The Peel with Turner Novak

Turner Novak
  • 4.6 (11)
  • TECHNOLOGY
  • UPDATED WEEKLY

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

  1. How US Healthcare Actually Works, the WWII Tax Loophole that Broke it Forever, and How AI Can Fix it | Nikhil Krishnan, Out of Pocket

    1D AGO

    How US Healthcare Actually Works, the WWII Tax Loophole that Broke it Forever, and How AI Can Fix it | Nikhil Krishnan, Out of Pocket

    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/

    1h 45m
  2. Sophia Amoruso on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders

    APR 2

    Sophia Amoruso on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders

    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/

    1h 32m
  3. Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi

    MAR 26

    Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi

    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/

    1h 32m
  4. Inside Hanover Park: Building an AI-Native Service Business, Growing to $15B in Assets

    MAR 18

    Inside Hanover Park: Building an AI-Native Service Business, Growing to $15B in Assets

    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/

    1h 12m
  5. Inside Canada’s Fastest Growing AI Company | Spellbook, Scott Stevenson

    MAR 12

    Inside Canada’s Fastest Growing AI Company | Spellbook, Scott Stevenson

    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/

    1h 36m
  6. Benchmark’s Chetan Puttagunta on the Past, Present, & Future of Software

    MAR 4

    Benchmark’s Chetan Puttagunta on the Past, Present, & Future of Software

    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/

    1h 30m
  7. Inside Serval: Building the System of Intelligence for IT | Jake Stauch

    FEB 27

    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/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/

    1h 25m
  8. Garry Tan on the Past, Present, and Future of YC

    FEB 19

    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.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/

    1h 24m
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4.6
out of 5
11 Ratings

About

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

Information

  • Creator
    Turner Novak
  • Years Active
    2023 - 2026
  • Episodes
    136
  • Rating
    Explicit
  • Copyright
    © Turner Novak
  • Show Website
    The Peel with Turner Novak

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