Show Notes
Our guest in this episode is Mike Fey, co-founder and CEO of Island, one of the fastest-growing cybersecurity companies. Founded just five years ago, Island has raised over $700 million in funding, crossed $5 billion valuation, and helped create an entirely new category: the Enterprise Browser.
Mike has scaled massive cybersecurity businesses. Over the course of his career, he has served as CTO of Intel Security and President of both Blue Coat and Symantec. Mike played a key role in some of the largest transactions in cybersecurity history, including Intel's $7.7 billion acquisition of McAfee, Symantec's $4.7 billion acquisition of Blue Coat, and Broadcom's $10.7 billion acquisition of Symantec's enterprise business.
After decades of leading some of the industry's largest security companies, Mike could have easily become an investor, advisor, or board member. Instead, he decided to start over from scratch. Together with co-founder Dan Amiga, he set out to challenge one of the most entrenched pieces of enterprise software: the browser. At first glance, building a browser company sounded like a terrible startup idea: enterprises already had Chrome, Edge, Safari, and countless security products protecting them. Yet Mike and the Island team believed that the browser was evolving into the primary workspace for modern employees and that whoever controlled the browser could fundamentally rethink security, productivity, and the future of work.
On Inside the Network, Mike shares the story behind Island's creation, why he initially rejected the idea before becoming convinced it could become a generational company, and how the team navigated the challenge of convincing enterprises to replace one of the most widely used pieces of software in the world.
We discuss category creation, the Innovator's Dilemma, building go-to-market organizations from scratch, fundraising strategy, and the lessons Mike learned from scaling businesses through more than $20 billion worth of acquisitions. He explains why founders often underestimate sales and go-to-market execution, how startups can use incumbents' strengths against them, and why market timing matters more than many entrepreneurs realize. We also dive into the impact of AI on enterprise software and cybersecurity, how AI is reshaping the role of the browser, and why Mike believes the browser will become the front door through which enterprises adopt and operationalize AI.
More from Inside the Network
Our guest in this episode is Sachin Nayyar, a rare founder who has built not one, but two major cybersecurity companies: Securonix and Saviynt. Even more unusually, for nearly a decade, he was building both at the same time. After Sachin's first company was acquired by Sun Microsystems, he became a millionaire in his twenties. Instead of experiencing the moment as the triumph most founders imagine, Sachin fell into depression. It became an early lesson in the difference between being in love with entrepreneurship and being in love with solving a problem, and that lesson shaped how he would approach company building, leadership, and his own health for the rest of his career. This also inspired him to found Live Your Best Life (LYBL), a holistic health-tech platform designed to help people understand and overcome chronic health conditions. Sachin went on to co-found Securonix, helping pioneer User and Entity Behavior Analytics (UEBA) and build the company into a major player in security analytics and SIEM. At the same time, Sachin was also building Saviynt, an identity security company that was bootstrapped for its first seven years and has since grown past $300 million in ARR and reached a valuation of more than $3 billion. On Inside the Network, Sachin shares what it was actually like to build two cybersecurity companies simultaneously, including commuting between Securonix in Dallas and Saviynt in Southern California. He talks candidly about burnout, why founders shouldn't treat exhaustion as a badge of honor, and the management mistake that slowed both companies down: waiting too long to bring experienced operators into the business. We also dive into Sachin's unconventional approach to financing companies. Rather than following the traditional Silicon Valley playbook, Saviynt was self-funded for more than seven years, using services to get close to customers and fund product development. Later, Sachin leaned heavily on private credit rather than raising equity when he believed the market was undervaluing the company. Sachin also explains why he never believed building a successful cybersecurity company required a Silicon Valley ZIP code, how he built major engineering organizations across Southern California, Texas, and India, and why founders should focus more on customers and conviction than on following the industry's standard startup playbook. Finally, we explore the next chapter of identity security. Sachin shares his thesis that AI creates an opportunity to move identity controls all the way to build time, embedding identity and access management directly into applications and AI agents. He explains why he still thinks of Saviynt as a “startup at scale,” how incumbents can compete with AI-native challengers, and why the explosion of machine identities may force the identity industry to rethink traditional per-user pricing models.
Our guest in this episode is Kyle Hanslovan, Co-Founder and CEO of Huntress. When Kyle started Huntress in 2015, most investors believed protecting small and mid-sized businesses wasn't a venture-scale opportunity. The contracts were too small, customer churn would be too high, and the market simply wasn't attractive enough. Kyle heard “no” more than 60 times from VCs before raising his first institutional round.
Our guest in this episode is Rob Lee, co-founder and CEO of Dragos. Two weeks ago, Accenture agreed to acquire a majority stake in Dragos as part of the massive, over $4 billion transaction that also included the acquisitions of runZero and NetRise. As luck would have it, we recorded this conversation just a few weeks before the announcement. Massive congratulations to Rob and to the entire teams of Dragos, runZero, and NetRise! When Rob started Dragos, most investors didn't believe critical infrastructure security was a venture-scale opportunity. Despite getting more than 100 rejections from investors, Rob stayed committed to his mission. Today, Dragos protects critical infrastructure around the world and has become one of the defining companies in industrial cybersecurity. This episode isn't simply about building a unicorn or leading a company to a massive exit. It's about building a company around a mission. Rob explains why Dragos exists to "safeguard civilization," why protecting critical infrastructure is fundamentally different from protecting enterprise IT, and why cybersecurity in operational technology is ultimately a public safety problem, not just a business problem. Throughout the conversation, Rob shares candid lessons from building Dragos over the past ten years. We discuss choosing investors, surviving VC rejections, scaling from three founders to more than 600 employees, building a founder-led culture, making difficult executive hiring decisions, expanding internationally, and why Rob believes founders should optimize for long-term mission rather than short-term valuation. We also dive deep into the future of critical infrastructure security. Rob explains how AI is changing operational technology, why cyber warfare is increasingly targeting civilian infrastructure, what keeps him awake at night as geopolitical tensions continue to rise, and why he believes the next generation of cybersecurity founders should pay far more attention to industrial systems than they do today. It’s a fascinating story about a founder who decided to build a mission-driven company instead of trying to optimize for an exit or the next funding round. By doing that, not only has he succeeded in building something lasting, but he also achieved a massive financial outcome.
This episode of Inside the Network is unique because it is our very first show recorded live on the RSAC 2026 stage in front of security leaders, startup founders, and identity experts. For this episode, we had the privilege of sitting down with one of the most accomplished founders in cybersecurity, founder and CEO of SailPoint, Mark McClain.
In this episode of Inside the Network, we sit down with Christina Cacioppo, Co-Founder and CEO of Vanta, the company that defined what is now known as trust management. What began as a scrappy effort to make SOC 2 less painful, has grown into one of the most important platforms in security and compliance.