Scott Wu is the co-founder and CEO of Cognition, the company behind Devin, the world’s first AI software engineer. On Friday last week they pulled off the acquisition of the year, acquiring Windsurf, following their licensing agreement with Google. Previously a world-class competitive programmer, he was a gold medalist at the International Olympiad in Informatics and a member of the U.S. Math and Physics Olympiad teams. Before Cognition, he was a founding engineer at Scale AI, helping shape the early AI infrastructure stack.
AGENDA:
00:00 – Why are founders walking away instead of going down with the ship?
01:05 – How did Cognition pull off the $220M Windsurf deal in just 72 hours?
04:45 – What really happened behind closed doors the weekend Windsurf was acquired?
07:15 – Did Google overlook a goldmine in the Windsurf team and IP?
09:00 – Who are the 100 people that secretly shape the future of AI?
12:30 – Can application startups ever gain leverage over foundation model giants like Anthropic?
14:15 – Is coding about to be replaced by simply describing what you want?
17:30 – 50% of new code is AI-written. Where does that go next?
20:45 – “We’ve gone from 0 to $80M ARR in 6 months. Quietly.”
25:00 – Are IDEs and agents just the training wheels for the real future of software engineering?
28:20 – If you could only back one—OpenAI or Anthropic—who’s the better bet?
30:00 – Why has Cognition kept its insane growth a secret… until now?
Agenda:
00:00 Windsurf was dead—then this deal changed everything
05:00 The Windsurf x Google x Cognition saga explained
09:00 The OpenAI deal collapsed—what really happened
15:00 FTC rules forced a brutal deal structure—who lost?
17:00 The investors’ returns: who actually made money?
21:30 Will Google’s corp dev team get fired over this?
23:00 Cognition’s genius $220M acquisition of Windsurf: Most brilliant Deal of the Year
26:00 The biggest recruiting flex in Silicon Valley this year
35:00 “Roll your own SaaS” is complete nonsense
38:00 Lovable vs Cursor vs Replit: who wins the coding war?
41:00 Why Lovable could be the ChatGPT of builders
44:00 Will these vibe-coded apps become durable businesses?
48:00 The shocking churn rates hidden inside AI SaaS
55:00 Are these $2B valuations actually... cheap?
56:30 Grok just destroyed GPT-4 in benchmarks—WTF?!
01:01:00 Why Grok might overtake OpenAI in the next 12 months
01:11:00 Meta just invested $3.5B in Ray-Bans—WTF?
01:12:30 Should every S&P 500 company buy Bitcoin now?
01:15:00 Will Meta kill open source? What happens to Llama 5?
Vlad Tenev is the Founder and CEO of Robinhood, the greatest story on Wall St of the last decade. In the previous 18 months, Robinhood has increased its net revenue by 58% to nearly $3B; a $500M loss in 2023 turned into a $1.1B profit in 2024. Robinhood’s stock is up roughly 4x, lifting their market cap to north of $80B. Today, Robinhood has nine lines of business that do over $100M in revenue.
Agenda:
00:00 – “Tokenization Is The Biggest Innovation in Finance”
03:28 – How Robinhood 4x’d Its Market Cap in 8 Months
06:40 – AI Writes 50% of All Net New Code at Robinhood
10:02 – Why Robinhood Built a Secret ChatGPT for Support
12:11 – The One Customer Type That Transformed the Business
15:29 – “CoreWeave Is Retail’s Way Into AI” — The Meme Stock Defense
18:05 – Inside Robinhood’s Tokenized Private Shares Product
21:23 – “Capital as a Service” — Vlad’s Wild Vision for Startup Fundraising
24:10 – The $100M Revenue Line Vlad Wishes He Could Kill
26:45 – Robinhood Is Building... Cash Delivery Trucks?!
29:55 – “We Were Shipping Nothing”: Vlad on the 2020–2022 Culture Crisis
33:20 – What Line of Business Will Be the Biggest For Vlad in 5 Years Time
35:11 – The One Competitor Vlad Actually Respects
36:55 – From Men’s Health to Japanese Toilets: Vlad’s Weirdest Quickfire Yet
38:40 – “I Was in the Dumps”: What 2022 Taught Vlad About Resilience
40:00 – Where Robinhood Is Headed: The Next Decade of Financial Infrastructure
Kieran Flanagan is the CMO at HubSpot, where he’s led the transformation of their growth strategy from SEO-led to multi-channel and AI-powered. Formerly SVP of Marketing, he helped scale HubSpot’s user base to millions and revenue past $2B. Before HubSpot, he drove breakout growth at Marketo and Salesforce. Kieran is one of the most respected voices in SaaS marketing and a pioneer in growth-driven content strategy.
Agenda:
00:03 – The Death of Growth Teams? Kieran's Wild Prediction
06:44 – AI Innovation Pods: The New Org Structure for Startups
10:18 – Email Personalization That Tripled Conversions
13:21 – From Software Budget to Labor Budget: The Shift is Happening
16:35 – The Big Lie: Why Autonomous Agents Still Suck
19:24 – The Secret Sauce Behind HubSpot’s Email AI Stack
21:44 – Segment-Based Marketing Is Dead. Enter Micro Audiences.
24:15 – Content Collapse: Why Google Organic Is Getting Torched
30:52 – The Future of AI SEO: 1 Product, 100 Pages, Infinite Prompts
33:16 – Memory = Moat: Why ChatGPT Is Becoming Unbeatable
35:46 – Prompt Engineering is the New Coding: Here's How to Win
41:03 – The Death of the Middle Manager Marketer
46:17 – OpenAI vs. Anthropic: Kieran’s $400M Bet
48:00 – Europe Is Falling Behind: The Harsh Truth on Regulation
52:39 – CMO Playbook 2025: Micro-Audiences, Creator-Led, AI at Scale
Agenda:
[00:00] The AI Talent Crisis No One’s Ready For
[03:00] Daniel Gross and Nat Friedman: Why Two Legendary VCs Walked Away From $1B to Join Meta
[12:00] Meta’s AI Talent Magnet: Will It Actually Work?
[15:00] Cursor Is Breaking the Market: Can Anyone Compete?
[18:30] OpenAI’s SBC Bombshell: More Stock Comp Than Revenue
[22:00] CoreWeave’s Power Play: Buying Their Landlords
[26:00] Is Circle Next to Go Shopping with Meme Equity?
[28:00] PE Is Back: The Olo Take-Private Explained
[35:00] Why Triple, Triple, Double, Double Is No Longer Sexy
[41:00] QSBS Hack: The Billionaire’s Tax Loophole You’re Missing
[48:00] Microsoft’s AI Layoffs: Salespeople Are Dead, Long Live Engineers
[50:00] “If You Need a Week to Learn AI, You Should Be Fired”
[53:00] Will Sequoia’s Sean Maguire Be Pushed Out? Place Your Bets
[57:00] Will There Be a Recession in 2025? Jason Bets $75K It’s a No
[1:00:00] Is Linda Yaccarino Still CEO of X by Year-End?
[1:03:00] Circle and CoreWeave’s Meme Rally: Real or Mirage?
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 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 celebrity experiences and luxury house draws. 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
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
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:
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:
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
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