Our Business Needed Couples Therapy
For the last 6 years Scotty and I have been building our businesses together. We flip about 15–20 houses a year and we’ve grown to 74 rental properties. On paper everything looks great.
Behind the scenes? It’s been a lot of growth and learning how differently we’re wired.
I tend to be all gas and no brakes. I love building new things, solving big problems, meeting new people, exploring what’s next. If something works, my first thought is, “Cool. Let’s double it and see what happens.” I get bored maintaining stuff that already works.
Scotty is the opposite in all the best ways. He’s phenomenal at building systems and executing. He makes ideas real. He hits the brakes so we don’t go bankrupt. Which, in hindsight, has been helpful.
It’s a great combo… once you understand it. But before you understand it, it can feel more like:
“TJ is reckless and doesn’t have the patience to finish anything.”
“Scotty is a pansy with no ambition.”
We never say that out loud, of course…
One thing we’ve always been committed to is putting our relationship first and the business second.
Before we went into business together, we’d heard all the horror stories about partnerships blowing up families. We’ve heard Dave Ramsey say a million times, “The only ship that won’t sail is a partnership.” So we went in knowing there would be storms. We just decided ahead of time how we’d handle them.
Recently, there’s been enough turbulence that we decided to get some outside perspective.
We spent an entire day with a business consultant walking through something called the Working Genius (more on this in a later post). 8:30AM to 4:30PM. All the cards go on the table and permission to be completely honest about what we’re both feeling. which is how we always operate anyway, but was good having someone there to referee.
It was basically couples therapy, but with cash flow statements.
A few big discoveries:
Scotty is drowning in operations. (We knew this. But we hadn’t fully unpacked it.) He can’t engage with my “what’s next” ideas because he’s buried in what we’re already doing. When you’re overwhelmed, the future just feels like more work that will be added to his already full plate.
I’m bored. Not because the business isn’t good. It is. But the machine we built runs pretty well without me. And I’m a builder. Maintenance is not my gift. When I’m forced to sit still, I get restless and honestly… not that useful. That’s when I start inventing new ideas that stress everyone out (except me, of course).
We’re under-prioritizing our lending business. We consistently have $2.5–3M loaned out and we turn away good borrowers because we don’t have enough capital. That’s dumb. The demand is there. We just need to scale it.
So here’s what we’re doing:
We’re hiring a Head of Operations.Yes. It was either this or get Scotty a pacemaker.
We need a very competent, systems-minded person to run a lot of day-to-day operations so Scotty can breathe again and operate in his strengths. The goal is for both of us to spend 75% of our time on what we love and what we’re actually good at. Right now Scotty only spends about 30% of his time in that world, and I only spend about 50%. Those numbers aren’t sustainable.
And we’re going on a fundraising sprint.
Our goal is to raise another $3M this year for the lending company. That can come in small chunks or big ones. Doesn’t matter. We are not picky. The demand is there. We just need more fuel.
And lastly… because I can’t sit still and we need something concrete to build…
We’re moving into short-term rentals (Airbnb).
We already own one in St. Charles County and the last two weeks of optimizing it showed us we’ve been leaving money on the table. There’s a lot to learn to become great operators in that space. So 2026 is our education year.
Later in the year, we’re converting one of our long-term rentals in O’Fallon into a STR. The numbers make sense and it gives us more reps operating in the space.
2027 we start buying strategically outside of the St. Louis market.
So that’s my update.
We’re still buying houses. We’re scaling lending. We’re hiring. We’re learning a lot. And we’re growing up as business partners…which just means we’re making fewer rookie mistakes and more professional ones.
It should be fun. We’ll keep you posted with our progress.
