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 riskWhy Juan believes high expectations only work when they're accompanied by unconditional loveWhat coaching children taught Juan about effort, failure and leadershipWhy the best leaders give people freedom to become uncomfortableHow boredom and uncertainty create opportunities for genuine creativityWhy Juan deliberately hires people who are willing to challenge himThe emotional reality of laying off employees who have done nothing wrongHow losing his brother-in-law during COVID nearly made Juan walk away from WhisticWhy founders must take responsibility when their decisions affect employees and their familiesWhat Juan learned from working alongside a CEO with a completely different leadership styleWhy he would choose to become CEO from day one if he could start Whistic againThe difference between taking risks and calculating risks differentlyWhy AI-generated code could threaten creativity and the development of future engineersThe leadership lesson Juan discovered in Radical CandorWhy 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 jobHow Ayoub became synonymous with GRC EngineeringWhy consistency mattered more than trying to manufacture viralityThe content system behind hundreds of ideas and more than a thousand postsWhy your audience should become relationships, not just followersHow to “niche down twice” until people associate one thing with youFinding and exploiting your genuine unfair advantagesWhy passion often follows competence instead of preceding itWhat visibility, influence, and access are actually useful forWhy 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 sameWhy FUD and cold outreach increasingly miss the markWhat early-stage companies should learn from their first customersWhy customer language matters more than category jargonThe real value of major event spend and badge scansWhy 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 burnoutWhy consistency often matters more than intensityThe impossible breadth of expertise expected from modern security leadersWhy business fluency becomes critical as your career growsWhat AI exposes about the way we structure teams and workWhy the next phase of cyber may require changing the system, not just adding better tools

At some point in your cybersecurity career, the skills that made you successful stop being the skills that move you forward. And according to this week’s guest, Adam Arellano, some of us may be a little more attached to our “technical” identity than we'd like to admit.

Adam is Field CTO at Harness, a longtime security practitioner, humanist, former social worker, leader, unapologetic wearer of kilts and heels, and one of the more unconventional thinkers you'll find wandering around a cybersecurity conference.

In this episode of Random Access Memories, Adam joins Jake Bernardes for a conversation about what happens when you stop following the career path you're supposed to follow and start figuring out what actually makes you different.

They talk about Adam's decision to be visibly weird and queer in an industry that still has plenty of sports coats, why representation can sometimes mean becoming the person your younger self needed to see, and why standing out isn't really about what you wear. It's about understanding the perspective, experience, and abilities you bring that nobody else does.

And then things got uncomfortable. Are senior cybersecurity leaders actually still technical?

Adam argues that technical expertise ages along with the technology you learned it on. If your hands-on expertise comes from 2006, calling yourself technical in 2026 may require an asterisk. And as practitioners move into leadership, Field CTO, Field CISO, and other positions of influence, the ability to communicate, understand people, and translate complexity may become far more valuable than staying the smartest person at the keyboard.

The conversation moves from punk rock to personal branding, social work to cybersecurity leadership, why disagreement is essential to good teams, and why surrounding yourself with people exactly like you might be one of the worst career decisions you can make.

And just when Jake thinks he's safely wrapping things up, Adam delivers some unsolicited therapy about success, anxiety, and our obsession with controlling outcomes.

Oh, and apparently Maui is a Disney princess…he makes a compelling case, trust us.

In this episode

Why Adam intentionally chooses to stand outBeing the representation your younger self didn't haveWhy following the standard cybersecurity career path isn't always the answerFinding the thing that's uniquely yours—and building around itRSA vs. Black Hat and BSides: has cybersecurity become too corporate?Punk rock, selling out, and why being effective can matter more than being righteousWhy senior cybersecurity practitioners may not be as technical as they thinkWhat happens to technical skills as your career moves into leadershipWhy communication becomes a critical technical-adjacent skillLearning human interaction the same way you'd learn a new technologyWhy you should surround yourself with people who aren't like youHow complementary strengths can create extraordinarily effective teamsWhy disagreement isn't dysfunctionUnderstanding the person receiving your message instead of simply changing how loudly you deliver itLetting go of success anxiety and the illusion that you can control every outcomeThe definitive argument for Maui as a Disney princess

Most leaders spend their careers trying to prove they're good at their jobs. But Assaf Keren does something different, he teaches his managers how he's failed.

The current CSO of Qualtrics and former CISO of PayPal has spent more than two decades in security, but some of his strongest beliefs about leadership didn't come from the things he got right. They came from burnout, bad decisions, difficult feedback, and learning to let go of the need to be the smartest person in the room.

In this episode of RAM, Assaf joins Jake Bernardes to talk about the stories behind his book and the leadership philosophy they created.

That includes asking employees to tell him when he's wrong, telling leadership what he intends to do instead of constantly asking permission, and an annual ritual his team has learned to dread: Assaf publicly grading his own performance. One year, he even went to his boss and asked to be rated lower. But some failures cost more than a performance review.

Early in his PayPal career, Assaf was working across Israel and the United States, essentially working two shifts every day. Good nights ended around 1 a.m. Bad ones at 3 or 4. Then he'd wake up and do it again.

He did that for a year.

Eventually he was physically ill, emotionally reactive, unable to think clearly, taking 15-minute power naps between meetings—and closer than he realized to leaving cybersecurity altogether.

Compounding that experience was something else he'd carried quietly for years: PTSD. During COVID, Assaf learned that an employee with PTSD was afraid to disclose what they were experiencing. So Assaf wrote a message to a PayPal Slack channel with roughly 40,000 people explaining his own experience.

Then he stared at it, for three days. His extended family didn't know. His colleagues didn't know. He worried his leaders might see him differently. 

Eventually, he pressed Enter, shut his laptop and walked away. Looking back, he says: “That was the moment I started healing.”

Memory 006 is a conversation about failure, burnout, vulnerability, mental health, ego and what it actually means to lead people through a profession built on uncertainty. 

In this episode:

Why Assaf calls English a low bandwidth language, and what it taught him about giving feedbackThe year he worked two full shifts a day, Tel Aviv mornings and US nights, until his body forced him to stopWhy he asked his own boss to rate his performance lower than expectedThe Slack message to 40,000 people that he sat on for three daysWhat a submarine commander's book taught him about intent based leadershipWhy he believes the entry level security career is disappearing, and what that means for the next generation of leaders

Rinki Sethi has spent nearly 25 years in cybersecurity, with stops at Walmart, eBay, Intuit, Palo Alto Networks, IBM, Rubrik, Twitter, Bill.com, and now Upwind.

But one of the most important moments in that career came when she almost walked away from cybersecurity entirely.

In this episode of Random Access Memories, Rinki joins Jake Bernardes to talk about the mentor who changed the trajectory of her career, why the people around you can matter more than the logo on your résumé, and what great leadership actually looks like when the goal isn't just building better programs, but building better people.

They also dig into a question cybersecurity is going to have to answer sooner rather than later: What happens to the next generation of security leaders when AI automates the jobs where so many of today's CISOs learned the fundamentals?

From the rise of the “builder” CISO to technical fluency in an AI-first world, Rinki and Jake explore how the role is changing, and why knowing how to ask the right questions may matter just as much as knowing how to write the code.

Then, they look beyond the CISO seat. Rinki shares why she co-founded Lockstep, what she's learned from investing and working with founders, and why she believes security practitioners should sit at the center of the cybersecurity ecosystem instead of simply being sold to buy it.

Her biggest lesson after decades in the industry is also one of the simplest: Don't just chase the company. Chase the people.

Because the jobs change, the titles change, and the technology definitely changes but the relationships you build along the way can change everything.

In this episode

The Walmart mentor who kept Rinki from leaving cybersecurityWhy great careers aren't necessarily built by chasing prestigious company namesWhat separates a true leader and mentor from someone who's simply managing peopleWhy tomorrow's CISOs may need a builder mindsetWhether AI actually makes everyone technical — or just makes it easier to build the wrong thingWhat happens when SOC, GRC, AppSec, and pentesting entry-level work gets automatedHow the CISO role is shifting from technical architect to business leader, communicator, and influencerRinki's move from traditional enterprise security into hypergrowth security at UpwindWhy she co-founded Lockstep and what investing taught her about the cybersecurity ecosystemWhy practitioners should have a bigger stake in the value they help createThe importance of understanding equity, cap tables, vesting, and startup economicsWhy networking and community aren't side quests — they're often where the next opportunity begins

What happens after you finally get the CISO job you've spent your career working toward, and realize you want something different?

Tim Chase made the move from operational CISO to Field CISO because he loved something specific about the job: talking to other security leaders, understanding their problems, sharing what he'd learned, and helping them find better answers.

But becoming a Field CISO introduced a different kind of pressure.

In this episode of RAM, Tim joins Jake Bernardes to talk about what the role actually looks like when you strip away the conference stages and LinkedIn posts: defending whether you're still a "real" CISO, pushing back when companies treat Field CISOs like salespeople with impressive Rolodexes, and trying to remain credible when your paycheck ultimately comes from a vendor.

They also get into the part of the job that's harder to see: the cost to your family.

It's a theme that came up with last week's guest, Avani Desai, too. Avani talked about one year when her career meant she saw her infant son only 50 days. For Tim, it's the conferences that overlap with the first week of school, the travel squeezed between kids' sports and date nights, and the guilt of knowing that being present somewhere often means being absent somewhere else.

Different careers. Same uncomfortable question: How much of your life are you willing to give your job?

Tim is a father of four with a working spouse. Being useful in the field means customers, conferences and teams constantly compete for his time. But every yes somewhere is a no somewhere else.

Sometimes that means squeezing family life between trips. Sometimes it means sitting at a hockey game feeling guilty because his wife is home putting four kids to bed. And every year, Black Hat somehow lands during his children's first week of school.

For Tim, being a great Field CISO isn't about being everywhere. It's about knowing where you're actually valuable, and having the discipline to say no everywhere else.

This is a conversation about trust, credibility, career identity, burnout, family, and why sometimes the best thing a Field CISO can tell a customer is: Don't buy our product.

In this episode

Why Tim left an operational CISO role after spending years getting thereWhether becoming a Field CISO is a progression, a lateral move—or a step backwardWhy some security leaders don't consider Field CISOs "real" CISOsWhether Tim would ever return to an operational CISO seatThe misconception that Field CISOs are salespeople with CISO networksWhy lived experience gives a Field CISO credibility with customersWhy solving the customer's problem has to matter more than selling your productTimes Tim has told prospects that his own company wasn't the right solutionWhy trust matters more than the product pitchThe travel and visibility expectations that come with being a Field CISOBalancing conferences and customer commitments with four kids and a working spouseWhy Tim refuses to become a "road warrior"The guilt that can come with being present professionally and absent personallyWhy saying no is part of staying effectiveWhat burnout looks like in a Field CISO role versus an operational security role

Avani Desai once believed she had to make an impossible choice: be a good mother or become an exceptional executive.

Today, she's CEO of Schellman, and she's building the kind of workplace she wishes she'd been able to see earlier in her career.

In this episode of RAM, Avani joins Jake Bernardes to talk about growing up as the daughter of immigrants, beginning her career as one of the only women in penetration testing, and eventually becoming one of fewer than ten women leading a top-100 CPA firm.

But this isn't really a story about becoming CEO.

It's about what happened along the way.

Avani opens up about being afraid to disclose her first pregnancy because she worried it could affect her next promotion, seeing her newborn son fewer than 50 days during his first year, and ultimately leaving a job she loved because she refused to sacrifice the kind of mother she wanted to be.

Then an opportunity at Schellman changed the equation.

Now, as CEO and mother of three, Avani is trying to make sure the people coming behind her never feel forced to make the same choice.

It's a conversation about ambition, representation, parenthood, leadership—and redefining what having it all actually means.

In this episode

Why Avani's father moved his family to America specifically to create more opportunities for his daughtersGoing from penetration tester to privacy, marketing, president, and ultimately CEOWhat it feels like to be the only woman—or woman of color—in the roomWhy Avani was afraid to tell colleagues she was pregnantThe impossible choice she felt forced to make between motherhood and her careerSeeing her son fewer than 50 days during his first yearWhy she ultimately left a job she genuinely lovedFinding a company where parenthood and ambition didn't have to competeWhy 70% of Schellman's executive leadership team is femaleWhy Avani believes representation isn't about celebrating being “the only”—it's about making sure you're not the lastHer approach to being fully present at work and fully present at homeWhy Schellman shuts down for three weeks every yearWhy “rest is not a reward after burnout. It is part of performance.”Building a leadership team strong enough that the CEO can make herself “irrelevant”

Chapters

00:00 – Meet Avani Desai
01:54 – Her hero: the father who sacrificed everything for his daughters
02:42 – Growing up as the daughter of immigrants
04:34 – Reinventing yourself without changing companies
06:35 – Being a female penetration tester in 2002
06:52 – Becoming one of the few women leading a top-100 CPA firm
07:34 – Why being “the only” isn't something to celebrate
08:04 – Being afraid to disclose her pregnancy
09:00 – The impossible choice: executive or mother?
09:47 – Seeing her son fewer than 50 days in his first year
10:18 – The opportunity that meant she didn't have to choose
10:55 – Building a leadership team that's 70% women
12:35 – Why Avani talks publicly about the good and the bad
13:12 – Can you actually “have it all”?
14:00 – Protecting the hours that belong to her family
21:38 – Why Schellman completely shuts down
22:26 – Why she rejects unlimited PTO
24:12 – “My job is to make me irrelevant”
24:30 – Why exhaustion shouldn't be a badge of honor
24:50 – Rest is part of performance

Everyone remembers the headlines, but very few know what happened after the cameras left.

Former Uber Chief Security Officer Joe Sullivan and his wife, Prathiba, join Jake for an honest conversation about what it was like to navigate one of cybersecurity's most public legal battles—not as a security leader, but as a family.

From media scrutiny and online speculation to preparing their children for the possibility of prison, Joe and Prathiba share the conversations that happened behind closed doors and the resilience that carried them through.

This isn't another breach retrospective. It's a story about marriage, community, parenthood, and what happens when your hardest professional moment becomes your family's burden too.

If you've ever wondered what leadership really costs, this episode is for you.

In this episode

What life looked like behind the headlines of the Uber incidentHow public scrutiny affects spouses and children—not just executivesNavigating fear, uncertainty, and the possibility of prison as a familyWhy community became their greatest source of strengthTeaching resilience, honesty, and courage through adversityHow hardship ultimately strengthened their marriage and reshaped their purpose

The Emotional and Strategic Resilience of a CISO: Insights from Tim Brown

In this episode, Tim Brown reflects on his extraordinary journey through one of the most high-profile cybersecurity breaches in history, his health scare, and how these experiences reshaped his outlook on leadership, community, and the future of cybersecurity.

Main Topics:

The human side of cybersecurity leadership and managing personal health amid high-pressure incidentsThe importance of community support, compartmentalization, and resilience in crisis situationsLessons learned from a major breach and regulatory challenges, including navigating SEC casesThe evolving role of the CISO in strategy, AI, and business impact awarenessThe benefits of pivoting careers and fostering innovation within the cybersecurity community

Timestamps:

00:00 - Introduction to Tim Brown and episode overview

01:09 - Tim’s background, heroes, and personal interests

02:25 - Handling a major breach and personal health during crisis

04:00 - Managing work-life separation during high-stress legal and public scrutiny

06:00 - Lessons from a prolonged SEC case and their impact on mindset

07:24 - Decision to fight SEC charges and the importance of integrity

09:00 - Recognizing physical health signals amid stress

10:37 - The role of recovery versus stress and mental well-being

12:36 - How the incident changed life priorities and outlook

14:36 - Reflecting on advice for cybersecurity professionals before a crisis

17:02 - Factors motivating the decision to fight legal battles

19:20 - Post-crisis career pivot and current roles with Team8

22:24 - Trends and challenges in the cybersecurity community, including AI and future skills

28:18 - Resilience, design, and strategic thinking in the evolving security landscape

36:44 - The importance of visionary thinking beyond immediate technical solutions

37:22 - Final reflections: whether to avoid hardship or embrace growth

38:46 - Closing remarks on community, leadership, and future directions

Resources & Links:

Team8CISO VillageTim Brown on LinkedInBook (The CISO Journey)

Connect with Tim Brown:

LinkedInTwitter

Tim emphasizes the importance of community, strategic thinking, resilience, and integrity in cybersecurity leadership. His journey highlights how personal experiences can reinforce professional purpose and community contribution.