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From 15 epsHost
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The Past, Present, and Future of Pre-Seed | Charles Hudson, Precursor
Jun 25, 2026
Unknown duration
Inside Elbow Grease, NYC's Hands-On Accelerator | Dan Teran, Gutter Capital
Jun 18, 2026
Unknown duration
The AI-Native GTM Playbook | Sam Blond, Monaco
Jun 11, 2026
1h 56m 48s
Inside the First Quant-Driven VC Fund | Nuno Goncalves Pedro, Chamaeleon
Jun 5, 2026
2h 01m 20s
15 Hot Takes on VC and AI from the 2026 Allocate Beyond Summit
May 29, 2026
1h 36m 35s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/25/26 | ![]() 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.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/ | — | ||||||
| 6/18/26 | ![]() 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.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) 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 HamiltonReferencedApply to Elbow Grease: https://forms.gutter.cc/eg0002-applicationElbow 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 DanLinkedIn: https://www.linkedin.com/in/danteran/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/ | — | ||||||
| 6/11/26 | ![]() The AI-Native GTM Playbook | Sam Blond, Monaco✨ | AI in salesGTM playbook+3 | Sam Blond | MonacoBrex+2 | — | AIsales+6 | Numeral | 1h 56m 48s | |
| 6/5/26 | ![]() Inside the First Quant-Driven VC Fund | Nuno Goncalves Pedro, Chamaeleon✨ | quant-driven venture capitaldata analysis in VC+3 | Nuno Goncalves Pedro | ChamaeleonRenTech | — | venture capitalquantitative analysis+3 | Numeral | 2h 01m 20s | |
| 5/29/26 | ![]() 15 Hot Takes on VC and AI from the 2026 Allocate Beyond Summit✨ | venture capitalAI+4 | Tripp JonesBryan Rosenblatt+10 | Allocate | Deer Valley Utah | venture capitalAI+5 | Numeral | 1h 36m 35s | |
| 5/24/26 | ![]() Building Got Easy. This Startup Solves What to Build | Alfred Wahlforss, Listen Labs✨ | AI customer researchstartup strategy+4 | Alfred Wahlforss | Listen LabsMicrosoft | — | AIcustomer research+6 | Numeral | 1h 13m 32s | |
| 5/15/26 | ![]() Inside the AI Sprint, Understanding Anthropic's Strategy | Tomasz Tunguz, Theory Ventures✨ | AI strategyinvestment in AI+4 | Tomasz Tunguz | Theory VenturesOpenAI+1 | — | AIAnthropic+7 | Numeral | 1h 32m 19s | |
| 5/7/26 | ![]() Cursor + Kalshi Seed Investor on Spotting Outlier Talent | Ali Partovi, Neo✨ | outlier talentinvesting+4 | Ali Partovi | NeoPayPal+5 | — | Neooutlier talent+5 | Numeral | 1h 56m 09s | |
| 4/30/26 | ![]() How a Hillbilly in Nevada Bootstrapped a $140M ARR Manufacturing Company | Jim Belosic, SendCutSend✨ | manufacturingbootstrapping+4 | Jim Belosic | SendCutSend | — | sheet metal manufacturingrevenue run rate+5 | Numeral | 1h 32m 17s | |
| 4/24/26 | ![]() The $5B Venture Growth Buyout Playbook | Alex Israel, Metropolis✨ | venture capitaltechnology+4 | Alex Israel | Metropolis | — | parking lotsgrowth buyout+4 | Numeral | 1h 29m 58s | |
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| 4/17/26 | ![]() How Agentic AI is Reshaping Science, Education, and the Economy | Karthik Duraisamy at the University of Michigan✨ | Agentic AIscientific discovery+4 | Karthik Duraisamy | University of MichiganInstitute of Agentic Computing+1 | — | Agentic AIscientific research+5 | Numeral | 1h 48m 30s | |
| 4/9/26 | ![]() How US Healthcare Actually Works, the WWII Tax Loophole that Broke it Forever, and How AI Can Fix it | Nikhil Krishnan, Out of Pocket✨ | US healthcare systemAI in healthcare+3 | Nikhil Krishnan | Out of Pocket | — | healthcareAI+5 | Numeral | 1h 45m 04s | |
| 4/2/26 | ![]() Sophia Amoruso on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders✨ | entrepreneurshipbootstrapping+5 | Sophia Amoruso | Nasty GalTrust Fund | — | Nasty GalTrust Fund+8 | Numeral | 1h 31m 38s | |
| 3/26/26 | ![]() Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi✨ | venture capitalAI in entrepreneurship+4 | Mike SmithNikhil Basu Trivedi | FootworkCanva+1 | — | Footworkventure capital+7 | FlexTURNER | 1h 32m 16s | |
| 3/18/26 | ![]() Inside Hanover Park: Building an AI-Native Service Business, Growing to $15B in Assets✨ | AI-native service businessfund administration+5 | Chris Hladczuk | Hanover ParkSahil Bloom+1 | — | AI-nativefund administration+5 | Numeral | 1h 11m 41s | |
| 3/12/26 | ![]() Inside Canada’s Fastest Growing AI Company | Spellbook, Scott Stevenson✨ | AIlegal technology+4 | Scott Stevenson | Cursor for lawyersMicrosoft Word plugin+3 | — | AIlegal software+6 | Numeral | 1h 35m 41s | |
| 3/4/26 | ![]() Benchmark’s Chetan Puttagunta on the Past, Present, & Future of Software✨ | software historyAI investments+5 | Chetan Puttagunta | BenchmarkMeta+1 | — | softwareAI+6 | Numeral | 1h 29m 33s | |
| 2/27/26 | ![]() Inside Serval: Building the System of Intelligence for IT | Jake Stauch | Jake Stauch is the Co-founder and CEO of Serval. Serval automates IT with AI.We talk taking on incumbents with an AI-native product, why IT departments haven’t had much automation historically, the 12+ month journey of landing their first customer, and how teams can increase talent density as they scale.Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com](https://www.numeral.xn--com-xw0a/)Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFzTimestamps:(0:14) AI-native employee support(5:15) How an early work trial almost ended the entire company(9:05) Why IT hasn’t had much automation(13:09) Vibe coding for IT professionals(15:31) Competing against publicly traded incumbents(23:32) Having less than three months of runway for seven years building his first hardware consumer health startup(33:15) Lessons from five years at Verkada(39:11) The single question that led birthed the idea for Serval(44:19) Navigating 12+ months of zero revenue(52:05) Knowing when not to pivot(55:15) Finally landing the first three customers(58:07) Getting pre-empted for a Series A(1:01:04) Getting a Series B term sheet the next day(1:05:54) How to structure design partnerships that convert(1:08:48) Building a mirror instead of system of record(1:13:49) Make the implementation part of the product(1:15:24) How to increase talent density as you scale(1:21:32) Why every new hire should help you recruitReferencedTry Serval: https://www.serval.com/Careers at Serval: https://www.serval.com/careersEpisode with Filip @ Verkada: https://www.youtube.com/watch?v=fXI3GdicIHwFollow JakeTwitter: https://x.com/jakeservalLinkedIn: https://www.linkedin.com/in/jakestauchFollow 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/ | — | ||||||
| 2/19/26 | ![]() Garry Tan on the Past, Present, and Future of YC | 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/ | — | ||||||
| 2/13/26 | ![]() Building the Wearable That Gets You Stronger | Miranda Nover, Co-founder of Fort Health | Miranda Nover is the Co-founder and CEO of Fort Health. Fort builds wearables that automatically track strength training for people who care about longevity.This is a new format I’m experimenting with. It’s the first time I’ve had a Banana portfolio company founder on the show while they’re still at the pre-seed stage. When I surveyed my subscribers a few weeks ago, you were most interested in more early stage VC-backed founders, and I’d love your feedback on what you think of this.Miranda is still very much working through the idea maze and iterating on the Fort product. We talk about the megatrends driving consumer health, why she’s building a company that helps people get stronger, and everything she’s learned getting a hardware company off the ground.She’s also in the middle of the current YC batch, and gives an inside look at what it’s been like and if she’d recommend it to other founders.Thank you to Numeral and Flex for supporting this episode.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:(3:37) Importance of strength training(6:34) Benefits of being strong(10:37) Evolution of Fort’s hardware(15:58) Automating workout tracking(19:29) Two types of strength trainers(25:30) Building the strength company(27:26) How healthcare is consumerizing(40:43) Lessons building batteries at Tesla(44:56) Hardest parts about building a hardware startup(51:01) Adventures in vibe coding(57:54) How to use Twitter as a founder(1:02:09) The launch video industrial complex(1:08:03) What it’s like doing YC(1:10:19) Selling crayons in 3rd grade, Lemonade stands(1:14:41) Miranda’s best vintage finds(1:16:44) How Turner evolved as a VC(1:22:22) Turner’s early social media PMF(1:28:53) Inventing shitpostingReferencedTry Fort: https://www.fort.cx/Follow MirandaTwitter: https://x.com/mirandanoverLinkedIn: https://www.linkedin.com/in/mirandanoverFollow 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/ | — | ||||||
| 2/5/26 | ![]() How Duo Security went Zero to $1B ARR in Ann Arbor | Dug Song, Jon Oberheide | 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/ | — | ||||||
| 1/28/26 | ![]() Building Real-Time Data Streaming for AI | Jacqueline Cheong, Co-founder and CEO of Artie | Jacqueline Cheong is the Co-founder and CEO of Artie.Artie moves data across your systems in real-time, and we talk about why that’s so important in the age of AI.It’s a lot harder than you’d think, as less than 5% of real-time data streaming projects are successful.I talked to a dozen people to prepare for this conversation, including Jared Friedman who worked with Jacqueline during YC, her sales coach Ras, and numerous Artie employees like A-nee-rud, Ryan, Sarah, Shangbing and Jacqueline’s co-founder Robin.We talk through how Robin built real-time data streaming at OpenDoor and Zendesk before they started Artie, and Jacqueline shares the sales playbook she learned going from hedge fund analyst to software CEO, including asking customers for their hardest problem and then solving it with the product.Artie just announced a $12 million Series A a few weeks before we published this episode. We talk about how they landed all of their early enterprise customers through cold outbound, how they structure and automate their prospecting with AI so they have no BDRs, and why they’re seeing customers switch to Artie even after building their own multi-million dollar real-time streaming projects in-house.I also asked Jacqueline what it’s like working with Standard Capital. They’re a new fund started by a group of YC partners, and it was fascinating to hear about the things they’ve borrowed from YC when investing at the Series A stage.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:(4:08) Artie: Real-time data streaming(5:13) Why moving data is so hard(9:14) Evolution of data warehouses(12:47) AI needs real-time data(18:44) Build vs buy in data streaming(22:51) How to build in a crowded market(26:26) Early focus on a specific hard problem(30:33) Acquiring enterprise customers from cold emails(32:51) Onboarding their first customer with no UI(35:46) Solving compliance and implementation(38:50) How to automate internal engineering, marketing, and ops(44:01) Building an AI-powered GTM pipeline and motion(46:52) Add your customers on iMessage, Slack, Teams(53:00) Starting Artie to solve their own problem(59:25) Discovering YC through a friend(1:02:20) Everything Jacqueline learned about sales(1:06:29) How to improve your sales discovery calls(1:10:08) Inside Artie’s $12m Series A(1:16:44) What its like working with Standard Capital(1:22:59) Jacqueline’s favorite bookReferencedTry Artie: https://artie.comCareers at Artie: https://www.artie.com/careersClay: https://www.clay.comPodcast with Tommy @ Alloy: https://www.youtube.com/watch?v=e7i8Wxklu-YYCombinator: https://www.ycombinator.comStandard Capital: https://www.standardcap.comFounding Sales: https://www.foundingsales.comThe Score Takes Care of Itself: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472Follow JacquelineTwitter: https://x.com/JacquelineSYC19LinkedIn: https://www.linkedin.com/in/jacqueline-cheongFollow 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/ | — | ||||||
| 1/22/26 | ![]() The State of AI: Rise of Reasoning, Surge in Chinese Open Source, Sovereign AI , How to Invest in AI Today | Nathan Benaich, Air Street Capital | 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/ | — | ||||||
| 1/15/26 | ![]() Building the $3B API That Didn’t Exist, Europe’s Regulation Problem | Marcelo Lebre, Co-founder of Remote | Marcelo Lebre is the Co-founder and President of Remote, the payroll and international employment company.Remote is one of today's most underrated software companies. We get into why payroll is such a hard problem, why most of the industry still runs on spreadsheets, the edge cases of software meeting government, and a diagnosis of Europe’s regulation problem.We also talk through the journey trying 8 different startup ideas before Remote, how COVID changed the business overnight, and what he’s learned about building culture and running remote teams.Thanks to Gillian O’Brien, Villi Iltchev, Andreas Klinger, Masha Bucher, and Marcelo’s co-founder Job for helping brainstorm topics for this.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:(3:22) Gaming with kids(6:05) Hundreds of millions in revenue in the most boring market(8:22) Payroll corporate spies(14:54) Why payroll tax is such a hard problem(19:46) Why tax is even more complicated outside the US(23:08) Legacy payroll still runs on manual spreadsheets(29:14) Remote’s unfair advantage in AI(31:40) Building the global payroll API that didn’t exist(38:06) Meeting his co-founder on a double date(42:04) Seven years of failed products before Remote(49:25) Launching Remote in 2019(52:39) Each year felt like a new apocalypse(59:25) Distributed teams must master async, document everything(1:02:42) Culture is what you tolerate(1:13:05) Europe's regulation problem and why it can't innovate(1:21:18) Why fundraising is so hard in Europe(1:28:23) Deleting spreadsheets to force automation(1:40:25) Burnout, health, fixing the system instead of grinding harder(1:47:57) Writing honestly about the hard parts of building companiesReferencedTry Remote: https://remote.com/Careers at Remote: https://remote.com/careersRemote Handbook: https://remotecom.notion.site/a3439c6ccaac4d5f8c7515c357345c11?v=8bb7f9be662f45da87ef4ab14a42be37The Toyota Way: https://www.amazon.com/Toyota-Way-Management-Principles-Manufacturer/dp/0071392319The Book of Five Rings: https://www.amazon.com/Book-Five-Rings-Miyamoto-Musashi/dp/1590309847Follow MarceloTwitter: https://x.com/marcelolebreLinkedIn: https://www.linkedin.com/in/marcelolebreFollow 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/ | — | ||||||
| 1/8/26 | ![]() Kevin Hartz | Backing Teen Founders, Lessons from the PayPal Mafia | 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/ | — | ||||||
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