The Peel with Turner Novak

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/

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/

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/