Avery Pennarun on Tailscale's Evolution: From Mesh VPN to AI Security Gateway
Corey Quinn sits down with Avery Pennarun, co-founder and CEO of Tailscale, for a deep dive into how the company is reinventing networking for the modern era. From finally making VPNs behave the way they should to tackling AI security with zero-click authentication, Avery shares candid insights on building infrastructure people actually love using, and love talking about.
They get into everything: surviving 100% year-over-year growth, why running on two tailnets at once is pure chaos, and how Tailscale makes “secure by default” feel effortless. Plus, they dig into why FreeBSD firewalls needed some tough love, the uncomfortable truth behind POCs, and even the surprisingly useful trick of turning your Apple TV into an exit node.
About Avery:
Avery Pennarun is the co-founder and CEO of Tailscale, where he’s redefining secure networking with a simple, Zero Trust approach. A veteran software engineer with experience ranging from startups to Google, he’s known for turning complex systems into approachable, user-friendly tools. His contributions to projects like wvdial, bup, and sshuttle reflect his belief that great technology should be both powerful and easy to use. With a mix of technical depth and dry humor, Avery shares insights on modern networking, internet evolution, and the realities of scaling a startup.
Highlights:
(0:00) Introduction to Tailscale and Security
(00:52) Sponsorship and Personal Experiences
(02:07) Technical Deep Dive into Tail Scale
(06:10) Challenges and Future of Tail Scale
(22:45) Building the Tail Net's API
(23:54) Connecting Cloud Providers with Tailscale
(25:22) Tailscale as a Security Solution
(26:44) Innovations and Future of Tailscale
Sponsored by:
duckbillhq.com
Discord’s Power Move, Slate’s Modular EVs & the “Act for Private Gain” | E2117
Today’s show: Jason, Alex, and Lon break down today’s top tech and startup stories — from Slate Auto’s customizable $25K EV truck to Discord’s major leadership shakeup ahead of a potential IPO. They also cover Uber’s self-driving push with Volkswagen, Perplexity AI’s aggressive growth moves, and why value-driven products are winning in a tough economy. Plus, Alex sits down with Tailscale CEO Avery Pennarun to unpack how they grew from 5K to 10K customers — and why fixing internet networking could spark the next huge wave of innovation.
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Timestamps:
(0:00) Jason, Lon and Alex kick off the show!
(3:26) Introduction and features of Bezos-backed EV truck company, Slate
(7:55) Market impact and value proposition of Slate's EV trucks
(9:48) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups
(14:04) EV features and market potential discussion
(17:42) Discord CEO steps down and IPO prospects
(20:19) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(24:00) Uber and Volkswagen's self-driving car partnership
(28:39) Superpower - The best founders know: better health = better business. Visit http://superpower.com/twist to skip the waitlist.
(30:00) Pace of self-driving car adoption and regulation
(37:20) Butterfly Effect secures Benchmark investment
(38:37) Perplexity and Motorola Razr partnership
(43:12) Jason's experience with Light Phone
(45:39) New York Times and Ziff Davis lawsuits against OpenAI
(50:09) Nonprofit structures and OpenAI's mission issues
(54:01) Founder Friday: Pitchfire and TACTUN's two-year plans
(1:02:28) Introduction to Tailscale and Avery Pennarun
(1:10:17) Tailscale's enterprise adoption
(1:21:13) Current Internet networking issues*
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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Links from episode:
Check out Tailscale: https://tailscale.com/
Check out Slate vehicles: https://www.slate.auto/en
Check out Not For Private Gain:https://notforprivategain.org/
Check out the Light Phone: https://www.thelightphone.com/
Check out Oregon lawmakers article: ****https://www.oregonlive.com/politics/2025/04/oregon-lawmakers-to-decide-whether-big-tech-should-pay-to-support-local-journalism.html
Check out Manus: https://manus.im/
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Follow Lon:
X: https://x.com/lons
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Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm
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Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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Thank you to our partners:
(9:48) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(20:19) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(28:39) Superpower - The best founders know: better health = better business. Visit http://superpower.com/twist to skip the waitlist.
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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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Check out Jason’s suite of newsletters: https://substack.com/@calacanis
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Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
The Magic of Tailscale with Avery Pennarun
About Avery
wvdial, bup, sshuttle, netselect, popularity-contest, redo, gfblip, GFiber, and now @Tailscale doing WireGuard mesh. Top search result for "epic treatise."
Links Referenced:
Webpage: https://tailscale.com
Tailscale Twitter: https://twitter.com/tailscale
Personal Twitter: https://twitter.com/apenwarr