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    Technology

    The Peel with Turner Novak

    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.

    Advertise

    Copyright: © Turner Novak

    • Apple Podcasts
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    • Spotify

    Latest Episodes:
    Inside the AI Sprint, Understanding Anthropic's Strategy | Tomasz Tunguz, Theory Ventures May 15, 2026
    Show notes

    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/


    Cursor + Kalshi Seed Investor on Spotting Outlier Talent | Ali Partovi, Neo May 07, 2026
    Show notes

    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/


    How a Hillbilly in Nevada Bootstrapped a $140M ARR Manufacturing Company | Jim Belosic, SendCutSend Apr 30, 2026
    Show notes

    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/


    The $5B Venture Growth Buyout Playbook | Alex Israel, Metropolis Apr 24, 2026
    Show notes

    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/


    How Agentic AI is Reshaping Science, Education, and the Economy | Karthik Duraisamy at the University of Michigan Apr 17, 2026
    Show notes

    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/


    How US Healthcare Actually Works, the WWII Tax Loophole that Broke it Forever, and How AI Can Fix it | Nikhil Krishnan, Out of Pocket Apr 09, 2026
    Show notes

    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 on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders Apr 02, 2026
    Show notes

    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/


    Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi Mar 26, 2026
    Show notes

    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/


    Inside Hanover Park: Building an AI-Native Service Business, Growing to $15B in Assets Mar 18, 2026
    Show notes

    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/


    Inside Canada’s Fastest Growing AI Company | Spellbook, Scott Stevenson Mar 12, 2026
    Show notes

    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/


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