Every investor has that moment where they wonder if Financial Guru Dave Ramsey is somewhere shaking his head.

If I called Dave Ramsey today and told him about our real estate portfolio, I already know how that call would go.

The Conversation (Probably)

Me: “Hey Dave, love your show. We’ve got 71 rental units worth around $11.5 million… and about $8 million in debt.”

Dave: "You’re an idiot.”

Me: “Okay… well technically they’re cash flowing…”

Dave: “SELL. HALF. OF. THEM. Pay the rest off as fast as you can. Live debt-free, young man!”

Me: “…Yes sir.”

The Truth Is… He’s Not Wrong

Here’s the thing: Dave’s advice works.

It’s also the only time yelling at strangers on the radio has changed lives

It’s simple, clear, and it’s made millions of families debt-free and financially stable.

But… he’s talking to the average person.

We’re not the average person.

We’re not the average person. We’re the exact type of people Dave uses as a cautionary tale between commercial breaks (not that that's a good thing, obviously).

However, our debt isn’t on depreciating assets like boats, cars, or bad Amazon decisions. It’s tied to assets that produce income, build equity, and (in theory) appreciate over time.

We’ve leveraged that debt to buy 71 properties, create jobs, and build something that outlives us (hopefully).

Still, when you start saying “eight million dollars in debt” out loud…

you start sweating a little.

The Debt Dilemma

Here’s what we’ve learned about debt:

• Leverage multiplies everything…including mistakes.

• At some point cashflow is more important than appreciation. It pays the bills and buys peace of mind.

• There's a balance between what makes the most sense on a spreadsheet (the math virtually always favors more leverage) and what makes the most sense in real life.

We’ve been wrestling with this tension for a while:

The Math Behind Our Reservation
To simplify our hesitation about going fully debt-free, here’s a real scenario:

Historically, St. Louis real estate appreciates about 4% per year.
Right now, we own $11.5M in property with $8M in loans, leaving $3.5M in equity.

If we keep leveraging:

• 4% appreciation on $11.5M = $460K per year in value growth.

If we sold most of our properties and went debt-free:

• We’d own just $3.5M in property.

• 4% appreciation = $140K per year.

That’s a $320K difference every single year, and that gap compounds over time.
In other words, leverage doesn’t just buy more property, it multiplies your upside.

• On one hand, we love the power of leverage.

• On the other hand, we know it’s unwise to be millions of dollars in debt, even if it’s “good debt”.

For years, our plan was “buy, renovate, refinance, repeat.”

And it worked.

We built a portfolio that cash-flows and grows.

But then we started asking a harder question:

“At what point does stability become more attractive than growth?”

The Hybrid Plan

After a lot of late-night talks (and Scotty’s stress spreadsheets), we landed on a hybrid approach:

We’re not going full Dave Ramsey… but we’re not ignoring him either.

Here’s our new goal:

• 2026: Pay off two rental properties in full.

• By 2028: Pay off one house every quarter.

(Unless the Fed drops rates 3%... in which case we'll tell Dave, who doesn't even know who we are, to shove it, and you can forget we ever wrote this newsletter.)

That means by 2028, we’ll have 10+ paid-off homes generating pure cashflow—no banks, no mountains of refinance paperwork.

We still believe in leverage. But now, we believe in sleeping well Just as much.

Because there’s a difference between being rich and being secure.

Our new philosophy is simple: use leverage to grow, use cashflow to pay down, use discipline to stay free.

The Balance

So yes, Dave… you’re right.

Debt-free is the goal.

Just not the “sell half of your houses tomorrow” kind.

We’re choosing progress over panic.

Slow, steady, and with a spreadsheet full of formulas that only Scotty understands.

We’ll still leverage.

We’ll still grow.

But we’ll mitigate risk as we go. .

Because financial freedom isn’t just about building an empire.

It’s about protecting ourselves and our families and making sure the future is in our hands, not the hands of a lender.

Until next time,

The Moe Bros

(TJ & Scotty — debt-free-ish, cashflow-happy, and working on our Ramsey redemption arc)

Speaking of Dave Ramsey… President Trump floated the idea of a 50-year mortgage this week and the internet is having a field day with it.