ChatGPT

Canva Co-Founder: AI Is Useless Without This 1 Skill

Jul 29, 2026 · 57:30

Cameron Adams, co-founder of Canva—now used by 250 million people monthly—argues that taste, not AI, is the new differentiator for creators. Adams describes Canva's founding story, where they delayed launch to polish the user experience, turning early social media managers into fanatical ambassadors. He explains that AI enables exploring ideas at scale, but the key skill is having the judgment to choose the right option and respond quickly to trends. Adams details Canva's AI evolution from text-to-image in 2022 to now solving end-to-end workflows like marketing campaigns. He also shares insights on co-founder dynamics, noting that Mel and Cliff excel at recognizing moments of change and rallying around a vision. The episode covers creators' need for taste, responsiveness, and managing multiple AI tools to stay relevant.

a16z Partner: Hollywood Is Secretly Replacing Films With AI

Jul 23, 2026 · 50:27

Justine Moore, a16z partner and early backer of ElevenLabs, explains why AI microdramas — short, vertical soap operas — are becoming the fastest-growing entertainment format, with China's microdrama market now larger than its domestic box office. She argues model quality has reached 90-95% of filming, making it cheaper and faster, and professional storytellers are now using it to create compelling narratives. Amazon and Netflix have announced programs for fully AI-generated animations. ElevenLabs, which she backed at Series A, has crossed $500M in ARR. She highlights consumer agents like Town that automate tasks such as warm intros and expense forwarding, and sees the biggest opportunity in serving less technically sophisticated users and vertical industries like marketing and architecture.

Reid Hoffman, LinkedIn Founder: 99% of People Are Using AI Wrong

Jul 19, 2026 · 1:00:42

Reid Hoffman, LinkedIn co-founder, argues most people underutilize AI by treating it as a search engine rather than an agentic workforce, predicting a shift where humans become managers of AI agent teams. He explains that Blitzscaling today means using AI to rapidly build and discard prototypes, while distribution remains a critical moat for startups. Hoffman warns that negative AI perception in the US and Europe risks ceding leadership to Asia, which embraces the cognitive Industrial Revolution. He highlights the importance of taste and judgment as skills that AI amplifies rather than replaces, and contrasts Anthropic's enterprise focus with OpenAI's consumer strength. Drawing from his decade on Microsoft's board, he shares Satya Nadella's lessons on rebuilding culture, corporate partnerships, and treating AI agents as employees that work for the company. Hoffman also spotlights applications in drug discovery (Manus AI) and personalized AI to maintain human connections.

Mark Manson: AI is a Better Writer Than You But Here’s What it Can’t Replace

Jul 16, 2026 · 44:11

Mark Manson, author of *The Subtle Art of Not Giving a F*ck* (20 million copies, 70+ languages), argues AI will render most human self-help obsolete because it's all language, and he's building an AI app called Purpose. He claims nonfiction book sales are down 20–30% due to AI, not podcasts, and that AI will write as well as him but cannot replace his unique blend of traits. Manson shares how he uses AI for research and business coaching, and outlines an AI-proof nonfiction book requires novel concepts, creative teaching, and trust-based verticals like dating and business. He reflects on how his book's message has shifted over a decade, noting people now over-invest in identities. His advice: find the 0.1% edge case where your specific experiences overlap, because that's what AI cannot replicate.

This Company Is Reinventing Venture Capital | Ben Miller CEO at Fundrise

Jun 28, 2026 · 50:44

Ben Miller, CEO of Fundrise, recounts how the 2008 crisis inspired him to democratize private markets, first through real estate and later venture capital (launched 2022), where they waited 12 months to deploy, investing in Vanta. He contrasts venture—regretting missed opportunities—with real estate—regretting bad deals—and argues that venture value-add is mostly overstated; team builds success. On AI, he says Anthropic is eating the application layer, making it hard for all but top labs, and predicts Mythos will unlock consumer apps; he notes upcoming IPOs of AI labs and SpaceX will reallocate $10 trillion, starving other sectors. He is bullish on longevity through his investment in Loyal, a dog longevity drug company, and sees human longevity within a decade. His admired AI leader is Dario Amodei for genuine concern about risks, and his personal trait is willingness to suffer.

Why We Sold To Grammarly | Rahul Vohra

Jun 21, 2026 · 1:01:18

Rahul Vohra, founder of Superhuman and now CEO of Superhuman Group after the company's acquisition by Grammarly, argues that email remains the most enduring layer of work identity and that AI will radically transform the inbox experience while distribution and taste-driven focus are the lasting moats in an era of near-zero software costs. He explains that email addresses are owned by companies and serve as the root identity and authentication unit, with professionals spending 3 billion hours daily on email. Voice features like Right With Voice on mobile now drive 30% of usage gains, and the 'Sent via Superhuman' signature still generates 20% of site traffic. The acquisition story reveals that Grammarly independently chose the Superhuman name via a branding agency, leading to the rare rebrand of the acquirer. Superhuman Group operates as a multi-product bundle ($15/$30 per month) spanning email, documents (Coder), writing agents (Grammarly), and proactive AI (Superhuman Go), with priorities on M&A to fill missing categories like chat. Vohra also angel-invests via Todd and Rahul Capital, backing companies like Loyal (which received FDA efficacy approval for a dog lifespan drug) and…

Replit's President & Head of AI | Michele Catasta

Jun 16, 2026 · 49:58

Replit's President Michele Catasta explains how the company evolved from a 15-year-old open source side project to powering 85% of Fortune 500 by launching the first vibe coding agent in 2024, before the term existed. He describes the initial rough launch that attracted candid feedback, the scramble to build an enterprise sales team when IT departments knocked, and the belief that the coding problem is nearly solved—shifting focus to integrations. Catasta argues that technical moats are less important than execution moats built from a decade of battle scars and user trust. He predicts 2026 will be the year of 'agent managers,' where every role involves managing multiple AI agents rather than single-threaded work. The Visa partnership exemplifies Replit's strategy of providing reliable building blocks for monetization, allowing vibe coders to add payments with a single prompt.

Inside Mercury's Founding Story | Co-Founder & CEO Immad Akhund

Jun 9, 2026 · 50:11

Immad Akhund, co-founder and CEO of Mercury, explains how the startup bank captured one in three U.S. startups by launching with product-market fit from day one—a million-dollar deposit arrived within four days from a stranger—and why legacy banks never stood a chance due to their focus on loans, expensive branch structures, and IT rather than engineering teams. Mercury raised $200M at a $5.2B valuation without needing the money, driven by 2.5x growth in Q1 2024 from AI-fueled entrepreneurship. Akhund details building trust as a moat, using small teams and Amazon's working-backwards process to launch AI features like Mercury Insights and Mercury Command, which let users run banking tasks inside AI tools. He dropped all one-on-ones after learning from Jensen Huang's 60 direct reports, favors optimistic curiosity, and angel-invests 250K checks in contrarian areas like space and deep tech.

Inside Gusto's Founding Story | Co-Founder & CTO Eddie Kim

Jun 6, 2026 · 54:31

Eddie Kim, co-founder and CTO of Gusto, reveals how the company grew from a 2012 YC startup called ZenPayroll to $1B in annual revenue and 500,000 customers by cracking the small business market against investor skepticism. He credits the 15-year co-founder relationship with Josh Reeves and Tomer London to shared values and radical directness, arguing that packaging feedback undermines trust. Kim describes building Gusto Co-Founder, an AI agent that automates back-office tasks via chat, with a team of five in eight weeks using Claude Code, embodying how the distinction between engineer and designer disappears. He calls the blank canvas problem AI's main barrier to mainstream adoption and predicts solopreneurs will thrive as AI enables anyone to become a builder.

5 Grand Slam Champion Maria Sharapova: Tennis Icon | Entrepreneur | Investor | New Media Creator

May 20, 2026 · 52:29

Maria Sharapova, five-time Grand Slam champion, reflects on her tennis career, emphasizing that most preparation happens when nobody's watching and that commitment to quality defined her proudest moments. She discusses the challenge of balancing fierce competition with personal boundaries, the business of sport and building a team, and how a shoulder injury in her early 20s first made her plan for a second act. Sharapova describes reinventing herself after retirement by taking a break and applying athletic lessons to entrepreneurship and her podcast 'Pretty Tough,' which explores the duality of grit and vulnerability. She shares her take on AI, noting its positive uses in sports like IBM's Wimbledon predictions and automated video analysis, but values human connection in media. In rapid-fire questions, she names Monica Seles and Steffi Graf as admired icons, Serena Williams as both the toughest opponent and a close friend who introduced her into the Tennis Hall of Fame, and says what makes her tough is the ability to say no.

How Many $10 Billion Startups Will There Be? | Eric Hippeau

May 13, 2026 · 57:21

Eric Hippeau, co-founder of Lerer Hippeau, argues that while AI is transforming tech faster than ever, startups must avoid being mere wrappers around foundational models, as they can be instantly disrupted. He explains that physical AI, combining hardware and AI in areas like robotics and defense, offers more defensible opportunities. Hippeau warns that the startup market is disconnected, with inflated seed valuations assuming many will reach $10B, but historically there's no market for hundreds of such companies. He discusses healthcare, where AI-driven diagnostics could make primary care nearly free, but political will is needed to overcome entrenched systems. On media, he shares lessons from building Huffington Post—keeping stories live and separating opinion—and predicts that AI could restore trust by providing verifiable facts. Hippeau also reveals he has rebuilt his firm's workflow around Anthropic's Claude, cites AR glasses as underrated, and notes that solo GPs must build teams to succeed.

Will AI Models Ever Compensate Creators? Tony Stubblebine (Medium CEO)

May 6, 2026 · 53:35

Tony Stubblebine, CEO of Medium, argues the creator economy is ending as AI slop floods public channels, but a writing renaissance is emerging where authentic expertise and private communities hold value. He details Medium's turnaround from losing $2.5M per month and $37M in debt to profitability, achieved by restructuring investor relationships and refocusing on human-written content. Stubblebine warns that AI companies like OpenAI created a 'prisoner's dilemma' by scraping content without compensation, pushing high-quality writing into walled gardens. He introduces Medium's new AI-assisted writing app TK and private blogging groups as responses to the era. The episode explores how creators must diversify revenue streams and reinvent themselves, while per-inference pricing standards like RSL slowly develop.

We Ignored Silicon Valley Advice for 3 Years | Nicolas Sharp (Attio)

Apr 30, 2026 · 57:49

Nicolas Sharp, co-founder of Attio, explains why the CRM startup spent 1,000 days building in stealth—a deliberate counter to the 'ship fast' philosophy he learned from a previous venture—and how that architectural investment now powers Attio's AI-native platform. He argues that the half-life of product-market fit has collapsed, forcing companies to simultaneously iterate and scale, and that Attio's high-resolution data pipelines are critical for deploying AI agents. Sharp also details how Attio used manual waitlist onboarding to validate demand, how fundraising expectations have risen dramatically (Attio raised $52M at Series B with accelerating growth), and why Europe is having a breakout moment as an AI hub, citing talent from DeepMind and Palantir as catalysts.

Why Andreessen Horowitz Is Still Betting Big On Crypto

Apr 22, 2026 · 50:25

Ali Yahya, general partner at Andreessen Horowitz (a16z), explains why AI and crypto are converging faster than predicted, with privacy emerging as a key defensive moat for crypto startups. He defines AGI as the point when an agent can be fully economically independent and outlines five stages of autonomous commerce, from automated payments to agent-to-agent transactions. Yahya is skeptical about AI agents trading for consumers—since everyone using ChatGPT eliminates alpha—but sees potential for professionals with proprietary data. He notes that a16z's 70-person platform team provides legal, research, and go-to-market support, and that the cost of entry has collapsed, letting founders test ideas with smaller teams before raising capital. He also highlights prediction markets, now legal in the US, as a growing category and recommends robotics as the next frontier, calling physical intelligence a 10–15 year arc offering time for newcomers to enter.

Students Will No Longer Be Taught By Teachers | Joleen Liang

Apr 15, 2026 · 46:16

Joleen Liang, co-founder of Squirrel AI, explains how its LAM engine—powered by over 20 billion learning behavior data points—replaces traditional teachers by handling 100% of knowledge transfer, turning instructors into data analysts and psychologists. She details how the Chinese Double Reduction policy in 2021 slashed revenue from $300 million to zero overnight, forcing a pivot to a hardware-integrated smart tablet and leading 80% of franchisees to convert $160 million in debt into company stock. The company now expands into the US with self-study centers and plans to introduce physical AI robot teachers within five years, while arguing that generic LLMs cannot deliver truly personalized education. Liang also shares how the co-founders maintained belief through the crisis, prioritizing health and exercise, and advises founders not to underestimate their abilities.

Yahoo Is Striking Back | CEO Shares The Latest

Apr 7, 2026 · 53:50

Yahoo CEO Jim Lanzone and SVP Eric Feng explain how Yahoo is striking back with AI-powered products like Scout and MyScout, leveraging its 700 million users and proprietary data to differentiate from generic chatbots. After being taken private by Apollo in 2021, Yahoo sold off non-core assets and restructured into GM-led units, cutting headcount by 50% while remaining profitable. The company owns its AI tech, using 30 years of search history and unique knowledge graphs to deliver accurate, citation-rich answers that send traffic to publishers, unlike other AI engines. They argue this approach is possible because Yahoo dominates categories like finance (#1) and sports (#2), each with 100M+ monthly users, and that AI is causing a seismic shift in search behavior (Google's lowest market share in a decade). The duo emphasizes that domain expertise now matters more than pure technical skills, and they are planning agentic features that move from information to action, such as booking trips or setting fantasy lineups, to increase user touchpoints from once a day to multiple times an hour.

Why Hand-Typing Code Will End Your Career in 2026

Mar 2, 2026 · 49:31

Dan Shipper, co-founder and CEO of Every, argues that AI agents like OpenClaw and vibe coding—prompting apps in English—are fundamentally reshaping how companies operate, from internal workflows to product development. Every, a 20-person company running four AI-native products (Quora, Spiral, Sparkle, Monologue), treats failed software experiments as content that builds distribution, and uses a 'two-slice team' approach where each product is managed by one person. Shipper details how he reclaimed the 'founder' title for legitimacy, the four-year 'flatline' period before the AI wave hit, and why over-hiring early is 'crazy—most of the time it doesn't end well.' He advises founders to automate every internal process with AI and build for both humans and agents.

A16Z Partner: Why "Just Capital" Is Not Enough Anymore (The Firm of 2030) | David Haber

Jan 25, 2026 · 56:58

David Haber, a16z general partner, argues most venture investors run funds but few build firms, and explains how a16z operates as a firm with compounding competitive advantage. The firm reinvests fees into a 600-person platform giving founders distribution, credibility, and leverage. Haber shares his founder story: Bond Street raised $900M in debt, sold to Goldman Sachs, teaching him inside a 40,000-person organization. On AI, he says software becomes labor, expanding TAM beyond IT spend—portfolio company Salient's voice agents achieve 50% better collection rates. He also highlights a16z's decentralized model with no single CIO, where specialist partners run divisions, making the firm more resilient than traditional funds.

He Built A $1.8B AI Company With No Experience | Max Junestrand

Dec 14, 2025 · 52:02

Max Junestrand, CEO of legal AI company Legora, explains how AI is rewiring the legal profession, arguing that not building in AI is the biggest career risk. Legora, which went through YC W25 and has raised $260M, doubles ARR every quarter by embedding with law firms to solve real problems. Junestrand details how AI adds a fourth step to the lawyer career ladder—junior associate, senior associate, partner, AI—pushing junior lawyers to focus on intelligence and client skills earlier. He describes Legora's shift from chat to large-scale document review and Word-native drafting, and predicts a move from billable hours to outcome-based pricing as AI automates more work. Junestrand also shares his fundraising approach: build a great business and investors come to you, with Legora's Series B closing in a week and Series C in a week and a half.

The Hidden Skill Behind Every Successful Founder | Lindsay Kaplan

Nov 30, 2025 · 37:06

Lindsay Kaplan, co-founder of Chief, explains how she and her co-founder Caroline built the women's executive network from cold emails that landed the first 200 members to a unicorn with tens of thousands on the waitlist. She details pivoting from in-person to digital in days during COVID, launching physical spaces, and the art of co-founder dynamics—emphasizing disagreement and complementary skills. Kaplan describes stepping down as operator after seven years, moving to VC at Next Wave NYC, and why she backs founders at the intersection of AI and real-world community, arguing that AI is a tool that cannot replicate in-person connection.

The Harsh Truth About Building a Startup in the AI Era | Anish Acharya

Nov 23, 2025 · 51:12

Anish Acharya, General Partner at a16z, argues the AI era has reopened consumer tech's biggest window since mobile, with consumers paying $200–$250 monthly for products like Gemini Ultra and ChatGPT. He warns founders against traps like thinking they're too late, noting AI code and legal will become entire industries with dozens of winners. Voice AI is an enterprise insertion point where agents already outperform humans at negotiation, while the next social platform will revolve around software creation rather than content. He dismisses the AI wrapper risk because multi-model products and fine-tuned data give startups defensibility, and advises founders to raise 24-month rounds focused on product, not marketing. Acharya also predicts 2026 will bring new distribution channels via OpenAI's Apps SDK, Apple's mini apps, and group chat discovery.

The AI Version of You Will Outperform You — Emad Mostaque

Nov 16, 2025 · 51:27

Emad Mostaque, founder of Stability AI and now Intelligent Internet, argues that within 1,000 days, AI will create digital twins that replace most cognitive jobs, but the bigger risk is cognitive colonialism—a handful of corporations controlling the AI layer closest to people. He explains why he left Stability after it reached 300 million downloads to build open, sovereign AI for healthcare, education, and government, citing a medical model that outperforms human doctors on benchmarks and runs on a laptop. Mostaque warns that graduate jobs are already disappearing, and by 2028 coding jobs as we know them will vanish, replaced by English-language AI. He advocates for universal basic AI alongside universal basic income, and announces Sage, an open-source policy engine for governments, and a ChatGPT alternative that routes through any model at cost. The episode details his vision for distributed civic AI funded via Foundation Coin, where compute goes toward helping people rather than maximizing profit.

This Is How AI Will Reshape Startups Forever | Henry Ward, Co-Founder of Carta

Nov 2, 2025 · 47:52

Henry Ward, co-founder and CEO of Carta, explains how AI is reshaping startups and Carta itself — inverting the source of truth back from data to paper by using LLMs to reconstruct cap tables from legal documents. He shares the early hack that got Carta its first users: offering discounted 409(a) valuations through VC portfolio companies. Ward advises founders to diligence investors by talking to founders who exited with them, warns that seed investors often turn on founders in M&A, and notes the VC market is becoming bimodal — large funds get larger while small emerging managers exploit niches. Carta is now expanding into private equity and credit, which he says are 6–8x larger than venture, and opening offices globally. He also recounts meeting Marc Andreessen, who admitted his firm made a mistake passing on earlier Carta rounds, exemplifying the humility Ward admires.

Spotify’s Early Investor Shares His Blueprint for Outlier Founders | PJ Pärson (Northzone)

Oct 26, 2025 · 46:20

PJ Pärson, Northzone partner and early Spotify investor, argues outlier founders combine existential intensity with adaptability to AI disruptions and must hire smarter people. He recounts meeting Daniel Ek in high school and how Northzone insisted Ek become Spotify's CEO, producing Sweden's most valuable company. Pärson breaks AI into infrastructure, application tools, and a coming wave of AI-native businesses, explaining Northzone focuses on complex B2B bets like healthcare AI. He notes European startup hubs now have critical mass—Stockholm hosts 50–60 fast-growing AI companies—but Europe lacks later-stage capital and a deep IPO market. He warns US visa changes could redirect talent to Europe if Europe fixes retention issues.

The Nas Daily Story

Aug 22, 2025 · 49:52

Nuseir Yassin, creator of Nas Daily and founder of Nas.io, explains how after 271 failed daily videos he finally broke through in Bangkok, then pivoted his entire content operation to AI—achieving 250 million views from 60 AI-generated videos. He argues that creators must stop building on social media 'quicksand' (only 3-5% of his 70 million follower revenue comes from platforms) and instead build real businesses. Nas.io, built with $10M+, lets anyone turn an idea into revenue within 24 hours using AI for design, ads, and customer acquisition. Yassin predicts the next big trend is internet capital markets—tokenizing ownership of real estate and companies so anyone globally can buy fractional shares. He also launched an entrepreneur fellowship giving 100 people $3,000 each to build businesses on the platform.

300 Million Downloads (Matt Rouif, Photoroom)

Aug 16, 2025 · 48:07

Matt Rouif, co-founder of Photoroom, explains how the photo editing app grew from a two-week prototype in 2019 to 300 million downloads and $20 million in annual revenue on only $2 million raised, becoming the largest AI image editing tool globally. He details early tactics like localizing in 10 languages and conducting customer interviews at McDonald's. COVID accelerated adoption as sellers moved online, and Photoroom's focus on trust—avoiding AI hallucinations in product shots—set it apart for e-commerce. Rouif shares plans for a video editing beta and personalized advertising at scale, where infinite marketing assets are tailored per user. He identifies trends: specialized AI models for mobile speed and trust, AI video maturing in 2025-2026, and personalized advertising that creates unique imagery for each segment.

How To Actually Vibe Code

Aug 8, 2025 · 59:19

Billy Howell demonstrates how to vibe-code a directory website for barbecue restaurants using AI tools like Replit, Lovable, and V0, taking the idea from a product requirements document to a functional prototype in under an hour. He explains that niche directories can be built in a weekend, monetized through ads or affiliate partnerships, and eventually sold via platforms like MicroAcquire. Beyond directories, Howell discusses three trends: employees using AI to build and sell custom software to their employers, unlocking nascent demand as every business gains access to tailored tools; and AI receptionists for local service businesses, citing a personal experience where he didn't realize he was talking to an AI until 20 seconds into the call. He recommends starting with a specific niche (e.g., HVAC or gyms) and using tools like Replit, Cursor, LiveKit, or VAPI to build custom solutions.

$16M Net ARR In Just Two Years (Maxime Barbier, Timeleft)

Aug 1, 2025 · 43:00

Maxime Barbier, co-founder of Timeleft, explains how his company that hosts dinners for strangers scaled from zero revenue to $16M net ARR in just two years by focusing on in-person connection amid a loneliness epidemic. After three years of failing with different concepts, Timeleft launched in May 2023 with 24 people in one city; today it serves 120,000 strangers monthly across 260 cities in 50 countries. Barbier attributes growth to performance marketing (40% of business is US) and a profitable acquisition model, avoiding 'empty calories' by ensuring users return. He details operational challenges of coordinating 30,000 dinners in 2,500 restaurants on a single Wednesday, and the expansion into new events like Thursday bar drinks and Saturday runs. Barbier also shares his views on why dating apps are declining (citing Bumble's share price drop from $62 to $6.50), arguing they create an illusion of choice and an 'Amazon Prime effect' that undermines real connection. The episode covers trends like tech as a new social frontier, friendship as the new dating, and the fall of dating apps.

The Founding Story Of Zapier (Wade Foster)

Jul 24, 2025 · 51:33

Wade Foster, co-founder of Zapier, recounts the company's 2011 founding as an integration tool born from a forum thread and bootstrapped to scale without raising beyond $1.3 million. He explains how early growth came from answering forum posts with a prototype that converted at 50% despite being poorly designed, and how the company maintained a 'don't hire till it hurts' philosophy. Foster details the decision to avoid VC because customer acquisition costs were low and the business was profitable within a year, achieving breakeven with only tiny monthly losses. He shares two Paul Graham lessons from Y Combinator: focus only on writing code and talking to customers, and target 10% week-over-week growth, which the company sustained for years. On AI, Foster notes that AI is Zapier's fastest-growing category at nearly 300% year-over-year, and the company now offers agents built by non-technical users through natural-language workflows. He argues that seat-based pricing is dying and predicts a shift to usage-based models, while identifying the biggest AI opportunity in legacy industries like healthcare that work with unstructured data.