Staring Into the Void

April 8, 2024

The day I sold my company, I thought I would never be unhappy again.

​I was on a private island off the coast of Croatia, celebrating with some of my closest friends. I had just met the woman who would become the love of my life.

​All of the work, all of the sacrifice had all culminated in that moment. That night was the single greatest night of sleep of my entire life. My bank account was full, my mind was finally at ease, and most importantly, I was free.

​Two short years later, I was so crippled by stress and anxiety that some days, I couldn’t even get out of bed because I didn’t want to face the day. I was losing $100,000 a month and watching as my bank account quickly drained toward zero. And even though I was still a multimillionaire on paper, I felt broke, and I was scared.

​But most importantly, I was ashamed. I couldn’t look at myself in the mirror because I had tasted freedom.

​And I blew it.


​After selling a company, a massive accomplishment often accompanied by a financial windfall and newfound freedom of time, the post-exit founder rides high on the wave of success.

However, this bliss is often short-lived. As the wave of joy subsides, the post-exit founder often faces a sense of loss of identity, purposelessness, and discomfort.

​Further, this is often exacerbated by a deep sense of shame for having these feelings at all—after all, they should finally be happy. Because these feelings feel unrelatable to the general population, this shame can further result in feelings of isolation and hopelessness.

​The result is that after a few months of discomfort, the founder often starts a new company, often one that looks similar or is adjacent to the old one, and gets back on the treadmill of long hours and deep stress of raising capital, hiring employees, and finding product market fit. Even if they are good at these skill sets, they find themselves wondering why they are even doing it in the first place—especially since they often don’t particularly need the money.

​Of course, when asked, they mask the discomfort by saying that they would be too bored in retirement or that they are driven by impact and solving problems, and that’s why they couldn’t sit still.

​And yet, mere months after their exit, they lie awake at night, crippled with anxiety, guilt, and even depression. 

I would know.

Staring into the void.

But I was lucky.

​A few years earlier, I had found the path of personal development. I met my first coach and the man who would eventually become my mentor, Phillip Mckernan, at a mastermind event. At the time, I had no idea what a coach was, not to mention that I could benefit from working with one.

​There was something deeply intriguing about him. The way he carried himself, the way he looked into people’s eyes without turning away.

There was something about his presence that was strangely both intimidating but warm and inviting at the same time.

​I approached him nervously, uncharacteristic for me, an entrepreneur who thought he was on top of the world. As someone who had built a successful investment firm, tested himself in combat, and knew how to cultivate peak performance, it wasn’t often that another man would elicit such feelings in me.

​Without prompting, I felt compelled to tell him that, for the first time, I wasn’t sure what to do. I was unsure about the future of our industry and my company’s place in it. I told him how I felt responsible for so many people and how much the pressure was getting to me.

“I’m a good guy, but I’m really starting to question myself,” I stammered, unsure of what I was even asking.

​“Are you?” he shot back unflinchingly.

​“Am I what?” I asked, a bit confused.

​“A good guy. Are you?”

​I was on my heels. No one had ever pierced me with a question like that.

​“Yes,” I answered softly.

​“Ok. Here’s my email. If you would like, you can reach out and we’ll book a chat.”

​He walked away, leaving me alone and wondering what exactly had just taken place.

I had no idea that conversation would set my life on a course I could have never imagined.

​Through my early work with Phillip, I first learned that while I had always fancied myself as confident and capable, I was, in fact, extraordinarily hard on myself.

​I dove into the work voraciously. Over the next few years, he expertly guided me through breakthrough after breakthrough on a journey of deep self-discovery.

​I learned the power of vulnerability, empathy, and the gift of truly holding space for another human.

​As a result, years later, as I was in the throes of my post-exit crisis, I knew that the best way to navigate a seemingly untenable situation was to share what I was going through.

And so I began to speak to people about my struggles. I talked openly about the feelings of shame, guilt, and anger at myself for letting this happen in the first place.

​Then, I decided to speak about my journey publicly. I asked for a keynote slot at the same Baby Bathwater event in Croatia, where I had met my wife two years earlier. I’m still sometimes amazed by that decision, as on the surface, there seemed to be very little upside to admitting that I had it all and I blew it. I was risking a lot, and my ego started to conjure images of public humiliation and the ridicule of my community.

​But I decided to speak anyway. My talk began with the famous internet meme, “I don’t know who needs to hear this, but…”

​I opened up about everything. I talked about how I was addicted to risk, deploying all of my post-exit earnings into deal after deal, including the final blow into the distressed company that was causing me all of the stress. I didn’t leave anything out. It was raw, it was vulnerable, and it was scary.

It turned out that quite a few people needed to hear it.

​After I finished, at least two dozen fellow founders lined up near the stage to talk to me. Each one thanked me and then opened up about their own journey. While not everyone had sold a company, they all had their own tale of wins, losses, and the wild swings in between.

​I learned an important lesson that day:

I am not alone.

​Entrepreneurship is hard. And so often, we make it even harder by suffering in silence.

​Since that day, I’ve spoken to hundreds of entrepreneurs about my wild post-exit ride.

​I even found a secret group comprised of well over a thousand post-exit founders. Within the group, there is even a separate chat appropriately titled “Am I Alone?” in which the members share the struggles that often accompany their success.

​Again and again, I’ve learned that my journey is hardly unique. In fact, it’s much closer to the norm. We sell a company, face a loss of identity, and then create some sort of self-sabotage out of the discomfort. The result is that, all too often, the situation becomes even more stressful than before the exit.

​The real tragedy is that within this cycle lies a missed opportunity.

​Selling a company comes with a gift:

The power of space.

​Most people will never have the opportunity to take time away from their daily grind, at least not while they are young enough to use it to its potential.

​The gift of unburdened freedom is a chance to sit in stillness and learn who we really are at a core level, without our external success, without our accomplishments, and without our constant busyness.

​When I finally took the time to sit and listen, I realized that I actually really like who I am.

​I’ll be forever grateful that I had Phillip to guide and mentor me through the process of coming home to myself.

If you’d like me to be that person for you, consider this your invitation.

​And remember, no matter where you are in your journey, whether you are riding high or going through it:

You are not alone.

​To sitting in stillness,


Did you enjoy this article? There’s more where that came from. Sign up for our newsletter to get these hard-earned insights and more delivered straight to your inbox.