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The Twenty Minute VC

Hosted by Harry Stebbings

The world's largest venture capital podcast. Harry Stebbings interviews the top VCs, founders, and operators in tech — from Sequoia's Doug Leone to Benchmark's Bill Gurley to Snowflake's Frank Slootman. Rapid-fire questions that cut to the essence of building.

76 episodes processed

Host Profile

Themes
business
Style

daily, 25m episodes

25 canon references20 curious36 novel

Episodes

# · Sep 10, 2026 · 01:18:07

Harry Stebbings discusses the week's biggest tech and venture capital stories: Jensen Huang's AGI claim, OpenAI's GPT Astra, AI safety debates, Tesla's robotaxi ambitions, venture deal drama, and startup funding rounds.

# · Sep 7, 2026 · 1h 10m
Jean-Denis Grèze

Jean-Denis 'JD' Grèze, founder of Town (reportedly raising at a $1B valuation), joins Harry Stebbings to discuss the AI assistant race. Grèze argues the assistant market is not a bubble because it addresses a real product failure—the fragmentation of work across hundreds of SaaS apps. He explains why Town bets on one universal AI assistant over multiple specialized ones, how they choose models to protect margins, and why the assistant that reduces mistakes to one in a thousand will win. The conversation covers competition with GrokBot, Instinct, and big tech; how AI has already changed hiring; and what it would take for Town to become a $100B company.

1 editorial
# · Sep 5, 2026 · 01:05:13
Cliff Weitzman

Cliff Weitzman, co-founder and CEO of Speechify, joins to discuss the strategic decision to build proprietary data centers rather than relying on cloud providers, and the competitive dynamics of the AI voice space. He explains how ElevenLabs leapfrogged Speechify and what that failure taught him about talent acquisition and focus. The conversation covers the hidden economics of GPU purchasing, why the screen will be replaced by voice as an interface, and how Weitzman plans to apply AI to cure his brother's disease.

3 editorial
# · Sep 3, 2026 · 01:17:40

Harry Stebbings discusses a packed week of AI and tech news, including Nvidia's blockbuster earnings and its pending acquisition of Hugging Face. He covers the escalating OpenAI-Musk feud, a massive AI-powered cyberattack, and the rising valuations of AI assistant and coding agent startups. The episode explores the concept of compound startups, Salesforce's AI pivot to Claude and outcome-based pricing, and the collapse of the Stripe-PayPal deal. Harry also touches on privacy concerns around police surveillance cameras in Texas.

10 editorial
# · Aug 31, 2026 · 01:03:37
Aaron Katz

Aaron Katz, CEO of ClickHouse, joins 20VC to explain why he believes the AI sector is not in a bubble, pointing to real revenue and transformative adoption. He explores how AI agents becoming software buyers will reshape enterprise sales, and why open models will dominate token volume despite enterprise caution. The conversation also covers talent competition, the future of remote work, the value of college, and the impact of AI on jobs, drawing on Katz's experience scaling Elastic and ClickHouse.

1 canon
# · Aug 29, 2026 · 1h 29m
Eno Reyes

Eno Reyes, Co-Founder and CTO of Factory, joins Harry Stebbings to discuss the rapidly evolving landscape of AI coding tools. The conversation covers whether Anthropic's coding business could reach a $2 trillion valuation, why the smartest AI models may also be the cheapest, and the fate of neo-labs in an overcrowded market. Other topics include the impact of continuous-learning models on platforms like Factory, whether American enterprises should work with open-source Chinese models, and how AI founders need to rethink what a great outcome looks like in this new era.

# · Aug 27, 2026 · 01:22:40

Harry Stebbings breaks down a blockbuster week in AI, starting with NVIDIA's $12B acquisition of Poolside and its investments in Mercor and Perplexity. He discusses OpenAI's confirmed 2027 IPO, Anthropic's bold $30 trillion revenue assumption, and Citadel's exit from its AI trade. The episode also covers the boom in open models, Stripe's reacceleration, and VC warnings that customer service, defense, and robotics are overinflated sectors.

# · Aug 24, 2026 · 01:18:41
Julien Bek

Julien Bek, Partner at Sequoia Capital, pulls back the curtain on the firm's investment committee dynamics, revealing lessons from legends like Don Valentine and Doug Leone and detailing how the SpaceX and Citadel deals went down. The conversation covers what Sequoia specifically looks for in founders—including why a flawless pitch can be a warning sign, how to judge exceptionalism in 30 minutes, and what a founder's childhood reveals. Bek also shares his contrarian takes on AI's impact: that agents becoming the customer will make UI irrelevant, that answer-engine optimization could surpass SEO, and that the next trillion-dollar company may masquerade as a services business.

2 novel
# · Aug 22, 2026 · 1h 6m
Jerry Murdock

Jerry Murdock of Insight Partners joins Harry Stebbings to discuss the state of the AI market, arguing that an AI valuation bubble will burst within the next 18 months and that half of all current 'neocloud' companies will disappear within 36 months. Murdock also assesses the competitive landscape among the major AI labs, suggesting open-source models will surpass closed-source leaders like OpenAI and Anthropic, while framing the rise of Chinese open-source AI as a much greater threat than chip exports. The conversation extends to the Mag 7, where Murdock makes a bull case for Microsoft and expresses deep skepticism about Meta's and Apple's AI strategies, warning of an impending cybersecurity crisis driven by AI-powered attacks.

3 novel2 editorial
# · Aug 20, 2026 · 01:13:12

Harry Stebbings analyzes a week of mega-deals in AI and enterprise software: SpaceX buys code editor Cursor for $60 billion; Stripe invests $7 billion in model aggregator OpenRouter; Anthropic turns its first profit on $11.5 billion quarterly revenue; Silver Lake acquires Workday for $43 billion; and Lovable and Higgsfield raise massive rounds at wildly different valuations. The episode examines the strategic logic behind these moves and what they signal about the state of AI, SaaS, and venture capital.

3 editorial
# · Aug 17, 2026 · 01:06:36
Andrew MacDonald

Andrew MacDonald, Uber's longest-serving employee and now President and COO, shares untold stories from the company's early days, including the brutal battle in China and lessons from Travis Kalanick. He explains why Uber chose to divest its self-driving unit to focus on core rides and delivery, and why markets like India and Brazil will delay a fully autonomous future. MacDonald also reveals an internal 'SWAT team' of 30 elite AI engineers and argues that companies that don't adopt frontier AI models risk being unbundled by competitors. Finally, he discusses why chat-based interfaces aren't the right solution for everything, echoing Airbnb's CEO Brian Chesky.

2 editorial
# · Aug 15, 2026 · 1h 18m
Matt Swulinski

Matt Swulinski, Head of Growth at Viktor and former growth lead at Wispr Flow and Superhuman, joins 20Growth to share his playbook for building a $100M growth engine. The conversation covers why SaaS founders should adopt e-commerce growth tactics, how product-led growth changes when AI agents become the customer, and the mechanics of paid acquisition—from building a tracking stack to producing 500 ads a month. Matt also breaks down referral programs, paywall loops, structuring an AI-native growth team, and which growth channels are most overrated and underrated in 2026.

# · Aug 13, 2026 · 1h 26m 39s

This episode of The Twenty Minute VC covers a series of major technology business stories: Canva's growth slowdown as AI costs escalate, a looming 'Great Software Reset' that will punish AI hesitancy, and valuation concerns for Canva alongside a liquidity trap for limited partners. The show also discusses Google's AI talent departures, why Google can't afford to cure Alzheimer's, political backlash against data centers, Elon Musk's $55BN Terrafab bet to reduce TSMC dependence, Revolut's $50BN CEO pay package, and AI shopping plus Atlassian's revival and Airtable's difficult sale.

# · Aug 10, 2026 · 59:59
Alex Atallah

Alex Atallah, founder and CEO of OpenRouter, joins to discuss the reported $10B acquisition by Stripe, the lessons he learned bootstrapping and scaling OpenSea, why the founding thesis of OpenRouter proved wrong, and whether AI model routing is being commoditized. The conversation also covers the impact of falling token prices on the business, the alarming rise of Chinese open models surpassing US counterparts, whether the routing layer will be swallowed by agent frameworks, and Atallah's perspective on the ethics of distillation.

1 canon2 editorial
# · Aug 8, 2026 · 1h 25m
David Frankel

David Frankel, Co-Founder of Founder Collective, shares his contrarian views on the venture capital landscape. He warns that current tech bubbles are larger than past ones and will lead to significant failures, calling multi‑stage seed funds a recipe for underperformance. He brands pro rata rights the 'original sin' of venture, argues that a dot‑com‑style crash is inevitable, and predicts China could overturn the dominance of OpenAI and Anthropic. He also makes bold long‑term bets: a world where driving is obsolete and chemotherapy seems prehistoric.

5 editorial
# · Aug 6, 2026 · 01:15:36
Nikesh Arora

Harry Stebbings hosts a news roundup with Nikesh Arora, CEO of Palo Alto Networks, covering major AI and tech developments. Airtable sold for $1.285 billion to Bending Spoons, Leo Aschenbrenner's book on AI safety sparked a $16 billion deal with Citadel, and Anthropic's models demonstrated alarming security breach capabilities. Moonshot AI raised $3.5 billion at a $35 billion valuation amid China's AI price war, Valar Atomics tripled to a $6 billion valuation with Sequoia's nuclear bet, and Big Tech earnings signaled the next phase of the AI gold rush with Palantir leading. Procore acquired DroneDeploy for $900 million and Scale AI reached $1.5 billion ARR after the Meta deal fallout.

# · Aug 3, 2026 · 1h 4m
Anastasios Angelopoulos

Anastasios Angelopoulos, CEO of AI model evaluation platform Arena, discusses the state of the AI industry. Topics include Chinese models surpassing US benchmarks, the commoditization of models, and why America's open-source community lags behind China. Angelopoulos shares his views on enterprise fears of frontier labs, stubborn inference costs, and the rise of AI-enabled cyberattacks. He also explores the survival odds for neo labs, data as a trillion-dollar market, and whether model providers will swallow the application layer.

# · Aug 1, 2026 · 01:03:41
Joon Sung Park

Joon Sung Park, founder and CEO of AI simulation startup Simile, joins Harry Stebbings to discuss the company's $300M raise and $2B valuation. He argues the best AI companies win through proprietary data acquisition and clear reward functions, and shares how Simile closed Fortune 500 deals worth $10 million in weeks. Park also explores the future of prediction markets and whether simulation will render traditional markets obsolete, before offering fundraising advice for founders.

4 editorial
# · Jul 30, 2026 · 01:17:30

Harry Stebbings breaks down a packed week in tech and venture capital. Topics include Jensen Huang's open-weights letter isolating Anthropic, Etched's bold $300M challenge to Nvidia, the market's bizarre reaction to Google Cloud's 82% growth, and Travis Kalanick's $1.7B raise for physical AI startup Atoms. He also examines the explosive debate between Mark Pincus and Jason Lemkin over whether founders should quit when things get too hard.

# · Jul 25, 2026 · 1h 37s
Osvald Nitski

Osvald Nitski, Chief Product Officer at Mercor, discusses the AI data marketplace's explosive growth and the future of the industry. Topics include whether open-source models threaten data providers, why large enterprises remain hesitant to work directly with frontier labs, and the shift toward small, specialized AI models. The conversation also covers Mercor’s customer concentration risk, AI-generated code fueling a cybersecurity arms race, and the timeline for robotics’ mainstream breakthrough moment.

1 canon1 novel
# · Jul 23, 2026 · 1h 23m
Harry Stebbings (host analysis)

Harry Stebbings examines whether Chinese AI models (Kimi, Qwen) pose a genuine threat to OpenAI and Anthropic, debates the merits of a US ban on Chinese open-source AI, analyzes OpenRouter's positioning as an AI routing layer, and unpacks the strategic implications of Stripe's potential acquisition of PayPal. The episode covers infrastructure-heavy AI trends, late-stage venture capital's dominance, and supply chain bottlenecks in semiconductor manufacturing.

1 novel3 editorial
# · Jul 20, 2026 · 1h 17m
Lin Qiao

Lin Qiao, CEO of Fireworks AI (valued at $17B with $1B+ ARR), argues that the future of AI is not centralized AGI but millions of specialized models optimized for specific tasks. He explains why inference—not training—is the real infrastructure opportunity, how open-source models commoditize proprietary advantage, and why token costs falling 10x will trigger 100x usage explosion. The conversation covers valuation realities for OpenAI and Anthropic, whether enterprises can safely use Chinese open models, and the routing layer that may emerge as AI's $100B bottleneck.

3 novel1 editorial
# · Jul 18, 2026 · 1h 27m
Fred Turner

Fred Turner, founder and CEO of Curative, discusses one of the most explosive growth stories in startup history: scaling a COVID testing business from zero to $5 billion in revenue in nine months, growing from 7 to 7,000 employees, and processing over 206,000 tests daily. The conversation spans Curative's pivot into health insurance, the role of AI in restructuring the business, and Turner's views on the future of work, healthcare incumbents, and nuclear energy.

1 novel2 editorial
# · Jul 16, 2026 · 1h 22m 51s
Harry Stebbings

Harry Stebbings breaks down the biggest tech and venture stories of the week. He covers Apple's lawsuit against OpenAI, Meta's renewed AI offensive, and the sustainability of AI infrastructure spending. The episode also examines SK Hynix's record IPO, Jason Calacanis's shift from seed to growth, and Greylock's new $1.5 billion fundraise against a backdrop of venture strategy debates.

# · Jul 13, 2026 · 57:20
Avishai Abrahami

Avishai Abrahami, co-founder and CEO of Wix, discusses the SaaS market's misunderstanding of AI's impact on platform businesses, the economics of AI-powered "vibe coding," the strategic challenges of Wix's Base44 acquisition and massive buyback program, and why most AI customer support startups fail. He argues that Wall Street fundamentally misvalues Wix's core business and makes a contrarian prediction about AI hype cycles.

1 novel4 editorial
# · Jul 11, 2026 · 54m 46s
Arvind Jain

Arvind Jain, CEO of Glean (valued at $7.2B), challenges the narrative around frontier AI models winning in enterprise. He argues that 90% of frontier AI capabilities are already commoditized, that OpenAI and Anthropic won't own the app layer, that teams will actually grow larger (not smaller) with AI, that Microsoft is the real competitive threat, and that enterprises are increasingly questioning AI ROI. He also discusses why AI companies are making billion-dollar mistakes on token spend, why founders must move immediately, and why America will likely win the AI race against China.

3 novel4 editorial
# · Jul 9, 2026 · 1h 23m
Harry Stebbings (host); analysis of Sam Altman, Alex Karp, Zuckerberg, Jensen Huang

Harry Stebbings unpacks three major AI industry shifts: Sam Altman's controversial proposal to give Trump a 5% stake in OpenAI as a political hedge, Alex Karp's warning that enterprise customers don't trust frontier AI models and question ROI, and the rise of Chinese open-source alternatives (DeepSeek, Kling) challenging Nvidia and Western AI dominance. The episode explores regulatory pressure on frontier AI, the AI funding bubble's disconnection from real adoption, and whether China is winning the open-source war.

5 editorial
# · Jul 4, 2026 · 1h 8m
Clay Bavor

Clay Bavor, Co-Founder of Sierra (a $15.8B enterprise AI company serving 40% of Fortune 50), discusses the future of frontier vs. open models, the emerging $100K token budget constraint for engineers, and why forward-deployed engineers are becoming critical infrastructure for enterprise AI. Sierra has raised $1.5B+ and surpassed $150M ARR, making it one of the fastest-growing enterprise software businesses in history.

1 novel3 editorial
# · Jul 2, 2026 · 1h 17m
Dario Amodei

Harry Stebbings interviews Anthropic CEO Dario Amodei on the state of AI business models, open-source competition, geopolitics, and market consolidation. The episode covers Coinbase's 50% AI spend cut as a signal of market maturation, Anthropic's stance against open-source commoditization, regulatory concerns around Chinese AI, Microsoft's strategic challenges, and the emerging mega-trend of SaaS roll-ups exemplified by Bending Spoons' IPO. Core themes: the AI market is shifting from hype to unit economics, proprietary models face existential threats from open-source, and consolidation will dominate 2026.

1 editorial
# · Jun 29, 2026 · 01:00:44
KR Sridhar

KR Sridhar, founder and CEO of Bloom Energy, discusses the company's role in powering the AI revolution amid surging data center demand. He explains why electricity, not AI models, will determine AI race winners, why the AI capex cycle is not a bubble, and his long-term bet that Bloom's distributed power would be essential for AI. The conversation covers his 'failure is never an option' mindset, leadership lessons from Andy Grove, and a vision of energy sovereignty where power moves to the edge of the grid.

1 editorial
# · Jun 27, 2026 · 57m 12s
Paul Erlanger

Paul Erlanger, CEO of social-first trading platform fomo, explains how he raised $94 million from Benchmark, Index Ventures, and USV while growing to 600,000 users with a team of just 17. He challenges conventional startup wisdom: Robinhood's super-app strategy is misguided, founder-style equity should replace salaries, and 1-on-1s are unnecessary overhead. Erlanger also argues that AI will collapse org charts, taste beats AI in consumer startups, and the future of investing belongs to social trading networks and creator economies.

4 editorial
# · Jun 25, 2026 · 1h 24m

In this solo episode of 20VC, Harry Stebbings breaks down the biggest shifts in AI: Anthropic poaching Google talent, DeepSeek's $50B raise, Apple's memory supply warning, the $725B return question from Wall Street, experiments with AI finance agents, the erosion of defensive moats, and why open source now threatens OpenAI more than Anthropic ever did.

1 novel2 editorial
# · Jun 22, 2026 · 1h 14m
Nikesh Arora

Nikesh Arora, CEO of Palo Alto Networks, argues that AI token prices will collapse 90% over the next 3-5 years, which is ultimately bullish for the industry. He challenges the current enterprise AI deployment model, claiming most companies are using AI completely wrong by treating it as a tool rather than a system of intelligence. Arora predicts that memory will become the primary moat in AI, that transaction-based models will dominate over advertising, and that AI applications will replace traditional SaaS workflows by introducing autonomous decision-making capabilities that software never had before.

1 novel2 editorial
# · Jun 20, 2026 · 1h 18m
Ryan Peterson

Ryan Peterson, founder and CEO of Flexport, discusses the logistics company's $8B valuation, $450M revenue, and 30% YoY growth. He challenges remote work as ineffective for company culture, shares the story of raising $1B from Masa Son in an hour-long meeting, and offers candid perspectives on founder traits, hiring mistakes, fundraising strategy, and the role of CEO personality in building enterprise value.

4 editorial
# · Jun 18, 2026 · 1h 25m
Harry Stebbings

Harry Stebbings unpacks a watershed week in tech: SpaceX's historic $2.7T IPO and Elon Musk's instant wealth surge; the US government banning Anthropic's Fable model mid-launch; Mistral's $20B valuation push and the sovereign AI arms race; Salesforce acquiring Fin for $3.6B as legacy SaaS faces an existential AI reckoning; and the great capital rotation away from software toward AI infrastructure. A masterclass in how regulatory action, geopolitical competition, and AI disruption are reshaping tech valuations in real time.

2 novel3 editorial
# · Jun 13, 2026 · 01:21:24
Matan Grinberg

Matan Grinberg, founder of AI lab Factory, joins Harry Stebbings to discuss the future of AI models, arguing that open-source will dominate and that current spending will face a reckoning. He introduces the concept of 'token maxing,' explains why he dismisses fears of AI-driven job loss, and predicts elite companies will treat talent like NBA athletes. The conversation also covers his unconventional path from string theory to Sequoia-backed founder.

1 canon2 novel
# · Jun 8, 2026 · 1h 6m
Roman Chernin

Roman Chernin, Co-Founder and Chief Business Officer of Nebius, discusses why the AI infrastructure market isn't a bubble despite explosive growth. The conversation covers open source's impact on OpenAI and Anthropic, Jevons Paradox and demand elasticity for compute, the shift from training to inference and agents, and how Nebius competes against hyperscalers with vastly more capital. A key insight: Nebius could sell 10x more compute if it existed, suggesting the actual bottleneck is supply, not demand.

1 canon1 novel2 editorial
# · Jun 6, 2026 · 54m 31s
Jacob Lauritzen

Jacob Lauritzen, CTO of Legora (a $5.6B enterprise AI startup that hit $100M ARR in 18 months), discusses the real bottlenecks in software development in 2026. The conversation moves beyond the 'AI will write all code' narrative to examine what actually breaks in hypergrowth: hiring product talent, system design over code generation, the death of the design phase, and what happens when you scale a 250-person product team. Token maxing—throwing more AI at code generation—isn't solving enterprise problems; the bottleneck has shifted entirely.

# · Jun 4, 2026 · 01:35:51
Harry Stebbings

Harry Stebbings explores the seismic shifts reshaping startup finance and AI adoption in 2026. The episode covers Anthropic's IPO filing, Cognition's $1 billion fundraise at $26 billion valuation, the token budgeting crisis sweeping corporate America, and the uncomfortable reality that AI automation is forcing companies to choose between cutting engineers or cutting tokens. Key tension: venture is celebrating AI winners while incumbent software faces margin compression, and the startup world's obsession with 9-9-6 work culture clashes with its own productivity dreams.

1 novel1 editorial
# · Jun 1, 2026 · 01:15:23
Brendan Foody

Brendan Foody, CEO of Mercor (a $10B data provider to OpenAI and other major AI labs), argues that value in AI will accrue to the infrastructure layer, not applications, because the model itself is the product. He discusses why AI won't cause labor displacement but will create entirely new job categories like agent training and evaluation, why token spend will exceed headcount spend within five years, and why application layer companies should be concerned about defensibility. The conversation covers Mercor's path to $1.5B ARR, the distinction between revenue and GMV, and the infrastructure-vs-applications dynamic reshaping AI economics.

3 novel
# · May 30, 2026 · 53m 18s
Nico Laqua

Nico Laqua, CEO of Corgi Insurance (a $2.6BN AI-native insurance startup), discusses building the most intense workplace culture in America — where the team works 7 days a week, the founder sleeps in the office, and 67% of early employees have Corgi tattoos. He covers university as wasted time, extreme hiring practices (work trials as stamina tests), the psychology of equity vs. cash compensation, pricing strategy lessons from Brian Chesky, and why he rejects traditional boards.

1 novel3 editorial
# · May 26, 2026 · 01:01:38
Andrew Feldman

Andrew Feldman, CEO of Cerebras Systems, discusses the semiconductor company's historic IPO and $70 billion market cap, driven by a $20 billion compute deal with OpenAI. The conversation spans infrastructure investment, the actual cost of AI tokens, competitive positioning of major tech companies, and systemic barriers to enterprise AI adoption—from memory pricing to legal friction.

1 novel3 editorial
# · May 23, 2026 · 1h 19m
Chad Peets, Chris Degnan

Chad Peets and Chris Degnan dissect the $100M CRO compensation bubble inflated by companies like Anthropic, expose why most salespeople are order takers rather than true closers, and map how AI is rewriting sales fundamentals from hiring to forecasting to deal structure. Degnan shares his playbook for scaling Snowflake to $4B ARR while Peets challenges conventional startup sales wisdom.

5 editorial
# · May 21, 2026 · 1h 21m 53s
Harry Stebbings (host, no external guest)

Harry Stebbings covers major tech industry moves: Anthropic's $30 billion fundraise at a $900 billion valuation with Andrej Karpathy joining as Chief AI Officer, SpaceX filing for the largest IPO in history, Cerebras' blockbuster public debut, and the hidden cost of mass tech layoffs. The episode examines AI compute scarcity, token economics, public market rebounds, and the political fallout from AI-driven workforce reductions.

2 editorial
# · May 18, 2026 · 1h 29m
Josh Browder

Josh Browder, founder of Browder Capital and DoNotPay, discusses how he turned a $100K Thiel Fellowship into a $10M angel portfolio by investing in founders like Micro (now unicorn-valued) and Owner.com. He shares his unconventional accelerator model—requiring founders to live with him at the Four Seasons until they raise their seed round—and reveals why young founders, founder psychology, and commitment signals matter more than credentials. The episode covers what VCs actually add (and don't), why university dropouts often outperform, and how early-stage founders are being assessed wrong.

3 novel6 editorial
# · May 16, 2026 · 01:04:37
Shiv Rao

Shiv Rao, CEO of Abridge (a $5.3B AI healthcare company), discusses the founder lessons that shaped the company's explosive growth from a five-year struggle to product-market fit. He breaks down how to know if foundation models will help or kill your company, the surprising role of USV's taste in music in their billion-dollar investment returns, what "founder mode" really means via Jensen Huang's example, and the non-negotiable sacrifices required to scale a healthcare AI company from 0 to 450 employees.

2 editorial
# · May 14, 2026 · 1h 18m

Harry Stebbings covers the latest in tech and VC news, including Anthropic's secondary sale restrictions and its massive $200B revenue commitment to Google, alongside its compute deal with Elon Musk. He discusses Goldman Sachs' prediction of a 24x surge in token consumption from AI agents, and the potential for AI labs to disrupt app layer verticals. The episode also breaks down public SaaS market movements, the competitive threat from startups like Clay commoditizing data businesses, and contrasts Ramp's high valuation with a peer's bankruptcy. It closes with a reflection on whether building a $20B company inevitably requires sacrificing mental health.

4 canon1 editorial
# · May 11, 2026 · 1h 14m
Patrick Forquer

Patrick Forquer, CRO of Legora, breaks down the economics of building a $100M ARR enterprise AI business in 18 months. The conversation covers how AI celebrity endorsements (Jude Law) generate qualified pipeline, why implementation is the real moat against competitors like Harvey, how to structure sales teams for AI products, and whether Legora's $5.5B valuation is justified or a bubble.

1 novel
# · May 9, 2026 · 1h 44m
Cliff Weitzman

Cliff Weitzman, founder and CEO of Speechify AI, discusses how he built a voice AI platform used by 60+ million people while managing dyslexia and ADHD. The episode covers his unconventional approach to hiring, AI-driven advertising, his learnings from studying 100 top CEOs, personal stories including stays with MrBeast and time in Ukraine, and his thesis that AI token costs will soon exceed employee salaries.

3 novel13 editorial
# · May 4, 2026 · 01:13:49
Tobi Lütke

Tobi Lütke, CEO of Shopify, discusses his reluctance to become CEO, the impact of AI on entrepreneurship and labor markets, and why he believes companies are using AI as a scapegoat for layoffs. He also critiques charitable giving inefficiency, government dysfunction, and Canada's political reaction to Trump, while offering career advice based on compound learning and skill differentiation.

7 editorial
# · May 2, 2026 · 1h 13m 20s
Becca Lindquist

Becca Lindquist, Head of Sales at Clay, pulls back the curtain on scaling a sales organization to over $100M ARR. She shares concrete frameworks for reading sales candidates' LinkedIn profiles, building effective compensation plans, and fostering high-performance culture without toxicity. The conversation also covers how AI is reshaping outbound sales, whether SDRs will be replaced, and why every rep must own their own pipeline.

# · Apr 30, 2026 · 1h 25m

Harry Stebbings breaks down a massive week in tech: Anthropic's $45B raise fails to secure sufficient compute, OpenAI's growth stalls despite GPT-5.5, China blocks a $2B AI acquisition, and Thoma Bravo gives up on Medallia. The episode explores the threads connecting AI hype, infrastructure bottlenecks, and the potential death of SaaS at the hands of agentic interfaces.

# · Apr 27, 2026 · 1h 20m
Adam Foroughi

Adam Foroughi, Co-Founder and CEO of Applovin, discusses what makes his company an exceptional software business—$160B market cap, $5.48B revenue, and $10M EBITDA per employee with 80%+ margins. The conversation covers founder motivation driven by winning rather than fear, how to build cultures of A-players, the role of AI in modern product development, the risks of mentorship for elite founders, and the controversial claim that kindness in business can slow you down. Foroughi also reflects on navigating a 92% stock decline and the future of recommendation engines.

15 editorial
# · Apr 25, 2026 · 46m 51s
Amjad Masad

Amjad Masad, CEO of Replit, discusses why AI coding models are hitting performance plateaus and why this matters for the future of development tools. He explains Replit's strategy of not building their own model, why product quality beats cost optimization, and makes a provocative case that the SaaS apocalypse—where AI displaces traditional software—is justified and inevitable. Masad also challenges narratives about IDEs being dead, addresses whether PMs survive the next 3-5 years, and reflects on what true product-market fit actually means.

3 editorial
# · Dec 17, 2024 · 28m
Harry Stebbings

Stebbings distills 10 lessons from interviewing 4,000+ founders, VCs, and operators over 9 years. Themes: speed beats perfection, relationships matter more than deals, and the best investors are perpetual students.

1 canon
# · Nov 18, 2024 · 62m
Demis Hassabis

Google DeepMind CEO Demis Hassabis fresh from winning the 2024 Nobel Prize in Chemistry for AlphaFold's protein structure predictions. Discusses the path from games (AlphaGo) to science (AlphaFold) to AGI.

1 canon
# · Nov 4, 2024 · 65m
Sam Altman

OpenAI CEO returns to discuss whether scaling laws will continue, the semiconductor supply chain, and which startup categories OpenAI will steamroll versus leave alone.

# · Oct 22, 2024 · 35m
Demis Hassabis

Demis Hassabis — fresh from winning the Nobel Prize for AlphaFold's protein structure predictions — discusses AI's potential to solve humanity's hardest scientific problems. From chess prodigy to DeepMind founder to Nobel laureate.

1 canon
# · Aug 6, 2024 · 24m
Harry Stebbings

Stebbings argues that the AI startup landscape is repeating the 2021 SaaS bubble: too much capital chasing too few defensible businesses. He estimates 90% of current AI startups will fail — not because AI doesn't work, but because they have no moat.

1 canon
# · Jul 22, 2024 · 52m
Harry Stebbings

Lisa Edgar of Top Tier Capital Partners on how limited partners evaluate venture fund managers. What LPs look for in first meetings, portfolio construction, fees, carry, and why most emerging managers fail.

# · Jun 18, 2024 · 22m
Harry Stebbings

Stebbings delivers a personal episode on founder mental health after several founders in his portfolio experienced burnout, depression, and substance abuse. He argues the VC industry's celebration of hustle culture is directly contributing to a mental health crisis.

1 canon
# · Jun 10, 2024 · 58m
Aaron Levie

Box CEO Aaron Levie on how enterprise companies are actually adopting AI — beyond the hype. Why most enterprise AI deployments fail, and how Box is rebuilding around AI-native workflows.

1 canon
# · May 7, 2024 · 30m
Sebastian Siemiatkowski

Klarna CEO Sebastian Siemiatkowski explains how Klarna replaced 700 customer service agents with AI in one month — reducing resolution time from 11 minutes to 2 minutes while improving customer satisfaction. The first major public company to quantify AI-driven workforce reduction.

1 canon
# · Apr 15, 2024 · 70m
Sam Altman

OpenAI CEO Sam Altman and COO Brad Lightcap discuss whether foundation models will be commoditized, the compute problem, and which companies will be steamrolled by OpenAI. A rare joint interview.

# · Mar 12, 2024 · 25m
Harry Stebbings

Harry Stebbings delivers his annual state-of-venture-capital analysis. Key themes: the IPO window is reopening, AI is consuming all available capital, and the venture industry itself is consolidating — fewer funds, larger sizes, less diversity.

1 canon
# · Mar 4, 2024 · 72m
Vinod Khosla

Vinod Khosla makes his provocative case that AI will replace 80% of current jobs within 25 years — and that this is good news. Discusses energy constraints, nuclear power, and the future of work.

# · Feb 26, 2024 · 60m
Harry Stebbings

Shore Capital Partners founder Justin Ishbia on building a top-performing PE firm, acquiring sports teams, and why the best companies are talent systems. A rare deep-dive into private equity from a practitioner's perspective.

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# · Feb 12, 2024 · 55m
Thomas Plantenga

Vinted CEO Thomas Plantenga on building Europe's largest secondhand fashion marketplace. How to create trust in peer-to-peer transactions, why Rule of 40 is misleading, and the unique dynamics of marketplace businesses.

# · Jan 17, 2024 · 48m
Harry Stebbings

Palantir CTO Shyam Sankar on why government defense procurement is broken, how AI is changing warfare, and why Silicon Valley needs to engage with national security rather than avoid it.

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# · Jan 16, 2024 · 28m
Gustav Söderström

Spotify's CTO Gustav Söderström explains how Discover Weekly, Release Radar, and Daily Mix use machine learning to predict musical taste better than users themselves. The algorithmic curation model that transformed how 600M+ people find music.

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# · Jan 12, 2024 · 66m
Keith Rabois

Keith Rabois discusses his move from Founders Fund to Khosla Ventures, the current state of venture capital, and why he believes the best companies are built during downturns. Deep dive into operator-to-investor transitions.

# · Oct 30, 2023 · 35m
Marc Andreessen

Marc Andreessen discusses his Techno-Optimist Manifesto — a provocative defense of technological progress against what he calls the 'decel' movement. Stebbings pushes on whether optimism can coexist with acknowledging tech's genuine harms.

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# · Sep 5, 2023 · 32m
Patrick Collison

Patrick Collison discusses Stripe's evolution from '7 lines of code' to processing $1T+ in payments annually. He explains why Stripe stayed private, his reading habits, and why he thinks the pace of scientific progress has slowed.

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# · Jun 20, 2023 · 26m
Tobi Lütke

Shopify CEO Tobi Lütke explains why the company deleted 12,000 recurring meetings from calendars — and why meetings are organizational debt that compounds silently. His programmer-CEO approach treats management systems like code: if it's not working, refactor it.

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# · Mar 14, 2023 · 30m
Bill Gurley

Benchmark's Bill Gurley — who led the investment in Uber, OpenTable, and Zillow — explains his framework for evaluating marketplace businesses. His core thesis: not all revenue is created equal. Revenue quality (recurring, high-margin, defensible) matters more than revenue quantity.

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# · Nov 15, 2022 · 28m
Frank Slootman

Frank Slootman — who took Data Domain, ServiceNow, and Snowflake from struggling to dominant — explains his 'Amp It Up' philosophy: most companies operate at a fraction of their potential. The solution: raise the tempo, sharpen the focus, and raise the bar on talent.

1 canon