The Peel with Turner Novak

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/

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/