Understanding What Works for You in Investing

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Deals on the Move

Last week, I put in an offer on a triplex. Today, I’m touring a single-family property that looks promising.

Momentum is building—properties are showing up, offers are going out, and I’m hopeful the first deal closes soon.

And in the middle of all this movement, I’ve been reflecting on my goals and strategy.

I think it’s worth sharing.

Rethinking My Circle of Competence

For years, I believed I could learn anything. My PhD is proof—set a goal, and I’ll either achieve it or decide it’s not worth chasing.

But that belief came with a hidden trap.

I’d take on things I thought would lead to success, only to burn out because I didn’t enjoy them. Burnout pushed my goals further away, which made me grind harder, which burned me out again. A brutal loop.

The good news is, I’ve been slowly stepping out of that trap.

Over time, my guiding question has shifted from “What’s the best?” to “What works?” to “What works for me?”

It sounds like a small change, but it’s been a big internal journey for me. One that led me to an answer I didn’t like at first.

Net Worth vs. Freedom

As of today, my net worth is $5.9M.

For a long time, I chased the highest possible returns because I thought anything less was poor capital allocation (i.e. lazy). And I sure as hell didn’t want to be labeled that.

But the thing about net worth: it doesn’t automatically translate to freedom.

Or happiness. And chasing a higher number puts me back on that same treadmill I burn out on.

Sure, I could liquidate everything, invest it at 3%, and collect $177K a year to sit on the couch and eat chips. But at 33, that would mean trading future growth for comfort now.

That’s the real tension: a tradeoff.

Income vs. Growth

Assets can give you income and growth, but rarely both in large amounts.

• High growth usually means low or no income.

• High income usually means low, no, or even negative growth.

A simple rule of thumb: the older you are, the more you should prioritize income over growth.

And while my age still points toward growth, I’ve been thinking…

Why not have both?

What’s Working for Me

I think I’ve worked out a real estate strategy that can outperform the S&P 500 while still giving me cash flow today.

While I’m still interested in buying businesses, there’s a big skills gap. And I’m not going to fill it overnight.

Real estate, on the other hand, fits me like a glove:

• I understand the business model

• It’s more passive than running a small business.

• I already have experience in the field.

• My natural talents help me mitigate risk

If you’re curious how I plan to beat that market using real estate, tune in for next week.

I’m dedicating the entire letter to laying out the process in full.

Happy investing,

—Dakota

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