Best The monkey is always Right Podcasts (2025)

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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 ... 1:11:17

1d ago1:11:17

1:11:17

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: In…

1
Fostering a Culture of Thought: Tactics for Modern Leaders 12:02

2d ago12:02

12:02

Diving beneath surface-level leadership advice, our conversation explores how to truly foster environments where thinking flourishes. We unpack two pivotal tactics from our new book that transform organizational culture: the power of reading and the counterintuitive approach of "staying stupid longer." Reading isn't just about information acquisiti…

1
Stolen Sausage Submarine 52:27

4d ago52:27

52:27

Kurt and Scotty talk about how the Chinese police corgi stole sausage from a child, a man flees police using submarine and noisy hungry frogs ruin farmer's life! Support this podcast by shopping our latest sponsor deals and promotions at this link: https://bit.ly/4a61tMk See omnystudio.com/listener for privacy information.…

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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 ... 1:01:32

5d ago1:01:32

1:01:32

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, Phil…

1
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 ... 1:17:24

7d ago1:17:24

1:17:24

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 part…

1
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 ... 1:13:57

9d ago1:13:57

1:13:57

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…

1
Unmasking the HR Urban Legend That's Killing Your Culture 16:03

9d ago16:03

16:03

Ever wondered why that technically brilliant hire turned out to be your biggest management headache? In our fascinating conversation Scott and Tammy reveal the critical blind spot in most hiring processes that leads organizations to repeatedly bring on problematic employees. The shocking truth? Skills and experience account for just 10-12% of what …

1
Mummy Sniffin Monkey F*ckin Beats with Kristen Schaal 1:07:00

11d ago1:07:00

1:07:00

Kristen Schaal joins Kurt and Scotty talk about how scientists taught monkeys to use money and first they stole and then sold sex, why mummies still smell nice and Steve Harvey gifted TV every year to teacher who said he would never get on TV! Support this podcast by shopping our latest sponsor deals and promotions at this link: https://bit.ly/4a61…

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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 ... 1:16:45

11d ago1:16:45

1:16:45

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:…

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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 ... 1:19:24

14d ago1:19:24

1:19:24

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 le…

1
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 ... 1:06:44

16d ago1:06:44

1:06:44

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:…

1
Can "Lazy Leadership" Help You? 26:16

16d ago26:16

26:16

Leadership transitions demand fundamental shifts in how we create value. Moving from frontline supervisor to executive means evolving from performing tasks to developing others who can multiply your impact exponentially. Yet this critical transformation trips up countless leaders who remain stuck in comfortable patterns of doing rather than teachin…

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Gone in 16 Seconds with Lili Trifilio 53:59

18d ago53:59

53:59

Lili Trifilio is back on Bananas! She talks to Kurt and Scotty about the time Andre the Giant let out a 16 second fart on The Princess Bride set, a toddler thinks John Wilkes Booth is hiding under her bed, China hosts first race of humans vs robots and a man steals 8 dump trucks! Support this podcast by shopping our latest sponsor deals and promoti…

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20VC: How We Made $800M on Coursera | We Lost Money on Uber and Made Money on Lyft | We Did 3x on Postmates in 18 Months | DPI is King, MOIC is BS | We Dodged Theranos and I Still Lost Millions with Larry ... 1:34:40

19d ago1:34:40

1:34:40

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 a…

1
20VC: SpaceX, Tesla, Neuralink: Elon’s Empire After the Firestorm | Are Circle and Coreweave Meme Stocks: IPO Analysis | Anduril Raises $2.6BN & Becomes Founders Fund's 1st and 2nd Largest Check Ever ... 1:16:12

23d ago1:16:12

1:16:12

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…

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There's Never Just One Right Answer: Moving Through Fear Together 16:06

23d ago16:06

16:06

Fear lies at the heart of resistance to organizational change. This revealing conversation explores how leaders can navigate the complex emotional landscape that emerges when teams face significant transitions. What makes change feel so threatening to many people? We unpack the psychology behind those fight-flight-freeze-appease responses that emer…

1
From Mouth to Butt in Japan 53:32

25d ago53:32

53:32

Kurt and Scotty talk about a museum in Japan where you can sniff animals butts, a Boston homeowner discovers his house is cut in half, food delivery driver tricks people into thinking he delivered a pizza to Mt. Fuji and snake falls in woman’s margarita! Support this podcast by shopping our latest sponsor deals and promotions at this link: https://…

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20VC: Fiverr CEO: ‘If You’re Not Adapting to AI, F* You. You’re Done | Why "Time to Copy" is the Most Important Metric in Startups Today | Why 99% of AI Companies Today Will Die | Why Governments Will ... 1:06:00

26d ago1:06:00

1:06:00

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…

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20VC: The Science of Storytelling: Three Steps to Master the Perfect Story | From Near Death Experience to Unicorn Startup: The Untold Story of Omaze with Matt Pohlson 1:25:51

29d ago1:25:51

1:25:51

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 st…

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20VC: Is Chamath Right: Is DPI The Only Thing That Matters | Does OpenAI Even Matter | Mary Meekers AI Report: The Analysis| IPO Breakdown: Chime, Circle & Thoma Bravo's New Fund 1:23:15

30d ago1:23:15

1:23:15

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…

1
Beyond the Easy Button 20:49

1M ago20:49

20:49

Scott and Tammy return from hiatus with exciting news—they've published a book called "Think" that addresses a pervasive modern problem: our collective habit of shallow thinking. Rather than suggesting people don't think at all, they observe that many of us operate with thinking "as deep as a parking lot puddle," functioning on autopilot and habitu…

1
Blowing it Up and Blowing it Out with Charlotte Dobre 48:18

1M ago48:18

48:18

Charlotte Dobre joins Kurt and Scotty to talk about a school forced to evacuate after kid brings grenade for show and tell, a TV anchor goes into labor on air and finishes entire morning broadcast, a postal carrier refuses to deliver mail to nudist colony and a postal worker arrested for DUI while on route! Support this podcast by shopping our late…

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20VC: Windsurf Founder on Will Model Companies Own the App Layer | Why Moats Do Not Exist in a World of AI | Why the Notion of Single Person $BN Companies is BS | Lovable vs Bolt & Cursor vs Windsurf ... 1:05:58

1M ago1:05:58

1:05:58

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 au…

1
20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best ... 1:18:34

1M ago1:18:34

1:18:34

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…

1
20VC: OpenAI's $6BN Jony Ive Deal | YC Is Both Chanel and Walmart—and Has Officially Won | Builder.ai Implodes and Hinge IPOs: Who Wins & Who Loses | Seed Is Easy. Series A Is Brutal & The Dirty Truth ... 1:19:44

1M ago1:19:44

1:19:44

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…

1
20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue ... 1:26:48

1M ago1:26:48

1:26:48

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 Zha…

1
Men are Psychopaths, Women Fall in Crevices 53:28

1M ago53:28

53:28

Kurt and Scotty talk about how psychopaths are more attractive, a woman falls into crevice trying to retrieve her cell phone, and a woman files for divorce after Chat GPT reads husbands affair in coffee grounds! Support this podcast by shopping our latest sponsor deals and promotions at this link: https://bit.ly/4a61tMk See omnystudio.com/listener …

1
20VC: ElevenLabs Head of Growth on Why You Do Not Need PMs | The 7-Part Launch Playbook That Gets 700K+ Views Per Product | The Truth About CAC, Payback & Performance Marketing in AI with Luke Harries 1:15:44

1M ago1:15:44

1:15:44

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 E…

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20VC: Chime IPO: The Breakdown | Why Fund Returners Are Not Enough & Seed is for Suckers | Are IPOs Dead & The Future of the Late Stage Private Market | Rippling vs. Deel Lawsuit: WTF Happens Now? 1:17:53

1M ago1:17:53

1:17:53

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…

1
Oh God My Phone 53:38

2M ago53:38

53:38

Kurt and Scotty talk about how in Finland mobile phone throwing is a national sport, a new MMA Jesus movie and a naked race! Support this podcast by shopping our latest sponsor deals and promotions at this link: https://bit.ly/4a61tMk See omnystudio.com/listener for privacy information.By Exactly Right and iHeartPodcasts

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20VC: Duolingo Co-Founder on Why $3M is Harder than $100M to Raise | Why You Should Always Take Tier 1 VCs Even at Worse Terms | Why Europe Can't Win Unless the US Screws Up | How AI Impacts the Future ... 1:31:43

2M ago1:31:43

1:31:43

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 Ferris…

1
20Product: Figma CPO on How Figma Builds Products: What Works, What Does Not | How Figma Does Testing and Product Reviews | The Future of Design, Engineering and Product with Yuhki Yamashita 1:01:51

2M ago1:01:51

1:01:51

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 product…

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20VC: Tiger Global Saved by OpenAI | Coatue's New Fund: Hype or Substance | Why SBF is the Greatest Investor of the Last 5 Years | Why Big Funds are Investing in Perplexity 1:14:37

2M ago1:14:37

1:14:37

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…

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Kindly Style Sea Steak with Mary Holland 52:30

2M ago52:30

52:30

Mary Holland joins Kurt and Scotty to talk about a man with brain implant asks for beer as first words, using the dishwasher to make a steak and a sea serpent chases vessel in kindly style! Support this podcast by shopping our latest sponsor deals and promotions at this link: https://bit.ly/4a61tMk See omnystudio.com/listener for privacy informatio…

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