Jacqueline Cheong is the Co-founder and CEO of Artie.

Artie moves data across your systems in real-time, and we talk about why that’s so important in the age of AI.

It’s a lot harder than you’d think, as less than 5% of real-time data streaming projects are successful.

I talked to a dozen people to prepare for this conversation, including Jared Friedman who worked with Jacqueline during YC, her sales coach Ras, and numerous Artie employees like A-nee-rud, Ryan, Sarah, Shangbing and Jacqueline’s co-founder Robin.

We talk through how Robin built real-time data streaming at OpenDoor and Zendesk before they started Artie, and Jacqueline shares the sales playbook she learned going from hedge fund analyst to software CEO, including asking customers for their hardest problem and then solving it with the product.

Artie just announced a $12 million Series A a few weeks before we published this episode. We talk about how they landed all of their early enterprise customers through cold outbound, how they structure and automate their prospecting with AI so they have no BDRs, and why they’re seeing customers switch to Artie even after building their own multi-million dollar real-time streaming projects in-house.

I also asked Jacqueline what it’s like working with Standard Capital. They’re a new fund started by a group of YC partners, and it was fascinating to hear about the things they’ve borrowed from YC when investing at the Series A stage.

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:

(4:08) Artie: Real-time data streaming

(5:13) Why moving data is so hard

(9:14) Evolution of data warehouses

(12:47) AI needs real-time data

(18:44) Build vs buy in data streaming

(22:51) How to build in a crowded market

(26:26) Early focus on a specific hard problem

(30:33) Acquiring enterprise customers from cold emails

(32:51) Onboarding their first customer with no UI

(35:46) Solving compliance and implementation

(38:50) How to automate internal engineering, marketing, and ops

(44:01) Building an AI-powered GTM pipeline and motion

(46:52) Add your customers on iMessage, Slack, Teams

(53:00) Starting Artie to solve their own problem

(59:25) Discovering YC through a friend

(1:02:20) Everything Jacqueline learned about sales

(1:06:29) How to improve your sales discovery calls

(1:10:08) Inside Artie’s $12m Series A

(1:16:44) What its like working with Standard Capital

(1:22:59) Jacqueline’s favorite book

Referenced

Try Artie: https://artie.com

Careers at Artie: https://www.artie.com/careers

Clay: https://www.clay.com

Podcast with Tommy @ Alloy: https://www.youtube.com/watch?v=e7i8Wxklu-Y

YCombinator: https://www.ycombinator.com

Standard Capital: https://www.standardcap.com

Founding Sales: https://www.foundingsales.com

The Score Takes Care of Itself: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472

Follow Jacqueline

Twitter: https://x.com/JacquelineSYC19

LinkedIn: https://www.linkedin.com/in/jacqueline-cheong

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/

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.

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:

(3:39) 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/

Zaid Rahman is the Co-founder and CEO of Flex.

Flex is the AI native private bank for high net worth middle market business owners, headlined by it’s 60-day interest free credit card for businesses.

Flex just announced their $60 million Series B, as well as their new consumer product, Flex Elite, which pits it head-to-head against Amex for the consumer spending of some of the wealthiest people in America. It's products now spans from when a business owner first generates revenue, all the way to when they spend that cash personally.

This conversation goes inside how the company scaled from zero to a $70 million revenue run rate in two years, and everything Zaid learned along the way.

Thank you to Eric Bahn at Hustle Fund, Jeff Morris Jr. at Chapter One, Andrew Ziperski at General Catalyst, and Jared Thomas and Ewan Steel at Flex for helping brainstorming topics for the conversation.

Timestamps:

(1:44) Raising $60m to fix business finance

(3:23) Flex Elite: Personal + Business banking

(4:48) Jumbo shrimps: powering 40% of US payroll

(9:16) The forgotten mid market business

(14:01) “Flex fuels ambition”

(16:08) How to serve entrepreneurs in middle America

(22:58) Flex’s 5-pillar product suite

(27:12) Starting Flex to help construction companies

(31:51) Using AI to lend to mid-market customers

(40:22) Power of multi-product in fintech

(43:53) Zero to $3B in volume in 18 months

(44:43) Raising a bear market Series A in 2023

(51:00) How referrals landed their first big customers

(55:07) Flex’s playbook for 85% organic growth

(1:01:15) Dissecting various accents

(1:04:22) Building a quiet luxury brand

(1:09:33) Importance of customer happiness

(1:12:43) Why CEO’s should be the top sales person

(1:13:58) Building lots of in-house software

(1:24:33) PMF is like operating a popular restaurant

(1:30:49) How to raise a debt facility

(1:34:48) Recruiting is so crucial for startups

(1:39:00) Why VC’s hate lending businesses

(1:45:14) Underserved vs Underbanked in fintech

(1:48:02) Why business owners want personal + business banking

(1:54:49) Acquiring Maza, leaning in to M&A

(2:02:53) Most fintech companies look the same

(2:08:35) Founder group therapy with Eric at Hustle Fund

(2:11:50) The Thiel Fellowship’s 10% unicorn hit rate

(2:15:52) Lesson from the ruler of Dubai

(2:19:24) Building Flex’s risk underwriting engine

(2:26:58) Flex’s AI opportunity

Referenced

Try Flex: https://www.flex.one

Careers at Flex: https://jobs.lever.co/Flex/

Basel III https://en.wikipedia.org/wiki/Basel_III

Linguistic TikTok account: https://www.tiktok.com/@zaydupree

Lazy luxury: most worn shoes on private jets: https://www.wsj.com/style/fashion/lazy-luxury-sneakers-are-these-the-most-worn-shoes-on-private-jets-7801be30

Follow Zaid

Twitter: https://x.com/zaidrmn

LinkedIn: https://www.linkedin.com/in/zaidrahman

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/

Matteo Franceschetti is the Co-founder and CEO of Eight Sleep.

Eight Sleep created one of the original breakout consumer health products in 2014, quietly building a business that’s raised over $300 million dollars and was reportedly free cash flow positive in the first half of 2025.

But things weren’t always easy, and Matteo shares the challenges of starting a hardware company, why hardware has stronger moats, and the fundraising mindset he adopted that eventually got Khosla Ventures and Founders Fund to invest.

We also get into the importance of sleep, how the company’s Sleep Butler uses AI to help you sleep better, and the big opportunity building more consumer health products.

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:

(2:18) Three pillars of health: sleep, nutrition, fitness

(4:02) Creating a sleep routine

(6:59) Importance of body temperature in sleep

(8:43) How Eight Sleep works

(12:14) Using AI to help you sleep

(18:35) The AWS outage

(24:12) It’s too hard to build in Europe

(28:09) Why hardware has stronger moats

(32:23) How to fundraise for a hardware company

(35:30) The opportunity in Sleep tech

(38:43) Hiring is easy when you have a mission

(40:37) How to fight jet lag

(43:03) Opportunities in women’s health

(45:54) Evolving from single purchase to subscription model

(47:12) Matteo’s personal health stack

(49:41) Racing sports cars

Referenced

Eight Sleep: https://www.eightsleep.com/

Compliant VC Meme Account: https://x.com/compliantvc

Follow Matteo

Twitter: https://x.com/m_franceschetti

LinkedIn: https://www.linkedin.com/in/matteofranceschetti/

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/

Rahul Vohra is the Founder and CEO of Superhuman Mail.

Rahul sold his company to Grammarly in July of 2025, which had just acquired Coda in 2024. Following the acquisitions, the combined companies rebranded to Superhuman in October of 2025.

And it’s quietly one of the most underrated businesses that no one is talking about, with over $700 million ARR and 40 million Daily Active Users. Grammarly spent 15+ years building integrations with over a million other products, that they’re now layering more AI products on top of.

We talk about Rahul’s journey building Superhuman, go inside the acquisition, all the lessons he’s learned from selling two companies, why you should design your product like a video game, and we also re-visit his famous quantitative guide to finding PMF.

Thanks to Todd Goldberg, Ed Sim, Shomik Ghosh, Ryan Hoover, and Rahul’s brother Gaurav Vohra for helping brainstorm topics for this conversation.

Thank you to Hanover Park for supporting this episode! Upgrade your fund admin to the 21st century https://www.hanoverpark.com/Turner

Timestamps:

(2:42) Inside the Superhuman acquisition

(11:09) Grammarly: $700M ARR, 40M DAUs

(18:53) How to sequence your product roadmap

(24:43) Vision for the new Superhuman

(32:43) Build your product like a video game

(38:24) Designing Karamja island in Runescape

(41:10) Build products like toys and games

(44:53) Starting a Machine Learning PhD in 2006

(48:49) Dropping out to start his first company

(50:47) Rapportive’s crazy accidental launch

(57:56) Meeting Superhuman co-founders

(1:02:17) Being 1 of 20 to access LinkedIn’s API

(1:06:38) Almost getting acquired by LinkedIn

(1:10:32) Nearly dieing, getting acquired with 2 weeks of runway

(1:20:08) Diligence from VCs vs Acquirers

(1:26:37) Rahul’s quantitative framework for PMF

(1:30:45) How to build an enduring brand

(1:31:51) Rahul’s AI-powered productivity stack

(1:35:01) Todd and Rahul’s angel fund

(1:36:45) We need more solo founders

Referenced

Superhuman: https://www.superhuman.com

Grammarly: https://www.grammarly.com

High Resolution Fundraising: https://paulgraham.com/hiresfund.html

High Resolution Fundraising: https://paulgraham.com/hiresfund.html

Superhuman Quantitative Framework for Finding PMF: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

Whisper Flow: https://wisprflow.ai

Follow Rahul

Twitter: https://x.com/rahulvohra

LinkedIn: https://www.linkedin.com/in/rahulvohra/

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/

Will Gaybrick is the President of Technology and Business at Stripe.

Stripe builds financial infrastructure for the internet, and if you’ve ever purchased a product online, you’ve probably used Stripe.

We talk about what Stripe’s doing in crypto and stablecoins, how AI is changing commerce and payments, how they’re thinking about going public, how they build products internally, and interesting data they’re seeing around AI-native companies, like how they’re growing 3.5x faster than SaaS companies.

Thank you to Claire Hughes Johnson, Josh Kushner, and Cosmin Nicolaescu for help brainstorming topics for the conversation.

Thank you to Numeral and Amplitude for sponsoring this episode.Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://www.numeral.com

Amplitude: Listen to users at scale with AI https://www.amplitude.com/AI-Feedback

Timestamps:

2:42 Will’s promotion

5:29 Build vs Buy in AI

6:39 Inside the Bridge acquisition

8:54 Stripe’s stablecoin strategy

11:20 Why building Stripe is so complicated

13:22 How Stripe builds new products

18:29 AI companies growing 3.5x faster than SaaS

22:58 New fraud vectors in AI businesses

25:19 Agentic commerce in ChatGPT

29:34 Building modular products

34:05 How Stripe uses AI internally

42:12 Building the first payments foundation model

48:23 Link, Stripe’s 200M user consumer product

56:52 Will Stripe ever IPO?

59:14 Blurring of private and public companies

1:03:39 Starting Hack Yale

1:08:23 Joining Thrive’s $5 million Fund 1

1:12:30 Low margin businesses are underrated

1:16:30 Joining Stripe as CFO

1:21:59 How Stripe’s go-to-market has evolved

1:25:56 Stripe’s margins

1:29:52 Why financial services are so hard to use

1:33:04 Lessons from Alan Mulally

Referenced

Stripe: https://stripe.com/

Careers at Stripe: https://stripe.com/jobs/search

Follow Will

Twitter: https://x.com/gaybrick

LinkedIn: https://www.linkedin.com/in/william-gaybrick-5730347

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/