20VC: The Twenty Minute VC
Fast, focused interviews with the top venture capitalists shaping AI investment. The pulse of where AI money is moving.
198 episodes curated
Episodes
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
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
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 IP
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
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 Re
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 Stag
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 | Su
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
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 Be
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 – Th
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
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
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
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
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:
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
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 Be
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 – T
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
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 O
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
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 Team
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 Futur
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 Du
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
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 OpenAI's New CEO: Non-Technical CEOs Running OpenAI 44:48 Why Big Funds are Investing in Perplexity 54:43 Why Clay Should Raise a Warchest and Go to War 01:00:05 The Impact of AI on Marketing and Sales
20VC Exclusive: Mercury Founder Launches First $26M Fund | Why Founders Should Take the Highest Price | Why Serial Entrepreneurs are Better | Why AI Is So Overhyped | The Future of Venture Capital wit
Immad Akhund is the CEO of Mercury. Launched in 2019, Mercury has raised $500M in funding from Sequoia, Coatue, CRV, Andreessen Horowitz and others. He is a former part-time partner at Y Combinator and is an active angel investor, with more than 350 investments in startups including Rippling, AirTable, Rappi, Applied Intuition, and Substack. In Today's Episode We Discuss: 04:38 Exclusive News: New Fund Announcement 05:15 Lessons from 350 Angel Investments 12:27 Why Founders Should Always Push for the Highest Price 14:40 Biggest Wins and Misses in Angel Investing 22:56 How Sequoia Came to Lead
20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce. In Today's Episode We Discuss: 02:50 "What I Learned from Failing Early as a CRO" 06:06 The Most