For most of my adult life, I worked inside institutions. Some were corporate. Some were mission-driven. Some were tied to national security. All of them offered the same thing: structure. A title. A team. A paycheck that showed up when it was supposed to.

On the side, I was always building something else — writing books, speaking, advising companies, growing my own firm. It felt ambitious, but safe. I had room to explore without actually risking anything. Health care was covered, bi-weekly checks came in, and my office was only a short drive away.

Then, abruptly (as things tend to do), everything changed.

A global charity I served as General Counsel began to unravel after geopolitical changes dried up its funding. Around the same time, Broadcom divested much of the Carbon Black division where I'd spent more than a decade helping organizations think through cyber risk. Two pillars went at once.

A steady paycheck provides reassurance. It's the oxygen you don't notice until someone hits the red button on the airlock and vents it all into space.

The Night the Numbers Didn't Work

One night, after the house went quiet, I opened a spreadsheet and tried to predict the future. Bank balances. Investments. Tuition. Property taxes. Groceries and gasoline. Every bill, down to the subscriptions I kept meaning to cancel. Set against what I hoped to earn, not what I knew was coming.

Of course, the numbers didn't add up.

There's a specific kind of silence when certainty leaves the room. I didn't sleep. I kept recalculating. I stared at the gap between what I projected and what was real, and it kept getting wider.

There were job offers sitting in my inbox. Good ones. I could have taken one and been fine. Instead, somewhere before dawn, I decided to keep going. To stop hedging and actually bet on myself. It didn't feel bold. It felt like the scariest thing I'd ever done.

Entrepreneurship looks glamorous from the outside. From the inside, it starts with a quiet room and a choice nobody else can make for you.

The Shock of Freedom

Everyone talks about the freedom of working for yourself. The flexibility. The independence. What nobody talks about is the silence.

When you leave an organization, you lose the background noise of shared purpose. Hallway conversations, the camaraderie of a team that takes some of the hits with you. When a proposal falls through, there's nobody else to absorb it. It lands on you, full weight. I felt the way I’d felt years ago when I left the FBI. A lot like I’d been exiled from family.

My first two years on my own, I worked harder than I ever had in the past. And I couldn't turn it off. When your time is your product, work never ceases atfive. Some nights I was still running through keynotes or client problems at two in the morning. Doubt doesn't keep business hours either.

But something else grows alongside it: a sense of real ownership. Over the work. Over the direction. Over what happens next.

Momentum and Its Hidden Cost

By most measures, these two years have gone well. My investigative firm The Georgetown Group grew. I raised my speaking fees. I co-founded a new cyber advisory company named NeXasure with people I trust. Over the past seven months I’ve sat for over 200 interviews, media hits and podcasts. My book Spies, Lies and Cybercrime came out to strong reviews and hit the national bestseller list.

And yet I still check the sales numbers like I'm waiting on a verdict. Every author does, I think. You put years into something and then watch a dashboard as if it's telling you whether it was worth it.

The book is doing better than I honestly expected — and a big part of that is this community. All of you. That's not something I say lightly. None of this gets built alone.

When you are the brand, the writer, the strategist, and the face of everything — there's no buffer. The good stuff hits you directly. So does the hard stuff. Both feel personal and they each keep you up at night.

The Strategic Recalibration

Two years without a net has changed how I think about almost everything.

Time is the most valuable commodity. You can make money, but never more time. Wasted hours have a real cost when every hour is yours to account for. Entrepreneurship sharpens your attention towards the ideas that matter the most.

And risk looks different up close. Every major move I've made has rolled a set of dice. Leaving stable roles. Turning down offers. Doubling down when the spreadsheet said otherwise. Risk never fells comfortable. But no one ever shot the moon without taking a gamble. And as my Granddad O’Neill used to say: “Money is like manure, Eric. I’t does no good unless you spread it around.”

Stronger Without the Net

These two years have been some of the best of my career. They've also transformed how I work and manage my time. Losing the institutional cushion surfaced things I needed to fix and pushed growth I wouldn't have chosen on my own. I'm more disciplined, more grateful, and clearer on what actually matters.

Security isn't permanent. Titles change. Companies restructure. The market doesn't care about your tenure. The only thing that travels with you is how well you adapt.

The leap of faith isn't for everyone. It comes with bad nights, numbers that won't cooperate, and stretches of real doubt. But it also comes with something most jobs can't offer: you own your time.

When the scaffolding comes down, what's left is who you are, what you know, and whether you're willing to back yourself.

Most of the time, that turns out to be enough. Thank you for joining me on this journey. Seventy-five issues and counting.

New reporting from the Wall Street Journal reveals that OpenAI’s internal systems flagged repeated violent discussions from Jesse Van Rootselaar on ChatGPT months before the tragic school shooting in Tumbler Ridge, B.C. More than a dozen employees reportedly urged leadership to alert Canadian authorities. The company instead banned the account, concluding it didn’t meet the “credible and imminent threat” threshold for law-enforcement referral.

Investigators also found that Van Rootselaar had created a violent Roblox game simulating a mass shooting in a mall before the attack.

So here’s the uncomfortable, necessary question:

When AI companies detect escalating violent behavior — across chatbot conversations and even user-created violent simulations — do they have a duty to report it?

Not just when a threat is minutes away. But when a pattern emerges that, combined with known warning signs already on law enforcement’s radar, could tip the balance toward a court-ordered mental health intervention.

AI platforms now see behavioral signals at scale that no institution in history has ever had access to. If those signals stay locked inside moderation dashboards, what exactly are we protecting — and at what cost?

The next tragedy will raise the same question. We should answer it now.

I wanted to bring a little levity into this issue, and then I found this story and couldn’t resist.

During the women’s cross-country team sprint qualifier at the 2026 Winter Olympics, as elite athletes from Croatia and Australia lunged toward the finish line, a dog casually trotted onto the course, glanced at the cameras, spotted the skiers, and decided this was now his race.

“Anybody lost their dog?” the announcers joked, adding that the “fairly nice mutt” wasn’t hindering anyone and that it was “one of those moments you have to laugh about.”

The pup sprinted alongside the exhausted Olympians, crossed the finish area with confidence, then did what any champion would do — sniffed the competitors and collected belly rubs from volunteers before wandering off.

Sweden took gold.

The dog took the internet!

Please Leave a 5-star review on Amazon or on Goodreads.

🎤  I’m on the road doing speaking events. If your company or organization is interested in bringing me to a stage in 2026, book me to speak at your next event.

If you’ve ever paused at an email, login alert, or message and thought, “Could this happen to me?”—my Linkedin Learning course is for you! Login and start learning here.

Join me for my next Surveillance 101 spy hunter event with the International Spy Museum on Friday, April 17, 2026!

George Washington wasn’t just the father of our country — he was America’s first spymaster. As the U.S. turns 250, most people will celebrate by visiting monuments. You’ll do something better. Your undercover operation begins at Tudor Place — the home of Washington’s step-granddaughter — where you’ll step into a live surveillance to hunt my spy. This is one of the most exclusive events in Washington, DC, and it happens only four times a year. In a small, high-intensity group, you’ll learn how to track a target without being detected, move through crowds invisibly, capture discreet intel, and sharpen your situational awareness while navigating the gardens, galleries, and shadowed streets of Georgetown. Then we’ll debrief over cocktails or mocktails like professionals. Register now! Spots are limited and fill up and sell out fast!

Meet Moya, a humanoid AI companion from Chinese robotics firm DroidUp. She’s 5’5”, built with silicone skin over a bone-and-muscle-like frame, walks with near-human gait, and even emits body heat between 32–36°C.

Moya can smile, wink, and make subtle facial expressions using dozens of micro-actuators in her face. She’s modular and customizable — hair, facial features, body form. Underneath it all, advanced AI keeps conversations flowing in real time, maintaining context so interactions feel continuous rather than scripted.

Robots already run warehouses and fold laundry. Moya signals something different: machines moving from utility to intimacy.

The question isn’t whether the tech works.

It’s what happens when loneliness meets lifelike code.

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