Random Access Memories

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

Juan Rodriguez grew up watching his mother go door to door selling stuffed animals in Mexico. When the family moved to America, she was still knocking on doors, but this time handing out business cards for her own company. Decades later, Juan founded Whistic. And unlike many first-time entrepreneurs, he wasn't particularly afraid of starting a business; he'd watched his mother do it his entire life.

In this episode of Random Access Memories, Juan joins Jake Bernardes for a deeply personal conversation about entrepreneurship, leadership, fatherhood and the uncomfortable realities of building a company.

This one is particularly personal for Jake, who worked alongside Juan at Whistic and credits him with fundamentally changing Jake's own approach to leadership. Juan explains why he gives employees enormous freedom while deliberately pushing them outside their comfort zones, why he wants people who challenge him rather than agree with him, and how the principles he uses to raise his children are remarkably similar to those he uses to run a business.

But building a company isn't always about growth, ambition and success. Juan opens up about the pain of laying off employees who had done absolutely nothing wrong, the responsibility he feels for the families affected by his decisions, and why he once offered his resignation rather than avoid accountability. He also shares how losing his brother-in-law during COVID brought him closer to walking away from Whistic than anything he'd experienced professionally.

Then they explore the complicated relationship between founders and CEOs: what Juan learned from handing leadership of his company to someone else, and why he would make a very different decision if he could start again.

And of course, they get into football, parenting, AI, why boredom might be essential to creativity, and Juan's seemingly impossible ambition to take an actual holiday.

Ultimately, this is a conversation about what leadership looks like when you genuinely care about the people you're responsible for. Because as Juan learned from reading Radical Candor, you can't hold people accountable if they don't believe you care about them.

But sometime the best thing a leader can do is simply be kind.

In this episode...
Growing up in Mexico and America, and how Juan's entrepreneurial mother shaped his attitude towards risk
Why Juan believes high expectations only work when they're accompanied by unconditional love
What coaching children taught Juan about effort, failure and leadership
Why the best leaders give people freedom to become uncomfortable
How boredom and uncertainty create opportunities for genuine creativity
Why Juan deliberately hires people who are willing to challenge him
The emotional reality of laying off employees who have done nothing wrong
How losing his brother-in-law during COVID nearly made Juan walk away from Whistic
Why founders must take responsibility when their decisions affect employees and their families
What Juan learned from working alongside a CEO with a completely different leadership style
Why he would choose to become CEO from day one if he could start Whistic again
The difference between taking risks and calculating risks differently
Why AI-generated code could threaten creativity and the development of future engineers
The leadership lesson Juan discovered in Radical Candor
Why kindness and accountability belong together

We hear the advice to build a personal brand all the time, and everyone wants to know the how. But Ayoub Fandi is a walking, (pretty) compelling argument that you might be asking the wrong question.

Ayoub went from working relatively quietly in GRC to becoming one of the people most closely associated with GRC Engineering, building an audience of tens of thousands, relationships with security leaders and founders across the industry, and a career where opportunities increasingly started finding him instead of the other way around.
In this episode of Random Access Memories, Ayoub joins Jake Bernardes to unpack how that actually happened, and refreshingly, there was no master plan to become an influencer. He started writing because writing forced him to understand what he actually thought, chose a very specific niche, kept showing up long after consistency stopped being exciting, and used the audience he built as a doorway to real relationships rather than treating follower count as the goal.

We get into Ayoub’s surprisingly sophisticated content engine, why the people behind his ideas matter more than the content itself, how to find an unfair advantage that actually fits who you are, and why “follow your passion” might actually be terrible career advice. 

Ayoub’s alternative is much more useful: passion often follows competence, but you have to stay with something long enough to become good before you can know whether you actually care about it.
Most importantly, Ayoub makes the distinction between becoming visible and becoming valuable. Influence can create leverage, but the point is deciding what you want that leverage to be for.

In this episode
Why writing publicly can make you better at your actual job
How Ayoub became synonymous with GRC Engineering
Why consistency mattered more than trying to manufacture virality
The content system behind hundreds of ideas and more than a thousand posts
Why your audience should become relationships, not just followers
How to “niche down twice” until people associate one thing with you
Finding and exploiting your genuine unfair advantages
Why passion often follows competence instead of preceding it
What visibility, influence, and access are actually useful for
Why knowing your personal “why” matters before you start chasing reach

Cybersecurity buyers have changed, while a lot of cybersecurity marketing…stayed in 2016. 😬

In this Random Access Memories Special, George Kamide and Jake Bernardes get into why so much cyber marketing still relies on the same tactics, assumptions, and messaging that worked years ago, even as the people buying security have become more informed, more connected, and much more skeptical.
George’s diagnosis is simple: there is a fear of original thought. Too many companies default to FUD, cold outreach, giant event spends, and category language that sounds nothing like the way customers actually describe the problem they are trying to solve. Meanwhile, buyers are comparing vendors, sharing experiences, and forming opinions in communities and conversations where the vendor is not even present.

For founders and marketers, George’s advice is less about doing more and more about paying closer attention. Become a fanatical anthropologist of your customers. Learn how they talk about your product when you are not in the room. Understand where they actually discover new technology, why they chose you, and what they tell their peers after the sale.

Because the best product does not automatically win, more badge scans do not automatically create demand, and louder marketing does not fix messaging that never understood the buyer in the first place.

In this special
Why cyber marketing has a fear of original thought
How buyer behavior changed while vendor tactics stayed largely the same
Why FUD and cold outreach increasingly miss the mark
What early-stage companies should learn from their first customers
Why customer language matters more than category jargon
The real value of major event spend and badge scans
Why reputation, service, and the people behind the product shape buying decisions

Burnout, ineffective execs, & AI taking over jobs. Cybersecurity did not get here because people were stupid. It got here because we built reactively, solving the threats, technologies, and business problems in front of us as they appeared.

The problem is that some of those assumptions have outlived the conditions that created them.

In this episode of Random Access Memories, George Kamide joins Jake Bernardes to talk about what happens when an industry built for constant change starts carrying too much legacy thinking. They get into burnout and the culture of overcommitment, why security leaders are still expected to prove impossible levels of technical breadth, and why understanding how your company actually makes money may matter more than another layer of expertise.
The conversation eventually turns to AI, not as a tool problem, but as an operating model problem. If technology can perform pieces of work dramatically faster than the human systems around it, then automating the task without rethinking the organization may just move the bottleneck somewhere else.
George’s argument is not that cyber was built wrong. It is that cyber was built for the problems we had, and we need to get better at recognizing when the objectives have outgrown the delivery model.
In this episode
Why cybersecurity and startup culture are unusually good at creating burnout
Why consistency often matters more than intensity
The impossible breadth of expertise expected from modern security leaders
Why business fluency becomes critical as your career grows
What AI exposes about the way we structure teams and work
Why the next phase of cyber may require changing the system, not just adding better tools