I Quit Being a CISO to Write a Newsletter | Mike Privette, Founder of Return on Security

Most cybersecurity professionals spend their careers trying to become a CISO. Mike Privette got there, decided he was more interested in something else, and eventually walked away to write a newsletter.Which sounds like a terrible career decision until you hear how it happened.This week on Random Access Memories, I sat down with Mike, founder of Return on Security, to talk about why he traded a successful cybersecurity career for something he'd originally started as a hobby.Mike spent years working his way through security engineering and leadership, but somewhere along the way became fascinated by the business of cybersecurity. Why were investors throwing money at certain companies? Why did some startups succeed while others disappeared? And why was nobody properly tracking what was happening?So he started collecting data, writing about it and sharing what he learned. His first personal blog post took six months to get through corporate communications. Six years later, he'd built something valuable enough to become his full-time career.But this conversation isn't really about newsletters.We talk about the fear of walking away from a career you've spent decades building, why people become trapped chasing the next promotion, and how moving his family from America to the UK changed Mike's perspective on money, success and what actually makes a good life.There's also a fascinating discussion about the financial side of cybersecurity. Where the investment money is going, whether we've created too many AI startups, why Mike wouldn't rush to invest in application security, and whether founders are building businesses to solve problems or simply hoping someone will buy them.We get into something I think a lot of people struggle with, particularly when they have young families. The years when your career demands the most from you are often the exact years your children need you most.Mike's decision to build something of his own wasn't just about doing work he enjoyed. It was also about having more control over his time and being present for his family.It's a conversation about taking risks, finding curiosity again and recognising that the career you've built doesn't have to be the career you finish with.Because sometimes success isn't another promotion, a bigger salary or a better job title.Sometimes it's having the freedom to do something completely different.In This Episode...Why Mike walked away from being a CISO to build Return on SecurityHow a personal hobby became a cybersecurity market intelligence businessWhy his first blog post took six months to get approved by corporate communicationsThe fear of abandoning a career you've spent years buildingDiscovering that building a business was more interesting than running another security programmeMoving his family from America to the UK and reconsidering what success looks likeWhy the American obsession with bigger salaries, houses and cars isn't necessarily a recipe for happinessThe uncomfortable relationship between career ambition and spending time with your childrenWhy Mike wanted more control over his life rather than another senior leadership positionWhere cybersecurity investment money is flowing and why Europe is becoming more importantWhether AI cybersecurity startups are solving genuine problems or simply wrapping existing modelsWhy Mike would be cautious about investing in application securityThe problem with founders building companies purely to get acquiredWhy a profitable business might be worth more than a billion-dollar exitMike's advice for anyone who's lost interest in their career but is afraid to try something different