The Peel with Turner Novak

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/

Alamin Uddin

Co-founder and CEO

NexHealth

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 1,000...

Anatoly Yakovenko

CEO & Co-founder

Solana LabsSolana

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 judg...

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 in...

Peter Rahal

Co-Founder and CEO

David ProteinRXBARDADavid

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...

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/

Charles Hudson

Managing Partner

Precursor Ventures

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/

Dan Teran

Co-Founder

Gutter CapitalEGElbow Grease

Sam Blond is the Co-founder and CEO of Monaco, the revenue engine for startups. Sam is one of the best sales operators in tech. He spent four years as CRO at Brex, where he helped scale it to a ~$12B valuation, ran sales at Zenefits before that, and got his start at EchoSign. If there’s a modern GTM playbook, Sam helped write it. Our conversation walks through how AI has rewritten a big chunk of it. But most importantly, we talk about what hasn’t changed. We get into the sales work AI is now better at than humans, and why Sam thinks 90% of startups misdiagnose their bottleneck as conversion when it’s really demand gen. He explains why he doesn’t measure early brand marketing at all and trusts anecdotes over attribution, walks through the full Monaco launch playbook including the Super Bowl box-truck story, and shares a rev-ops insight from Brex, including how they figured out a specific ICP converted at 4x the rate of another. 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) Scaling Brex to $12B (1:14) How AI speeds up prospecting and TAM building (5:19) Using AI to get more leverage (9:15) Incubating Monaco at Founders Fund (12:56) Innovator’s dilemma in AI (15:57) Why AI companies build full platforms, not wedge products (23:30) Revenue is just a math equation (27:18) Two ways AI increases conversion rates (36:56) AI will never replace spending time with customers (39:46) Don’t measure the impact of brand marketing (49:03) Your marketing must be different (and hard) (58:39) Customer discovery calls and working with design partners (1:03:03) The zero to 100 launch (1:11:00) Monaco’s launch playbook (1:19:00) Send gifts that are unique and social (1:22:17) Naming your company (1:28:04) Founders should send early outbound (1:32:38) How multi-channel augments AI outbound (1:39:42) Using intent signals and outreach timing to increase conversions (1:43:28) Two common ways founders mess up when scaling revenue (1:50:22) Monaco’s Forward Deployed AE's Referenced Try Monaco: https://www.monaco.com/ Careers at Monaco: https://jobs.ashbyhq.com/monaco Sam’s launch post: https://x.com/samdblond/status/2026420015793320129?s=20 Follow Sam Twitter: https://x.com/samdblond LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/ 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/

Sam Blond

Former CRO

BrexFounders FundMonaco

Nuno Goncalves Pedro is the Founder and Managing Partner at Chamaeleon. He won't describe it this way, but I'd call Chamaeleon something like "The RenTech of VC." Chamaeleon is built around its proprietary data platform, Mantis, which borrows tools like factor analysis from public-market investors and operates more like a quant hedge fund than a traditional venture firm. We talk through a bunch of data that cuts against the common narrative in venture, including why repeat founders aren't always the safer bet, why sub-$100m funds catch the majority of fund-returning deals, and why 10x might be a better target than 100x. 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. https://www.merge.dev/agent-handler/employees Timestamps: (1:00) When 1st time founders outperform serial entrepreneurs (8:05) Mantis: factor-driven quant model for VC (18:33) Why most VC’s are not data-driven (22:28) Top 1% VC fund performance (27:41) Early customer sentiment stronger success indicator than PMF or Team (34:09) Importance of co-investors on performance (39:42) Sub-$100M funds capture 70% of fund-returning deals each year (43:53) The Neolab AI bubble (52:16) Marketing games that VC’s play (55:22) Most investors are not high conviction (56:43) Startups not raising for at least 3 years are 5x less likely to succeed. 10x less likely at 5 years. (1:00:19) Emerging managers have lowest LP interest in the last 15 years (1:11:19) LP capital is much less concentrated than in 2011 (1:16:28) The importance of remaining relevant (1:21:01) You must lean into your unique edge as an investor (1:23:18) Pros/Cons of an alumni network venture strategy (1:28:29) Specialist funds outperform generalists (with a catch) (1:35:22) The data says go for 10x, not 100x returns (1:41:41) Should you start or join a VC firm today? (1:48:07) Nuno’s collection of 270+ phones (1:53:16) Racing cars (and winning championships) Referenced Chamaeleon: https://www.chamaeleon.vc/ Tech Deciphered Podcast https://decipheredshow.com/ Say It With Charts: https://www.amazon.com/Say-Charts-Executives-Visual-Communication/dp/007136997X How To Lie With Charts: https://www.amazon.com/How-Charts-Gerald-Everett-Jones/dp/1419651439 Redmagic Phone: https://redmagic.gg/ ASUS Rog phone: https://rog.asus.com/phones/rog-phone-model/ Follow Nuno LinkedIn: https://www.linkedin.com/in/ngpedro/ 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/

Nuno Goncalves Pedro

Founder and Managing Partner

Chamaeleon

I just attended Allocate’s Beyond Summit in Deer Valley Utah. It was a peek into what the top VC's and LP’s are thinking about right now. Allocate asked me to record an episode of the show, live from the conference. So I asked everyone “What’s your hottest take on the VC market today?” Thank you to Numeral, Flex, and Amplitude 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 Timestamps: (1:22) Seed investing is dead (Tripp Jones, Uncork) (5:56) Seed is not dead (Bryan Rosenblatt, Sandlot) (13:19) Most consensus era of VC ever (Nate Williams, Union) (18:02) Taking the Power Law Pill (Pratyush Buddiga, Susa Ventures) (29:15) The 2nd-time founder premium is dead (Matt Cohen, Ripple Ventures) (32:46) AI will crush intelligence labor (Clark Cheng, Merrimac) (42:25) New deep tech investors will lose their shirts (Sunil Nagaraj, Ubiquity Ventures) (46:39) ChatGPT for robotics is still 15 years away (Sungjoon Cho, Fortitude Ventures) (52:07) The app layer ARR reckoning (Josh Christensen, Mercato) (58:30) The AI bubble will pop in Q2/Q3 (Amias Gerety, QED) (1:08:22) Most individuals do VC wrong (Jon Oberheide) (1:15:25) Allocators have become too allocator-y (Dan Feder, University of Michigan) (1:20:55) LP’s should value information, not just returns (Ben Ivey, Marshall Street) (1:24:09) Upcoming litigation of Russian doll SPVs (Asher Siddiqui, Song United) (1:30:13) Why retail needs private market access (Sarah Pinto Peyronel, Robinhood Ventures) Referenced https://beyondsummit.allocate.co/ Tripp Jones, Uncork Capital Twitter: https://x.com/thistrippjones Bryan Rosenblatt, Sandlot Twitter: https://x.com/BRosenblatt4 Nate Williams, Union Twitter: https://x.com/naywilliams Pratyush Buddiga, Susa Ventures Twitter: https://x.com/pratyushbuddiga Matt Cohen, Ripple Ventures Twitter: https://x.com/mattybcohen Clark Cheng, Merrimac LinkedIn: https://www.linkedin.com/in/clark-cheng-cfa-frm-caia-a411535 Sunil Nagaraj, Ubiquity Ventures Twitter: https://x.com/sunilnagaraj Sungjoon Cho, Fortitude Ventures Twitter: https://x.com/josungjoon Josh Christensen, Mercato LinkedIn: https://www.linkedin.com/in/joshjdmba/ Amias Gerety, QED Twitter: https://x.com/amiasmg Jon Oberheide Twitter: https://x.com/jonoberheide Dan Feder, Michigan LinkedIn: https://www.linkedin.com/in/danfeder Ben Ivey, Marshall Street LinkedIn: https://www.linkedin.com/in/benivey Asher Siddiqui, Song United LinkedIn: https://www.linkedin.com/in/ashersiddiqui Sarah Pinto Peyronel, Robinhood Ventures Twitter: https://x.com/SPintoPeyronel *This podcast is produced by Allocate for informational and educational purposes only and is intended for institutional, accredited, and qualified investors. Nothing discussed constitutes an offer to sell or solicitation to purchase any security or advisory service, and nothing should be construed as legal, tax, or investment advice. Any offering will be made only pursuant to applicable confidential offering documents. Views expressed by participants are their own and subject to change. Any discussion of target returns, projected outcomes, IRRs, MOICs, or other performance metrics is hypothetical and illustrative only and should not be relied upon as an indication of future performance. Investments in private funds are speculative, illiquid, and involve substantial risk, including possible loss of the entire investment. Past performance is not indicative of future results. Certain guests may have financial or other interests in the opportunities discussed. Allocate Management Company, LLC is an SEC-registered investment adviser. Registration does not imply any level of skill, training, or SEC endorsement. Please consult your own advisors before making any investment decision.*

Alfred Wallforss is the Co-founder of Listen Labs, the AI customer research company. Companies like Microsoft use Listen to run AI-powered customer interviews, and Alfred talks about how they first landed them as a customer at a pitch competition. We talk why startups should pursue enterprise customers early on, why 85% of survey answers are random clicks, how AI is changing the $140B market research industry, leveraging VC’s for customer intros, how to stand out when recruiting as a startup, and hiring for obsession. Thank you to Numeral, Flex, and Amplitude 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 Timestamps: (0:14) Listen: AI customer research tool (7:30) Fraud is a big problem in customer research (9:06) The $140B customer survey industry (12:08) Why running customer surveys is so hard (16:03) AGI will never replace humans (18:25) Surveys vs interviews (21:13) Importance of emotion in data collection (22:54) Using AI interviews to get product feedback (26:15) Building digital twins creates better data (32:22) Outperforming generic AI tools (34:17) Sweetgreen’s Max Protein Bowl (36:09) Jevon’s Paradox in customer research (40:37) Quantitative vs qualitative (42:38) Landing Microsoft as an early customer (44:50) Targeting enterprise customers from day 1 (48:05) Building a VC customer intro leaderboard (51:53) Recruiting with billboard games (57:20) Hiring for obsession (1:02:07) Alfred’s favorite movies (1:03:53) Listen’s custom agent harness (1:06:24) Velocity Fellowship for Swedes moving to SF (1:08:34) Growing up with entrepreneurial older brother (1:09:46) No shoes in the office Referenced Try Listen: https://listenlabs.ai/ Careers at Listen: https://listenlabs.ai/careers Sweetgreen protein bowls: https://listenlabs.ai/case-studies/sweetgreen Toni Erdmann: https://www.imdb.com/title/tt4048272/ Episode with Erik @ Modal: https://www.thespl.it/p/building-ai-native-infrastructure Follow Alfred Twitter: https://x.com/itsalfredw LinkedIn: https://www.linkedin.com/in/wahlforss 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/

Alfred Wahlforss

Co-Founder and CEO

Listen Labs

Tomasz Tunguz is the Founder and General Partner of Theory Ventures. We talk about today’s “all out sprint” in AI, Anthropic’s strategy, the three layers of AI business models, how AI compares to prior technologies, where to invest in AI today, and what Theory looks for in new investments. Thank you to Numeral, Flex, and Amplitude 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 Timestamps: (0:42) The “all out sprint” in AI today (1:40) Why GPU prices are up 116% in six weeks (6:34) AI infra end-state: “We’ll over build” (9:12) Tokenmaxxing, and why AI needs to get more efficient (15:48) AI models will resemble pharma more than software (19:52) Why Anthropic still trades at a discount (25:42) Anthropic’s strategy: commoditize the compliments (30:29) Why OpenClaw is so strategic for OpenAI (34:08) The three layers of AI business models (38:18) Where to invest in AI today (45:49) Who will survive SaaSpocalypse? (52:15) Comparing AI’s impact to historical technology cycles (57:34) How new technology historically impacts jobs (1:05:58) Where AI is underrated today (1:10:41) How people are actually buying AI products (1:14:06) Why Theory’s investing in ads, inference, and email (1:16:24) 2026 IPO pipeline, how VC has changed over 20 years (1:20:56) What Theory looks for in new investments (1:22:32) Starting Theory Ventures in 2022 (1:25:39) Running a monte carlo analysis to determine portfolio construction (1:27:54) Tomasz personal AI projects Referenced Theory Ventures: https://theoryvc.com/ Tomasz Blog: https://tomtunguz.com/ Follow Tomasz Twitter: https://x.com/ttunguz LinkedIn: https://www.linkedin.com/in/tomasztunguz 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/

Tomasz Tunguz

Founder and Partner

Theory VenturesRedpoint Ventures

Ali Partovi is the Co-founder and CEO of Neo. Neo started in 2017 as a network for the top college students. Neo is a “people-first” investor, a thesis it developed missing out on early investments in PayPal and Google at three employees. Neo has since invested in the Seed rounds of Cursor and Kalshi, and Ali shares everything he’s learned about spotting outlier talent, how to hire the best people, how computer science is the best business education, and why the best entrepreneurs start young. Special thanks to Hadi Partovi, Fuzzy Khosrowshahi, Alan Shusterman, and Claire Shorall for their help brainstorming topics for Ali. Thank you to Numeral, Flex, and Amplitude 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 Timestamps: (0:09) Neo’s two 10x funds (2:19) Missing PayPal led to Neo (9:32) Not investing in Google at 3 employees (11:31) Backing Facebook despite the idea (13:01) Starting Neo to help top college students (17:21) How to identify outlier talent (24:38) Neo’s coding test (27:41) Bootstrapping the first cohort of Neo Scholars (34:58) How Cognition President Russel Kaplan changed Neo forever (39:21) Starting Neo after talking to Steph Curry (46:42) Launching [Code.org](http://Code.org) to teach 20M kids to code (59:38) Is coding still relevant in 2026? (1:03:43) How to hire outlier talent (1:07:25) Why you should aggressively apply for one job (1:11:09) Neo Residency: $750k uncapped (1:19:51) Growing up in Iran during the revolution (1:26:03) Impact of the immigrant mentality (1:29:15) Most entrepreneurial roots start very young (1:39:18) Lessons investing in Cursor + Kalshi seed rounds (1:50:27) Confession: a podcast about failure (1:52:36) Fucking up a $50m deal by lying to Steve Jobs Referenced Neo: https://neo.com/ Neo Scholars Application: https://neo.com/scholars Neo Residency: https://neo.com/residency Code.org: https://code.org/ Lying to Steve Jobs: https://x.com/apartovi/status/1447251334814523392 Losing a deal with Yahoo: https://x.com/apartovi/status/1449856639331340289 Follow Ali Twitter: https://x.com/apartovi LinkedIn: https://www.linkedin.com/in/apartovi/ 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/

Ali Partovi

CEO

Neo

Jim Belosic is the Co-founder and CEO of SendCutSend, a sheet metal manufacturing business he bootstrapped to a $140 million revenue run rate in eight years. We talk building a manufacturing business in the US, creative ways he financed the company early on, using speed and trust to compete with overseas competitors, lessons from restaurants, and why you can’t run a factory from a spreadsheet. Thank you to Numeral, Flex, and Amplitude for supporting this episode Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com Timestamps: (0:16) Automating sheet metal manufacturing (5:59) Zero to $140 million ARR in 8 years (7:58) Acquiring a $750k laser with $0 (13:38) Automating factories is like baking cookies (15:17) Being legible to capital (17:31) Unlocking custom, low order manufacturing with software (20:00) Building more factories instead of selling the software (24:50) Run your company like a lemonade stand (28:30) Raising an angel round in 2021 as a safety net (33:21) SendCutSend’s unique bottoms-up GTM (38:24) Fun coupons (40:12) Building a moat with speed and trust 45:55) How US factories can beat China (47:40) Gaslight product launches (52:05) Lessons from non-manufacturing businesses (55:19) You can’t run a factory from a spreadsheet (58:10) Using data in manufacturing (59:50) Lessons from Factorio (1:03:17) Unlocking a negative cash conversion cycle (1:06:14) You need to resist automating everything (1:13:51) Surviving COVID with six weeks of cash (1:15:47) Solving the US skilled labor shortage (1:26:17) Teaching kids about manufacturing Referenced SendCutSend: https://sendcutsend.com/ Careers at SendCutSend: https://sendcutsend.com/careers Sandy Kory: https://www.linkedin.com/in/sandykory Horizon VC: https://www.horizon.vc/ Concrete Canoe Competitions: https://www.asce.org/communities/student-members/conferences/asce-concrete-canoe-competition Follow Jim Twitter: https://x.com/jimbelosic LinkedIn: https://www.linkedin.com/in/belosic 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/

Jim Belosic

Co-Founder & CEO

ShortStackSendCutSend

Alex Israel is the Co-founder and CEO of Metropolis.He unpacks the unique strategy they used as a tech startup to rollup parking lots and become the largest parking operator in the world.Thank you to Will Quist, Yoni Rechtman, Adam Bain, and Jamie Siminoff for their help brainstorming topics for the conversation.Thank you to Numeral, Flex, and Amplitude for supporting this episodeNumeral: The end-to-end platform for sales tax and compliance https://www.numeral.comFlex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFzAmplitude: AI analytics, all you have to do is ask https://www.amplitude.comTimestamps:(1:10) Helping 50m Americans park(4:00) Building “Buy Now” for the physical world(9:02) Real-world checkout technology that works(16:07) Why parking never institutionalized as an asset class(18:34) Using tech to make parking assets more valuable(21:53) Parking lots as autonomous robotics hubs(29:07) Going to film school, working at MTV(30:55) Starting his first parking data company(33:47) Culture of pranking each other(36:27) A Fortune 500 CEO convinced him to start a 2nd parking company(42:55) Realizing they couldn’t sell to real estate operators(46:09) Acquiring a company 10x their size to jumpstart GTM(50:20) How to do a successful AI growth buyout(54:48) Revenue growth must be driven by technology(1:00:33) Why companies should do growth buyouts(1:03:55) Being legible to capital(1:09:16) You need creativity to take risks(1:13:30) AI is the first ever disruption to skilled labor(1:19:14) CEO challenges growing zero to 23,000 employees(1:24:31) Alex’ personal AI stackReferencedMetropolis: https://www.metropolis.io/Careers at Metropolis: https://www.metropolis.io/careersRoy Amara: https://en.wikipedia.org/wiki/Roy_AmaraFollow AlexTwitter: https://x.com/Alex__IsraelLinkedIn: https://www.linkedin.com/in/alex-israelFollow 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/

Alex Israel

Co-founder and CEO

Metropolis

Karthik Duraisamy is a professor at the University of Michigan. He is co-leading U of M's newly created Institute of Agentic Computing, the first of its kind. The institute will serve researchers and developers building agentic AI infrastructure to advance scientific discovery, engineering, and the knowledge economy. It will also be a central node for managing developers and maintainers of the OpenClaw platform. Karthik's research spans a broad spectrum of computational science and engineering, including new modeling approaches for complex physical systems, numerical methods, algorithms and uncertainty quantification. This is the first conversation Karthik’s had going deep on the institute. We talk about using AI to advance scientific research, two new discoveries announced yesterday, how universities work, how AI is impacting students and education, and his advice for young people. Thank you to Numeral, Flex, and Amplitude for supporting this episode Numeral: The end-to-end platform for sales tax and compliance https://www.numeral.com](https://www.numeral.com/ Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com Timestamps: (0:25) The Institute for Agentic Computing (4:27) OpenClaw Foundation and Lobster Compute Company (8:19) How Universities actually work (12:33) ClawCon in Ann Arbor (15:24) Two scientific discoveries made with ScienceClaw (20:06) How AI is speeding up scientific discovery (25:42) Supporting AI and OpenClaw development (29:55) Why universities function like VC funds (34:29) How Universities get money from the government (40:55) Why some academics believe AI is a fad (46:17) Biggest bottlenecks in AI today (49:26) How AI will change the world (53:10) Karthik's Code Red advice for students (59:19) Separating learning and doing (1:03:10) Ways COVID and AI impacted college students (1:14:53) How the role of universities is changing (1:23:21) Why college classes suffered from grade inflation (1:26:05) How AI is actually impacting the job market (1:32:49) Karthik’s advice for students (1:39:16) Winning two NCAA basketball national championships (1:43:04) Almost dying in the Grand Teton National Park Referenced More on Karthik: https://aero.engin.umich.edu/people/duraisamy-karthik/ Institute for Agentic Computing: https://record.umich.edu/articles/u-m-launches-institute-for-agentic-computing/ ClawCon Announcement: OpenClaw: https://openclaw.ai/ ScienceClaw: http://scienceclaw.science/ MIT OpenCourseWare: https://ocw.mit.edu/ ASU iPhone video: https://www.youtube.com/watch?v=qqfk7-3iN-U Follow Karthik LinkedIn: https://www.linkedin.com/in/karthik-duraisamy-66705025 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/

Karthik Duraisamy

Professor

University of Michigan

Nikhil Krishnan is the Founder of Out of Pocket, a media company that makes understanding healthcare more entertaining and accessible. We spend 100 minutes talking about how the US healthcare system actually works, how World War II changed it forever, all the ways AI is seeing real adoption across the industry, and most common bad startup ideas in healthcare. Thank you to Numeral, Flex, and Amplitude for supporting this episode Numeral: The end-to-end platform for sales tax and compliance [https://www.numeral.com](https://www.numeral.com/) Flex: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz Amplitude: AI analytics, all you have to do is ask [https://www.amplitude.com](https://www.amplitude.com/) Timestamps: (1:23) How the US healthcare system works (4:26) Why US healthcare is different from the rest of the world (12:01) Why healthcare costs keep going up (15:58) Core problem: is healthcare a marketplace or not? (21:04) How money flows + Two-way price negotiation (27:34) Why payments are seeing early AI adoption (30:08) How AI could change healthcare delivery (35:40) Doctor’s are trapped on a productivity hamster wheel (39:28) How incentives shape healthcare delivery (43:53) Healthcare is an implicit jobs program in the US (48:45) Areas AI is overhyped, worst healthcare startups (55:30) Consumerization of healthcare (1:01:58) Rise of Peptides, understanding risks and downsides (1:09:35) Why all medical software is so bad (1:11:58) How to do enterprise sales in healthcare (1:14:51) The battle forming between Scribes, Search, and EMRs (1:18:33) Why we need more physician independence (1:26:51) Starting Out of Pocket in February of 2020 (1:2912) Write to meet your audience (1:37:54) Using AI as a content creator (1:42:13) How to get started writing on the internet Referenced Out of Pocket: https://www.outofpocket.health/ Doctronic: https://www.doctronic.ai/ Follow Nikhil Twitter: https://x.com/nikillinit LinkedIn: https://www.linkedin.com/in/thinkboi/ 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/

Nikhil Krishnan

Founder

Out-of-Pocket

Sophia Amoruso is the Founder of Nasty Gal and Trust Fund, an early stage venture capital firm. We talk through her journey of starting Nasty Gal as an Ebay store in 2006 to sell vintage clothing, bootstrapping it to $28 million in revenue, raising $50 million, scaling it to $120 million and a massive team, turning down a $400 million acquisition offer, and ultimately declaring bankruptcy. She takes us inside what it was like to fail so publicly, what she’d do differently next time around, lessons from building the brand, and why she started her VC firm Trust Fund to back the next generation of founders building consequential companies. 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: Sign-up for Flex Elite with code TURNER, get $1,000 https://form.typeform.com/to/Rx9rTjFz Amplitude: AI analytics, all you have to do is ask https://www.amplitude.com Merge: Every modal. One API. Total control. Check out Merge Gateway https://www.merge.dev/gateway Timestamps: (0:59) Selling vintage on Ebay while working at an art school (04:31) Lessons in marketing and perceived value (12:38) Knowing when to make your first hire (18:31) Borrowing from others to build a unique brand (25:17) Growing to $120m revenue in seven years (27:24) Sharing the pitch deck that raised $50m (30:17) Mistakes scaling to 100’s of employees too fast (34:48) Downsides of raising at too high of a valuation (39:56) Why being a CEO is fun (42:57) Declaring bankruptcy (50:38) How it feels to fail publicly (54:41) Writing a book, Netflix series, starting the Girlboss movement (59:13) How to create a new brand in 2026 (1:05:34) Starting Trust Fund to invest and help founders (1:13:45) Raising $5m from a poker game (1:18:47) Sophia asks for Turner’s LP pitch (1:26:53) Traits of the best founders Trust Fund: https://www.trustfund.vc/ Pitch Trust Fund: https://www.trustfund.vc/pitches Nasty Gal: https://www.nastygal.com/ Follow Sophia Instagram: https://www.instagram.com/sophiaamoruso Twitter: https://x.com/sophiaamoruso LinkedIn: https://www.linkedin.com/in/sophiaamoruso Website: https://www.sophiaamoruso.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/

Sophia Amoruso

Founder

TrustFund VCTrust FundGirlbossNasty GalGirlboss Media

Nikhil Basu Trivedi and Mike Smith are the Co-founders of Footwork where they invest up to $15 million in Seed and Series A rounds. This is the first time they've ever sat down to record a conversation together on video. We talk about starting the firm in 2020, their secret sauce for working with founders, lessons investing in Canva’s Seed round, scaling Stitch Fix from $0 to $1B revenue in five years with $17m in capital, why AI will enable a new wave of entrepreneurship, and how public company boards are discussing AI today. Thank you to Tony Staehelin, Andrew Riesen, and Hunter Walk for helping brainstorming topics for the conversation. Thank you to Flex for supporting this episode. Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (0:24) Starting Footwork from a tweet in 2021 (3:11) Difference between startup and public company boards (4:52) 20-40% of board meetings are now about AI (7:48) How Footwork’s investing in AI today (10:37) AI will enable millions of new entrepreneurs (15:04) 37 questions to ask when starting a VC firm (17:40) Importance of differences (23:08) The pace of VC is faster than operating (26:26) Footwork’s secret sauce (2x board seats, 1-pager) (31:59) Investors should talk to and help employees (37:05) Building an equal-carry partnership (39:33) How Footwork makes decisions (43:21) Navigating short-termism and politics in VC firms (51:18) “You’re only as good as your next investment” (53:30) Characteristics of great founders (58:13) Canva’s Seed pitch in 2014 (1:02:54) Joining Stitch Fix as 4th employee (1:06:40) Scaling Stitch Fix $0 to $1B revenue in five years with $17m in capital (1:16:48) Raising from Bill Gurley after a failed Series A (1:19:40) Footwork’s office near YC (1:22:10) Opportunities in consumer health (1:25:20) Using flash mobs to win deals (1:26:15) Dad life Referenced Footwork: https://www.footwork.vc/ Anything: https://www.anything.com/ Table22: https://www.table22.com/ Canva: https://www.canva.com/ Stitch Fix: https://www.stitchfix.com/ Honeydew: https://www.honeydew.com/ Follow Mike Twitter: https://x.com/msmith492 LinkedIn: https://www.linkedin.com/in/michaelcsmith1 Follow Nikhil Twitter: https://x.com/nbt LinkedIn: https://www.linkedin.com/in/nikhilbt Substack: https://nbt.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/

Nikhil Basu Trivedi

Co-Founder and General Partner

FootworkShasta Ventures

Mike Smith

Co-founder

Footwork

Chris Hladczuk is the Co-founder and CEO of Hanover Park, the AI-native fund administrator, vertically integrating fund administration, portfolio management, and LP experience for finance and investment teams. Chris is the 2nd ever returning guest of the show, and is fresh off announcing Hanover’s $27m Series A. We go inside the round, their explosive growth, why they built their own general ledger from scratch, and how that enabled them to build incredible AI products for investment firms that touch over $100 trillion in assets. Thanks to Sahil Bloom, and Chad + Pratyush at Susa for help brainstorming topics for this conversation. 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.com Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (0:37) Financial infrastructure for investment firms (1:35) Hanover Park’s $27m Series A (5:30) AI-enabled services businesses (9:07) Productizing the service layer (11:30) Helping CFO’s and investors use AI (13:46) Building a general ledger from scratch (18:03) Compete against companies with IT departments (19:55) Hiring in an unsexy industry (21:30) Live in constant paranoia of your customers (25:19) Gongs, music in the office, blizzard commutes (28:54) Friday night hackathons (30:54) Automating onboarding and manual admin work (35:05) Real-time visibility on all data (38:07) Always get on the plane (40:36) Turning customers into raving fans (43:45) Using polite persistence in sales (47:36) How to master founder-led content (51:29) 99% of advice is wrong in AI era (54:21) Importance of one-way vs two-way doors (56:11) Growing from VC into PE and Private Credit (1:00:36) When to turn down new customers (1:02:22) Becoming a customers most important vendor (1:04:00) Chris’ personal AI stack (1:07:41) Hanover Park’s MCP Referenced Try Hanover Park: https://www.hanoverpark.com/ Careers at Hanover Park: https://jobs.ashbyhq.com/hanover-park First episode with Chris: https://www.youtube.com/watch?v=7lomqcrFNv8 Artie: https://www.artie.com/ Episode with Jacqueline @ Artie: https://www.youtube.com/watch?v=6fd1YKsBaq0 Granola: https://www.granola.ai/ Claude Cowork: https://claude.com/product/cowork HubSpot: https://www.hubspot.com/ Attio: https://attio.com/ Monaco: https://www.monaco.com/ Follow Chris Twitter: https://x.com/chrishlad LinkedIn: https://www.linkedin.com/in/chris-hladczuk-b09204153 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/

Chris Hladczuk

Co-founder and CEO

Hanover ParkHAHanover

Scott Stevenson is the Co-founder and CEO of Spellbook. Spellbook is an AI copilot for contract review and drafting, essentially “Cursor for lawyers.” They have 4,000 customers in 80 countries, and to my knowledge is the fastest growing AI company in Canada, and the largest company in the world built on a Microsoft Word plugin. Scott has been building in legal AI longer than almost anyone. We talk about why legal software was essentially untouched before LLM’s, why the market is so hot right now, if it’s sustainable, and how Spellbook navigates product differentiation compared to horizontal AI products like ChatGPT. We talk about why fine-tuning your own models was one of the biggest mistakes early AI companies made, how to build a network effect as a vertical AI product, and Spellbook’s philosophy of “Don’t sharpen your axe when the chainsaw is coming out tomorrow”. Spellbook spent a few years finding PMF before really taking off in 2022, and Scott shares their playbook for launching over 100 product experiments in three years, how to know when to lean in, and what it’s been like scaling Spellbook post-PMF. 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.com Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (0:30) Spellbook: “Cursor for Contracts” (3:08) Building the world’s largest Microsoft Word plugin (14:06) Why legal software was untouched before LLMs (18:32) $30 trillion moves through contracts annually (20:51) Why ChatGPT won’t replace vertical tools (25:15) Fine-tuning was the biggest mistake in AI (30:00) Differences between pro and amateur gamers (37:38) Top-down vs. bottoms-up in legal AI (42:27) The long-tail of legal AI software (47:24) Building for models that don’t exist yet (51:20) Skating where the puck is going (1:01:35) The legal bill that cost 50% of his bank account (1:09:33) Testing 100 landing pages in 3 years (1:14:06) The moment Spellbook hit PMF (1:19:17) Building new brands for each product experiment (1:23:10) Raising a Series B with a tweet (1:27:41) What Scott learned from Keith Rabois (1:31:16) Scott's favorite new AI tool Referenced Spellbook: https://www.spellbook.legal/ Careers at Spellbook: https://www.spellbook.legal/careers Playing to Win by David Sirlin: https://www.amazon.com/Playing-Win-becoming-David-Sirlin/dp/1413498817 Find the Fast Moving Water by NFX: https://www.nfx.com/post/find-the-fast-moving-water Spellbook’s case study with Replit: https://replit.com/customers/spellbook Twin: https://twin.so/ Follow Scott Twitter: https://x.com/scottastevenson LinkedIn: https://www.linkedin.com/in/scottas Blog: https://blog.scottstevenson.net/ 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/

Scott Stevenson

Co-founder and CEO

Spellbook

Chetan Puttagunta is a General Partner at Benchmark. We talk about investing in Manus, the AI company that went from zero to $100M ARR in eight months and was recently acquired by Meta. We also talk through the full history of application software, from mainframes to client-server, to the internet to cloud, why each wave reduced the barrier to entry and created an explosion in the number of new software, why legacy SaaS companies are making the same mistake on-prem vendors made at the dawn of the cloud, why software companies should be making big AI acquisitions, and how public market investors are begging private AI companies to go public. We also talk about what Benchmark actually looks for in founders, how they make decisions, and why his last two investments were consumer AI and crypto. Thanks to Sam Ross and Everett Randle for helping brainstorm topics for this conversation. Thanks you to Numeral and Flex for supporting this episode. Try Numeral, the end-to-end platform for sales tax and compliance: https://www.numeral.com Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (0:08) Inside the $2.5B Manus acquisition (6:24) Manus' three main use cases (11:08) Taking heat on Twitter (15:10) Starting to tweet about software in 2018 (22:50) The history of application software (29:15) Benchmark’s 25x Fund 7 (31:33) SaaS incumbents got too dominant by 2020 (31:48) Going all-in on AI software in 2022 (39:31) Benchmark didn’t invest in the big AI labs (40:48) How cloud companies beat on-prem competitors (44:33) Why AI companies will beat legacy cloud competitors (50:04) Software incumbents should make big AI acquisitions (57:35) Why incumbents have not bought more AI companies (1:04:43) Public markets are starving for AI companies (1:10:14) Inside Benchmark’s fund strategy (1:14:14) Benchmark’s history of non-traditional VC rounds (1:17:56) Is the 20% ownership model outdated? (1:19:20) Chetan’s rebirth as a consumer investor (1:22:39) What Benchmark looks for in founders (1:25:01) AI coding and gross margins Referenced Benchmark: https://benchmark.com/ Eric Vishria’s podcast episode: https://www.youtube.com/watch?v=I-5IsqFgrZM Workday S-1: https://www.sec.gov/Archives/edgar/data/1327811/000119312512375787/d385110ds1.htm Innovator's Dilemma: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Business-Essentials/dp/0060521996 Try FOMO: https://apps.apple.com/us/app/fomo-never-miss-out/id6741115427 Follow Chetan Twitter: https://x.com/chetanp LinkedIn: https://www.linkedin.com/in/chetanputtagunta 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/

Chetan Puttagunta

General Partner

BenchmarkBenchmark CapitalNEA

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/Rx9rTjFz Timestamps: (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 recruit Referenced Try Serval: https://www.serval.com/ Careers at Serval: https://www.serval.com/careers Episode with Filip @ Verkada: https://www.youtube.com/watch?v=fXI3GdicIHw Follow Jake Twitter: https://x.com/jakeserval LinkedIn: https://www.linkedin.com/in/jakestauch 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/

Jake Stauch

Founder and CEO

Serval

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.com⁠ Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (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 optimism Referenced Y 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=XQoFbvyWEy8 Follow Aaron Levie on X: https://x.com/levie Follow Gary Twitter: https://x.com/garytan LinkedIn: https://www.linkedin.com/in/garytan/ 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/

Garry Tan

President and CEO

Y CombinatorInitialized Capital

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.com Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (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 shitposting Referenced Try Fort: https://www.fort.cx/ Follow Miranda Twitter: https://x.com/mirandanover LinkedIn: https://www.linkedin.com/in/mirandanover 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/

Miranda Nover

Co-founder and CEO

Fort Health

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/Rx9rTjFz Timestamps: (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 ecosystem Referenced Duo 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 Dug Twitter: https://x.com/dugsong LinkedIn: https://www.linkedin.com/in/dugsong Follow Jon Twitter: https://x.com/jonoberheide LinkedIn: https://www.linkedin.com/in/jono 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/

Dug Song

Co-Founder & CEO

Duo Security

Jon Oberheide

Co-founder

Duo Security

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.com⁠ Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (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 book Referenced Try Artie: https://artie.com Careers at Artie: https://www.artie.com/careers Clay: https://www.clay.com Podcast with Tommy @ Alloy: https://www.youtube.com/watch?v=e7i8Wxklu-Y YCombinator: https://www.ycombinator.com Standard Capital: https://www.standardcap.com Founding Sales: https://www.foundingsales.com The Score Takes Care of Itself: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472 Follow Jacqueline Twitter: https://x.com/JacquelineSYC19 LinkedIn: https://www.linkedin.com/in/jacqueline-cheong 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/

Jacqueline Cheong

Co-founder and CEO

Artie

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.com⁠ Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (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 Federer Referenced State of AI Report: https://www.stateof.ai The Thinking Game Documentary: https://www.youtube.com/watch?v=d95J8yzvjbQ V7: https://www.v7labs.com Follow NathanTwitter: https://x.com/nathanbenaichLinkedIn: https://www.linkedin.com/in/nathanbenaich Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: 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/

Nathan Benaich

Founder

Air Street Capital

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.com⁠ Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (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 companies Referenced Try Remote: https://remote.com/ Careers at Remote: https://remote.com/careers Remote Handbook: https://remotecom.notion.site/a3439c6ccaac4d5f8c7515c357345c11?v=8bb7f9be662f45da87ef4ab14a42be37 The Toyota Way: https://www.amazon.com/Toyota-Way-Management-Principles-Manufacturer/dp/0071392319 The Book of Five Rings: https://www.amazon.com/Book-Five-Rings-Miyamoto-Musashi/dp/1590309847 Follow Marcelo Twitter: https://x.com/marcelolebre LinkedIn: https://www.linkedin.com/in/marcelolebre 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/

Marcelo Lebre

Co-founder and President

Remote

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.com⁠ Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (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 started Referenced https://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/0060742763 20% 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 Kevin Twitter: https://x.com/kevinhartz LinkedIn: https://www.linkedin.com/in/hartz 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/

Kevin Hartz

Co-founder & Chairman

EventbriteA*Founders Fund