The Peel with Turner Novak

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 2014, 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.

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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
LinkedIn: https://www.linkedin.com/in/jono
Follow Turner

Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak

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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.

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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

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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

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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

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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

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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

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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

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