20VC: Tony Fadell "The Father of The iPod" on Mentors, Self-Doubt, Vulnerability, His Relationship To Money, Why Entrepreneurs Need to Be Coachable, Why VCs Need To Be More Direct & Why The First Trillionaire Will Innovate Around Climate Change

20VC: Tony Fadell "The Father of The iPod" on Mentors, Self-Doubt, Vulnerability, His Relationship To Money, Why Entrepreneurs Need to Be Coachable, Why VCs Need To Be More Direct & Why The First Trillionaire Will Innovate Around Climate Change

Tony Fadell, often referred to as "the father of the iPod," is currently Principal @ Future Shape, a global investment and advisory firm coaching engineers and scientists working on foundational deep technology. Prior to Future Shape, Tony was the Founder & CEO @ Nest Labs, the company was ultimately acquired by Google for a reported $3.2Bn. Before Nest, Tony spent an incredible 9 years at Apple Inc, where, as SVP of Apple's iPod division, he led the team that created the first 18 generations of the iPod and the first three generations of the iPhone. Fun facts, Tony has filed more than 300 patents for his work and is also a prolific angel investor having invested in the likes of mmhmm and Nothing to name a few.

In Today's Episode With Tony Fadell You Will Learn:

I. The building blocks of an entrepreneur

What was the moment that Tony realised that he wanted to be an entrepreneur?

"I got my first money when I was in third grade, because I had an egg route. We'd go get eggs from the farmer, and I'd load them in my wagon. Then my younger brother and I would go door to door around the neighborhood, and we'd sell eggs. And that was an every week or every other week situation. And I got money in my hands. And I was like, Oh my God, I can do whatever I want with that money – I don't have to ask anybody, I can just do it. And so that was the level of freedom that, especially when you're young, feels really cool. And then as I got older, I started to buy Atari video game cartridges for my 2600 (yes, I'm that old!), and that was really, really fun too."

What was the biggest lesson that Tony learned from his father on sales and building trusted relationships?

"And he said, very clearly, Look, this is a relationship. If I make this person successful, he's gonna want to come back to me over, and over, and over. But if I sell him something and it doesn't sell, and he has to discount and he loses money, he's not going to come back. Even if I don't have the right product, I'll tell him where to go to get the right product they're looking for, or if they're picking the wrong one, I'll tell them, here's the right one, because my job is to make them successful. Because if they're successful, they'll come back to me year after year after year. And even when we have a down year, they're going to trust me, and they're going to come back."

II. Reflections on experience

How does Tony Fadell think about and assess his own relationship to money? How has it changed over the years?

"So my relationship to money now is that it's just a means to make change happen. And so literally, for me, I can just have a backpack, my computer, my phone, a couple of roller bags with my clothes. And that's enough to live life with my family. I don't need all this other stuff. COVID taught me that even further."

How does Tony determine true friendships vs transactional relationships?

"If it's not a reference – if it's not coming from somebody saying, Hey, you really need to meet this person – I take everything with a grain of salt. With anybody who comes to me cold, I think they probably want something. I try to find that out through the network, Do you know this person? What are they about?"

III. Tony Fadell on becoming a mentor

Why does Tony Fadell believe that founders have to be "coachable"?

"I think anybody who's trying to do something that the world has never seen before, or trying to work with people who are, they'd better be coachable. Because you're going to be so narrowly focused, you're going to be so heads down, you're going to be so on a mission, that sometimes you'll be blinded, and you'll need somebody to come from left field and go, Wait a second, dude, you're not thinking about this right."

What are the core signs that an individual is coachable?

  1. Trustworthiness

2. Willingness to listen

What does Tony believe is the right way to deliver advice without fluff?

"First, it's about trust. You have to be able to have a trusted relationship with somebody. And second, there are different ways of delivering a message. You can deliver a message the first time in an iron-fist-in-a-velvet-glove kind of way. But sometimes the velvet glove is going to come off."

How do people make mistakes when giving advice?

"I'm in too many board meetings; we have over 200 investments. I've seen all kinds of different CEOs and different boards, where the investors don't want to feel like they're going to get a bad rep because the CEO is going to say something if they say something negative."

What does Tony Fadell advise founders when it comes to finding mentors?

"Usually, a really great mentor is going to be highly selective. They're going to be like, I don't want to work with you. They only have so much time for people who are actually coachable."

What are the characteristics of the best mentors?

"You're gonna have tough love with them, you're gonna say things that they don't want to hear, you're not going to be liked all the time. Hopefully, one day, you'll be respected if not liked. And that's what it means to be a mentor."

IV. Changing perceptions

How does Tony assess his own relationship to self-doubt?

"Everyone goes through imposter syndrome. Everyone does. We all have gone through it, I go through it. Because you know what, when you're doing stuff you've never done before, and you're changing the world, no one else has done it either. No one else has done it either. That means it's okay. And I always say, if you don't have butterflies in your stomach each day, you're either not paying attention, or you're not pushing hard enough and taking enough risk."

What are Tony's views on failure?

"Now, there's taking stupid risks versus risk mitigation and taking calculated risks. But you should always be living on the edge of pushing yourself because that's where the growth is, that's where the change is happening."

Does one learn more from success than from failure?

"How we do and change the world is through the same method. We go do, and then we fail, and then we learn from that, and then we do again."

What does Tony mean when he says, "do, fail, learn."

"Look, it's do, fail, learn; do, fail, learn. There's no such thing as learn and then you're able to do. No, no, no. When you really learn in life is after you've tried to do it."

What is the right way for entrepreneurs to present their boldest of ambitions?

"Look at Elon now. If he was pitching what he's doing now 15 years ago, people would go, No way! A few people, like Jurvetson and others, said, Yeah, sure, okay, great. But very few people would get behind that huge boldness."

"So what they do is – and this is what I've had to do – they start and just pitch that simple 'What's the next three to four years look like?' and never tell anybody about the big picture. Because you scare most people off."

How do investors need to change how they think about ambition and upside?

5.) Why does Tony believe the first trillionaire will originate from the climate change space? Why is the majority of plastics recycling total BS today? Why does Tony believe we need to fundamentally transform our economies? How do funding markets need to change to fund this structural reshaping of society?

Jaksot(1391)

20VC: Scott Galloway on Are Billionaires Happy & The Impact of Money on Psychology and Self-Worth | Becoming a Better Father & Husband | Why We Should Drink More and Not Work From Home | The Tinder Effect & How it Makes Young Men Radical

20VC: Scott Galloway on Are Billionaires Happy & The Impact of Money on Psychology and Self-Worth | Becoming a Better Father & Husband | Why We Should Drink More and Not Work From Home | The Tinder Effect & How it Makes Young Men Radical

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

7 Heinä 1h 10min

20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents

20VC: Figma's IPO: The Full Breakdown | Index Returns $3.5BN on Two Deals | Why Melio's $2.5BN Acquisition is "Discouraging" | Asana's New CEO and the Great Founder Exodus | Oracle's $30BN AI Deal and What it Means for Incumbents

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

3 Heinä 1h 11min

20VC: Inside KKR's Monster $8BN European Fund | The $500M Turkey Gamble That Went Wrong | Do Andreessen & General Catalyst Scare KKR? | Will AI Kill the PE Model? | Can The PE Model Survive without IPOs and Where is the Liquidity with Philip Freise

20VC: Inside KKR's Monster $8BN European Fund | The $500M Turkey Gamble That Went Wrong | Do Andreessen & General Catalyst Scare KKR? | Will AI Kill the PE Model? | Can The PE Model Survive without IPOs and Where is the Liquidity with Philip Freise

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

30 Kesä 1h 1min

20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

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

27 Kesä 1h 17min

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

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

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?

26 Kesä 1h 13min

20VC: The Wild Story Raising $450M From Masa and Softbank | Why My Biggest Mistakes Came From Listening to VCs | Why 100 VCs Turned Us Down | Why European Founders Are Tougher Than US Founders with Johannes Reck, GetYourGuide

20VC: The Wild Story Raising $450M From Masa and Softbank | Why My Biggest Mistakes Came From Listening to VCs | Why 100 VCs Turned Us Down | Why European Founders Are Tougher Than US Founders with Johannes Reck, GetYourGuide

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?

23 Kesä 1h 16min

20Product: How Duolingo Build Product 10x Faster with AI | Duolingo's Biggest Lessons on Paywalls, Push Notifications and In-App Purchases | Why Small Teams are the Future of Product | Why PMs Will Become Extinct with Cem Kansu, CPO @ Duolingo

20Product: How Duolingo Build Product 10x Faster with AI | Duolingo's Biggest Lessons on Paywalls, Push Notifications and In-App Purchases | Why Small Teams are the Future of Product | Why PMs Will Become Extinct with Cem Kansu, CPO @ Duolingo

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

20 Kesä 1h 19min

20VC: Scale's $14.8BN Acquisition: Is Scale a Dead Man Walking / What Did Meta Buy | Chime IPO: Are IPOs Hotter Than Ever | Ramp Hits $16BN Diluting Only 1% | Salesforce, Slack and Dropbox Falling Behind: Are Incumbents Losing Ground

20VC: Scale's $14.8BN Acquisition: Is Scale a Dead Man Walking / What Did Meta Buy | Chime IPO: Are IPOs Hotter Than Ever | Ramp Hits $16BN Diluting Only 1% | Salesforce, Slack and Dropbox Falling Behind: Are Incumbents Losing Ground

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.

19 Kesä 1h 6min

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