Community Isn't a Mailing List...Build Trust, Not Leads | Jason Cenamor, CISO Society & Confide Group

Jason Cenamor didn't set out to build one of cybersecurity's most active CISO communities. In fact, the CISO Society was supposed to be a side project while he built an entirely different business.
That business didn't work out. The money ran out, Jason went back to full-time employment, and he assumed the community would eventually disappear.
Instead, it grew.
In this episode of Random Access Memories, Jason joins Jake Bernardes to talk about building the CISO Society, the business behind it, and why genuine relationships have become one of the most valuable things you can invest in during your career.
We get into how the community started, why Jason deliberately avoided turning its members into a product, and the difficult balance between building something valuable for CISOs and making enough money to keep it running.
There's also a fairly uncomfortable conversation about how cybersecurity vendors approach communities.
Too many companies still see CISOs as logos, budgets and potential sales opportunities. They spend enormous amounts of money on conferences, dinners and sponsorships, then wonder why they can't immediately attribute revenue to the investment.
Jason argues that they're missing the point. Relationships take time, trust isn't something you can buy, and sometimes the most valuable outcome of an event is a conversation that doesn't turn into business for another year.
We also talk about why so many security professionals underestimate the importance of their networks, particularly when they're looking for their next job. Jason admits he spent years avoiding the networking side of the industry before realising how much he'd underestimated it.
And we explore something I've experienced throughout my own career: the people willing to introduce you to someone, challenge your thinking or offer advice can have a far greater impact than another certification or another impressive company name on your CV.
It's a conversation about entrepreneurship, community, trust, mentorship and the importance of putting yourself out there, even when it feels uncomfortable.
Plus, we somehow manage to spend an unreasonable amount of time discussing pizza ovens, expensive bicycles and Jason's alternative career as a Formula 1 driver.
In this episode...
How a side project became one of cybersecurity's most engaged CISO communities
Why Jason's original business failed while the CISO Society continued growing
The importance of building a community that belongs to its members, not its founder
Why Jason decided against charging CISOs membership fees
How to monetise a community without turning its members into a product
Why CISOs increasingly trust their peers over analysts and traditional industry research
The thinking behind Confide Group and helping CISOs navigate an increasingly noisy vendor market
Why Jason thinks traditional cybersecurity conferences and panels are fundamentally broken
The problem with conferences where speaking opportunities depend on sponsorship
Why smaller, experience-led events are often more valuable than traditional conferences
Why vendors need to stop measuring every relationship against immediate pipeline and revenue
The importance of saying no to sponsors, even when they're offering significant money
Why your professional network could be the most valuable asset in your career
How mentoring creates opportunities for both the mentor and the person being mentored
Why getting into the room is often the hardest and most important step