The Peel with Turner Novak

Turner Novak
  • 4.6 (11)
  • TECHNOLOGY
  • UPDATED WEEKLY

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.

  1. How Duo Security went Zero to $1B ARR in Ann Arbor | Dug Song, Jon Oberheide

    FEB 5

    How Duo Security went Zero to $1B ARR in Ann Arbor | Dug Song, Jon Oberheide

    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 and company culture helped them win in a crowded cybersecurity market. We talk growing up in the early hacking culture of the 90s, why most security tools are painful to use, sizing their market, solving for non-consumption of a product, and how Duo flipped the model by designing for end users instead of security teams. We talk about staying in Michigan instead of moving to Silicon Valley, and why staying out of the tech bubble helped them execute. We break down the mechanics of scaling from zero to $100 million in ARR, everything they learned integrating with Cisco, and why more founders should build outside of San Francisco. A quick thank you ex-Duo employees Zack Urlocker, Ash Devata, and Katie Kilroy for their help brainstorming topics for the conversation. Try Numeral, the end-to-end platform for sales tax and compliance: [https://www.numeral.com](https://www.numeral.com/) Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (4:49) Meeting from Dug’s Wi-Fi honeypot (7:33) 90’s hacking culture and cybersecurity’s wild west (14:49) How the internet was born in Ann Arbor (18:58) Staying in Michigan instead of moving to Silicon Valley (31:20) Philosophy on leadership and team building (39:48) What makes a good engineering leader (44:01) Starting Duo to make security easier (45:22) Why most security products suck (48:36) How fixing account takeover became a $1B ARR company (59:10) TAM, competition, fixing the non-consumption of security (1:04:04) Being a radical advocate for the customer (1:08:35) Duo’s pizza sales play (1:12:45) Branding lessons from Anthropic, Tesla, Cliff Bar (1:17:47) When to say no to customers (1:21:27) Importance of culture when scaling (1:27:56) Duo’s role in uncovering the SolarWinds breach (1:31:29) Scaling to $100M ARR on $14M burned (1:39:30) Inside the $2.35B Cisco acquisition (1:44:02) What big companies get wrong about customers (1:51:53) Building Michigan’s startup ecosystem Referenced Duo Security: [https://duo.com](https://duo.com/) Cisco: [https://www.cisco.com](https://www.cisco.com/) University of Michigan: [https://umich.edu](https://umich.edu/) Follow Dug Twitter: https://x.com/dugsong LinkedIn: https://www.linkedin.com/in/dugsong Follow Jon Twitter: https://x.com/jonoberheide LinkedIn: https://www.linkedin.com/in/jono 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/

    2h 9m
  2. Building Real-Time Data Streaming for AI | Jacqueline Cheong, Co-founder and CEO of Artie

    JAN 28

    Building Real-Time Data Streaming for AI | Jacqueline Cheong, Co-founder and CEO of Artie

    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/

    1h 27m
  3. The State of AI: Rise of Reasoning, Surge in Chinese Open Source, Sovereign AI , How to Invest in AI Today | Nathan Benaich, Air Street Capital

    JAN 22

    The State of AI: Rise of Reasoning, Surge in Chinese Open Source, Sovereign AI , How to Invest in AI Today | Nathan Benaich, Air Street Capital

    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/

    2h 23m

  4. JAN 15

    Building the $3B API That Didn’t Exist, Europe’s Regulation Problem | Marcelo Lebre, Co-founder of Remote

    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/

    1h 52m
  5. Kevin Hartz | Backing Teen Founders, Lessons from the PayPal Mafia

    JAN 8

    Kevin Hartz | Backing Teen Founders, Lessons from the PayPal Mafia

    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/

    1h 28m
  6. Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick, Investing in 100+ Startups per Year with Jason Calacanis

    12/18/2025

    Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick, Investing in 100+ Startups per Year with Jason Calacanis

    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

    1h 43m
  7. Why the Future of Software is AI and Human Collaboration | Steven Fabre, Co-founder and CEO, Liveblocks

    12/11/2025

    Why the Future of Software is AI and Human Collaboration | Steven Fabre, Co-founder and CEO, Liveblocks

    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/

    1h 37m
  8. Building Flex, the AI Private Bank with CEO Zaid Rahman

    12/04/2025

    Building Flex, the AI Private Bank with CEO Zaid Rahman

    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/

    2h 32m
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4.6
out of 5
11 Ratings

About

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.

Information

  • Creator
    Turner Novak
  • Years Active
    2023 - 2026
  • Episodes
    127
  • Rating
    Explicit
  • Copyright
    © Turner Novak
  • Show Website
    The Peel with Turner Novak

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