Most people think that once you sell a company, you ride off into the sunset. The truth is a lot messier. And before you roll your eyes—"Oh, poor successful guy struggling to find purpose"—let me be clear: this isn't one of those newsletters. I'm not writing for sympathy. I have deep purpose—I live for my two daughters.
But this is a lesson in humility. In what happens when your identity has been tied to growth, chaos, and challenge… and then all that slows down. The truth is, the growing doesn't stop just because you reach what you thought was the top of the mountain.
So what do you do next?
After selling my agency, I figured I'd take my experience, capital, and momentum and apply them to new ventures—stack more wins, move faster, go bigger. But reality had other plans.
The first post-exit business I started was a fragrance company. I teamed up with a co-founder, but things didn't play out how we hoped. My brother-in-law eventually stepped in to run it. I wrote a big check—well into the six figures—and recently, we sold the business and got our investment back.
But here's the truth: it just wasn't fun. We were constantly fighting for survival:
Rising customer acquisition costs on Meta
Dealing with manufacturers in China
Unexpected tariffs that crushed our margins
Nonstop customer service issues
It was a grind from start to finish. And in the middle of all that, I kept asking myself: Why am I doing this? Why didn't I aim bigger? Why didn't I build something I was truly passionate about—something I believed in deeply?
It felt like I had taken all this post-exit momentum and pointed it in the wrong direction.
Then came a telehealth venture. I invested over $250K—and lost it all. We spent way too much money upfront before we even got to market. Branding, website, tech infrastructure—it all added up fast. We were six figures deep before we even tested product-market fit. Add to that the legal costs of staying compliant with all the healthcare regulations...
We completely underestimated the amount of capital it takes just to get a business live, let alone profitable. We moved too fast, partnered with the wrong group, and couldn't make the unit economics work.
Another hard lesson: great ideas mean nothing without execution, timing, and cost control.
I also had a vision for The Next Chapter podcast. Still not launched. And a new kind of founder community—a modern answer to YPO or Tiger21—focused on curated, purpose-driven experiences for people navigating big life and business shifts. That hasn't come to life yet either.
I haven’t been a great investor—especially when it comes to investing my time in things I truly care about.
The hardest part about post-exit life isn't the lack of money or ideas. It's the fog of figuring out what's worth pouring yourself into again—and what will give you a return not just on capital, but on purpose.
It doesn't matter how much success you have in any venture, as humans what we crave most beyond purpose is PROGRESS. Just because you haven't achieved or aren't where you want to be in life, doesn't mean you won't get there.
We all need a game to play.
We all need to feel like we're using our gifts.
What do you think? Have you ever learned valuable business lessons from unlikely sources? Hit reply and let me know – I read every response.
