The Peel with Turner Novak

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/

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/

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/

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/

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/