Episodes featuring 20VC with Harry Stebbings

Browse episodes where 20VC with Harry Stebbings appears as host or guest. View all episodes →

20VC with Harry Stebbings
The Most Intense Workplace Culture in America | The Journey from $0 to $2.6BN Valuation
20VC with Harry Stebbings · with Nico Laqua · May 30, 2026 · 2 recommendations

Nico Laqua, CEO of Corgi Insurance, talks with Harry Stebbings about building a $2.6B company through extreme work culture, hiring practices, and fundraising strategy.

20VC with Harry Stebbings
OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds
20VC with Harry Stebbings · with Jason Lemkin, Rory O'Driscoll · May 28, 2026 · 2 recommendations

Harry Stebbings, Jason Lemkin, and Rory O'Driscoll discuss OpenAI's S1 filing, SpaceX's IPO, and Anthropic's rapid revenue growth relative to OpenAI.

20VC with Harry Stebbings
Cerebras CEO on the Future of Data Centres, Token Costs & Memory | Should US Companies Sell to China
20VC with Harry Stebbings · with Andrew Feldman · May 26, 2026 · 9 products mentioned

Cerebras CEO Andrew Feldman talks with Harry Stebbings about why AI infrastructure demand is outpacing supply, and what that means for chip design, memory, energy, and US-China policy.

20VC with Harry Stebbings
Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow
20VC with Harry Stebbings · with Chad Peets, Chris Degnan · May 23, 2026 · 1 recommendation

Sales leaders Chad Peets and Chris Degnan join Harry Stebbings to discuss how to build strong sales teams, why to avoid hiring from big-name companies, and how to think about quotas and revenue metrics.

20VC with Harry Stebbings
Andrej Karpathy Joins Anthropic | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1
20VC with Harry Stebbings · May 21, 2026 · 9 products mentioned

The 20VC hosts break down a big week in AI and tech, covering Anthropic's $900B valuation, Andrej Karpathy joining Anthropic, Cerebras's 68% IPO pop, and SpaceX's planned $1.75T listing.

20VC with Harry Stebbings
The One Man Accelerator at The Four Seasons & Why VCs Can Be Sharks | Josh Browder
20VC with Harry Stebbings · with Josh Browder · May 18, 2026 · 15 products mentioned

Josh Browder, founder of DoNotPay, talks with Harry Stebbings about spotting real founders, avoiding VC traps, and running a lean, profitable startup.

20VC with Harry Stebbings
The Five Year Desert to Product Market Fit and a $5.3BN Valuation | Shiv Rao, Founder @ Abridge
20VC with Harry Stebbings · with Shiv Rao · May 16, 2026 · 5 recommendations

Shiv Rao, founder of Abridge, talks with Harry Stebbings about surviving five years before reaching a $5.3B valuation by building AI that captures doctor-patient conversations in healthcare.

20VC with Harry Stebbings
Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN
20VC with Harry Stebbings · with Ramp Raises · May 14, 2026 · 10 products mentioned

Harry Stebbings, Jason and Rory discuss Anthropic's compute deals with SpaceX and Google, its crackdown on secondary share sales, the Cerebras IPO, Ramp's $40 billion raise, and why slowing software companies are...

20VC with Harry Stebbings
Inside Legora: Jude Law Generated $50M Pipeline | Are They Undervalued at $5.5BN? | Patrick Forquer
20VC with Harry Stebbings · with Patrick Forquer · May 11, 2026 · 4 recommendations

Patrick Forquer, CRO of Legora, joins Harry Stebbings to discuss how Legora built a fast-moving enterprise sales operation, including generating $50M in pipeline in one month.

20VC with Harry Stebbings
Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries
20VC with Harry Stebbings · with Cliff Weitzman · May 09, 2026 · 7 recommendations

Cliff Weitzman, CEO of Speechify, joins Harry Stebbings to share lessons from meeting 100 top consumer CEOs, covering growth testing, AI-native engineering, and hiring for grit.

20VC with Harry Stebbings
Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down
20VC with Harry Stebbings · with Rory O'Driscoll, Jason Lemkin · May 07, 2026 · 1 recommendation

Harry Stebbings, Rory O'Driscoll, and Jason Lemkin break down Big Tech earnings, the Anthropic fundraise, and what it all means for AI valuations and IPO timing.

20VC with Harry Stebbings
Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada
20VC with Harry Stebbings · with Tobi Lütke · May 04, 2026 · 6 recommendations

Shopify CEO Tobi Lütke talks with Harry Stebbings about AI, layoffs, wealth creation, and why bad incentives matter more than bad technology.

20VC with Harry Stebbings
Inside Clay's Sales Playbook | Becca Lindquist
20VC with Harry Stebbings · with Becca Lindquist · May 02, 2026 · 2 recommendations

Becca Lindquist, Head of Sales at Clay, walks through the playbook that took the company to $100M+ ARR, covering hiring, compensation, deal qualification, and AI's role in sales.

20VC with Harry Stebbings
Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors
20VC with Harry Stebbings · with Jason Lemkin, Rory O'Driscoll · Apr 30, 2026 · 2 recommendations

Jason Lemkin and Rory O'Driscoll discuss Anthropic's $45B raise, Thoma Bravo handing Medallia back to creditors, and how AI agents could upend SaaS business models.

20VC with Harry Stebbings
$160B Market Cap, $5.48B Revenue, $10M EBITDA Per Head: Inside AppLovin’s Profit Engine
20VC with Harry Stebbings · with Adam Foroughi · Apr 27, 2026 · 6 products mentioned

AppLovin CEO Adam Foroughi talks with Harry Stebbings about scaling to a $160B market cap, surviving a 92% stock collapse, and running a lean, cash-focused business.

20VC with Harry Stebbings
Replit CEO: Why the SaaS Apocalypse is Justified & Why Coding Models are Plateauing | Amjad Masad
20VC with Harry Stebbings · with Amjad Masad · Apr 25, 2026 · 1 recommendation

Replit CEO Amjad Masad talks with Harry Stebbings about why AI coding tools threaten traditional SaaS, how to pick and combine AI models, and why coding models are hitting a ceiling.

20VC with Harry Stebbings
Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead?
20VC with Harry Stebbings · with Jason Lemkin, Rory O'Driscoll · Apr 23, 2026 · 1 recommendation

Harry Stebbings, Jason Lemkin, and Rory O'Driscoll discuss Cursor's $60B acquisition, Anthropic hitting a $1T secondary valuation, and which legacy design tools AI could make obsolete.

20VC with Harry Stebbings
Are SaaS Companies Cooked: Which Thrive & Which Die | Aaron Levie
20VC with Harry Stebbings · with Aaron Levie · Apr 20, 2026 · 10 products mentioned

Box CEO Aaron Levie joins Harry Stebbings to argue that AI agents will create more engineering, legal and operations jobs, and that software built on business logic and strong APIs can thrive.

20VC with Harry Stebbings
Jake Paul: Traditional VC is Toast & Attention is More Valuable than Cash
20VC with Harry Stebbings · with Jake Paul, Geoffrey Woo · Apr 18, 2026 · 1 recommendation

Jake Paul and Geoffrey Woo join Harry Stebbings to explain how their fund Antifund uses Jake's audience and cultural instincts to compete with traditional venture capital.

20VC with Harry Stebbings
SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race?
20VC with Harry Stebbings · with Jason Lemkin, Rory O'Driscoll · Apr 16, 2026 · 1 recommendation

Harry Stebbings, Jason Lemkin, and Rory O'Driscoll discuss the state of AI, what it means for SaaS companies, and whether SpaceX's $2 trillion valuation makes sense.