The Peel with Turner Novak

Charles Hudson started Precursor Ventures in 2015, and helped create pre-seed as a category.Ten years and hundreds of Day 0 checks later, few investors have backed as many first-time founders, making him the perfect person to talk through the state of the category today.We talk about why this is the hardest moment for pre-seed/seed investing he can remember, why sitting out of bubbles can be more dangerous than joining, how he hands his junior team real money to make their own bets, and urgency and “the last $250k effect”.Thank you to Numeral, Flex, Amplitude, and Merge for supporting this episode.Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.comFlex: Get premium banking and a net 60 day credit card at 0% APY https://home.flex.one/referral/bananacapitalAmplitude: AI analytics, all you have to do is ask https://www.amplitude.comMerge: Every modal. One API. Total control. Check out Merge’s Agent Handler. merge.dev/turnerTimestamps:(0:00) Is Pre-Seed dead?(4:15) Do round names matter anymore?(12:27) Multi-stage signaling risk doesn’t exist(16:42) Smart LP’s love multi-stage funds(22:03) Is the traditional Seed model broken?(26:31) Velocity of capital deployment drives all incentives(30:30) How to compete with megafunds at early stage(34:24) Megafunds have Seed funds in a vice-grip(38:34) “The best Series A’s are all expensive"(39:33) Are we doing 2021 all over again?(41:53) It’s safer to participate in bubbles than sit out(47:35) Price you pay is everything(50:22) The system incentivizes an addiction to consensus(55:22) High valuation + high CapEx grows AUM(59:56) How Precursor actually invests today(1:01:32) Precursor’s Principal investor program(1:05:56) Deciding when to selling your winners(1:10:53) Raising as a pre-consensus founder(1:12:39) What Charles looks for in founders(1:17:20) What it’s actually like to start a fund(1:20:56) Misconceptions of first-time fund managers(1:26:22) 300+ LP meetings to raise Precursor Fund 1(1:29:24) The single tweak to his pitch that raised the fund(1:31:54) Precursor’s evolution over time(1:34:57) The second desert of venture capital(1:37:34) The last $250k effectReferencedPrecursor: https://precursorvc.com/a16z’s State of Markets report https://x.com/TurnerNovak/status/2015830796393742599?s=20Follow CharlesTwitter: https://x.com/chudsonLinkedIn: https://www.linkedin.com/in/chudsonCharles Substack: https://chudson.substack.com/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Gary Tan is the President and CEO of Y Combinator.YC is the startup accelerator behind companies like Airbnb, Stripe, Coinbase, Reddit, Twitch, and thousands more. According to Garry, they’ve invested in 20% of all startups worth $5B or more started since 2012.Gary has lived every side of the YC ecosystem. He went through YC as a founder, later became a partner, started Initialized Capital where he backed companies like Coinbase and Instacart, and then returned to lead YC.We walk through the different “eras” of YC, from the early Paul Graham and Jessica Livingston days in Cambridge, to scaling in San Francisco, to today’s push back toward in person community and what Gary calls “founder mode” for the organization itself.We also talk about why the Bay Area still matters so much for startups, what’s happening with California taxes and policy, and why Gary has gotten more involved in local politics to keep it the best place for founders to build companies.Then we go deep on the parts of startups people don’t talk about enough. Co-founder conflict, rage quitting, therapy and coaching, and why companies inevitably take on the personality and emotional patterns of their founders.We also cover what YC looks for in applications, how the 13 week batch is structured, how Demo Day really works, how to choose the right investors, and what Gary thinks the next phase of YC looks like, including helping founders even after Series A.At the end, Gary shares his personal AI workflow, including meta prompting, comparing outputs across models, and the tools he uses every day to think and build faster.Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:05) Moving from Winnipeg to California as a kid(1:35) How YC interviews work(2:55) The first batch in 2005(6:46) Why YC moved from Boston to SF(8:17) California’s Billionaire Tax(11:00) Tech should care about public policies(17:01) Going direct to your audience(20:28) The 2nd Era of YC(24:01) Rage quitting Palantir, learning to understand himself(32:41) Co-founder conflict kills most startups(35:15) Joining YC as a group partner(37:22) Initialized Fund 1 (55x DPI)(39:44) Why Garry went back to lead YC(42:44) YC funds 20% of all $5B+ companies(44:30) Lessons from Brian Chesky(48:01) Garry’s thoughts on YC rejection(51:41) How to get into YC(58:03) What it’s like inside a 13-week YC batch(1:02:23) 20% of YC is hard tech(1:05:55) YC's 3rd era: founder mode, re-batching(1:07:56) Escaping the matrix(1:11:26) Garry's personal AI stack(1:20:25) Tech optimismReferencedY Combinator: https://www.ycombinator.com/Initialized Capital: https://initialized.com/Torch: https://torch.io/Perplexity: https://www.perplexity.ai/Anthropic: https://www.anthropic.com/OpenAI: https://openai.com/Airbnb: https://www.airbnb.com/Kyle Vogt on his new startup: https://www.youtube.com/watch?v=XQoFbvyWEy8Follow Aaron Levie on X: https://x.com/levieFollow GaryTwitter: https://x.com/garytanLinkedIn: https://www.linkedin.com/in/garytan/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Dug Song and Jon Oberheide are the co-founders of Duo Security.If you’ve never heard of Duo, it might be one of the most underrated software stories of all-time.Starting in 2010, they burned only $14 million to hit $100m in ARR, were acquired by Cisco for $2.35 billion in 2018, and now rumored to be doing over $1 billion in ARR inside Cisco 16 years later.We talk about how they built one of the most capital efficient SaaS companies ever from Ann Arbor, Michigan, and how their focus on the customer and company culture helped them win in a crowded cybersecurity market.We talk growing up in the early hacking culture of the 90s, why most security tools are painful to use, sizing their market, solving for non-consumption of a product, and how Duo flipped the model by designing for end users instead of security teams.We talk about staying in Michigan instead of moving to Silicon Valley, and why staying out of the tech bubble helped them execute.We break down the mechanics of scaling from zero to $100 million in ARR, everything they learned integrating with Cisco, and why more founders should build outside of San Francisco. A quick thank you ex-Duo employees Zack Urlocker, Ash Devata, and Katie Kilroy for their help brainstorming topics for the conversation.Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com](https://www.numeral.com/)Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(4:49) Meeting from Dug’s Wi-Fi honeypot(7:33) 90’s hacking culture and cybersecurity’s wild west(14:49) How the internet was born in Ann Arbor(18:58) Staying in Michigan instead of moving to Silicon Valley(31:20) Philosophy on leadership and team building(39:48) What makes a good engineering leader(44:01) Starting Duo to make security easier(45:22) Why most security products suck(48:36) How fixing account takeover became a $1B ARR company(59:10) TAM, competition, fixing the non-consumption of security(1:04:04) Being a radical advocate for the customer(1:08:35) Duo’s pizza sales play(1:12:45) Branding lessons from Anthropic, Tesla, Cliff Bar(1:17:47) When to say no to customers(1:21:27) Importance of culture when scaling(1:27:56) Duo’s role in uncovering the SolarWinds breach(1:31:29) Scaling to $100M ARR on $14M burned(1:39:30) Inside the $2.35B Cisco acquisition(1:44:02) What big companies get wrong about customers(1:51:53) Building Michigan’s startup ecosystemReferencedDuo Security: [https://duo.com](https://duo.com/)Cisco: [https://www.cisco.com](https://www.cisco.com/)University of Michigan: [https://umich.edu](https://umich.edu/)Follow DugTwitter: https://x.com/dugsongLinkedIn: https://www.linkedin.com/in/dugsongFollow JonTwitter: https://x.com/jonoberheideLinkedIn: https://www.linkedin.com/in/jonoFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Nathan Benaich is the founder of Air Street Capital and author of the State of AI report. On its eighth year, the report is a year-long effort on the biggest things happening in AI, across research, industry, politics, and safety.This episode covers the biggest takeaways from the latest report, like the rise in reasoning, the surge in China’s open source models, where AI is working in practice, the rise of sovereign AI, where he thinks value will actually accrue over the long-term, if we’re in an AI bubble, and how he’s investing in AI today at Air Street.Thanks to Nico at Adjacent and Dan at Michigan for helping brainstorm topics for Nathan.Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(3:39) State of AI 2025(6:22) Takeaway #1: Reasoning & tool calling(13:01) Takeaway #2: Rise of Chinese open source(15:25) Open vs closed source models(26:46) Takeaway #3: AI revenue is real(27:51) Takeaway #4: Sovereign AI(36:44) Are we in an AI bubble?(59:23) Starting Air Street Capital(1:05:18) Raising Fund 1(1:16:20) Air Street portfolio strategy(1:25:15) When and who Nathan decides to invest(1:35:04) How important are AI benchmarks?(1:39:31) When to train your own models(1:45:56) Rise of European defense tech(2:01:43) Nathan’s personal AI stack(2:07:32) Is niching down too risky?(2:16:12) Nadal vs FedererReferencedState of AI Report: https://www.stateof.aiThe Thinking Game Documentary: https://www.youtube.com/watch?v=d95J8yzvjbQV7: https://www.v7labs.comFollow NathanTwitter: https://x.com/nathanbenaichLinkedIn: https://www.linkedin.com/in/nathanbenaichFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron.Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re still early, and lessons today’s breakout AI companies can learn from those that survived the Dot Com Crash.Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at A* is invested in teenagers, and he shares how he identifies outlier talent so early, from Seed investments in Airbnb, PayPal, and Pinterest, to many of today’s hottest AI companies.He also shares the insane story of investing 100% of the proceeds from his first startup into PayPal’s Seed round, how PayPal’s early fraud systems inspired Palantir, what he learned from the PayPal Mafia, from Peter Thiel, and what makes Founders Fund special.We also talk about how he and his wife recently had two babies, five months apart, using genome screening and surrogates.Thanks to Ramtin Naimi, Navya Gudimetla, and Bennett Siegel for helping brainstorm topics for the conversation.Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(4:25) Power shift from VC’s to founders since the 90’s(9:08) AI is the mother of all bubbles(12:40) Why AI is still underhyped(14:10) What Kevin and A* are investing in today(16:02) Investing 100% of his first startups proceeds in PayPal’s Seed round(21:21) What made the PayPal Mafia special(23:37) Parallels between the 90’s and today(26:40) What makes Founders Fund special(35:07) How Palantir evolved from PayPal’s fraud models(39:06) Building Xoom on the PayPal API(43:38) Lessons between Kevin’s 1st and 2nd startups(46:52) Starting Eventbrite off early PayPal API app(51:51) Eventbrite’s hidden TAM challenge(53:49) Selling Eventbrite to Bending Spoons(54:59) Investing 20% of A* in teenage founders(1:02:33) Incubating Sauron, the home security company(1:08:44) Making breakfast for our kids(1:13:33) Having kids with genome screening and surrogates(1:20:31) Collecting art, how to get startedReferencedhttps://www.a-star.co/https://www.eventbrite.com/https://www.xoom.com/https://www.sauron.systems/https://www.orchidhealth.com/Setting the Table by Danny Meyer: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/006074276320% of fund in teenage founders: https://techcrunch.com/2025/10/18/this-top-vc-bet-close-to-20-of-his-fund-on-teenagers-heres-why/https://nypost.com/2025/12/14/us-news/xu-bo-chinese-billionaire-reportedly-sires-more-than-100-kids/Follow KevinTwitter: https://x.com/kevinhartzLinkedIn: https://www.linkedin.com/in/hartzFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/