One night at my son’s flag football game, I watched him walk to center field for the coin toss. He came back puzzled that his coach was happy they 'lost' the toss, but it reminded me of exactly where I was this summer. I was staring at a 50/50 chance between two life paths: the freedom to build and experiment on my own momentum, or the structured ownership of an existing business (with all the cash flow and tethered schedules that come with it). When the acquisition financing fell through, the coin finally landed, and the feeling that followed wasn't what I expected.

Four months in and it is officially back to the drawing board (insert crowd gasps). After weeks of due diligence and narrowing it down to one local bank, we just couldn't find a financing plan that didn't involve over-leveraging our personal assets or becoming accidental landlords. It is a frustrating turn, but the data doesn't lie. While the acquisition path hit a snag, it has opened up a massive window for Radio Chatter and some upcoming overlanding expeditions. Here is how the 'failed' deal is actually shaping the next phase of this transition.

Three months in and the data is starting to tell a story (one that involves a lot more due diligence than I originally anticipated). While June felt different from May, my time allocation stayed surprisingly consistent, even as we moved into the heavy lifting of financial and operational deep dives for a potential acquisition. Between getting Apple’s approval for the Radio Chatter app and navigating the 'crazy' variables of bank underwriting, I am learning that this journey is less about a single leap and more about managing a dozen moving parts at once.

There is a lot of buzz out there about buying a business (thanks to the social media influencers who make it look like a weekend hobby), but I’m here to tell you it isn't all it’s cracked up to be. From the grueling timelines and the 'cash drain' of the search phase to the legal minefields of asset vs. stock sales, the acquisition journey is a mountain of work before you even get the keys. If you aren't prepared to build a team of experts or handle the anxiety of a deal falling through, you might want to stick to the W2 life.

“It must be nice to be able to afford to quit your job.” I’ve heard this more than once (and no, I didn’t win the lottery or flip a double middle finger to my boss on the way out). The truth is that this transition was a calculated move rooted in decades of discipline and a heavy dose of the FIRE movement. But even with a solid foundation, being in the 'search phase' means watching your cash slowly drain while you hunt for the right deal. Here is how we prepared for this leap and the scenario planning I’m doing now to make sure the math actually stays mathing.

One of the biggest reasons I left corporate America was to escape bureaucracy and regain my creative freedom, so the last thing I wanted was another boss (even if that boss is a franchisor). Following the 'Venmo Challenge'—looking at where we already spend the most money—I set my sights on a local business I’ve respected for years. I sent the letter, braced for the 'no,' and actually got a response. It wasn't a deal, but it was a start. Here is what I learned from my first official strikeout in the world of business acquisition.

I recently saw a post claiming that you shouldn’t buy a business if you haven’t built one from scratch (a pointed question about where your 'point of reference' comes from). As someone leaving corporate to do exactly that, it got me thinking. From my time as a process improvement engineer in healthcare to stepping into subject-matter-blind roles, I’ve learned that corporate life is a fertile training ground if you approach it with the right mindset. I might not be a 'starter' who loves a blank canvas, but I am a 'builder'—and there is a massive difference between the two.

I’m not going to lie, I’ve had doubts recently (not about leaving corporate, but about the path I’ve chosen). After a nudge from my coach, I reached out to six businesses, but instead of feeling energized, I felt nothing. I’m realizing that while 'boring businesses' are the darling of the ETA world, they don’t always align with the leadership leverage I’m actually seeking. Here is how that realization led to a major pivot for my partnership and a potential cliffhanger for what comes next.

Most people ask me what business I’m going to start (usually while my wife rolls her eyes at my hundredth idea), but the truth is, I’m not starting one at all. I’m looking to buy one. It’s called Entrepreneurship Through Acquisition (ETA), and it’s about skipping the high-risk 'startup struggle' to step into a business that already has customers, employees, and cash flow. Here is why I believe buying is better than building from zero.