The Peel with Turner Novak

Nathan Benaich is the founder of Air Street Capital and author of the State of AI report. On its eighth year, the report is a year-long effort on the biggest things happening in AI, across research, industry, politics, and safety.
This episode covers the biggest takeaways from the latest report, like the rise in reasoning, the surge in China’s open source models, where AI is working in practice, the rise of sovereign AI, where he thinks value will actually accrue over the long-term, if we’re in an AI bubble, and how he’s investing in AI today at Air Street.
Thanks to Nico at Adjacent and Dan at Michigan for helping brainstorm topics for Nathan.

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Timestamps:
(3:39) State of AI 2025
(6:22) Takeaway #1: Reasoning & tool calling
(13:01) Takeaway #2: Rise of Chinese open source
(15:25) Open vs closed source models
(26:46) Takeaway #3: AI revenue is real
(27:51) Takeaway #4: Sovereign AI
(36:44) Are we in an AI bubble?
(59:23) Starting Air Street Capital
(1:05:18) Raising Fund 1
(1:16:20) Air Street portfolio strategy
(1:25:15) When and who Nathan decides to invest
(1:35:04) How important are AI benchmarks?
(1:39:31) When to train your own models
(1:45:56) Rise of European defense tech
(2:01:43) Nathan’s personal AI stack
(2:07:32) Is niching down too risky?
(2:16:12) Nadal vs Federer

Referenced
State of AI Report: https://www.stateof.ai
The Thinking Game Documentary: https://www.youtube.com/watch?v=d95J8yzvjbQ
V7: https://www.v7labs.com

Follow NathanTwitter: https://x.com/nathanbenaichLinkedIn: https://www.linkedin.com/in/nathanbenaich

Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: 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/

Marcelo Lebre is the Co-founder and President of Remote, the payroll and international employment company.

Remote is one of today's most underrated software companies. We get into why payroll is such a hard problem, why most of the industry still runs on spreadsheets, the edge cases of software meeting government, and a diagnosis of Europe’s regulation problem.

We also talk through the journey trying 8 different startup ideas before Remote, how COVID changed the business overnight, and what he’s learned about building culture and running remote teams.

Thanks to Gillian O’Brien, Villi Iltchev, Andreas Klinger, Masha Bucher, and Marcelo’s co-founder Job for helping brainstorm topics for this.

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:
(3:22) Gaming with kids
(6:05) Hundreds of millions in revenue in the most boring market
(8:22) Payroll corporate spies
(14:54) Why payroll tax is such a hard problem
(19:46) Why tax is even more complicated outside the US
(23:08) Legacy payroll still runs on manual spreadsheets
(29:14) Remote’s unfair advantage in AI
(31:40) Building the global payroll API that didn’t exist
(38:06) Meeting his co-founder on a double date
(42:04) Seven years of failed products before Remote
(49:25) Launching Remote in 2019
(52:39) Each year felt like a new apocalypse
(59:25) Distributed teams must master async, document everything
(1:02:42) Culture is what you tolerate
(1:13:05) Europe's regulation problem and why it can't innovate
(1:21:18) Why fundraising is so hard in Europe
(1:28:23) Deleting spreadsheets to force automation
(1:40:25) Burnout, health, fixing the system instead of grinding harder
(1:47:57) Writing honestly about the hard parts of building companies

Referenced
Try Remote: https://remote.com/
Careers at Remote: https://remote.com/careers
Remote Handbook: https://remotecom.notion.site/a3439c6ccaac4d5f8c7515c357345c11?v=8bb7f9be662f45da87ef4ab14a42be37
The Toyota Way: https://www.amazon.com/Toyota-Way-Management-Principles-Manufacturer/dp/0071392319
The Book of Five Rings: https://www.amazon.com/Book-Five-Rings-Miyamoto-Musashi/dp/1590309847

Follow Marcelo
Twitter: https://x.com/marcelolebre
LinkedIn: https://www.linkedin.com/in/marcelolebre

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/

Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron.

Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re still early, and lessons today’s breakout AI companies can learn from those that survived the Dot Com Crash.

Kevin is a big proponent of backing young founders. A significant percentage of his latest fund at A* is invested in teenagers, and he shares how he identifies outlier talent so early, from Seed investments in Airbnb, PayPal, and Pinterest, to many of today’s hottest AI companies.

He also shares the insane story of investing 100% of the proceeds from his first startup into PayPal’s Seed round, how PayPal’s early fraud systems inspired Palantir, what he learned from the PayPal Mafia, from Peter Thiel, and what makes Founders Fund special.

We also talk about how he and his wife recently had two babies, five months apart, using genome screening and surrogates.

Thanks to Ramtin Naimi, Navya Gudimetla, and Bennett Siegel for helping brainstorm topics for the conversation.

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:
(4:25) Power shift from VC’s to founders since the 90’s
(9:08) AI is the mother of all bubbles
(12:40) Why AI is still underhyped
(14:10) What Kevin and A* are investing in today
(16:02) Investing 100% of his first startups proceeds in PayPal’s Seed round
(21:21) What made the PayPal Mafia special
(23:37) Parallels between the 90’s and today
(26:40) What makes Founders Fund special
(35:07) How Palantir evolved from PayPal’s fraud models
(39:06) Building Xoom on the PayPal API
(43:38) Lessons between Kevin’s 1st and 2nd startups
(46:52) Starting Eventbrite off early PayPal API app
(51:51) Eventbrite’s hidden TAM challenge
(53:49) Selling Eventbrite to Bending Spoons
(54:59) Investing 20% of A* in teenage founders
(1:02:33) Incubating Sauron, the home security company
(1:08:44) Making breakfast for our kids
(1:13:33) Having kids with genome screening and surrogates
(1:20:31) Collecting art, how to get started

Referenced
https://www.a-star.co/
https://www.eventbrite.com/
https://www.xoom.com/
https://www.sauron.systems/
https://www.orchidhealth.com/
Setting the Table by Danny Meyer: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763
20% of fund in teenage founders: https://techcrunch.com/2025/10/18/this-top-vc-bet-close-to-20-of-his-fund-on-teenagers-heres-why/
https://nypost.com/2025/12/14/us-news/xu-bo-chinese-billionaire-reportedly-sires-more-than-100-kids/

Follow Kevin
Twitter: https://x.com/kevinhartz
LinkedIn: https://www.linkedin.com/in/hartz

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/

Jason Calacanis is the host of the All-In Podcast, This Week in Startups, co-founder of the Launch Accelerator, and the “3rd or 4th investor in uber”.

We go inside the origins of All-In, how they decide what to talk about each week, and if Jason thinks it helped swing the election.

We also talk lesson from starting 7 media companies over the past three decades, what he's learned from studying the world's best interviewers, joining Sequoia’s first scout program, his investing strategy at Launch, the story of being the “3rd or 4th investor in Uber", what people underestimate about Elon, and what it was like inside the Twitter buyout in 2022.

Thank you to Austin Petersmith for helping brainstorming topics for the conversation.

Thanks to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠

Timestamps:
(3:34) Interviewing lessons from Oprah, Charlie Rose
(6:48) How to ask good questions
(12:20) Jason’s favorite upcoming podcasters
(17:57) Starting 7 media companies
(22:50) How he'd start a new media company today
(27:56) In-person experiences, “Bang Bang” in Japan
(32:44) Vinyl bars, smartphones, mental health
(38:41) Origin of the All-In Podcast
(42:58) All-In’s influence on the 2024 Election
(46:58) Why All-In got so political
(52:35) Media lessons from Trump
(55:01) Joining Sequoia’s very first scout program
(57:55) Jason’s VC investing strategy
(1:03:55) How Launch competes with other accelerators
(1:08:46) Fundraising is a numbers game
(1:13:06) Investing in Uber and Robinhood Seed rounds
(1:18:31) Origin of “3rd or 4th investor in Uber” meme
(1:20:57) How Jason got the first Model S
(1:26:19) What people underestimate about Elon
(1:27:37) Inside the Twitter takeover
(1:31:44) Career advice for young people
(1:35:22) Jason’s experience taking GLP-1’s
(1:40:05) How All-in picks topics each week

Referenced
Howie: ⁠https://howie.com/⁠
All-In Podcast: ⁠https://allin.com/⁠
Bret Easton Ellis (Podcast): ⁠https://www.breteastonellis.com/podcast⁠
Red Scare (Podcast): ⁠https://en.wikipedia.org/wiki/Red_Scare_(podcast)⁠
Preet Berrara (Podcast): ⁠https://cafe.com/stay-tuned-podcast/⁠
Adam Friedland Show: ⁠https://www.youtube.com/c/TheAdamFriedlandShow⁠
The Insider (Movie): ⁠https://www.imdb.com/title/tt0140352/⁠
Launch: ⁠https://www.launch.co/⁠
Ro: ⁠https://ro.co/⁠

Follow Jason
Twitter: ⁠https://twitter.com/Jason⁠
LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis/⁠

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

Steven Fabre is the Co-founder and CEO of Liveblocks.

Liveblocks builds ready-made AI copilots and collaboration for your product, and Steven is one of my smartest friends on how people are actually using AI on a day-to-day basis.

We talk about what most people get wrong when trying to build AI-native software, how to treat it as more than just a copilot that sits on top of your product, and what he’s learned about how large enterprises are actually buying and using AI right now.

We also talk through Liveblocks journey of evolving from real-time human collaboration components into one that also incorporates AI, what he’s learned going from a designer to a CEO, and how he rebuilt the company after his co-founder stepped away.

Thank you to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠

Timestamps:
(2:17) Liveblocks: Infrastructure for people + AI
(6:08) Wrong ways to add AI to software
(8:05) Why humans and AI must collaborate
(12:35) How AI will change software UI
(18:58) AI search optimization
(26:20) How to get #1 on Product Hunt
(32:33) Liveblocks 1.0 to 3.0 evolution
(36:40) Why collaboration software is so hard
(38:38) How customers use Liveblocks
(42:36) Hiring a coach to get better at sales
(47:07) Steven’s biggest enterprise sales mistakes
(50:28) How AI changes GTM and funding milestones
(57:57) Going from a designer to a CEO
(1:01:06) How Liveblocks first started
(1:04:56) Importance of design in company building
(1:06:51) Learning to become a CEO
(1:12:29) When his co-founder left 5 years in
(1:15:49) Becoming stronger hiring a new Head of Engineering
(1:22:10) Remote culture: what doesn’t work
(1:24:08) Remote culture: what does work
(1:26:47) Importance of autonomy on remote teams
(1:28:05) Most underrated basketball players
(1:33:38) ACL injury that kickstarted his first business

Referenced
Liveblocks: https://liveblocks.io/
Careers at Liveblocks: https://join.team/liveblocks

Follow Steven
Twitter: https://x.com/stevenfabre
LinkedIn: https://www.linkedin.com/in/steven-fabre-5510bb38

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/