11:30 – The INSANE Story Behind Duolingo's Viral Chess Launch 14:42 – Why Smaller Teams Are the Future of Product 17:20 – Duolingo's AI Playbook: How They're Building 10x Faster 20:05 – Will Engineers Even Exist in 5 Years? Cem Gets Real 26:10 – Do AI Tools Have ANY Defensibility? Cem Doesn't Hold Back 29:00 – Why Duolingo Took So Long to Monetize (And What They Learned) 33:05 – Cem on Killing Ads, Tasteful Monetization, and Investor Doubt 38:30 – The Secret to Duolingo's Paywall Strategy (And What Not to Do) 42:05 – Cem's Weirdest Retention Hack? A Single Emoji… 46:25 – The Crazy Science Behind Push Notifications at Duolingo 50:00 – In-App Purchases Done Right: GEMS, Freeze, and the Psychology of Value 53:15 – Why Cem Thinks Daily Retention Is the King Metric 55:10 – The ONE Product Feature That Changed Duolingo Forever 57:45 – Will Duolingo Become the Disney of Gen Z? 01:00:00 – Dating on Duolingo?! Cem Reacts to Harry's Craziest Product Ideas 01:03:45 – Cem's Biggest Product Mistakes — And What He'd Kill Tomorrow 01:12:00 – The One Thing Every PM Must Do to Survive the AI Wave 01:14:00 – Duolingo in 20 Years: Cem's Wildest Vision Yet  

Agenda: 00:00 – Meta's $14.8B Deal for Scale: The Analysis 05:40 – Will Scale Lose Their $800M ARR? Will All Customers Leave? 13:00 – Who is the Winner from All Scale Customers Leaving? 21:30 – Who Made the Most Money From Scale? 24:00 – LPs Just Got $14B Back. Are They Reinvesting? 26:45 – Chime IPO: The Breakdown 29:20 – Ramp Hits $16B Valuation: Are We Back in 2021? 31:10 – Ramp vs Brex vs Mercury: Who's the Real Winner? 34:00 – Gusto Going Public with $900M in ARR??? 36:40 – Dropbox vs Glean: Can the Old Guard Survive the AI Wave? 38:50 – Is Slack Dead as a Platform? Salesforce Shutdown Slack API? 41:15 – Will China Dominate AI? The Bets Are In 43:00 – S&P Prediction, iPhone Assembly in the US, and Rory's Rants Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.  

Larry Aschebrook is the Founder and Managing Partner of G Squared in what is one of the wildest stories of venture capital. Larry started G Squared with nothing, dialling for dollars having personally invested in Twitter and Uber. In his first fund, Larry made sizable bets into SpaceX, Palantir, Alibaba and Twitter. Larry has also had mega losses along the way (discussed in the show) in Getir, 23andme and more. Today, Larry manages over $5BN and has invested in all the best from Wiz to Spotify to Revolut and Anthropic.  Agenda: 00:00 – From Broke to Billion-Dollar Bets 03:40 – The $800M Coursera Windfall 06:10 – Lyft Made Millions, Uber Lost $50M 09:05 – “We Fcked Up”: The Billion-Dollar Vintage 11:50 – How a $150M Spotify Bet Made a Billion 15:10 – The Gut Call That Dodged Theranos 18:00 – Vampires vs Zombies: The Coming Startup Purge 20:30 – When Success Almost Killed the Firm 24:20 – DPI Is King, MOIC Is Bullsht 27:40 – Why I'd Buy Anthropic at $61BN Today 30:05 – Losing $70M on 23andMe 32:10 – The Janitor of Venture Capital 34:00 – The Getir Deal That Nearly Broke Me 36:25 – Does Money Actually Make You Happy? 39:00 – What Cal Ripken Jr. Taught Me About Venture  

Agenda: 00:03 – Circle's IPO: Investors Just Left $BNs on the Table 00:06 – CoreWeave & Circle: Are We Back to Meme Stock Madness? 00:11 – Should Stripe and Databricks Finally Go Public? 00:17 – US Stock Markets: How They DOMINATE the Global Game 00:21 – 50% of Unicorns Are DOOMED. What Happens Now? 00:25 – Founders Fund Just Dropped $1B on Anduril. Why?! 00:29 – What Would You Do If LPs Let You Go Wild? 00:36 – What Missing Out on Millions for Docusign Taught Rory 00:44 – Cursor is 20% of SaaS Spend: The Shocking Data Behind the SaaS Slowdown 00:47 – AI vs. SaaS: The Great Budget War Begins 00:48 – Can AI Take Budget from the Talent Budget or Will It Remain in Software Budgets? 00:56 – SpaceX, Tesla, Neuralink: Elon's Empire After the Firestorm Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.  

Micha Kaufman is the Founder and CEO of Fiverr, the leading online marketplace for freelance services. Fiverr has had an insane ride in the public markets, in 2019 the company went public with a $650M market cap, at their peak that hit over $8BN. Today, facing a wave of AI, the company has a market cap of $1.121BN on an estimated $430M EOY revenues. Prior to co-founding Fiverr, Micha successfully founded and led several startups over the last 30 years.  In Today's Episode We Discuss:  00:00 – “Fuck you. It's not my job to make you better.” Micha's viral internal email that sparked a company-wide awakening 05:00 – The real reason Micha thinks Fiverr is vulnerable to AI 07:00 – “Replace 100% of your job with AI”: Micha's challenge to every employee 11:00 – The brutal truth about entitlement in the modern workforce 13:00 – Wake the f*** up: Micha on the crisis of work ethic and ambition 15:00 – “Too many startups, zero value”: Why AI is the new dot-com bubble 17:00 – The time-to-clone has collapsed: Why your startup can be copied in 10 days 21:00 – Why distribution, not code, is the moat that matters now 23:00 – The new game of investing: Why backing “missionaries” is all that counts 25:00 – The seed investment Micha wrote off… that became his biggest win 38:00 – “Being a CEO today is like captaining a ship in a storm” 39:00 – Will governments take control of AI? The Manhattan Project analogy 42:00 – The rise of AI superpowers—and the brutal decline of everyone else 46:00 – The single-person unicorn: Is it real? Micha says yes 47:00 – Why Micha's hiring more engineers—not fewer 48:00 – Marketing is being disrupted faster than engineering. Here's how 54:00 – What cost Micha wants to cut—but can't 56:00 – Why Micha would tell his kid: “Don't go to university” 57:00 – The business Fiverr could have built before OnlyFans—and why they didn't 59:00 – How Micha decides every year whether he should still be CEO 01:00:00 – The ultimate metric: When meaning matters more than happiness  

Matt Pohlson is the co-founder and Chairman of Omaze, the most insane story in startups that you have never heard. From near death experience to working with Arnold Schwarzenegger, George Clooney and The Pope. Omaze has raised over $200 million for charity by offering once-in-a-lifetime experiences with celebrities and icons. He's a master storyteller, a purpose-driven builder, and one of the most creative entrepreneurs in modern philanthropy. In Today's Episode We Discuss: 00:00 — He Died for 4 Minutes… Then Built a $400M Startup 04:00 — The Magic Johnson Moment That Sparked Omaze 06:30 — From $780 to $1.7M: The Breaking Bad Campaign That Changed Everything 09:00 — Star Wars, Schwarzenegger, and Selling Dreams 13:00 — He Flatlined in Surgery… And Everything Changed 18:00 — How Near-Death Killed Fear and Transformed His Leadership 22:00 — Why Fear Isn't Real — And How to Beat It 24:00 — The $250K Bet That Changed Omaze's Business Forever 27:00 — Launching Houses: The Pivot to $100M+ Revenue 34:00 — The Science of Storytelling: Make the Customer the Hero 38:00 — Why TV Still Works: $35M Ad Spend Secrets 45:00 — How They Almost Went Out of Business—Twice 50:00 — The Deck That Saved Omaze Mid-COVID 53:00 — Loneliness, Therapy, and the CEO Mental Game 55:00 — From Self-Doubt to Self-Love: The Hoffman Process 58:00 — How to Lead With Story, Science, and Soul 1:02:00 — Should Omaze Go Public? Matt's Unfiltered Take 1:05:00 — Addiction, Ambition, and Why Fulfillment Can Kill Hunger 1:10:00 — Revenue Per Employee: $7M a Head! 1:15:00 — Matt's 10-Year Vision: Fortune 500. #1 in Charity. Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.  

Agenda: 00:00 – The Most Unfiltered Episode Ever Begins 03:30 – Does OpenAI Even Matter? Sam Lessin Says Maybe Not. 05:45 – TVPI Is Bullshit?  09:20 – Asset Gatherers vs Real Investors: Who Actually Wins? 12:15 – The Death of the Billion-Dollar VC Fund? 16:00 – Mid-Tier VC Funds Are Getting Annihilated 21:00 – Chime: Great Exit or Missed Opportunity? 27:00 – The War on Relevance: What Companies Truly Matter? 33:00 – If You're Not a Billion-Dollar Company, Do You Even Count? 37:10 – Mary Meeker's AI Report: What Everyone Missed 39:50 – $600B in AI CapEx—Where Is the Revenue?! 43:40 – What Could Trigger the First AI Crash? 51:10 – The Existential Dread Missing in Most B2B Startups 58:30 – Will AI Reduce Your Startup to Just a Pipe? 01:01:10 – IPO Market Is Back: What Actually Matters Now? 01:06:50 – YC Startups at $60M Valuations: How Should You Play It? 01:10:00 – Why 3% Ownership Could Still Work—Maybe 01:11:30 – Will Elon Still Be Tesla CEO by 2027? Place Your Bets 01:14:10 – Will Meta Release a Closed AI Model? And Does It Even Matter? 01:17:30 – The Real Challenge of Managing 11 Companies and 58 Kids Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.    

Varun Mohan is the CEO and Co-Founder of Windsurf, the leading AI-native IDE, which has over a million users and generates over 50% of all committed software across thousands of companies. Prior to Windsurf, Varun graduated with a Master's in Computer Science from MIT and led a team at Nuro focused on large-scale deep learning infrastructure for autonomous vehicles. Today's Agenda: [00:00] The $3B Startup That Only Happend on the Third Pivot [05:12] When to Give Up vs When To Stick at It [08:55] “Never Fall in Love With Your Idea” — Here's Why [10:38] What Founders Get Wrong About Being First [13:52] What Would Windsurf Do If They Had Unlimited Resources [16:45] Will Lovable and Bolt Ultimately Compete with Windsurf and Cursor [19:25] The Product Development Rule That Breaks All Startup Rules [21:20] The Cold Truth About Moats in the AI Era [24:30] The OpenAI Question You're Not Supposed to Ask [32:50] Who Actually Counts as an Engineer in 5 Years? [35:10] Will Product Managers Even Exist in 2030? [37:30] Async Agents Are Coming—But Most Will Fail.. Why? [41:00] The Truth About Agent-Only Workflows [44:20] The One Area of Engineering That AI Will Eat Next [46:12] What Cursor Got Right (That Windsurf Didn't) [47:55] Are LLM APIs Already Commoditized? [50:30] Why Anthropic Won't Win by Default [52:10] Should Model Companies Own the App Layer? [58:05] What Does Varun Want to be Remembered For?    

Kyle Norton is the Chief Revenue Officer at Owner.com, where he scaled revenue from $2M to $40M ARR in under 3 years while selling to one of the toughest markets: SMB restaurants. Before Owner, Kyle led sales at Shopify, where he helped architect one of the most operationally elite GTM orgs in SaaS.  Agenda: 00:00 – From Shopify to $40M ARR at Owner.com 06:40 – Why Founders Who Skip Sales Get Burned 11:50 – 90% Inbound, Then 70% Outbound — And Why Neither Is Enough 17:40 – How to Use AI in Sales to Massively Increase Outbound 24:30 – BDRs Don't Get Paid for Demos. Only Closed Revenue. 30:50 – The 3-Part Sales Scorecard That Replaced My Gut 36:20 – I Posted a Job on LinkedIn and Got 1,200 Applicants 42:15 – I Fired a Rep on Day 11. Here's Why. 49:40 – We Don't Do Pipeline Reviews. The Secret... 55:00 – The One Call Close Script That Wins in 99% of Cases 1:03:10 – Why YouTube Is Our Underrated Growth Weapon 1:14:30 – Sales Is a Personal Development Exercise Disguised as a Career 1:20:45 – The Night We Closed Until 1AM and Hit the Number  

Agenda: 00:00 – Why “Fund Returners” Are a Myth in Late-Stage VC 05:02 – Builder.ai Implodes: $500M Gone & Fraud Allegations Begin 11:40 – The Dirty Truth About Late-Stage Venture Math 15:57 – The Hinge IPO: Who Won, Who Lost, and Why It's a Game Changer 23:03 – The Chime Bombshell: Late-Stage VCs Forced to Crystallize Huge Losses 27:14 – Why YC Is Both Chanel and Walmart—and Has Officially Won 33:41 – Seed Is Easy. Series A Is Brutal. Here's Why 39:50 – The Silent Killer: How Dilution Is Screwing VCs Without Them Realizing 46:04 – OpenAI's $6B Jony Ive Deal: Genius or Delusion? 50:47 – Does OpenAI Win the Hardware War 1:02:09 – Duolingo, Klarna, and the Truth About AI Layoffs 1:13:10 – Only 20% of Unicorns Are Real. The Other 80%? Zombies 1:15:44 – Why 2021 Had an IPO Every Day — And Why That Won't Return Soon 1:18:00 – Quickfire: AGI Dates, Half-Trillionaires, and Trump Tax Moves  

Airwallex is the most insane story in startups: The best angel investment ever: The angel that turned $1M into $1BN. One of the world's best VCs pulled a term sheet and lost $1BN.  The company turned down a $1.2BN offer from Stripe.  The company scaled to $1BN in transaction volume in 9 months.  The company has never not grown 100% in a year.  Jack Zhang is the Co-Founder and CEO of Airwallex, one of the world's fastest-growing global payments and financial infrastructure companies. Since founding the company in 2015, Jack has scaled Airwallex to over $130B in annual payment volume, $720M in ARR, and a global team of 1,800+ employees. Under his leadership, Airwallex has raised over $1.2BN from investors including Square Peg, Lone Pine, and Tencent.  In Today's Episode We Discuss: 00:00 – The Best Angel Investment Ever: From $1M to $1BN 06:55 – From Lemon Factory and Petrol Station to Billionaire: The Early Days 15:20 – $5M side hustle while working full-time: how Jack did it 24:45 – Failing Three Times Before Product-Market-Fit 31:00 – The Term Sheet That Got Pulled and Lost Matrix $1BN 34:40 – Why We Rejected Stripe's $1.2BN Acquisition Offer 49:05 – 0-$1B transaction volume in 9 months: How Shein Saved Airwallex 1:03:40 – We F****** Up Scaling internationally... & Burnt $200M/year 1:08:00 – When COVID hit, they lost 50% of revenue overnight 1:11:45 – Why Jack raised at 6x revenue and is now buying back stock himself 1:15:00 – The truth about secondaries and how much is “enough” 1:18:00 – The hiring mistakes that almost broke the culture 1:20:15 – Why Jack is Taking Out a Line of Debt for $70M  

Luke Harries is Head of Growth at ElevenLabs, where he leads marketing, product, engineering, and developer experience. ElevenLabs has raised $281M with the latest round pricing the company at $3.3B valuation. Previously, Luke held roles at PostHog and Microsoft, and is also an angel investor supporting startups like Lovable and Runna. In Today's Episode We Discuss: 00:00 – The $3.3B Growth Engine Behind ElevenLabs 04:55 – Why Luke Said “No” to Investing in ElevenLabs (and Why He Was Wrong) 15:40 – How ElevenLabs Makes a Horizontal Product Strategy Work 20:15 – How to Build Sharded Growth Teams That Actually Scale 26:30 – The 7-Part Launch Playbook That Gets 700K+ Views Per Product 33:00 – The Truth About CAC, Payback, and Performance Marketing in AI 39:05 – SEO Isn't Dead: The Mini-Tool Strategy You Should Steal 44:10 – Kill Your Inbound SDRs—The Case for Voice AI in Sales 48:40 – Why You Don't Need PMs and the Rise of Growth-Led Product Teams  

Agenda: 04:34 Chime's IPO Announcement: Who Wins & Who Loses 06:28 The Lopphole That Means Chime Has a Better Business than JP Morgan 10:51 Why Investors Who Invested at $25BN Will Make Money When it IPOs at $12BN 18:59 Are IPOs Dead & The Future of the Late Stage Private Market 27:32 Exits are Larger Than Ever: So What? What Happens? Who Wins? Who Loses? 40:51 Is Europe Totally F******* 43:48 Challenges of Going Public & What Needs to Change? 46:12 OpenAI's Future and Predictions 49:45 Rippling vs. Deel Lawsuit: Is Deel Screwed? 59:28 Why So Many Companies Are About To Become Database Companies 01:08:07 The Future of Salesforce: Buy or Sell? 01:13:28 Quickfire Round Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.    

Severin Hacker is the Co-Founder and CTO of Duolingo, the world's most downloaded education app with over 100 million monthly users. Since its 2021 IPO, Duolingo has reached a market cap of $20BN. The company has raised over $183M from top-tier investors including CapitalG, Kleiner Perkins, Union Square Ventures, NEA, Ashton Kutcher, and Tim Ferriss. Severin is also an active angel investor, with standout bets including Decagon, one of the fastest-growing AI-native dev shops globally. Items Mentioned In Today's Episode:  00:00 – Why It's Harder to Raise $3M Than $100M 02:10 – The Real Reason Duolingo Couldn't Have Started in Europe 04:40 – Duolingo's AI Pivot: What “AI-First” Actually Means 07:00 – The 12-Year Bottleneck Duolingo Crushed with AI 11:40 – How Duolingo Uses AI Internally (and Why They Love Cursor) 13:30 – Where AI Still Sucks (Especially in Engineering) 16:00 – Will AI Kill the CS Degree? Severin's Surprising Take 18:00 – The End of Work? UBI, Purpose, and the Future of Labor 25:20 – OpenAI vs Duolingo: Are They Coming for Language Learning? 29:20 – Duolingo's Biggest Mistake: “We Waited Too Long on This…” 39:30 – Duolingo's Secret Sauce: What Investors Always Get Wrong 45:00 – Would You Go Public Today? Severin's Surprising Answer 49:00 – Best and Worst Parts of Going Public—A Rare Honest Take 51:00 – Should Europe Give Up? Severin's Unfiltered Opinion 56:00 – Harsh Truth: “Europe Can't Win Unless the U.S. Screws Up” 59:10 – Why Founders Have to Move to the US to Optimise Their Chance of Success 1:01:00 – Why Union Square Was the Only VC to Say Yes 1:03:00 – The Real Value of Tier 1 VCs (Even at Worse Terms) 1:05:00 – From PhD Student to Billionaire: Does Money Buy Happiness?  1:09:00 – Why Severin Sometimes Lies About His Job 1:10:20 – Founder Marriage Advice: “Write a Contract” 1:11:50 – How to Pick a Life Partner – Severin's Tuesday Night Test 20VC: Duolingo Co-Founder on The Doomed Future of Europe, Reflections on Money, Marriage and the Future of AI

Yuhki Yamashita is the Chief Product Officer at Figma, where he leads the development of one of the world's most beloved design platforms. Previously, he was Head of Product at Uber, overseeing the core rider experience used by millions globally. A master of product storytelling and team-building, Yuhki has redefined how world-class digital products are built and scaled. Items Mentioned in Today's Episode:  04:30 – "Simple is Lazy?" — Yuhki Challenges Product Dogma 07:45 – The Secret Behind Figma's New Product Ideas (Hint: Users Hack It First) 09:00 – From Hack Week to Roadmap: How New Figma Products Are Born 10:00 – Are PRDs Dead? Yuhki's Spicy Take on the Death of Specs 12:30 – The ‘Screenshot Test': Can Your Product Explain Itself in 1 Frame? 14:15 – Code Layers and ‘Living Designs'—This Demo Blew Everyone's Mind 15:30 – Designers vs Coders: Who Really Owns the Future of Product? 17:45 – The Most Controversial Product Decision Inside Figma 19:00 – Why Figma's Org Structure Could Kill the PM Role (For Real) 21:00 – Should Everyone Be a Designer and a Builder Now? 23:15 – Will Figma Have Fewer Engineers in 5 Years? 24:00 – Cursor, Windsurf & AI Coding Tools—What Figma Engineers Really Use 25:30 – AI's Dual Power: Lowering the Floor, Raising the Ceiling 27:00 – Figma's Biggest Product Flop? Yuhki Owns It 29:30 – The Magic of Product Storytelling—Even for Boring Compliance Tools 31:00 – Why Joy Must Be in the Product (and How Figma Bakes It In) 33:00 – Does Product Market Fit Even Mean Anything in 2025? 35:30 – Is Great Design Enough? Or Is It ALL About Distribution? 37:15 – Dylan's Secret to Early Growth: Hacking Design Twitter 39:00 – Community Mistakes Startups Keep Making 41:00 – The One Thing Yuhki Wishes He Could Change at Figma 43:00 – Should They Have Launched 4 Products at Once? Time Will Tell 45:00 – When Do You Know a New Product Is Doomed? 46:30 – Why Designers Still Don't Ship What They Design (and How to Fix It) 48:00 – From Uber to Figma: Yuhki's Playbook for Massive Product Swings 53:00 – The Adobe Deal Breakup—How Figma Rallied 56:00 – What Yuhki Needs to Improve as a Leader (His Own Feedback Review) 58:00 – The Product Leader He Admires Most—and Why 59:30 – What Figma Still Gets Wrong About Product Culture Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.

Items Mentioned in Today's Episode: 04:11 Owner's New $120M Round at $1BN 06:05 Why Series A is F****** Today 14:55 Could Tiger Global Be Saved by OpenAI and Scale 22:43 Why SBF is the Greatest Investor of the Last Decade 31:34 Why No Individuals Should Invest in Venture Funds 36:27 Why Microsoft Laying 3% of Their Workforce Off is not Enough 41:38 OpenAI's New CEO: Non-Technical CEOs Running OpenAI 44:48 Why Big Funds are Investing in Perplexity 54:43 Why Clay Should Raise a Warchest and Go to War 01:00:05 The Impact of AI on Marketing and Sales  

Immad Akhund is the CEO of Mercury. Launched in 2019, Mercury has raised $500M in funding from Sequoia, Coatue, CRV, Andreessen Horowitz and others. He is a former part-time partner at Y Combinator and is an active angel investor, with more than 350 investments in startups including Rippling, AirTable, Rappi, Applied Intuition, and Substack. In Today's Episode We Discuss: 04:38 Exclusive News: New Fund Announcement 05:15 Lessons from 350 Angel Investments 12:27 Why Founders Should Always Push for the Highest Price 14:40 Biggest Wins and Misses in Angel Investing 22:56 How Sequoia Came to Lead the Series C for Mercury 31:32 Why Move From Angel to VC 33:41 Is It Wrong For Founders to Also Have Funds with LP Capital? 36:28 AI Investments: Overhyped or Worthwhile? 41:14 Raising a First Time Fund: Challenges & Surprises 49:47 The Future of Venture Capital 54:36 Quickfire Questions and Reflections  

Eléonore Crespo is the Co-Founder and CEO @ Pigment, one of Europe's fastest-growing companies. With Pigment, Eleonore has raised over $397M from the best in the world including ICONIQ, Greenoaks and IVP to name a few. Prior to Pigment, Eléonore was on the other side of the table as an investor with Index Ventures. In Today's Episode We Discuss:  [04:10] “I had 3 surgeries. That's when I knew I had to become a founder.” [06:50] Why Index Ventures isn't on her cap table [08:40] Eleonore's CIA-style co-founder hunt (she literally made a target list) [11:50] Co-CEOs: “We talk 3x a day. That's our superpower.” [13:30] The boutique coffee metaphor for product excellence [15:40] Yuri Milner's 4 traits of legendary founders (one is shocking) [17:30] “Hiring is everything. I hunt talent like a football scout.” [19:00] Wild Olympic Games story → led to hiring a top CFO [24:50] How she filters out title-chasers and political hires [29:30] “Too much process? I make teams list the dumbest ones.” [33:00] Her blunt answer on whether Europe can produce scale execs [35:00] Why she raised so much money… even when they didn't need it [38:50] Board power is real: “They can fire you. I've seen it.” [43:30] Rob Ward's counter-cyclical advice: double down during a downturn [44:50] “We closed a massive US deal… at 2am… while drenched in rain.” [47:10] Selling into the US as a European founder—her full playbook [50:20] The hardest part of being a CEO no one talks about [54:00] “Children remind you what happiness is.” [56:30] “I don't fast. That would make me unhappy.” On longevity culture [59:20] Why her husband knows nothing about Pigment [01:04:20] “Forget $50B. I want to build a $200B company.” Follow Eleonore Crespo LinkedIn: Eleonore Crespo Pigment: pigment.com Subscribe to 20VC for more conversations with the world's best founders and investors.  

Today's Topics: 04:44 Analysis of $3 Billion Windsurf Acquisition 12:39 Will Mega Funds Win the Future of Venture Capital 18:39 Does Every Fund Have to do Pre-Seed to Win Series A and B Today 27:53 Why AI Will Create Massive Unemployment 31:06 The $100,000 Bet on the Future of Work  35:52 Why Venture Has Become a Bundled Good 37:52 Why Stage Specific Firms Will Win: a16z vs Benchmark 40:16 What Does Harvard Losing It's For Profit Status Mean for Venture 42:57 Why AI is Maiming and Not Killing Growth Companies on the Path to IPO 45:41 Decagon Raises 100x ARR: The Breakdown 52:50 Why VCs Are Upside Junkies and What That Means Today 01:03:37 Olo Looking to Sell: What Happens When Public Companies Want to Sell  

Bucky Moore is a Partner @ Lightspeed Venture Partners, announced exclusively in the show today on 20VC. Prior to Lightspeed, Bucky spent an incredibly successful 7 years at Kleiner Perkins working with Mamoon Hamid to build one of the most successful early stage firms of the last decade. Bucky has made investments in the likes of Prisma, Netlify, Browserbase and more.  In Today's Episode We Discuss: 03:07 Big News: Joining Lightspeed Venture Partners 04:09 Why Mega Platforms Will Win the Next 10 Years of VC 09:33 Are Foundation Model Companies Good Venture Investments 16:04 What Applications Will Model Providers Buy/Build? What Will They Not? 22:03 How to Approach Price Sensitivity in a World of AI 28:25 Why is it BS to do Market Sizing When Making Investments in AI 34:03 Is the Future of VC Domain Specialization 38:38 How to Know What Company Wins in Super Competitive Markets 41:06 Why Every Firm Has to do Pre-Seed To Win in VC Today? 44:43 The Risks of Multi-Stage Investing: Is Signalling Risk Real? 48:53 Investing Lessons from Leading Rounds in Glean and Windsurf 56:54 Quick Fire Round: Lessons from Mamoon, Fave CEO, Next 10 Years  

Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce.  In Today's Episode We Discuss:  02:50 “What I Learned from Failing Early as a CRO” 06:06 The Most Effective Sales Strategy and the BS Sales Methodology 06:55 How to Build Sales Processes from Scratch 12:28 When and How to do Verticalised Sales Teams 14:15 How to Become World Class as Sales Prospecting and Outbound 17:21 How to Use Proof of Concepts to Win Enterprise Deals 22:04 Enterprise vs. Self-Serve: Both or One and How 30:09 Building a Sales Team from Scratch 37:39 Structuring the Hiring Process 41:14 How Founders F*** Up Hiring in Sales 46:25 Handling Salary and Title Expectations 51:36 How to Run Effective Deal Cycles 57:06:07 How to do Onboarding for New Sales Hires 59:07:48 How to do Post Mortems in Sales Processes 01:04:24 Negotiating Enterprise Deals 01:08:04 Quick Fire Round: Sales Tactics and Strategies  

In Today's Episode We Discuss: 03:56 Why The Risk Lever Has Been Turned Higher than Ever in VC 06:04 Why IRR is the Hardest Thing to Control 09:36 Is Lack of Liquidity Short Term Temporary or Long Term Structural 12:17 Why Fund Returners Are Not Good Enough Anymore 16:03 Sequoia: The Best Strategy at the Worst Time 26:30 What it Takes to be Good at Series A and B Today 34:14 Only Three Company Types Survive AI 41:35 ServiceNow: 25% Pop, WTF Happened 45:29 Palantir and SAP Ripping: Do Incumbents Win AI 49:43 Are Benchmark Wrong to Invest in Chinese Made Manus 01:00:52 Geopolitical Risks in Investments 01:11:36 European vs. US Tech Culture  

Taavet Hinrikus is a Partner at Plural, the early-stage fund that backs the most ambitious founders on a mission to change the world through technology. He co-founded Wise in 2010, where he was CEO and later Chairman, which went public in the first-ever direct listing in Europe in 2021. Prior to that, Taavet was Skype's Director of Strategy until 2008, having joined as its first employee. He's been an active investor for more than a decade,with personal investments in the likes of Bolt and Synthesia. In Today's Show We Discuss: 04:08 VCs are Spreadsheet Monkeys 05:41 Why Banker European VCs Suck More Than The Others 11:20 Why Serial Entrepreneurs Are Better 14:48 Why the 2:20 Fee and Carry Model in VC is Broken 18:01 What are the Biggest Ways VC Investment Decision-Making is Broken 28:26 Why is it BS when VC Firms Need Every Partner to Meet the Founder 31:24 When and Why Will Founders Realise Multi-Stage Firms are Bad Early Investors 34:35 Why Does Europe Need to Build it's Own Tech Now More Than Ever 37:24 Will Putin Invade More European Countries 39:29 What are the Dangers of Having US Made Tech in Europe 47:12 How Does the Change in Relationship Between the US and Europe Impact How We Build Our Tech Ecosystem? 52:36 Quick Fire Questions and Reflections  

Mayur Gupta is currently the CMO at Kraken, one of the largest crypto platforms in the world. Prior to that, he lead Marketing, Business Transformation and Growth at Gannett - USA Today Network, led Growth at Spotify and was the CMO at Freshly which eventually got acquired by Nestle. He was the first ever Chief Marketing Technologist at Kimberly Clark. In Today's Episode We Discuss: 03:25 Biggest Growth Lessons from Spotify 08:21 Role of Marketing in Product-Led Companies 13:35 How to Build a Growth Engine 20:40 Organic vs. Paid Growth Strategies 27:36 The Branding Dilemma: Performance vs. Brand Marketing 28:37 Creating Demand: The Role of Upper Funnel Marketing 29:35 Balancing Investment: Immediate vs Long Term Bets 30:03 Channel Saturation and Experimentation 31:42 Growth Strategies and Performance Metrics 34:54 Growth: Big Swings or Moving % Points 40:04 Successful Growth Experiments and Tactics 44:56 Quick Fire Questions and Final Thoughts  

In Today's Show We Discuss:  04:49 Breaking Down the $3BN Windsurf Acquisition 06:18 Why Sam Altman is Playing a Master Game 12:40 Why Multi-Stage Funds are Destroying Seed Managers 21:52 Are Endowment Funds F****** 27:38 What Would Rory Do If He Was CFO of an Ivy League Endowment Fund 43:38 The Denominator Effect and It's Impact on Venture Allocations 49:36 Why Revenue Multiple is BS & What You Need to Know 51:34 The Rise of AI Rollup Plays & Are They Good Businesses 55:29 Competitive Markets: How to Make Money in Them? 01:02:58 Why If You Can Guarantee 5x, You Should Always Do the Deal 01:11:56 Is SF The Only Place to Be Building Today  

Jason Wilk is the Founder and CEO of Dave, the greatest turnaround in the public markets of the last 12 months. Dave went public with a market cap of $4BN, just months later the company had a market cap of $50M. Today, they are back with a market cap of $1.1BN. In 2024, CNBC named Dave the best-performing financial stock in the country, achieving 900% growth. In Today's Episode We Discuss:  04:09 Do Rich Founders Make Better Founders 07:45 The Best Performing Fund Would Only Invest in YC Founders on Their Second Time 11:25 “We Went Public Too Late, It Was a Big Mistake” 17:53 Why Did Jason Choose to SPAC?  24:21 Why Does Jason Believe SPACs are Unfairly Demonised and Will Comeback? 29:47 How Does AI Change the Margin Structure of the Next Generation of Companies 33:14 Is Trump Better for Business than a Biden Administration? 38:35 Are We Heading into a Recession? Predictions for Next 12 Months? 46:26 Why Have No Neobanks Reached the Heights of Revolut in the US? 48:08 Why is the Opportunity in Low Income Banking Not High Income in the US? 50:07 Why Short Sellers Should Be Stopped and How Immoral They Are  

Rich Socher is the Founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of the AI startup MetaMind, which Salesforce acquired in 2016. He is widely recognised as having brought neural networks into the field of natural language processing, inventing the most widely used word vectors, contextual vectors and prompt engineering. He has over 150,000 citations and served as an adjunct professor in the computer science department at Stanford. In Today's Episode We Discuss: 04:10 Winners & Losers: OpenAI, Gemini, Claude 08:59 How Partnerships Could Decide the Winners in AI 12:42 China vs US: Who Wins the War for AI 25:50 How Society and Economics Needs to Change in a World of AI 34:04 What Jobs Will Be Replaced, What Will Not 36:04 How Europe Needs to Change It's Approach to AI 41:06 How AI Will Change Health and Longevity 43:10 AI in Consumer and Enterprise Markets 49:30 Quantum Computing and AI Misconceptions 56:57 Longevity, Personal Reflections, and Future Outlook  

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more.  Rory O'Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. In Today's Episode We Discuss: 04:23 What is Wrong with Billionaires on Twitter: Are They Depressed? 08:49 Why Does product Market Fit Mean Less Than Ever 11:50 Why is Venture Capital More Risky Than Ever and No One is Discussing It 16:17 Will Private Equity Save a Generation of SaaS Companies and VCs 23:53 a16z's $20BN Fund: Seriously? 31:29 Why Josh Kushner and Thrive Capital are Masters of the World 38:21 Why is Seed Investing for Suckers 45:49 Why Are $50 Million Seed Funds Useless 46:21 Founders Fund Raises $4.6BN: Analysis 52:00 How WIll LPs Change Their Approach to Venture in the Next Five Years 59:53 When Will IPOs Comeback? 01:09:15 Why Does it Not Make Sense for the Best Companies to IPO 01:09:51 Lost Ethics and Morals in Founder Secondaries and Term Sheets 01:22:58 Quickfire: OpenAI, Cursor, Deel vs Rippling      

Victor Lazarte is a General Partner @ Benchmark, one of the mot renowned venture firms in the world. At Benchmark, Victor has led deals into the likes of HeyGen and Mercor. As an angel, he was the first investor and board member of Brex, and as a Founder he scaled Wildlife Studios, bootstrapping into the largest gaming company in LatAm, with about 4 billion downloads.  In Today's Episode We Discuss: 04:10 Lessons Scaling Wildlife Studios to 4BN Downloads 04:49 Why Predicting the Future is Wrong When Starting a Company 07:11 Three Different Categories of Company in an AI World: Who Wins & Loses? 09:25 Why You Should Always Ask What a Founder Does in Their Free Time? 17:30 Two Traits That All the Best Founders Have? 23:17 Why If You Start a Company in SF You are 1,000x More Likely to be Successful? 35:30 Why Spreadsheet SaaS Investing is Dead 36:10 Why Replacing Humans is the Most Exciting Opportunity in AI 37:02 Why Knowledge Work Will Be Destroyed and What Happens Then? 37:30 Why China is a Stabilising Force for the US 38:59 China vs. US: The AI Race 42:33 Why All Students Today Should Study Computer Science 44:38 Why Portfolio Construction is BS 47:04 What Makes Peter Fenton One of the Best Ever 51:31 Why Duolingo Will Be One of the Most Valuable Companies in the World 01:00:17 Quick Fire Round: Insights and Predictions  

Aatish Nayak is the Head of Product at Harvey where he oversees product vision, strategy, design, analytics, marketing, and support. This is his third hypergrowth AI unicorn having previously held product leadership roles at Scale AI from 40 to 800 people, and Shield AI from 20 to 100 people.  In Today's Episode We Discuss: 04:21 Biggest Product Lessons from Scale AI 7:18 Why Product Managers Are Wrong: They are not the CEO of the Product 12:28 Why Market Selection is More Important than Anything Else 16:40 If Distribution is King then Product is President 22:06 Effective Product Strategy and Execution 26:24 How to Write the Best PRDs 31:01 Balancing New Features and Technical Debt 33:17 Analysing Retrospectives and Postmortems 33:55 Introduction to Pre-mortems 38:25 Biggest Product Mistakes and Lessons Learned 41:40 Evaluating AI Models and Lessons Learned 45:03 The Future of AI in Product Management 55:21 What Should Product People Learn to Win in a World of AI 59:37 The AI Talent War in San Francisco 01:01:26 Quickfire Round  

Tom Hulme is a General Partner @ GV and leads GV's European investing. He has led rounds in Monzo, Nothing, GoCardless, Lemonade, Snyk and is widely considered one of the best investors in Europe.  Stan Boland is one of the most successful and respected entrepreneurs in the UK.  In 1999, he co-founded Element 14 which was acquired by Broadcom in 2000 for $640 million. Following this, Boland co-founded Icera Inc. in 2002, a fabless semiconductor company which he sold to Nvidia for $367 million.  In Today's Discussion We Cover: 04:26 Is The UK's Biggest Problem a Talent Problem 09:50 Why We Need to Flood the UK With Venture Capital 10:38 What Europe Can Learn from Stripe and the Collisons 15:21 How the UK Can Use Visas to Retain the Best Talent 16:46 Why the Government Needs to Put 10x More Cash Into Fund of Funds 24:32 Is the London Stock Exchange F****** and Does it Matter? 34:38 What The UK Can Learn From Sequoia and the Norwegian Sovereign Wealth Fund 40:42 What is a “National Goal for Wealth Creation” & How Do We Implement It? 48:10 What are the Most Broken Elements of the UK Tax Regime 52:11 Is It Stupid to Remove the Non-Dom Tax Status 53:15 Why is Now the Time to Be Bullish on China 01:00:19 Biggest Lessons from Working with Jensen Huang 01:08:04 Quick Fire Round: Insights and Predictions    

Ernest Garcia is the Co-Founder and CEO @ Carvana. Under Ernie's leadership, Carvana went from a back-of-the-napkin idea to a $50+ billion public company, became the fastest-growing online used car retailer in U.S. history, and landed on the Fortune 500 in under 10 years. However, it was not all up and to the right, in 2022, the stock plummeted 99% to a market cap of just $400M. Today they are back with a market cap of $35BN, that is a 100x in the public markets and selling 400,000 cars sold annually, with a logistics network that rivals Amazon.  In Today's Episode with Ernie Garcia We Discuss:  04:12 Are all great founders just “stubborn egomaniacs”? 06:55 How Carvana Almost Died on Several Occasions 08:46 Is Carvana's Inability to get VC Funding a Sign the VC Model is Broken? 11:58 Operators vs. Strategists: What Hires Can Make or Break a Company? 21:46 Billionaire's Biggest Lessons on Parenting 26:52 Is Life About Happiness or Achieving 32:21 The Reality of Being a Public Company CEO 39:07 Why Companies Should Go Public  43:55 Why You Should Price Your IPO to Perfection with No Pop 50:50 “What I Wish I Had Known About Debt in Building Carvana” 52:32 Quick Fire Round: Favourite CEO, Marriage Advice, Carvana in 10 Years  

Ishan Mukherjee is the Co-Founder/CEO of Rox, a Sequoia-backed AI-powered sales productivity platform. Before Rox, he was the Chief Growth Officer at New Relic where he scaled the self-serve business from $0-$100M in ARR. Prior to New Relic, Ishan founded Pixie Labs (acq by New Relic). Before that he led product at Siri Knowledge Graph at Apple, Lattice Data (acquired by Apple), Premise Data, and Amazon Robotics. Ishan was also an early engineer in Kiva (acquired by Amazon) where he joined after graduating from MIT. In Today's Episode We Discuss: 04:50 Biggest Lessons Scaling New Relic's PLG to $100M in ARR 05:59 How to Do PLG and Enterprise at the Same Time 07:00 How to do Content in a PLG World 08:50 Performance Marketing or Organic Content: What Works for PLG 10:27 Why You Should Stop Marketing at Events 11:47 Why SEM is a Cartel 14:15 Why Unpaid Design Partners are BS 17:17 How AI Changes the World of Enterprise Sales: Commit-Based vs. Usage-Based  20:49 How to do Sales Compensation Plans 24:44 How to Ramp New Sales Reps 25:03 The Impact of AI on Sales Research 29:18 How to do Deep Customer Research in an AI World 35:56 Changing Spending Patterns in SaaS 41:41 Retention and Churn in Enterprise AI 43:31 The Future of Sales Teams with AI 44:45 Hiring and Scaling Sales Teams 54:28 Quickfire    

Welcome to The Daily Deal — the new show with Harry Stebbings and Jason Lemkin, where we break down the biggest stories in tech, venture, and B2B. From market meltdowns to billion-dollar raises, wild valuations, and the drama behind the deals. We're covering it all! Plus, we'll be joined by some incredible guests to go deeper on the moves shaping the future of our industry.  Today we discuss:  Tech stocks were hammered in late trading today in response to the Trump administration's plans to levy tariffs of between 10% and 49% on imported goods, with Apple shares falling more than 6%. Rippling Deal: Illegal or Hustle? Emergence Raises $1B for B2B Investments Cursor, Replit, Windsurf: Who Wins? Lots of gen AI startups are crossing into the $100M ARR club. The latest entrant is talent marketplace Mercor, last valued at $2B. Is triple triple double double dead? ScaleAI at $25B: Pricey or Potential?  Discussion with Bhavin Shah @ Moveworks: ServiceNow Acquires Moveworks for $2.5B: AI Craze Continues Sequoia Makes 25x on Wiz: Is M&A Open Again? USD Stablecoin issuer Circle has filed to go public. The company, which has raised $1.2 billion in VC money, reported $1.7 billion in 2024 revenue, with $155.7 million in net income. Oracle Cloud Revenue Up 23%: Old Guard Wins in AI? Salesforce Customers Love AgentForce, But Will They Pay? Dustin Moskovitz Retires from Asana: Is SaaS Too Tough? Discussion with Andrew Feldman @ Cerebras: Coreweave's Redemption Provision: A Time Bomb for Coatue? Can OpenAI's $12B Deal Save Coreweave from $5B Loss? OpenAI Won't Profit Until $127B in Annual Revenue A lot of young founders raising big in chips; bullish or bullshit?    

Kevin Scott is the CTO of Microsoft, where he leads the company's AI and technology strategy at global scale and played a pivotal role in Microsoft's partnership with OpenAI. Prior to Microsoft, Kevin spent six years at Linkedin as SVP of Engineering. Kevin has also enjoyed advisory positions with Pinterest, Box, Code.org and more.  In Today's Episode We Discuss: 04:10 Where is Enduring Value in a World of AI 10:53 Why Scaling Laws are BS 12:26 What is the Bottleneck Today: Data, Compute or Algorithms 15:38: In 10 Years Time: What % of Data Usage will be Synthetic 20:04 How Will AI Agents Evolve Over the Next Five Years 23:34: Deepseek Evalution: Do We Underestimate China 28:34 The Future of Software Development 31:53 The Thing That Most Excites Me in AI is Tech Debt 35:01 Leadership Lessons from Satya Nadella 41:13 Quickfire Round  

Dame Julia Hoggett is the CEO of the London Stock Exchange. Julia previously worked at the UK's Financial Conduct Authority as Director of Market Oversight and Head of Wholesale Banking Supervision. In Today's Episode We Discuss: 04:25 How to Become CEO of a National Stock Exchange 05:36 Why The Domestic Economy is F***** Despite the Boom in Financial Services 06:45 How Pension Fund Reform Dmaaged the UK Economy 09:31 Should the UK Copy the Canadian Pension Fund Structure 16:30 Will the Best Companies Like Revolut and Monzo List in London 24:17 Why Are Revolut Wrong to Want to List in the US 27:32 Are Companies Priced Lower in the UK vs US 32:05 Why is Stamp Duty a Perversity We Have to Change 35:46 Why is the Way the UK Thinks About Financial Services So Wrong 40:31 Quick Fire Round: Insights and Reflections  

Mitchell Green is the Founder and Managing Partner of Lead Edge Capital. Mitchell has led or co-led investments in companies including Alibaba, Asana, Benchling, ByteDance, Duo Security, Grafana, Mindbody, and Xamarin, among several others. In Today's Episode We Discuss: 04:31 How Bessemer Taught Me The One Golden Rule of Investing 06:48 Why AI Infrastrcture is the Worst Investment to Make 08:51 Why it is Comical to think there will be $BN one person companies? 09:26 WTF Happens To The Cohort of SaaS Companies With Slow Growth, Not Yet Profitable and $50M-$200M in Revenue 16:12 What is the Biggest Problem with the IPO Market 23:24 When is the Right Time to Sell in VC and How a Generation F******* it Up 27:37 Biggest Advice to Smaller Emerging Managers 40:13 The One Question That Tells You if a Business is Good 43:01 Why LPs are More Important than Founders 45:03 One Question Every LP Should Ask Their VCs 46:03 Why TikTok Does Not Matter to ByteDance and It Is a Screaming Buy 51:30 Why We Drastically Underestimate the Power of Chinese AI? 55:18 Why Social Media is the Most Dangerous Thing in Society 01:00:07 Quick Fire Questions  

Andrew Feldman is the Co-Founder and CEO @ Cerebras, the fastest AI inference + training platform in the world. In Sept 2024 the company filed to go public off the back of a rumoured $1BN deal with G42 in the UAE. Andrew is the leading expert for all things inference.  In Today's Episode We Discuss: 04:23 Where Was AI Landscape in 2015 When Cerebras Founded 05:57 NVIDIA's Biggest Strength Has Become Their Biggest Weakness 07:09 What Happens to the Cost of Inference? 08:55 Why Are AI Algorithms So Inefficient? 20:30 Why is it Total BS That We Have Hit Scaling Laws? 23:07 What Will Be the Ratio of Synthetic to Human Data Used in 5 Years? 31:37 What Specifically Was So Impressive About Deepseek? 31:51 Why is Distillation Not Wrong and OpenAI Need to Look in the Mirror? 32:34 Where Will Value Accrue in a World of AI? 34:08 How Will NVIDIA's Market Position Change Over the Next Five Years? 39:59 Why is the CUDA Lockin for NVIDIA BS? What is Their Weakness? 40:46 Why is Trump Better for Business than Biden? 49:41 Do We Underestimate China in a World of AI? 52:33 What is the Most Underappreciated Segment of AI? 54:00 Quickfire Round  

Elias Torres is the Co-Founder and CEO of Agency, the AI agent for customer success teams. Prior to Agency, Elias was the Co-Founder of Drift, a company he sold to Vista for $1.2BN Before that he started Performable, which he sold to Hubspot.  In Today's Episode We Discuss: 03:50 Do Rich Founders Make Better Founders: How Backgrounds Shape You 06:23 Speed: Why are Incumbents Slower than Ever 10:00 Quality: Why are Incumbents Worse than Ever 25:34 Why Was Selling Drift For $1.2BN a Massive Failure 33:30 How Did a Cushy Culture Kill Drift 37:01 What They Never Tell You About Selling for $1.2BN 41:08 How to Hire F******* Rockstars 46:52 The Biggest Mistakes Founders Make in Hiring 54:52 Everything You Think You Know About Working Parents is Wrong 01:02:00 Quickfire  

Peter Singlehurst is the Head of Private Companies at Baillie Gifford. He has led research on a wide range of private investments including Epic Games, Bending Spoons, Anduril, Solugen, Scopely, and Grammarly, as well as a number of private holdings that have since transitioned to the public markets such as Airbnb, Affirm, Warby Parker, Wise and Tempus AI.  In Today's Episode with Peter We Discuss: 04:24 How I Accidentally Came to Manage One of the Largest Private Investment Firms in the World 07:29 What I Learned Losing 100s of $Ms  10:22 The 10 Questions Baillie Gifford Needs to Answer to Make an Investment 15:53 Why We Did Not Double Down in Stripe and Turned Down Coinbase 33:10 The ByteDance Investment Case 36:33 Why Would Any Good Company Go Public Today 39:19 Growth Stage Investing Trends 40:46 How Anduril Becomes a $200BN Company 45:39 Is 2024 Different to the Madness of 2021 and 2022 47:18 The Decision-Making Process Inside a $217BN Firm 49:00 How Does Re-Investment Decision-Making Differ from Original Investments 55:56 Future of Growth Equity Investing 58:12 Quick Fire Questions  

Yamini Rangan is the CEO at HubSpot. The $32BN juggernaut that has revenues of $2.6BN, over 247,000 customers and 8,200 employees. Prior to Hubspot, Yamini served as Chief Customer Officer at Dropbox, and before Dropbox, she was VP of Sales Strategy and Operations at Workday.  In Today's Episode We Discuss: 04:16 Taking Over the CEO Role from the Founders 07:58 Wartime vs Peacetime CEOship 11:18 How to Scale Into Enterprise: What Everyone Gets Wrong 22:20 Why is B2B Not Winner Take All 29:33 How Does Hubspot Compete Against Salesforce 33:26 Where Does Value Accrue in a World of AI 37:40 How Does Yamini Use AI Everyday 41:17 What Does Hubspot Do When It's Core SEO Channel Dies 44:10 Quickfire Round: Satya Nadella, Parenting Advice, Biggest Concern 51:35 Closing Thoughts and Reflections  

Matt Biilmann is the Co-Founder and CEO @ Netlify. Under his leadership, Netlify has become one of the fastest-growing platforms for modern web development. Matt recently introduced agent experience (AX), a new way of thinking about how software is built and experienced in the AI era. Matt is also known for coining Jamstack, a concept that redefined how developers build for the web.  In Today's Episode We Discuss:  03:43 How Does the Design Process Change When Designing For Agents 06:27 How Does the Product Building Process Change When Building for Agents 12:52 Will AI Kill SaaS Tools 16:12 If Prototyping Becomes Phase 1: Does Figma Survive? 17:35 Is Chat the Best Interface for a World of AI 21:52 Why AI Services Will Be One of the Biggest Economies 27:24 Open vs. Closed Platforms in an Agent-First World 31:09 Specialization of Large Language Models 35:13 Shifting Labor Costs to Agent Spend 36:28 The Future of Stripe and What Happens with 100M Developers in the World 38:39 Quickfire Round: Insights and Predictions  

Niklas Östberg is the Founder and CEO of Delivery Hero, a global juggernaut now present in over 70 countries across four continents. In Q4 2024, the company announced GMV of $49BN with $12.8BN in revenue and $750M in EBITDA. They have made an astonishing 35+ acquisitions including $2BN for Glovo. Before launching Delivery Hero, Niklas co-founded Pizza.nu, leading its expansion across Sweden, Poland, Finland, and Austria. In Today's Episode We Discuss: 04:09 How Skiing Prepared Me For Life As An Entrepreneur 10:12 Losing $200M on Gorillas Investment 17:58 Quick Commerce: Does the Business Model Work? 25:09 How to Master M&A: Lessons from 35 Acquisitions 31:45 Evaluating Acquisitions: The Glovo Example 32:39 Cohort Analysis: Lessons from $49BN in GMV 34:35 Growth Strategies: What Worked? What Did Not Work? 38:27 Competing Against Uber and Doordash 41:40 Is Cash a Weapon in the War for Food Delivery 44:29 Why Are Emerging Markets a Good Investment? 48:21 Why Are European Markets Broken? Are Regulators Killing Europe? 51:57 Quickfire Round: Insights and Reflections

Jake Saper is a General Partner @ Emergence Capital, one of the leading venture firms of the last 20 years. Their many wins include being early investors in Salesforce, Zoom, Veeva and more. In total, the firm has invested $2BN and returned an astonishing $8BN in cash with much more to come.  In Today's Episode We Discuss: 04:45 The Zoom Investment Story 10:21 Founder, Market, Traction: Rank Them 26:37 Why Market Pull is the Most Important Thing and How to Know 27:23 Are the Best Deals Always Expensive? 28:25 What is the One Framework Emergence Use for Every Investment 29:08 Lessons from the 16x DPI Zoom Fund 30:44 Why Does Every Partner Do Reference Calls on Every Deal? 35:16 We Have Lied to SaaS Founders: The Revenue Rules Changed 37:53 Where Will Value Accrue in a World of AI?  41:37 Three Reasons Why AI Will Not Replace Vertical SaaS 46:38 Who Wins in AI: Startups or Incumbents? 50:09 Why Should Every Company Aim to Be a “Board Discussion” 55:12 Why is Jake Worried About AI's FTX Moment? 56:00 What Losing Billions on Salesforce Taught Us About Selling 01:00:07 Why Most VC Partnerships are Broken 01:03:07 Grok vs Anthropic vs OpenAI: Buy and Sell? 01:14:25 Quickfire Round: Insights and Reflections  

Julian Teixeira is the Chief Revenue Officer at 1Password, where he has grown B2B revenue over 8x and scaled a team of more than 450 in go-to-market. 1Password set the record for the largest raise in Canadian history at the start of 2022 and has raised nearly $1B in capital throughout his time with the company. Prior to 1Password, Julian served as the head of global sales at Lightspeed Commerce, a company he helped scale from startup to IPO and through over 10 acquisitions throughout his decade-long tenure.  In Today's Episode We Discuss: 04:27 Sales Lessons from Scaling to $1BN in ARR 05:20 How to Create and Master a Sales Playbook 07:53 Lessons on First Sales Hires 09:41 Setting Goals and Targets for Sales Teams 13:22 The Reality of Tech Sales Today 16:19 Evaluating and Managing Sales Reps 19:07 Outbound Prospecting and Pipeline Generation 22:22 Hunter vs. Farmer Sales Models 24:15 Compensation and Specialization in Sales Teams 28:56 Outbound vs Inbound Sales 32:47 Pipeline and Deal Reviews 37:37 Sales Tech Stack and Tools 38:40 Maintaining Sales Morale 44:55 Are Remote Sales Teams Less Effective 46:44 Final Thoughts and Advice This episode is brought to you by Capchase, helping SaaS companies grow without dilution. Learn more at capchase.com/20vc