
Ep 16. The Accidental Entreprenuer w/ Alan Shimel. CEO Techstrong Group
Alan Shimel didn't plan on becoming cybersecurity media's kingmaker—he planned on being a lawyer. He passed the bar at 23, and the only thing that made him "tech savvy" in a New York law office was knowing WordPerfect better than anyone else in the building. But a home lab, a pair of 386 machines that needed to talk to each other, and a front-row seat to the birth of the web pulled him sideways into hosting, then into StillSecure as a founding executive going head-to-head with the people who would build Qualys and Tenable, and eventually into building the media empire behind DevOps.com, Security Boulevard, and TechStrong TV. In this episode, Alan—founder and CEO of TechStrong Group—tells Mehul the unfiltered version of that path: the $49.95-a-month hosting hustle that grew to 5,000 sites in 18 months, the dinner where Gene Kim first pitched him The Phoenix Project, the FeedBurner sale that accidentally handed him the Security Bloggers Network, and why he thinks the entire "open source vs. closed source AI" fight is really an argument about open weights. He also gets refreshingly blunt about Google's zero-click AI Overviews breaking the deal that funded the open web, and why the future of IT and journalism alike comes down to imagination—the one thing he doesn't think AI has.
- Transcript