On grip, fear, and the kind of conviction that actually costs something.

We own $13 million worth of real estate.

I'm not saying that to brag. I'm saying it because it sounds like a very good reason to relax. And it's exactly the kind of thing that can quietly paralyze you.

Here's the math: 25 years from now, the tenants will have paid those properties off. The values will likely have tripled. And without adding a single door, Scotty and I will be sitting on roughly $40 million in paid-off real estate (and paid off real estate cash flows quite well.)

That's Future T.J.'s very comfortable problem. Current T.J. would like some operating capital.

None of that future equity helps us today. Not one dollar. And if we spend the next decade protecting that prize instead of investing in what we're building right now, we'll still arrive at our $40 million moment. We'll just get there knowing we wasted our potential because we played it safe.

The grip

Scotty and I have been having a hard conversation lately.

From the day we started this business, we believed long-term rentals were our ticket to wealth. Every flip, every loan, every early morning existed so we could buy more rentals. So when we get one, we hold it like it's the last rental they're ever going to make. Selling one doesn't feel like a transaction. It feels like handing back a piece of the future.

That instinct got us to 75 doors. But somewhere along the way, "never let them go" stopped being a strategy and became a reflex.

So we had to ask ourselves: are we operating out of conviction or fear?

It's fear. Fear that if we let go of what's working, we might never get it back. Fear that the next bet won't pay off. Fear that the version of us we're betting on won't show up.

Holding an asset because the math says hold is discipline. Holding it because you can't stomach letting go is fear dressed up as discipline.

So the real question isn't "is the investment sound?" It's: are we worth betting on?

What the bet actually looks like

• Several more short-term rentals (Airbnb’s), each requiring us to leave substantial capital in the deal.

• Personal coaches for both of us. Mine for vision. Scotty's for operations and team leadership.

• Help with content, so we can get what's in our heads out into the world.

• Paying to be part of a high level mastermind full of guys who think and bet big.

Total bill: at least $500K. Or roughly 2700 years of Netflix subscriptions.

Here's the part that stings. We have four rentals with $530K of equity just sitting there (more on that in a future newsletter about return on equity). And we've been protecting that equity like it's the irreplaceable part of this business.

It isn't. We are.

Every smart person I know who's building something real is investing ahead of where they are. Committing first, then rising to meet the commitment. Betting on yourself sounds very inspiring on Instagram. It's considerably less inspiring when somebody sends you the wiring instructions.

What the money actually buys

For me, it buys freedom to raise capital, cast vision, build the brand, and push this team to move faster. Right now I spend a lot of time pushing us to do more and move faster, but we don’t have the help we need or the systems setup to accomplish that.

For Scotty, whose genius is designing the machine, not being the machine, it buys his way out from under tasks that shouldn't require him at all. He should be leading the team, not giving every task the full Scotty experience.

So we have equity. We have a decision. And we have a question we can't avoid: do we believe that a year from now, with coaches, new STRs producing revenue, and the right people around us, this business won't just be okay, but better than it's ever been?

I do. And if I believe that, I don't get to hedge. You can't half-bet on yourself. You either place the bet or you don't.

My guess (and I'm willing to be wrong) is that two years from now, this is the moment we'll point to. Not because we did something reckless. Because we finally stopped playing it safe with a future God never promised us anyway.

Your challenge

What are you holding onto that's actually holding you back? Are you protecting an asset, or protecting yourself from the discomfort of betting on who you could become?

Sometimes wisdom says "hold on." Sometimes fear says the exact same thing.

We're about to find out what we're made of.

— T.J.

As usual, let this be a reminder that if these two adult children can build a business and make things happen, so can you. Let’s get to it.