Posted about 1 month ago

I Lost Money in 2021 — Here’s What I’m Doing Differently in 2025+

Let me say something most syndicators won’t:
I lost money.
Not on every deal. But enough of them. When you have done 2 Billion dollars of deals you are going to have them... hint for new LPs, trouble is most new syndicators on their first dozen or two projects are not going to have long of a run rate yet.

And not because I was lazy, careless, or chasing shiny objects.
I was doing what most of us were doing 2016 - 2021—playing the hand we were dealt in a frothy, rate-suppressed market (which I believe things are different past 2023 with the FED not dropping rates under 3%).

Some of those deals looked great on paper. Great markets, strong value-add plans, solid teams. But the timing was wrong.

When Optimism Becomes a Liability

I was trained as an engineer. I like plans. I like order. I like to believe that if we just execute, things will work out.

But real estate doesn’t always care about your spreadsheet.

The Lesson: You Can’t Out-Operate Bad Timing

We always talk about “time in the market beats timing the market.”

I don’t believe that anymore.

I had deals with stellar operations—but purchased at peak pricing. They’re stuck, barely hanging on. Meanwhile, less sexy deals I bought in 2016 and 2018? Still kicking off strong cash flow.

Entry point matters. A lot.

So in 2025, I’m approaching things differently.

Here’s What I’m Doing Now (Maybe You Should Too)

I’m underwriting like it’s 2009 again.
That means higher exit caps, and NO assuming cap rate compression to make a deal work.
I’m only backing operators who’ve taken a punch.
I want scars, not just shiny pitch decks.
I’m diversifying by vintage.
Not just by sponsor or market. Having exposure across different years saved me. If all your deals are from 2021, you’re not diversified—you’re concentrated.
I’m focused on asymmetric upside.
Buying into cleaner, simpler deals in a dislocated market. If this is truly the bottom, I’d rather step in now than try to time perfection. Dare I saw dollar cost average to take a term from the equities world I left in 2015 when I cashed out my 401K.

The Punchline: Be Honest With Yourself

I’m not sharing this to fish for sympathy or save face.

I’m sharing this because I’ve seen too many investors pretend everything’s fine when they’re bleeding quietly. I'm a LP too in deals with the gurus and its the same thing there just they are not openly talking about it. That’s not me, I plan to stay in the game and learn the lessons for the next go around will be something different.

If you’re sitting on the sidelines right now, I don’t blame you. But ask yourself: Are you being cautious… or just afraid?

Because if this is our 2010 moment, the next few years could define the next decade of your investing life.