The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

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