The Peel with Turner Novak

Hosted by Turner Novak

Technology

Website RSS feed

Episodes

155

Latest episode

Aug 2026

Language

About the show

Exploring the world’s greatest startup stories. Get a behind the scenes look into the founding stories of your favorite companies. Learn how the industries they operate in actually work, and learn playbooks and tactics you can use to launch and scale your own business.

Listen to episodes

60 recent

August 24, 2026Episode 1551 hr 27 min

Brex’s 1st Employee On Thinking Like a Founder | Michael Tannenbaum, CEO of Figure

Michael Tannenbaum is the CEO of Figure, the blockchain lending company he took public in 2025. He was employee #1 at Brex, and before that ran the mortgage business at SoFi. Mike Cagney, who founded both SoFi and Figure, pulled him back to take Figure public in 2025. This is a conversation on how to think and act like a founder, the framework he uses to run Figure, plus a look at how a lending business works under the hood, why he ran the broken mortgage business at SoFi to prove himself, the time Masa offered him a billion dollars, how he nearly walking away from Brex right before they launched, inside the SVB collapse, how Figure originates loans for $1,000 instead of $12,000, their recent Kiavi acquisition, and the gas station test his dad taught him. Thank you to Mike Cagney, Art Levy, and Sam Blond for helping brainstorm topics for the conversation! Thanks to this episodes sponsors! Numeral: Sales tax on autopilot https://www.numeral.com Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital Amplitude: AI analytics https://www.amplitude.com Merge: Every model, one API https://www.merge.dev/turner Monaco: The revenue engine for startups https://www.monaco.com/ Timestamps: (0:00) From Brex employee #1 to public-company CEO (1:28) Operating vs managing a career (3:23) Why he took the worst business at SoFi (9:33) The Big Rock framework (11:02) How to get real customer feedback (14:58) The best nose for value in fintech (17:49) Why banking the affluent beats down-market (21:12) Figure: cutting mortgage cost from $12k to $1k (25:41) Do you actually need to use blockchain? (28:03) Why memecoins took over crypto (32:17) Masa's billion-dollar offer (36:29) Leaving SoFi for two kids in a kitchen (39:05) Six months from almost quitting to a unicorn (44:09) The finance guy who ran Brex's marketing (47:03) Inside Brex during the SVB collapse (51:09) The two SoFi insights behind Figure (54:40) From direct-to-consumer to B2B marketplace (56:41) AI can’t get you better credit ratings (58:50) Figure is a modern Fannie Mae (1:01:28) Buyers who commit before the loan exists (1:03:59) Following customers into new products (1:06:35) Buying Kiavi, the fix-and-flip leader (1:12:15) Why more fintech’s don't become marketplaces (1:14:46) The AI risk in outsourcing customer acquisition (1:18:23) What going public actually takes (1:20:14) Life as a public-company CEO (1:22:38) Getting shorted (1:24:12) The gas station test (1:25:42) The reverse pyramid of big corporates Referenced Figure: https://www.figure.com/ Careers at Figure: https://www.figure.com/careers/ Kiavi: https://www.kiavi.com/ Follow Michael Twitter: https://x.com/MBTannenbaum LinkedIn: https://www.linkedin.com/in/michaeltannenbaum/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

August 14, 2026Episode 1551 hr 21 min

Re-founding a Company for the AI Era | Shensi Ding, Merge

Shensi Ding is the co-founder and CEO of Merge, the connective infrastructure that plugs into every tool. Merge started in 2020 building integrations, watched its first customers die off, then rebuilt itself twice for the AI era. Not many founders talk this honestly about tearing up their company. A lot of lessons for others trying to do the same. We get into why integrations turned out to be so important in AI, the night-shift 5-11pm build of their AI transformation, almost hiring a foreign spy, why Shensi thinks founders with an EA are moving too slow, the Embarrassment Framework, why 60% of public MCP servers quietly fail, vibe coding a dinner bot that 10x'd their customer events, and why 6% of Merge employees get married. Thanks to this episodes sponsors! Numeral: Sales tax on autopilot https://www.numeral.com Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital Amplitude: AI analytics https://www.amplitude.com Merge: Every model, one API https://www.merge.dev/turner Monaco: The revenue engine for startups https://www.monaco.com/ Timestamps: (0:00) Something broke every year since 2020 (2:22) How Merge went all-in on AI on nights and weekends (5:40) New launches got faster (8:32) Building connective infrastructure for AI (10:51) The dinner where Merge started (13:11) Six months of research before a line of code (19:00) Almost hiring a foreign spy (20:48) Merge’s 6% marriage rate (22:50) Hiring enthusiastic, nice, smart people (28:02) Early stage founders don’t need an EA (31:27) Shortcuts are a mentality (33:01) The AI tool that 10x'd their customer dinners (38:33) Marketing became an engineering function (40:51) Starting with SMB and climbing the logo ladder (42:07) How the product went cross-category (44:16) Launching Agent Handler and a new pricing model (46:47) Every product should be multi-model (49:58) Why most MCP servers don’t work (53:31) Startups should go all-in on enterprise (57:00) The hardest things are most defensible (1:00:26) Say "psycho shit" to be memorable (1:05:47) The Embarrassment Framework (1:10:23) Frank Slootman and being okay with being disliked (1:12:48) Giving feedback got scarier at 100 people (1:14:01) What only the CEO can do (1:19:44) The best marketing is not doing what everyone else does Referenced Try Merge: https://merge.dev/turner Careers at Merge: https://www.merge.dev/careers Follow Shesi Twitter: https://x.com/shensi LinkedIn: https://www.linkedin.com/in/shensiding Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

August 7, 2026Episode 1541 hr 43 min

The 18x Midas Lister Betting $3B on AI (and calling most of it fake) | Navin Chaddha, Mayfield

Navin Chaddha is the Managing Partner at Mayfield. He’s made the Forbes Midas List 18 times, and thinks a lot of the AI revenue everyone's chasing right now is fake. Mayfield is a 56-year-old firm that backs founders at the paper-and-pencil stage. They’re investing $3 billion into AI, but Navin warns the market is overcapitalized by a factor of 10x. We get into what’s actually going on with the $1B+ funding rounds, the $25 trillion of value AI has to justify, the dangers of FOMO, how he separates vibe revenue from real revenue, backing vertical models instead of horizontal ones, why inference will dwarf training, how a startup actually beats a $100 billion incumbent, the people x-ray behind his founder bets, what cricket taught him about running a company, lessons being the last founder to IPO before the Dot Com Crash, what he learned working with Satya Nadella, and the unfinished business still driving him. Thanks to this episodes sponsors! Numeral: Sales tax on autopilot https://www.numeral.com Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital Amplitude: AI analytics https://www.amplitude.com Merge: Every model, one API https://www.merge.dev/turner Monaco: The revenue engine for startups https://www.monaco.com/ Timestamps: 0:00 Lumilens: Zero to $3B revenue in 14 months 0:50 Connecting GPU's is AI's next bottleneck 5:07 Mayfield: investing $3B in AI and semiconductors 9:39 Where a $1B round actually gets spent 12:51 The six-layer AI stack, and who needs mega-rounds 15:00 Why AI is overcapitalized by 10x 17:47 FOMO is for sheep 21:13 Vibe revenue vs real revenue 22:45 Backing vertical models 24:22 The best firms have one North Star 27:18 Are semiconductors still cyclical? 29:10 Why inference will dwarf training 31:19 What happens after every infra build-out 36:27 2 billion Gemini users isn't real AI adoption 38:21 What a correction does to AI stocks 40:46 How FOMO pulls VC's into hot categories 44:13 What Navin looks for in founders 50:23 Why "everyone hates this category" can be a buy signal 54:12 The argument against the cloud everyone got wrong 57:20 What white-collar work AI teammates will take 1:01:45 How AI startups beat incumbents 1:06:54 Why startups die of indigestion 1:11:49 Mayfield’s secret formula: people-first 1:19:18 What cricket taught Navin about building companies 1:23:17 Dropping out of Stanford to start VXtreme 1:29:22 Blitzscaling to blitz-failing: the last IPO before the Dot-Com Crash 1:31:25 Joining Mayfield instead of starting a 4th company 1:33:29 Unfinished business (backing a $1T company) 1:35:54 Could you tell Satya would run Microsoft? 1:38:58 Investors he respects, founders he missed Referenced Mayfield: https://www.mayfield.com/ Lumilens: https://lumilens.com/ Lumilens Raises $700M: https://www.wsj.com/tech/startup-raises-700-million-to-replace-data-center-wires-with-light-adc74358?mod=e2twd Built to Last by Jim Collins: https://www.amazon.com/s?k=built+to+last+-+jim+collins&adgrpid=186020621003&hvadid=779535177756&hvdev=c&hvexpln=0&hvlocphy=9218885&hvnetw=g&hvocijid=9037174021105194159--&hvqmt=e&hvrand=9037174021105194159&hvtargid=kwd-362242264527&hydadcr=21907_13365950_10662&mcid=f1dd2c5deb5539b7afc6bcdfee5613c8&tag=googhydr-20&ref=pd_sl_4b3f3t1l23_e Follow Navin LinkedIn: https://www.linkedin.com/in/navinchaddha Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

July 30, 2026Episode 1532 hr 9 min

Healthcare Skipped The Internet And Went Straight To AI | Alamin Uddin, NexHealth

Alamin Uddin is the co-founder and CEO of NexHealth. Today, NexHealth’s healthcare infrastructure serves 89 million patients. But at one point, the company had $4,000 in the bank and a maxed-out Amex card. We talk about why 75% of dentists still keep a server in the closet, how healthcare skipped the internet, cloud, and mobile and went straight to AI, why most healthcare systems have no API, funding the company with side hustles, the $36k customer pre-pay that saved the business, how 81% of new AI healthcare startups are built on NexHealth, where he thinks AI value actually accrues, and outlasting OpenAI. Thanks to this episodes sponsors! Numeral: Sales tax on autopilot https://www.numeral.com Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital Amplitude: AI analytics https://www.amplitude.com Merge: Every model, one API https://www.merge.dev/turner Monaco: The revenue engine for startups https://www.monaco.com/ Timestamps: (0:00) Healthcare skipped 3 platform shifts and went straight to AI (4:10) 75% of dentists still have on-prem servers (10:05) How data interoperability holds back healthcare innovation (16:02) Why everyone blames Epic (20:15) Building the developer platform for healthcare (24:36) Why everyone fails to fix the problem (29:11) Fragmented markets enabled developer platforms (32:32) Working as a receptionist at a doctor’s office (36:13) Building a prototype on Twilio (39:15) How incumbents went from blocking to partnering (46:05) Canvassing Soho dentists door-to-door (53:47) Reverse-engineering 40-year old databases (56:21) Funding NexHealth with side hustles for two years (57:30) The scheduling wedge no one could match (1:02:20) Raising $391k from professors and customers (1:03:46) Running out of cash, why customers kept churning (1:07:45) $4,000 in the bank and a maxed-out Amex (1:11:12) The $36k pre-pay that saved the company (1:13:24) NexHealth’s three businesses today (1:20:18) Payments and the “admin-day” problem (1:26:15) 72% sales win rate (1:28:27) The term sheet signed the week before COVID (1:30:26) Spending half the Series A on an acquisition (1:33:47) Raising $176M they didn't need (1:37:28) Why starting before 2022 is an advantage (1:42:22) Where AI value accrues: chips, models, the action layer (1:44:55) 81% of AI products are built on NexHealth (1:48:24) Staying patient for three years after ChatGPT (1:51:25) Competitors building on their API (1:54:02) “We’re a tech company, not healthcare company” (1:56:09) Hiring from outside healthcare (1:58:34) Shoes, email over Slack (2:01:21) What AI changed inside the company (2:04:16) Inspiration from Microsoft in 1977 - 1990 Referenced NexHealth: https://www.nexhealth.com/ Build on NexHealth: https://docs.nexhealth.com/ Careers at NexHealth: https://www.nexhealth.com/careers The Secret 3-Step Master Plan to Cure Healthcare: https://www.notboring.co/p/the-secret-3-step-master-plan-to Follow Alamin Twitter: https://x.com/alfromnexhealth LinkedIn: https://www.linkedin.com/in/alamin-uddin-95284889 Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

July 23, 2026Episode 1521 hr 25 min

Inside Solana's Plan to Replace Wall Street | Anatoly Yakovenko, Solana

Anatoly Yakovenko is the co-founder of Solana, the fastest scaled blockchain in the world. We start by talking about how non-US residents were trading SpaceX on Solana pre-IPO, and which parlayed into the last 130 years of US financial markets. We then get into how Solana is removing eight layers of middlemen that make-up the legacy financial system, whether you actually need to use blockchain to do this, the 4am inspiration to start Solana, how Solana was 10,000x faster than Bitcoin, why a16z passed on investing then paid a 1,000x higher price, how launching Solana at the bottom of the market right as COVID hit led to their success, why AI won’t take your job, growing up sharing one toilet with four families in the USSR, and playing competitive underwater hockey. Thanks to this episodes sponsors! Numeral : Sales tax on autopilot https://www.numeral.com Flex : Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital Amplitude : AI analytics https://www.amplitude.com Merge : Every model, one API https://www.merge.dev/turner Monaco : The revenue engine for startups https://www.monaco.com/ Timestamps: (0:00) Trading SpaceX on Solana (3:02) Why Wall Street runs on 100 year old tech (10:51) US dominance created demand for tokenized stocks (13:58) Complexity reduces risk of the financial system (15:51) Do you need to use blockchain? (18:34) Privacy tradeoffs of public ledgers (23:45) Making a 10,000x faster blockchain (30:05) A new data structure based on time (32:54) Trading was Solana’s first use case (37:41) Advice from his wife that led to Solana (40:05) Why a16z passed (then paid up 1,000x) (43:50) Rejection and COVID led to Solana’s fast adoption (48:30) Best time to launch is the bottom of a market (52:56) Why Bitcoin and Ethereum were so slow (57:38) Rebuilding Solana with Alpenglow (1:01:23) 35% of all stablecoin volume runs on Solana (1:04:26) Motors replaced 200 billion jobs, AI will replace 100 billion (1:08:17) It’s selfish to protest data centers (1:10:11) Growing up in the USSR: one toilet, four families (1:12:27) Culture shock moving to the US (1:13:23) Government spending is fake GDP (1:15:49) Playing competitive underwater hockey (1:18:01) Armani at Backpack (1:19:23) How Solana survived the FTX collapse (1:22:47) There won’t be massive AI job loss Referenced Solana: https://solana.com/ Jobs at Solana: https://jobs.solana.com/companies/solana-foundation-2 Slow Ventures: https://slow.co/ Foundation Capital: https://foundationcapital.com/ Multicoin: https://multicoin.capital/ Follow Anatoly Twitter: https://x.com/toly?lang=en LinkedIn: https://www.linkedin.com/in/anatoly-yakovenko Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

July 17, 2026Episode 1511 hr 28 min

The Hidden Layer Every AI Agent Runs On | Tony Holdstock-Brown, Inngest

Tony Holdstock-Brown is the co-founder and CEO of Inngest, the durable execution platform that quietly powers your favorite AI agents. We get into why agents work in a demo and die in production, building their own cloud to get 20x lower cost, growing 35x after AWS and Cloudflare copied them, growing a dev tools company without a personal brand or Twitter account, why he thinks evals today are like “asking the criminal if they committed the crime”, and the thing they built to score 100% of your production agents without paying for LLM as a judge. Thank you to Numeral, Flex, Amplitude, Merge, and Monaco for supporting this episode. Numeral: Sales tax on autopilot https://www.numeral.com Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital Amplitude: AI analytics https://www.amplitude.com Merge: Every model, one API https://www.merge.dev/turner Monaco: The revenue engine for startups https://www.monaco.com/ Timestamps: (0:00) The hidden infra layer every AI agent runs on (1:46) Building complex chains of logic (3:31) Why agent SDK's don't go far enough (4:49) Healthcare was the original event-driven nightmare (6:32) Storing traces on your infrastructure enables self-improving loops (14:26) Why Inngest was already in the right place for AI (15:49) Score agents off product events, not LLM's (17:31) The OpenAI copy-paste signal (21:24) Swap in LLMs and cut costs 20x (23:44) How customers pulled the product forward (25:41) Orchestration belongs outside the sandbox (29:48) Building a neocloud to cut costs 20x (32:09) Most neoclouds just resell AWS (32:54) All AI infrastructure is converging (34:49) Why Claude can't just build your backend (36:44) How to build a software factory (39:12) Agents are a lottery you get addicted to (42:44) Loops must exist until AGI hits (45:38) If models keep getting better, why orchestrate? (48:28) When incumbents steal your features (52:30) Why you can't vibe code infrastructure (55:54) Why Tony has no personal brand (59:38) Dev tools GTM without Twitter (1:03:20) Lessons from the founder of DuckDuckGo (1:10:39) Truth as a company value (1:13:08) Taking too long adapting to AI (1:15:10) Startups are 100% R&D (1:17:19) Ali from Databricks (1:19:03) Writing his own code, Voice-to-text with local models (1:23:53) Evals are batshit insane Referenced Inngest: https://www.inngest.com/ Principles by Ray Dalio: https://www.amazon.com/dp/1501124021?lv=shuf&channelId=500&plpRedirect=mhFallback Traction - How Any Startup Can Achieve Explosive Customer Growth: https://www.amazon.com/dp/1591848369?lv=shuf&channelId=500&plpRedirect=mhFallback Follow Tony Twitter: https://x.com/itstonyhb LinkedIn: https://www.linkedin.com/in/tonyhb/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

July 10, 2026Episode 1501 hr 28 min

Rebuilding a $600M Company From Scratch | Peter Rahal, David

Peter Rahal is the Founder and CEO of David. Before David, he built RXBAR in his parents' basement with $10k and sold it to Kellogg for $600M. We get into why he basically rebuilt the same company again, how buying his own ingredient supplier made a food business venture-backable, why RXBAR's paleo positioning was a trap, the EPG fat technology behind David, how GLP-1’s have changed diet trends forever, selling cans of fish as a marketing weapon, the lawsuit that got him 120M impressions in a week, and why he studies fashion houses instead of food companies. Thank you to Numeral, Flex, Amplitude, and Merge for supporting this episode. Numeral: Sales tax on autopilot https://www.numeral.com Flex: Premium banking, 60-day credit, 0% APR https://home.flex.one/referral/bananacapital Amplitude: AI analytics https://www.amplitude.com Merge: Every model, one API https://www.merge.dev/turner Timestamps: (0:00) David: Tools to increase muscle, decrease fat (2:24) Making nutrition evidence-based, not ideological (4:27) $300M revenue in year two (5:19) Why he rebuilt the same company again (7:12) Do what you're already good at (9:57) In food, the only edge is brand (12:13) The RXBAR playbook and $600M exit (14:20) RXBAR's original positioning was too fragile (15:25) Designing David from first principles (18:22) Why people don't eat protein bars (19:33) Building a multi-brand company that lasts (25:44) How EPG made David venture-backable (29:44) The Medici name and structure (31:38) Food entrepreneurs are Luddites (33:37) Why Big Food can't innovate (38:21) Beverage is a better business than food (40:34) Deciding which products to launch (43:21) GLP-1's ended diet trends forever (48:09) Looking good is the new status symbol (51:30) Sleep first, exercise second, nutrition third (54:35) Brand is just a unique human being (59:05) Humor travels (1:01:09) Marketing is finding mispriced attention (1:06:35) When to bail on a marketing trend (1:09:05) What makes a good meme (1:10:00) Why David sold cans of fish (1:13:30) How to navigate a lawsuit (1:17:02) 120M impressions from a lawsuit (1:18:52) Lessons from Bezos and Brad Jacobs (1:23:30) Why the best brands are fashion and beauty (1:25:00) Women set culture Referenced David: https://davidprotein.com/ EPG / Epogee: https://epogee.com/ Whoop: https://www.whoop.com/ Oura: https://ouraring.com/ Fort: https://fort.cx/ David Rumors TikTok: https://www.tiktok.com/@davidprotein/video/7616855415875210510 Founders Podcast: https://www.founderspodcast.com/ How to Make a Few Billion Dollars by Brad Jacobs: https://www.amazon.com/How-Make-Few-Billion-Dollars/dp/B0CHTQP25T Follow Peter Twitter: https://x.com/PeterRahal LinkedIn: https://www.linkedin.com/in/peter-rahal-037bba43 Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

July 3, 2026Episode 1491 hr 45 min

Inside Goldman’s $22B Bet on Venture Capital | Hans Swildens, Industry Ventures

Hans Swildens started Industry Ventures in 2000, and this is his first podcast since selling it to Goldman Sachs in 2026. Hans has been buying venture secondaries longer than almost anyone, and the combined business is one of the largest VC portfolios in the world: 525 firms, 1,600 funds, and over $22B in capital commitments. We get into why he sold to Goldman, the barbell market quietly killing middle-stage venture, how VC's are manufacturing their own exits, why most seed funds without a real angle have 5 years left, the LP base that's a completely different species every fund cycle, how he started Industry by acquiring funds at 99% discounts during the Dot Com Collapse, the day he passed on a multi-billion-dollar data center, and why the secondary market may eventually be multiples the size of the primary market. Thank you to Zach Coelius, Will Quist, Emily Zheng, and Andrea McGee for help brainstorming topics for the conversation. 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.com Flex: Get premium banking and a net 60 day credit card at 0% APR https://home.flex.one/referral/bananacapital Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com Merge: Every model. One API. Total control. Check out Merge’s Agent Handler. merge.dev/turner Timestamps: (0:00) Inside Goldman’s $22B venture bet (7:57) 1,600 funds over 525 firms (11:11) Why scale lets you “see the cube” (14:17) Most humbling lesson in 26 years (16:19) Three types of Seed funds (18:47) LP's evolve every fund cycle (22:00) VC is a sales game (24:38) A strong CRM is non-negotiable (29:06) Buying secondaries during the Dot Com Collapse (31:33) Triangulating opinions across GP’s, founders, and LP’s (37:22) Seed without differentiation doesn’t work (42:16) Biggest mistakes by first-time GP’s (44:31) Buying Enron’s VC portfolio at a 99% discount (50:15) Entrepreneurial finance is underappreciated (52:15) Why asset managers are acquiring venture firms (58:47) Why it’s hard to start venture programs (1:03:20) Secondaries: $250M to $150B market in 25 years (1:08:06) Continuation funds & debt structured secondaries (1:12:02) “Secondaries might be multiples bigger than primaries” (1:19:52) How to structure secondary transactions (1:26:00) What happens after SpaceX, OpenAI, Anthropic IPO’s (1:30:35) How Seed survives the asset manager era (1:35:16) How to manufacture liquidity (1:41:41) How AI is impacting secondary markets Referenced Industry Ventures: https://www.industryventures.com/ How Big Is The Secondary Market for Venture Capital?: https://www.industryventures.com/insight/2023-2025e-how-big-is-the-secondary-market-for-venture-capital/ Exploring the Growth of Venture Secondaries: https://www.chronograph.pe/exploring-the-growth-of-venture-secondaries/ Pitchbook’s US Secondaries Market Watch: https://pitchbook.com/news/reports/2025-annual-us-vc-secondary-market-watch Follow Hans Twitter: https://x.com/HansSwildens LinkedIn: https://www.linkedin.com/in/hansswildens Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

June 25, 2026Episode 1471 hr 42 min

The Past, Present, and Future of Pre-Seed | Charles Hudson, Precursor

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.com Flex: Get premium banking and a net 60 day credit card at 0% APY https://home.flex.one/referral/bananacapital Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com Merge: Every modal. One API. Total control. Check out Merge’s Agent Handler. merge.dev/turner Timestamps: (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 effect Referenced Precursor: https://precursorvc.com/ a16z’s State of Markets report https://x.com/TurnerNovak/status/2015830796393742599?s=20 Follow Charles Twitter: https://x.com/chudson LinkedIn: https://www.linkedin.com/in/chudson Charles Substack: https://chudson.substack.com/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

June 18, 2026Episode 1471 hr 48 min

Inside Elbow Grease, NYC's Hands-On Accelerator | Dan Teran, Gutter Capital

Dan Teran is the co-founder Gutter Capital, a concentrated seed fund in NYC, and Elbow Grease, the accelerator that puts 15 startups in one building and helps build their teams for them. Gutter just announced a $75M Fund III and opened applications for the second Elbow Grease batch (apply below by July 31st) We get into starting an accelerator when there’s already a hundred of them, why Gutter prefers very concentrated portfolios, what it was actually like selling Managed by Q to WeWork, why raising a fund turned out to be harder than selling a company, why he thinks startups should form a board and use OKR’s from day one, and the time he went big-wave surfing with Adam Neumann and Laird Hamilton. Thank you to James Gettinger, Satya Patel, Abhinav Kapur, and JT White for help brainstorming topics for the conversation. 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.com Flex: Get premium banking and a net 60 day credit card at 0% APY https://home.flex.one/referral/bananacapital Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com Merge: Every modal. One API. Total control. Check out Merge’s Agent Handler. merge.dev/turner Timestamps: (0:00) Elbow Grease: NYC’s new accelerator (7:39) Building a small, hands-on, in-person experience (13:39) Recruiting 100 people into portfolio companies (16:25) Portfolio concentration makes investors more helpful (24:58) Why raising Fund 1 was so hard (28:08) Advice for new fund managers (30:30) “Hiring today is as competitive as ever” (32:23) Selling Managed By Q to WeWork (35:23) “Never raise too much money” (39:43) Almost buying his company back from WeWork in Feb 2020 (43:50) Starting Gutter Capital in the depths of COVID (49:34) Funding angel investing with gambling proceeds (52:39) Behind the name “Gutter Capital” (54:49) “Raising a fund is like getting punched in the face” (59:03) Writing long LP letters (1:06:45) Investing in real world problems (1:09:48) What a Gutter founder looks like (1:12:46) How Gutter makes new investments (1:18:41) Importance of customer calls at pre-seed (1:21:59) Evolution of NYC tech over last 15 years (1:26:15) Why you should form a board at Seed (1:28:29) How to run a Seed stage board meeting (1:34:04) Sharing carry with portfolio founders (1:35:56) The best founders need lots of help (1:39:30) Big wave surfing with Adam Neumann and Laird Hamilton Referenced Apply to Elbow Grease: https://forms.gutter.cc/eg0002-application Elbow Grease: https://elbowgrease.cc/ Gutter Capital: https://www.gutter.cc/ WeWork Acquires Managed By Q: https://techcrunch.com/2019/04/03/wework-acquires-managed-by-q/ Follow Dan LinkedIn: https://www.linkedin.com/in/danteran/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/