I started with less than most. At eighteen I was on my own in a small Kentucky town with 34 cents to my name and no secure place to rest my head. I mention it once and move on, but everything about how I build traces back to that starting point.
The Kentucky National Guard was my way forward. I played a year of college football, and I enlisted as an infantry soldier and ended up serving alongside the 20th Special Forces Group (Airborne), where I learned what a quiet professional looks like. A counterdrug assignment paid for my first flight training, which led to Army flight school. The Army also gave me the operating system I still run every deal through: understand what can go wrong, have a plan for it, brief the contingencies, then execute.
The real estate side started with a book a mentor handed me while I was working security at a bar in Lexington: Rich Dad Poor Dad. Not a sophisticated playbook, but a different way of thinking about money and ownership, and a rabbit hole I never climbed out of. Mentorship has shaped everything since. Jeff Scott, a former 767 line check airman, is the reason I fly professionally at all. He lit a fire under me, and I knocked out my ratings in about five months.
My first deal was a triplex in Kentucky, bought sight unseen during flight school using a VA loan. I had to kick out two tenants within the first month. I renovated it myself and slept on an air mattress in the unit while I worked. That triplex turned into more Kentucky projects, where I made my first mistakes, built my first real portfolio, and proved this could be more than a side hustle. I’ve made many mistakes along the way that have turned into great lessons, and I share what I’ve learned so others can hopefully step above those growing pains.
A move to California changed the scale of my thinking. I got around people building serious companies and raising serious capital in a small, tight-knit mastermind, and realized the ceiling I’d put on myself was way too low. I stopped thinking about the next property and started thinking about the next ten, twenty, thirty years.
Today I fly a senior airline schedule for a major U.S. carrier and lead AK Capital Investments with my wife, Alyssa, and my development partner, Lukas Bondy, across residential rental properties, commercial buildings, and co-GP positions in ground-up development and senior living. I’m still a pilot. I’m also a full-time investor. And I’m sure I have plenty of mistakes left to make.
I don’t pick sponsors off a list. I build the deals and own a piece of them.
The goal was never to stop working. The goal is enough control over your life that work becomes a choice. For me that comes down to five freedoms: time, location, financial, relationships, and purpose. I don’t have all five yet either. That’s what I’m building toward.