20VC: Nat Friedman and Daniel Gross Bought with Zuck's $100BN AI Budget | Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens | Why Larry Ellison is the Smartest Man in Tech | Substance or Sizzle: What is Real and What is BS in AI

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 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.