Mike Fey: From Symantec to Island and building a $5B category leader

9 Jun 2026 · 66 min
Inside the Network

9 Jun 2026 · 66 min

0:00

In this Inside the Network episode, hosts Sid Trivedi, Ross Halediuk, and Mahendra Ramasinghani interview Mike Fey, co‑founder and CEO of Island, an enterprise‑browser startup valued at over $5 billion. The conversation traces Fey’s career—from early software work at Lockheed Martin, through product‑focused roles at Mercury and Opsware, a seven‑year stint at McAfee, leading Blue Coat’s growth and its $5 billion sale to Symantec, and steering Symantec’s enterprise business before its $10 billion acquisition by Broadcom. Fey explains why he left large enterprises to start Island, the technical and market rationale for an enterprise‑browser that becomes a control plane, and how timing (Chromium’s dominance, COVID‑driven remote work, and AI) created a unique window. He discusses product‑market fit, the importance of end‑user experience, the innovator’s dilemma, go‑to‑market choices (direct vs. channel), scaling a sales organization, fundraising tactics, and leadership principles such as love‑based leadership, deliberate decision‑making, and the role of a benevolent dictator. The episode ends with Fey’s vision of an AI‑enabled browser and a single piece of advice for founders: celebrate small wins to sustain the marathon of building a cybersecurity company.

Chapters

More from Jon

1:06:36
Podcast

Kyle Hanslovan: Building Huntress into a $3B+ unicorn by securing the 99%

2mo ago
1:02:02
Podcast

Rob Lee: Building Dragos into a multi-billion-dollar mission-driven cybersecurity company

3mo ago
1:02:02
Podcast

Rob Lee: Building Dragos into a multi-billion-dollar mission-driven cybersecurity company

3mo ago
1:06:17
Podcast

Mike Fey: From Symantec to Island and building a $5B category leader

4mo ago
PodcastNo Password Required Podcast Episode 63 — Jon Schipp
Podcast

No Password Required Podcast Episode 63 — Jon Schipp

4mo ago
52:22
Podcast

Mark McClain: Winning as an incumbent at SailPoint in the age of AI

5mo ago
52:22
Podcast

Mark McClain: Winning as an incumbent at SailPoint in the age of AI

5mo ago
52:05
Podcast

Christina Cacioppo: From Y Combinator to redefining trust in cybersecurity with Vanta

6mo ago
52:05
Podcast

Christina Cacioppo: From Y Combinator to redefining trust in cybersecurity with Vanta

6mo ago
53:09
Podcast

Sanjay Beri: Playing the long game and building Netskope into a public cybersecurity powerhouse

7mo ago
53:09
Podcast

Sanjay Beri: Playing the long game and building Netskope into a public cybersecurity powerhouse

7mo ago
See all content