Everyone likes to talk about their biggest wins.
But you learn more from the losses — especially when they cost you a few thousand dollars and a bit of pride.

In this episode, I sat down with my dad, Steve, to talk through our dumbest investments — what went wrong, what we learned, and how to keep your portfolio from making the same mistakes.

This one came from Peter Lynch, the guy who ran the Magellan Fund: “Invest in what you know.”

My dad broke that rule twice — and both times, it cost him.

First, he chased small gold miners — companies that looked shiny but had no clear reporting. Then he went bigger, buying into a Russian mining stock paying a 4% dividend.

Six months later, U.S.–Russia relations collapsed. That stock — and his $4,000 — were frozen overnight.

Lesson: If you don’t understand it, or you can’t check its health easily, it’s not an investment — it’s a bet.

Steve divides his investing into three buckets:

But during 2019–2021, he broke his own rule — loading up on speculative miners.

Result: a flat portfolio while the S&P 500 gained almost 50%.

The lesson? Stick to your system. Discipline beats prediction every time.

If we had to sum it up:

Greed is the most expensive teacher there is.

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Dan:
Welcome back to Millennial & Boomer Money Concepts.
This is where a Millennial son — that’s me — and my Boomer dad — that’s Steve — break down money concepts to make them simple and help you invest with confidence.

Dan:
Everyone loves sharing their biggest wins.
Today, we flipped it — we’re talking about our dumbest investments and what they taught us.

Steve:
We’ll make it philosophical. I’ve made bad investments, but more importantly, I broke my own principles twice. Let’s talk about those.

Dan:
Alright, Rule #1?

Steve:
It’s not mine — it’s Peter Lynch’s: “Invest in what you know.”

Steve:
I ignored that. I went deep into small miners, gold and silver companies. The problem is, you can’t really see what’s happening with those. There’s no regular reporting, and when updates come, they’re full of jargon.

Then I bought a Russian mining stock — looked great, paid a 4% dividend — until the U.S. cut ties with Russia. That $4,000 investment? Gone. I still technically own the shares but can’t sell them.

Dan:
So, rubles up in flames?

Steve:
Exactly. If I had a Russian relative, maybe I could do something, but it’s gone.

Dan:
So that’s Rule #1 broken — what about Rule #2?

Steve:
Rule #2 is about allocation. I split my money three ways: speculative, growth, and “sleep well at night.”
Speculative is no more than 10%, growth 30%, and SWANs 60%. But for three years, I ignored that.

From 2019 to 2021, my portfolio was 40% speculative. I made 11% in 2019, lost 10% in 2020, made 5% in 2021 — basically flat. Meanwhile, the S&P 500 gained about 50% over the same period.

Dan:
So, in poker terms, the house won.

Steve:
Pretty much. I tried to hit big but ended up treading water.

Dan:
And the takeaway?

Steve:
Stick to your allocation. Don’t let greed talk you into being “special.” Discipline wins.

Dan:
So in short: don’t chase what you don’t understand, stay disciplined, and focus on process over prediction.

Steve:
Exactly. I got greedy and paid the price.

Dan:
We’ve all been there.
If you’ve made a dumb money move, join the MBMC Skool Community, share it, and we’ll all learn together — maybe even feature yours in a future episode.