{"id":25337,"date":"2025-10-09T13:52:19","date_gmt":"2025-10-09T17:52:19","guid":{"rendered":"https:\/\/www.insightpartners.com\/?p=25337"},"modified":"2026-03-10T12:06:08","modified_gmt":"2026-03-10T16:06:08","slug":"tailscale-leadership-story","status":"publish","type":"post","link":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/","title":{"rendered":"How Tailscale is building the new internet"},"content":{"rendered":"<p><span style=\"font-weight: 400;\">Cofounder and CEO <\/span><a href=\"https:\/\/www.linkedin.com\/in\/apenwarr\/?originalSubdomain=ca\"><span style=\"font-weight: 400;\">Avery Pennarun<\/span><\/a><span style=\"font-weight: 400;\"> didn\u2019t set out to be a tech entrepreneur; what he really likes is coding. It\u2019s something of an understatement from someone who sold his college startup (Net Integration Technologies, or <\/span><span style=\"font-weight: 400;\">Nitix<\/span><span style=\"font-weight: 400;\">, a network server appliance for small businesses) to IBM, worked as a senior staff software engineer for Google for nearly eight years, and is now running a networking company that underpins much of the AI industry.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">With <\/span><a href=\"https:\/\/tailscale.com\/\"><span style=\"font-weight: 400;\">Tailscale<\/span><\/a><span style=\"font-weight: 400;\">, he\u2019s building not just a better virtual private network (VPN), but a new internet.<br \/>\n<\/span><br \/>\n<iframe loading=\"lazy\" title=\"YouTube video player\" src=\"https:\/\/www.youtube.com\/embed\/jyYumOXLIsY?si=H275UQ_u4tGlxM9M\" width=\"800\" height=\"450\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<h2>Making the easy things easy<\/h2>\n<p><span style=\"font-weight: 400;\">The idea for Tailscale emerged from a contrarian observation: Not everything needs to operate at internet scale.\u00a0<\/span><\/p>\n<blockquote>\n<p style=\"padding-left: 40px;\"><i><span style=\"font-weight: 400;\">\u201cToo many people are assuming that everything they build is going to scale to a billion users and a billion compute nodes. Almost nobody actually has that problem.\u201d\u00a0<\/span><\/i><\/p>\n<\/blockquote>\n<p><span style=\"font-weight: 400;\">Even at companies that do, like Google, most of the work is on a smaller scale: an internal dashboard, an HR tool, a database instance, a build system. But basic connectivity and security tasks for those systems still take most of the time and energy to build.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">That struck Pennarun and his cofounders <\/span><a href=\"https:\/\/www.linkedin.com\/in\/dfcarney\/?originalSubdomain=ca\"><span style=\"font-weight: 400;\">David Carney<\/span><\/a><span style=\"font-weight: 400;\"> and <\/span><a href=\"https:\/\/www.linkedin.com\/in\/crawshaw\/\"><span style=\"font-weight: 400;\">David Crawshaw<\/span><\/a><span style=\"font-weight: 400;\"> \u2014 former colleagues from previous startups and Google \u2014 as the place to start building.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">They saw teams spending 90% of their time just dealing with connectivity and security when building an internal tool, and only 10% of their time actually building the tool itself.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cNobody actually wants to do networking except a small group of people that we call network engineers,\u201d says Pennarun. \u201cFor everybody else, the network is an obstacle that\u2019s stopping their job from getting done.\u201d<\/span><\/p>\n<p><span style=\"font-weight: 400;\">So in 2019, they set out to remove the obstacle, and \u201cmake easy things easy,\u201d says Pennarun. That principle became Tailscale\u2019s north star.<\/span><\/p>\n<h2>Building for developers<\/h2>\n<p><span style=\"font-weight: 400;\">The team built a peer-to-peer, zero-configuration VPN that could be launched by anyone, installed on any device, and work from anywhere, without the long setup times and complexity of traditional VPNs. It was something that let users create secure, encrypted, and authenticated networks between any number of devices, without needing centralized infrastructure or complex firewall management.<\/span><\/p>\n<p><a href=\"https:\/\/tailscale.com\/blog\/tailscale-launch\"><span style=\"font-weight: 400;\">Released in 2020<\/span><\/a><span style=\"font-weight: 400;\">, it was well-timed. COVID-19 meant employees were looking for ways to connect remotely and securely to their workspaces. But what made Tailscale stick was that it was built for developers, not security teams.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cThose are the teams that have really concrete value they need to deliver,\u201d says Pennarun. \u201cIt&#8217;s like, \u2018I need this right now in order to solve this problem right now\u2019. And then Tailscale is also a security product, but it has this grounding in reality, which a lot of security products don\u2019t.\u201d<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Developers were using it at home, bringing it into work to solve some engineering problem, and then quietly rolling it out across the team \u2014 before getting the attention of the security team.<\/span><\/p>\n<h2>Solving security by accident<\/h2>\n<p><span style=\"font-weight: 400;\">\u201cThe engineers were just trying to solve their problems, and ended up solving them in a more secure way, kind of by accident,\u201d says Pennarun. \u201cAnd then CISOs get excited about it, because now the default way of doing things is better than what it used to be.\u201d<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Tailscale didn\u2019t market itself as a security product, but it was one. Security is baked in. The VPN is identity-centric, end-to-end encrypted, doesn\u2019t trust the physical network \u2014 the core tenets of zero-trust networking.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cOften we&#8217;ll end up doing the presentation halfway through the purchasing process,\u201d says Pennarun. \u201cThe security team gets involved, and they listen to us for half an hour, and then someone&#8217;s like, \u2018Wait a minute, is this zero-trust networking?\u2019 And we\u2019re like, \u2018Yeah, yeah, it is.\u2019\u201d<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Traditionally, companies would buy a VPN and a firewall as separate products. Tailscale merges those two things together, solving connectivity and security at the same time.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">This also helps security teams flip their image from gatekeepers to enablers.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cSecurity teams kind of suffer from a reputation issue, which is that their job is to prevent your work from getting done,\u201d says Pennarun. \u201cTailscale changes the formula, where the default becomes the secure thing to do.\u201d<\/span><\/p>\n<blockquote>\n<p style=\"padding-left: 40px;\"><i><span style=\"font-weight: 400;\">\u201cWhen security teams approve of or recommend Tailscale, they can be the good guys instead of the bad guys.\u201d<\/span><\/i><\/p>\n<\/blockquote>\n<h2>Building the new internet<\/h2>\n<p><span style=\"font-weight: 400;\">What makes Tailscale different isn\u2019t just how it works, but where it works. Instead of sitting on top of layer seven of the <\/span><a href=\"https:\/\/www.ibm.com\/think\/topics\/osi-model\"><span style=\"font-weight: 400;\">networking stack<\/span><\/a><span style=\"font-weight: 400;\"> (application), it operates much lower down the stack, at layer three (network). This allows it to simplify rather than add complexity.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cNobody nowadays knows how to build something further down in the stack because they\u2019ve all been trained to just add more layers on top to create the system that they want,\u201d says Pennarun. \u201cWhen you try to solve a problem by adding more layers, you can do it, but the system gets bigger and bigger and more complex.\u201d\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Tailscale embeds the security technology that\u2019s usually applied much higher up the stack \u2014 cryptography, identity, firewall traversal \u2014 way down at the network layer, minimizing the need for the extra layers and complexity on top.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">As one user told Pennarun, \u201cTailscale makes the internet feel like what you thought the internet would feel like, before you learned how the internet works.\u201d That\u2019s the ambition: a simpler, more secure internet, built on a better foundation.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cWe have every company size, from two employees to tens of thousands of employees using Tailscale,\u201d says Pennarun.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cYou can have this one thing and roll it out to everybody, and it works equally well for everybody. And that&#8217;s because the metaphor is really the internet, right? We are all on the internet.\u201d<\/span><\/p>\n<blockquote>\n<p style=\"padding-left: 40px;\"><i><span style=\"font-weight: 400;\">\u201cTailscale is what I call the new internet, where we finally fix some of the problems with the old internet without breaking how the old internet works.\u201d<\/span><\/i><\/p>\n<\/blockquote>\n<p><span style=\"font-weight: 400;\">It\u2019s a vision that Insight Partners backed early, co-leading the company\u2019s <\/span><a href=\"https:\/\/www.insightpartners.com\/ideas\/tailscale-raises-100-million-series-b-to-fix-the-internet-with-its-zero-trust-vpn-for-modern-devops-teams\/\"><span style=\"font-weight: 400;\">$100M Series B<\/span><\/a><span style=\"font-weight: 400;\"> in 2022.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cOne of the things I liked about Insight is, first of all, they&#8217;re extremely quantitatively data-oriented, while still understanding that we were, at the time, very much a startup-stage company. So they were expecting us to grow into a growth-stage company, which we have now. But they were also willing to help us all the way along,\u201d says Pennarun.\u00a0<\/span><\/p>\n<blockquote>\n<p style=\"padding-left: 40px;\"><i><span style=\"font-weight: 400;\">\u201cI wanted an investor that understood that transition and also the phase that comes after that.\u201d<\/span><\/i><\/p>\n<\/blockquote>\n<p><span style=\"font-weight: 400;\">Speaking of the partnership at the time, Insight Managing Director <\/span><a href=\"https:\/\/www.insightpartners.com\/team\/rebecca-liu-doyle\/\"><span style=\"font-weight: 400;\">Rebecca Liu-Doyle<\/span><\/a> <a href=\"https:\/\/www.insightpartners.com\/ideas\/tailscale-raises-100-million-series-b-to-fix-the-internet-with-its-zero-trust-vpn-for-modern-devops-teams\/\"><span style=\"font-weight: 400;\">said<\/span><\/a><span style=\"font-weight: 400;\">: \u201cTailscale is ringing in a new paradigm of secure networking \u2014 one that is centered around intuitive design and user delight. Tailscale has captured the minds, and more importantly, the hearts, of developers within organizations of all sizes.\u201d<\/span><\/p>\n<h2>\u201cWe accidentally won the entire AI networking market\u201d<\/h2>\n<p><span style=\"font-weight: 400;\">By March 2024, the company had <\/span><a href=\"https:\/\/betakit.com\/tailscale-hits-10000-paid-business-clients-after-doubling-customer-base-in-past-10-months\/\"><span style=\"font-weight: 400;\">5,000 paying business customers<\/span><\/a><span style=\"font-weight: 400;\">. Ten months later, it had more than doubled its customer base. In January 2025, Tailscale surpassed <\/span><a href=\"https:\/\/tailscale.com\/blog\/welcome-grace-lin-10000-customers\"><span style=\"font-weight: 400;\">10,000 business customers<\/span><\/a><span style=\"font-weight: 400;\"> \u2014 ranging from small firms to Fortune 500 companies \u2014 and over <\/span><a href=\"https:\/\/betakit.com\/tailscale-hits-10000-paid-business-clients-after-doubling-customer-base-in-past-10-months\/\"><span style=\"font-weight: 400;\">500,000 weekly active users<\/span><\/a><span style=\"font-weight: 400;\">, with a total active user base in the millions.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">A big part of that recent growth has been driven by AI startups, like Cohere, Mistral, Hugging Face, Groq, and Perplexity.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">\u201cEvery AI company has what we call a multi-cloud problem,\u201d explains Pennarun. \u201cThey have a GPU in one place where they got a good price for it, and they have everything else, probably in AWS, where the highest quality stuff is. And now they need to connect these two things together.\u201d<\/span><\/p>\n<p><span style=\"font-weight: 400;\">In other words, every AI company has a big networking problem because they have to transfer vast amounts of data between many machines across multiple cloud providers. And, given the amount of personal data they process, they also face access control, compliance, cryptography, identity, and privacy concerns. It\u2019s the ideal use case for Tailscale.<\/span><\/p>\n<p><span style=\"font-weight: 400;\">And thanks to the tight-knit nature of the community, the word spread fast. \u201cWe had accidentally won the entire AI market for networking software,\u201d jokes Pennarun.<\/span><\/p>\n<h2>Solving a billion-dollar problem<\/h2>\n<p><span style=\"font-weight: 400;\">Looking ahead, Pennarun believes that AI will further collapse connectivity and security. \u201cIn the next three to five years in security, we\u2019re going to see a little bit of consolidation on how people connect one thing to another,\u201d he predicts.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400;\">That might be a self-serving answer, he admits, \u201cbut I think it\u2019s going to be precipitated by this AI movement where suddenly everybody needs to be able to plug their AI into the other AI, and the other one, and the other one \u2014 and connect them all together.\u201d His vision is to simply have one solution that \u201cworks equally well for everybody.\u201d<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Since each of those AIs will need access to internal, potentially sensitive data, \u201cthere needs to be standards for how this stuff works,\u201d he adds. \u201cMCP [<\/span><a href=\"https:\/\/modelcontextprotocol.io\/overview\"><span style=\"font-weight: 400;\">Model Context Protocol<\/span><\/a><span style=\"font-weight: 400;\">] is the first step in that standard. But MCP has this limitation that if your thing is behind a firewall, it can&#8217;t connect to it.\u201d<\/span><\/p>\n<p><span style=\"font-weight: 400;\">Tailscale might not have set out to solve the billion-node problem, but it&#8217;s well on its way.<\/span><\/p>\n<hr \/>\n<p><em>Note: Insight Partners has invested in Tailscale.<\/em><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Cofounder and CEO Avery Pennarun didn\u2019t set out to be a tech entrepreneur; what he really likes is coding. It\u2019s something of an understatement from someone who sold his college startup (Net Integration Technologies, or Nitix, a network server appliance for small businesses) to IBM, worked as a senior staff software engineer for Google for [&hellip;]<\/p>\n","protected":false},"author":36,"featured_media":25340,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[21,35,132],"tags":[163],"class_list":["post-25337","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-article","category-post-format-video","category-software-leaders","tag-rsa-cybersecurity","topic-stories","domain-cybersecurity"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v23.1 (Yoast SEO v23.1) - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>How Tailscale is building the new internet | Insight Partners<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"How Tailscale is building the new internet\" \/>\n<meta property=\"og:description\" content=\"Cofounder and CEO Avery Pennarun didn\u2019t set out to be a tech entrepreneur; what he really likes is coding. It\u2019s something of an understatement from someone who sold his college startup (Net Integration Technologies, or Nitix, a network server appliance for small businesses) to IBM, worked as a senior staff software engineer for Google for [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/\" \/>\n<meta property=\"og:site_name\" content=\"Insight Partners\" \/>\n<meta property=\"article:published_time\" content=\"2025-10-09T17:52:19+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-03-10T16:06:08+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg\" \/>\n\t<meta property=\"og:image:width\" content=\"1280\" \/>\n\t<meta property=\"og:image:height\" content=\"720\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/jpeg\" \/>\n<meta name=\"author\" content=\"Cecilia Beard\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:creator\" content=\"@insightpartners\" \/>\n<meta name=\"twitter:site\" content=\"@insightpartners\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Cecilia Beard\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"7 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#article\",\"isPartOf\":{\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/\"},\"author\":{\"name\":\"Cecilia Beard\",\"@id\":\"https:\/\/www.insightpartners.com\/#\/schema\/person\/d7857b7d2815e82ba1d4d475aeed306b\"},\"headline\":\"How Tailscale is building the new internet\",\"datePublished\":\"2025-10-09T17:52:19+00:00\",\"dateModified\":\"2026-03-10T16:06:08+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/\"},\"wordCount\":1519,\"publisher\":{\"@id\":\"https:\/\/www.insightpartners.com\/#organization\"},\"image\":{\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg\",\"keywords\":[\"RSA Cybersecurity\"],\"articleSection\":[\"Article\",\"Video\",\"Leadership\"],\"inLanguage\":\"en-US\"},{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/\",\"url\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/\",\"name\":\"How Tailscale is building the new internet | Insight Partners\",\"isPartOf\":{\"@id\":\"https:\/\/www.insightpartners.com\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage\"},\"image\":{\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg\",\"datePublished\":\"2025-10-09T17:52:19+00:00\",\"dateModified\":\"2026-03-10T16:06:08+00:00\",\"breadcrumb\":{\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage\",\"url\":\"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg\",\"contentUrl\":\"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg\",\"width\":1280,\"height\":720},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\/\/www.insightpartners.com\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"How Tailscale is building the new internet\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/www.insightpartners.com\/#website\",\"url\":\"https:\/\/www.insightpartners.com\/\",\"name\":\"Insight Partners\",\"description\":\"Scaling the Future of AI\",\"publisher\":{\"@id\":\"https:\/\/www.insightpartners.com\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\/\/www.insightpartners.com\/?s={search_term_string}\"},\"query-input\":\"required name=search_term_string\"}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\/\/www.insightpartners.com\/#organization\",\"name\":\"Insight Partners\",\"url\":\"https:\/\/www.insightpartners.com\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/www.insightpartners.com\/#\/schema\/logo\/image\/\",\"url\":\"https:\/\/insightpartners.com\/wp-content\/uploads\/2023\/01\/Inisghtpartners.png\",\"contentUrl\":\"https:\/\/insightpartners.com\/wp-content\/uploads\/2023\/01\/Inisghtpartners.png\",\"width\":1255,\"height\":650,\"caption\":\"Insight Partners\"},\"image\":{\"@id\":\"https:\/\/www.insightpartners.com\/#\/schema\/logo\/image\/\"},\"sameAs\":[\"https:\/\/x.com\/insightpartners\",\"https:\/\/www.linkedin.com\/company\/insight--partners\"]},{\"@type\":\"Person\",\"@id\":\"https:\/\/www.insightpartners.com\/#\/schema\/person\/d7857b7d2815e82ba1d4d475aeed306b\",\"name\":\"Cecilia Beard\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/www.insightpartners.com\/#\/schema\/person\/image\/\",\"url\":\"https:\/\/secure.gravatar.com\/avatar\/0d0e55b6770f21853aed3bf363445379?s=96&d=mm&r=g\",\"contentUrl\":\"https:\/\/secure.gravatar.com\/avatar\/0d0e55b6770f21853aed3bf363445379?s=96&d=mm&r=g\",\"caption\":\"Cecilia Beard\"}}]}<\/script>\n<!-- \/ Yoast SEO Premium plugin. -->","yoast_head_json":{"title":"How Tailscale is building the new internet | Insight Partners","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/","og_locale":"en_US","og_type":"article","og_title":"How Tailscale is building the new internet","og_description":"Cofounder and CEO Avery Pennarun didn\u2019t set out to be a tech entrepreneur; what he really likes is coding. It\u2019s something of an understatement from someone who sold his college startup (Net Integration Technologies, or Nitix, a network server appliance for small businesses) to IBM, worked as a senior staff software engineer for Google for [&hellip;]","og_url":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/","og_site_name":"Insight Partners","article_published_time":"2025-10-09T17:52:19+00:00","article_modified_time":"2026-03-10T16:06:08+00:00","og_image":[{"width":1280,"height":720,"url":"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg","type":"image\/jpeg"}],"author":"Cecilia Beard","twitter_card":"summary_large_image","twitter_creator":"@insightpartners","twitter_site":"@insightpartners","twitter_misc":{"Written by":"Cecilia Beard","Est. reading time":"7 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#article","isPartOf":{"@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/"},"author":{"name":"Cecilia Beard","@id":"https:\/\/www.insightpartners.com\/#\/schema\/person\/d7857b7d2815e82ba1d4d475aeed306b"},"headline":"How Tailscale is building the new internet","datePublished":"2025-10-09T17:52:19+00:00","dateModified":"2026-03-10T16:06:08+00:00","mainEntityOfPage":{"@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/"},"wordCount":1519,"publisher":{"@id":"https:\/\/www.insightpartners.com\/#organization"},"image":{"@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage"},"thumbnailUrl":"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg","keywords":["RSA Cybersecurity"],"articleSection":["Article","Video","Leadership"],"inLanguage":"en-US"},{"@type":"WebPage","@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/","url":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/","name":"How Tailscale is building the new internet | Insight Partners","isPartOf":{"@id":"https:\/\/www.insightpartners.com\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage"},"image":{"@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage"},"thumbnailUrl":"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg","datePublished":"2025-10-09T17:52:19+00:00","dateModified":"2026-03-10T16:06:08+00:00","breadcrumb":{"@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#primaryimage","url":"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg","contentUrl":"https:\/\/www.insightpartners.com\/wp-content\/uploads\/2025\/09\/RSA-Thumbnails-3.jpg","width":1280,"height":720},{"@type":"BreadcrumbList","@id":"https:\/\/www.insightpartners.com\/ideas\/tailscale-leadership-story\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.insightpartners.com\/"},{"@type":"ListItem","position":2,"name":"How Tailscale is building the new internet"}]},{"@type":"WebSite","@id":"https:\/\/www.insightpartners.com\/#website","url":"https:\/\/www.insightpartners.com\/","name":"Insight Partners","description":"Scaling the Future of AI","publisher":{"@id":"https:\/\/www.insightpartners.com\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.insightpartners.com\/?s={search_term_string}"},"query-input":"required name=search_term_string"}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.insightpartners.com\/#organization","name":"Insight Partners","url":"https:\/\/www.insightpartners.com\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.insightpartners.com\/#\/schema\/logo\/image\/","url":"https:\/\/insightpartners.com\/wp-content\/uploads\/2023\/01\/Inisghtpartners.png","contentUrl":"https:\/\/insightpartners.com\/wp-content\/uploads\/2023\/01\/Inisghtpartners.png","width":1255,"height":650,"caption":"Insight Partners"},"image":{"@id":"https:\/\/www.insightpartners.com\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/x.com\/insightpartners","https:\/\/www.linkedin.com\/company\/insight--partners"]},{"@type":"Person","@id":"https:\/\/www.insightpartners.com\/#\/schema\/person\/d7857b7d2815e82ba1d4d475aeed306b","name":"Cecilia Beard","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.insightpartners.com\/#\/schema\/person\/image\/","url":"https:\/\/secure.gravatar.com\/avatar\/0d0e55b6770f21853aed3bf363445379?s=96&d=mm&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/0d0e55b6770f21853aed3bf363445379?s=96&d=mm&r=g","caption":"Cecilia Beard"}}]}},"_links":{"self":[{"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/posts\/25337"}],"collection":[{"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/users\/36"}],"replies":[{"embeddable":true,"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/comments?post=25337"}],"version-history":[{"count":7,"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/posts\/25337\/revisions"}],"predecessor-version":[{"id":25481,"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/posts\/25337\/revisions\/25481"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/media\/25340"}],"wp:attachment":[{"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/media?parent=25337"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/categories?post=25337"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.insightpartners.com\/wp-json\/wp\/v2\/tags?post=25337"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}