The Peel with Turner Novak

Mike Smith, operator-turned-investor who scaled Stitch Fix, and Nikhil Basu Trivedi, venture investor who backed Canva, chat about founding Footwork and their hands-on approach. They discuss AI driving a new wave of solo entrepreneurs. They explain Footwork’s two-seat board model, the one-pager they share with founders, and how investing pace differs from operating.

Chris Hladczuk, Co-founder and CEO of Hanover Park, built an AI-native fund administration firm that rapidly scaled to billions in assets. He discusses raising a $27M round, why they built a custom general ledger, and how AI agents automate onboarding, reporting, and complex fund accounting. Expect stories on founder-led sales, weekly demo rituals, and turning customers into raving fans.

Scott Stevenson, co-founder and CEO of Spellbook — an AI copilot for contract review and drafting built as a Microsoft Word plugin. He discusses how Spellbook automates contract autocomplete and review, why legal software lagged before LLMs, the limits of generic tools like ChatGPT for law, and the product experiments and PMF playbook that scaled Spellbook to thousands of customers.

Chetan Puttagunta, General Partner at Benchmark known for investing in software and AI startups. He recounts discovering Manus and its rapid $100M ARR growth. He traces the history of application software and how cloud and AI changed barriers to entry. He explains why incumbents should buy AI startups and what Benchmark looks for when backing founders.

Jake Stauch, Co-founder and CEO of Serval, builds an AI platform that automates IT and employee support. He discusses taking on incumbents with an AI-native product. He recounts an early work-trial crisis that reshaped security. He explains vibe-coding (natural language to TypeScript), why IT automation lagged, and how making implementation part of the product helps land customers.

Garry Tan, President and CEO of Y Combinator and co-founder of Initialized Capital, is a long-time founder and investor. He traces YC’s eras and why the Bay Area still matters. He discusses California policy, founders’ mental health and cofounder conflict. He explains YC’s 13-week structure, Demo Day, application advice, and his AI workflow and meta-prompting techniques.

Miranda Nover, co-founder and CEO of Fort Health and former Tesla mechanical engineer, builds wearables that automatically track strength training for longevity. She talks about why strength matters for health, the limits of wrist trackers, sensor tradeoffs like EMG versus motion, and the challenges of launching a hardware startup while in YC.

Dug Song, serial cybersecurity entrepreneur who built Duo into a high-growth company, and Jon Oberheide, security researcher and former Duo CTO with a University of Michigan roots. They recount early hacker culture, why they stayed in Ann Arbor, designing security for end users, product-led growth from SMBs to enterprise, capital-efficient scaling, and integrating with Cisco.

Jacqueline Cheong, co-founder and CEO of Artie, builds real-time data streaming infrastructure for analytics and AI. She discusses why moving data is surprisingly hard and how real-time feeds power AI and agents. Jacqueline also covers how Artie wins enterprise customers, automates prospecting with AI, and the tradeoffs of building versus buying streaming systems.

In this discussion, Nathan Benaich, founder of Air Street Capital and author of the influential State of AI report, delves into groundbreaking trends shaping the AI landscape. He discusses the shift toward reasoning and tool calling in AI models, and the significant rise of Chinese open-source projects. The conversation also touches on the reality of AI monetization and the emergence of sovereign AI strategies driven by geopolitical motives. Benaich reflects on whether we are in an AI bubble and shares insights on AI investments and opportunities in Europe’s defense sector.