Shows
SHIFTSecuring AI’s FutureDeveloping and scaling AI systems brings new security challenges, and companies are scrambling to figure out just how to handle some of the more pressing ones.I was recently joined on stage by co-founders from two Canadian unicorns, Cohere and Tailscale, to dig into these challenges at Web Summit Vancouver.We Meet: Avery Pennarun, Co-founder & CEO, Tailscale Ivan Zhang, Co-founder, Cohere Credits:This episode of SHIFT was produced by Jennifer Strong with help from Emma Cillekens. It was mixed by Garret Lang, with...2025-07-0917 min
Sand Hill Road2025 Summer VC Reading ListIt's our annual tradition—venture capitalists and startup founders share the books that shaped them. From sci-fi and civil rights to artificial intelligence and management, this year's reading list offers insight into the minds of Silicon Valley’s most thoughtful leaders.Highlights include:Master of the Senate by Robert Caro, recommended by Casber Wang of Sapphire Ventures for its deep exploration of power and politicsTraffic by Ben Smith, cited by Joe Alalou of Daring Ventures as essential reading on how the social web shaped our modern worldThe Sentence by Loui...2025-06-2608 min
A Product Market Fit Show | Startup Podcast for FoundersHow his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of TailscaleAvery Pennarun raised $160M for Tailscale—without even meaning to. What started as a small, simple project exploded into an unstoppable force in network connectivity and security. This episode reveals exactly how Avery turned a tiny seed round into millions of dollars in ARR, powered by nothing more than word-of-mouth and an obsession with solving everyday developer headaches. Learn why your startup idea is probably wrong (and why that’s okay), how Tailscale found explosive product-market fit, and why the biggest opportunities are hiding in the “smallest” problems. If you’re an early-stage founder looking for practical insights, game-changing growth hac...2025-06-0950 min
Startup Builders & BackersFrom Startup to Scale: How Tailscale Built a Billion-Dollar Business with Simplicity at Its CoreWhat does it take to turn a bold idea into a billion-dollar company during one of the most unpredictable periods in recent history? In this episode of Startup Builders and Backers, we meet Avery Pennarun, Co-founder and CEO of Tailscale, who shares how a lean networking startup found its stride in the middle of a global pandemic and reshaped expectations for what secure connectivity can look like.Before founding Tailscale in 2019, Avery had already built and sold a company to IBM, worked closely with senior leadership at Alphabet, and led engineering efforts at Google Fiber. His experience...2025-05-1732 min
This Week in StartupsDiscord’s Power Move, Slate’s Modular EVs & the “Act for Private Gain” | E2117Today’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.*Timestamps:(0:00) Jason, Lon and A...2025-04-261h 25
Spotlight OnIt’s Time to Build a Better Internet, with Tailscale CEO Avery PennarunOne thing we like about working with repeat founders is that they’re decisive about how they do and do not want to build their company. Take Avery Pennarun, CEO of Tailscale. Even before he knew what Tailscale would be, he knew he wanted to: build products as simply as possible, avoid selling software only at the enterprise level, focus on winning small segments before expanding, and not waste time “innovating” executive team structure. Clearly, it’s working: the company is redefining the network security category, and recently hit 10,000 paid customers after doubling its customer base in 10 months. Listening to Amit...2025-03-0437 min
Parempaa designia kaikilleKäyttäjiesi halut vs. tarpeetAvery Pennarun sanoo blogikirjoituksessaan SimSWE 4: Wants, needs, and chasm-crossing (https://apenwarr.ca/log/20211024), että startup voi menestyä vain jos se keskittyy yhteen haluun eli yhteen markkinasegmenttiin ja täyttää niiden käyttäjien kaikki tarpeet mahdollisimman hyvin ja kattavasti. Käymme läpi blogikirjoituksen omasta näkökulmastamme ja toteamme toisaalta, että se jäsentää asiaa hyvin ja toisaalta että sitä voi soveltaa omaan työhönsä. ---Podcastin muut jaksot löytyvät Podcastin sivustolta ja yleisimmiltä Podcast-alustoilta.Tavoitat meidät osoitteesta palaute@designkaikille.fi Kysele, haasta ja kommentoi! Luemme kaikki palautteet.2025-02-1549 min
Apple @ WorkCatching up with Tailscale CEO Avery PennarunApple @ Work is exclusively brought to you by Mosyle, the only Apple Unified Platform. Mosyle is the only solution that integrates in a single professional-grade platform all the solutions necessary to seamlessly and automatically deploy, manage & protect Apple devices at work. Over 45,000 organizations trust Mosyle to make millions of Apple devices work-ready with no effort and at an affordable cost. Request your EXTENDED TRIAL today and understand why Mosyle is everything you need to work with Apple.
In this episode of Apple @ Work, I talk with Avery Pennarun, CEO and Co-Founder of Tailscale, about the benefits of the...2025-02-1122 min
Smashing SecurityHacks on the high seas, and how your home can be stolen under your noseAn Italian hacker makes the grade and ends up in choppy waters, and hear true stories of title deed transfer scams.All this and more is discussed in the latest edition of the award-winning "Smashing Security" podcast by computer security veterans Graham Cluley and Carole Theriault.Plus - don't miss our featured interview with Avery Pennarun of Tailscale.Warning: This podcast may contain nuts, adult themes, and rude language.Episode links:Report from Corriere Di Bologna newspaper.Caro Musk, assumi subito l’hacker quindicenne di Cesena – Il Foglio.15-Year-Old Hacker Dive...2025-01-2349 min
AWS re:Think PodcastEpisode 33: Rethinking Network Connectivity and Security in the Cloud with TailscaleIn this episode, Tailscale CEO Avery Pennarun joins us to discuss VPNs, network connectivity and security in the cloud era. We talk about hub & spoke vs full mesh networks as well current and future trends in networking. Avery also talks about how Tailscale’s approach to networking helps make setting up secure networks between devices and the cloud easier than before. For more info on Tailscale check out:tailscale.comAWS Hosts: Nolan Chen & Malini ChatterjeeEmail Your Feedback: rethinkpodcast@amazon.com2024-11-1829 min
The Security Podcast of Silicon ValleyAvery Pennarun, Co-Founder and CEO of Tailscale, the Anti-Google: Rebuilding a Secure Internet from the Bottom-UpDon't miss this blend of technology, ambition, and forward-thinking only of The Security Podcast of Silicon Valley, a YSecurity.io production, as we dive into Avery Pennarun's journey, the Co-Founder and CEO of Tailscale, from starting his first company in college to selling it to IBM, taking a detour at Google, and eventually creating what's known as the anti-Google of cyber startups, Tailscale. Avery gives us a candid look at the evolution of a billion-dollar valuation company. Discover how Tailscale became the first security infrastructure product adopted bottom-up by individual engineers rather than imposed from the top down. Join...2024-05-0145 min
Open Source Startup PodcastE127: Reimagining VPNs with TailscaleAvery Pennarun is Co-Founder & CEO of Tailscale, the Wireguard-based VPN that reimagines secure, private networks.
Tailscale has raised $115M from investors including Heavybit, Accel, CRV, and Insight.
In this episode, we dig into what caused the team to reimagine zero trust security at the networking level, why they focus both on individual developers and large enterprises with a bottoms-up and top-down business model, why they leaned into the VPN comparison, how they create a personal tone for their blog & more! 2024-04-1743 min
Tech Beats UnpluggedEp04: "Networking in the Cloud Part 1" (with Jose Moreno)👨🏽🚀 Welcome to Episode 04 of "Tech Beats unplugged"
This time, we dared to tackle the big, yet exciting topic which is "𝐍𝐞𝐭𝐰𝐨𝐫𝐤𝐢𝐧𝐠 𝐢𝐧 𝐭𝐡𝐞 𝐜𝐥𝐨𝐮𝐝", and to help us with this challenge we summoned our expert and networking GURU "Jose Moreno" all the way from Munich Germany.
As an Azure Principal Engineer at Microsoft, he comes to share his knowledge and demystify all those mysterious networking concepts, answering questions you never dared to ask in the universe of SDN and cloud networking😀( SDWAN, Hub&Spoke, migrations, Cloud lies, you name it).
🌟 We’re so excited to share our latest tech Beats show with you🧡!
We hope you'll enjoy it!!!
Top...2024-04-171h 16
Sand Hill RoadAccel Invests in TailscaleEntrepreneur Avery Pennarun and Accel's Amit Kumar talk about leaving big companies to chase new adventures.
2023-12-0821 min
Tech Talks DailyTailscale Co-founder & CEO Shares His Startup JourneyToday's episode of the Tech Talks Daily Podcast is indeed an inspirational one. We have Avery Pennarun, the Co-founder and CEO of Tailscale, a security networking startup that's not just making waves but has also garnered a valuation of over $1 billion CAD. Avery's journey is nothing short of incredible, having consulted Alphabet's senior leadership, led Google Fiber's gigabit WiFi and platform analytics team, and even sold his startup, Net Integration Technologies (Nitix), to IBM in 2008. Tailscale, launched in 2019, found itself confronting the unprecedented challenges of a global pandemic. Yet, not only did it survive, but it thrived...2023-10-2132 min
The Next Stage podcast by Web SummitFighting bad bots with good botsThe term ‘bot’ often evokes a sense of annoyance, scepticism, or even dread. Whether it’s trending hashtags manipulated by an army of automated accounts, or your X (fka Twitter) feed being inundated with political propaganda, bots have gained a reputation as digital pests.
But what if they could be used for good in cybersecurity?
In this episode of the Next Stage, Signifyd co-founder and CEO Rajesh Ramanand and Avery Pennarun, co-founder and CEO of Tailscale, talk about employing bots as a proxy for the user and doing automated tasks on their behalf, including fighting scam bo...2023-10-1719 min
All AboardUnlocking Zero Trust Networking with Tailscale’s Avery PennarunWith the rise of the distributed workforce came the need for better remote connectivity. Traditional VPNs have fallen short.In this episode of the All Aboard Podcast, Alex chats with Avery Pennarun, CEO and Co-Founder at Tailscale. Founded in 2019, Tailscale uses mesh networking technology to help companies ditch their VPN and provide access to critical infrastructure and resources without sacrificing speed, scalability, or performance.What’s inside:Avery shares the accidental origin story of how Tailscale was foundedHow and why traditional VPNs are falling short for the remote first worldHow Ta...2023-06-1531 min
The dojo.live show / Interviews with Visionaries Shaping Travel TechBetter Living Through Small NetworksHow did the open Internet grow up to be such a dangerous place? Why don't security and privacy ever seem to get any better? Is there a better way? View the full video interview here.
Avery Pennarun started his first startup back in university, sold it to IBM 8 years later, worked on Google Wallet and Google Fiber for several years, started several open source projects (netselect, wvdial, bup, sshuttle, popularity-contest, and others), and sometimes writes popular blog posts about systems design. His latest startup, Tailscale, aims to make the Internet work the way it was always supposed...2022-10-1933 min
Heavybit Podcast Network Master FeedThe Kubelist Podcast - Ep. #33, Tailscale with Avery PennarunIn episode 33 of The Kubelist Podcast, Marc and Benjie speak with Avery Pennarun of Tailscale. This conversation explores VPNs, mesh-overlay networks, Tailscale's use cases, the relationship between scaling and architecture, and unparalleled lessons from Avery’s 20+ years in development.2022-10-191h 03
Heavybit PodcastsEp. #33, Tailscale with Avery PennarunIn episode 33 of The Kubelist Podcast, Marc and Benjie speak with Avery Pennarun of Tailscale. This conversation explores VPNs, mesh-overlay networks, Tailscale’s use cases, the relationship between scaling and architecture, and unparalleled lessons from Avery’s 20+ years in development.The post appeared first on Heavybit.2022-10-191h 03
The Kubelist PodcastEp. #33, Tailscale with Avery PennarunIn episode 33 of The Kubelist Podcast, Marc and Benjie speak with Avery Pennarun of Tailscale. This conversation explores VPNs, mesh-overlay networks, Tailscale’s use cases, the relationship between scaling and architecture, and unparalleled lessons from Avery’s 20+ years in development.The post appeared first on Heavybit.2022-10-191h 03
DealMakers: Entrepreneur | Startups | Venture CapitalAvery Pennarun On Selling His College Startup To IBM And Raising $115 Million To Build A Secure NetworkAvery Pennarun launched his first successful startup in college. He is now on his second tech startup, and investors have been more than eager to help fund it. The venture, Tailscale has attracted funding from top-tier investors like Accel, Heavybit, Insight Partners, and Uncork Capital.
2022-07-1434 min
The Business of Open SourceTailscale and Market Segmentation with Avery PennarunToday I’m chatting with Avery Pennarun, CEO of Tailscale. Tailscale is a VPN service that makes devices and applications accessible anywhere in the world by enabling encrypted point-to-point connections using the open source WireGuard protocol. Avery begins by talking about his experience building a start-up while he was a college student and how things have changed as he leads his current start-up. Avery recommends the book “Crossing the Chasm” and we discuss market segmentation as it relates to creating a successful start-up. Avery explains how Tailscale has been successful in implementing market segmentation strategies. We conclude our conversation by tal...2022-05-2535 min
LINUX Unplugged458: NVIDIA's New ViewNVIDIA is open-sourcing their GPU drivers, but there are a few things you need to know. Plus, we get some exclusive insights into Tailscale from one of its co-founders.Special Guests: Avery Pennarun and Christian F.K. Schaller.Sponsored By:Linode Cloud Hosting: A special offer for all Linux Unplugged Podcast listeners and new Linode customers, visit linode.com/unplugged, and receive $100 towards your new account. Bitwarden: Bitwarden is the easiest way for businesses and individuals to store, share, and sync sensitive data.Support LINUX UnpluggedLinks:After losing contact...2022-05-161h 07
All Jupiter Broadcasting ShowsNVIDIA's New View | LINUX Unplugged 458NVIDIA is open-sourcing their GPU drivers, but there are a few things you need to know. Plus, we get some exclusive insights into Tailscale from one of its co-founders.Special Guests: Avery Pennarun and Christian F.K. Schaller.Sponsored By:Linode Cloud Hosting: A special offer for all Linux Unplugged Podcast listeners and new Linode customers, visit linode.com/unplugged, and receive $100 towards your new account. Bitwarden: Bitwarden is the easiest way for businesses and individuals to store, share, and sync sensitive data.Support LINUX UnpluggedLinks:After losing...2022-05-1500 min
Screaming in the CloudThe Magic of Tailscale with Avery PennarunAbout Averywvdial, 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.comTailscale Twitter: https://twitter.com/tailscalePersonal Twitter: https://twitter.com/apenwarr2022-05-0441 min
Security Cryptography WhateverTailscale with Avery Pennarun and Brad Fitzpatrick“Can I Tailscale my Chromecast?” You love Tailscale, I love Tailscale, we loved talking to Avery Pennarun and Brad Fitzpatrick from Tailscale about, I dunno, Go generics. Oh, and TAILSCALE! And DNS. And WASM.Transcript:https://securitycryptographywhatever.com/2022/01/15/tailscale-with-avery-pennarun-brad-fitzpatrick/People:Avery Pennarun (@apenwarr)Brad Fitzpatrick (@bradfitz)Deirdre Connolly (@durumcrustulum)Thomas Ptacek (@tqbf)David Adrian (@davidcadrian)@SCWPodLinks:DERP server: https://github.com/tailscale/tailscale/tree/main/derphttps://xtermjs.org/The Tail at Scale : https://research.google/pubs/pub40801/Raft: https://raft.github.io/Litestream: https://lite...2022-01-151h 18
Hanselminutes with Scott HanselmanCan networking be simple? with Tailscale's Avery PennarunDouble NAT? Triple NAT? Opening Ports, punching holes in firewalls, it's all so complex, right? Does it have to be? Scott talks to Tailscale's Avery Pennarun and asks "can networking be simple?" Avery and his team believes it can with a new take on networking. Personal mesh-style VPNs with tech like WireGuard over a faster, leaner, cleaner, and simpler way to share your network with your team.
2021-02-0433 min
Troubleshooting AgileScoring Briefing and Back BriefingFollowing on further from Avery Pennarun's intriguing article on "what executives do", we ask how, exactly, executives (and others!) can trigger action, if they are not themselves going to carry it out? It turns out we've covered our favourite technique for this before - Bungay's Briefing and Back Briefing - but this time we have a scoring checklist that can help you use the technique, and two new stories about successful and unsuccessful delegation.
SHOW LINKS:
- What do executives do, anyway? by Pennarun: https://apenwarr.ca/log/20190926 and Hacker News discussion: https://news.ycombinator.com/item?id=21088425
- Art...2019-10-0918 minTroubleshooting AgileWhat Are Leaders Good For, Anyway?We respond to an intriguing and dense article from Avery Pennarun about what executives do. He takes us back to Andy Grove’s classic High Output Management and we reflect on the leverage leaders can use, how they and their staff can fool themselves into thinking they have the right information, and a mindset exercise to help you find “unknown unknowns”.
SHOW LINKS:
- What do executives do, anyway? by Pennarun: https://apenwarr.ca/log/20190926 and Hacker News discussion: https://news.ycombinator.com/item?id=21088425
- Andy Grove, High Output Management: https://www.amazon.co.uk/High-Output-Management-Andrew-Grove/dp/0679762884
- Art of Act...2019-10-0218 min