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PODCAST

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.

technology

All Episodes

01:45:04

How US Healthcare Actually Works, the WWII Tax...

The Peel with Turner Novak ·

2026/04/09

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 episodeNumeral: The end-to-end platform for sales tax and compliance

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01:31:38

Sophia Amoruso on Bootstrapping Nasty Gal to $120M...

The Peel with Turner Novak ·

2026/04/02

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

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01:32:16

Footwork’s Secret Sauce | Mike Smith and Nikhil Basu...

The Peel with Turner Novak ·

2026/03/26

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

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01:11:41

Inside Hanover Park: Building an AI-Native Service...

The Peel with Turner Novak ·

2026/03/18

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

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01:35:41

Inside Canada’s Fastest Growing AI Company |...

The Peel with Turner Novak ·

2026/03/12

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

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01:29:33

Benchmark’s Chetan Puttagunta on the Past, Present &...

The Peel with Turner Novak ·

2026/03/04

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

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01:25:20

Inside Serval: Building the System of Intelligence...

The Peel with Turner Novak ·

2026/02/27

Jake Stauch is the Co-founder and CEO of Serval. Serval automates IT with AI.We talk taking on incumbents with an AI-native product, why IT departments haven’t had much automation historically, the 12+ month journey of landing their first customer, and how teams can increase talent density as they scale.Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com⁠](https://www.numeral.xn--com-xw0a/)Sign-up for Flex Elite with code TURNER, get $1,000:

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01:23:57

Garry Tan on the Past, Present, and Future of YC

The Peel with Turner Novak ·

2026/02/19

Gary Tan is the President and CEO of Y Combinator.YC is the startup accelerator behind companies like Airbnb, Stripe, Coinbase, Reddit, Twitch, and thousands more. According to Garry, they’ve invested in 20% of all startups worth $5B or more started since 2012.Gary has lived every side of the YC ecosystem. He went through YC as a founder, later became a partner, started Initialized Capital where he backed companies like Coinbase and Instacart, and then returned to lead YC.We walk through the

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01:34:32

Building the Wearable That Gets You Stronger |...

The Peel with Turner Novak ·

2026/02/13

Miranda Nover is the Co-founder and CEO of Fort Health. Fort builds wearables that automatically track strength training for people who care about longevity.This is a new format I’m experimenting with. It’s the first time I’ve had a Banana portfolio company founder on the show while they’re still at the pre-seed stage. When I surveyed my subscribers a few weeks ago, you were most interested in more early stage VC-backed founders, and I’d love your feedback on what you think of this.Miranda is still

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02:08:32

How Duo Security went Zero to $1B ARR in Ann Arbor |...

The Peel with Turner Novak ·

2026/02/05

Dug Song and Jon Oberheide are the co-founders of Duo Security.If you’ve never heard of Duo, it might be one of the most underrated software stories of all-time.Starting in 2010, they burned only $14 million to hit $100m in ARR, were acquired by Cisco for $2.35 billion in 2018, and now rumored to be doing over $1 billion in ARR inside Cisco 16 years later.We talk about how they built one of the most capital efficient SaaS companies ever from Ann Arbor, Michigan, and how their focus on the customer

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01:26:55

Building Real-Time Data Streaming for AI | Jacqueline...

The Peel with Turner Novak ·

2026/01/28

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

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02:23:22

The State of AI: Rise of Reasoning, Surge in Chinese...

The Peel with Turner Novak ·

2026/01/22

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

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01:52:16

Building the $3B API That Didn’t Exist, Europe’s...

The Peel with Turner Novak ·

2026/01/15

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

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01:27:54

Kevin Hartz | Backing Teen Founders, Lessons from the...

The Peel with Turner Novak ·

2026/01/08

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

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01:43:20

Inside the All-In Podcast: Lessons from Elon, Trump,...

The Peel with Turner Novak ·

2025/12/18

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

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01:37:21

Why the Future of Software is AI and Human...

The Peel with Turner Novak ·

2025/12/11

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

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02:32:14

Building Flex, the AI Private Bank with CEO Zaid Rahman

The Peel with Turner Novak ·

2025/12/04

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

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00:53:03

Inside Eight Sleep | Using AI to Sleep Better | CEO...

The Peel with Turner Novak ·

2025/11/25

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

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01:39:39

Inside the New Superhuman: $700M ARR, 40M Daily Users...

The Peel with Turner Novak ·

2025/11/20

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

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01:36:08

Inside Stripe: Stablecoins, AI, and (not) Going...

The Peel with Turner Novak ·

2025/11/13

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

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137 results

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