How I Went From Penny‑Stock Humiliation to Outperforming My Managed IRA — And Why the Comparison Was Never Fair
As I step into 2026, I wanted my first post of the year to be something real — not polished, not performative, just honest. This isn't a victory lap or a highlight reel. It's a look back at the mistakes that shaped me, the lessons that stuck, and the quiet realizations that changed how I invest and how I think. If sharing this helps someone else navigate their own financial journey with a little more clarity and a little less fear, then it's worth putting into the world.
How It Started: The Paris Hilton Penny‑Stock Disaster
If I'm being honest, my investing journey didn't start a decade ago — it started back in the Scottrade days, when I bought a Paris Hilton penny stock and learned the true meaning of humiliation.
Most people begin their investing careers with index funds. I began with a pump‑and‑dump tied to a "modeling/entertainment" company that slapped Paris Hilton's name on it like a clearance sticker.
And the worst part? I bought it because a friend gave me what sounded like an insider tip — the kind of whispered "trust me, this one's going to pop" advice that preys on every beginner's FOMO. It was the first of two times in my life I let fear of missing out override common sense. (The second was the 2008 real estate crash, when I over‑leveraged myself into a personal demolition derby.)
This was my first "career" in stock trading. It lasted about five minutes.
I watched that thing spike, collapse, and take my dignity with it. After that, I sold everything else (thankfully at a profit), closed the chapter, and walked away from the markets like a character in a movie who'd just survived an explosion.
But I never stopped watching.
2020: The Year the Market Broke… and I Recognized the Pattern
When the pandemic hit the stock market in March 2020, the market didn't just wobble — it collapsed in a way that felt eerily familiar.
Because this wasn't my first rodeo.
Black Monday — October 19, 1987
The Dot‑Com Bust — 2000 to 2002
The 2008–2009 real estate crash, which I personally fell victim to with a full‑blown "get rich" FOMO mindset that wiped me out
So when the world panicked in 2020, I didn't see chaos. I saw a pattern.
Every major collapse I'd witnessed had the same rhythm:
And this time, I wasn't the rookie. I wasn't the one chasing hype. I wasn't the one getting swept up in the fear.
I combined everything I'd learned from decades of watching market cycles with the fundamentals I’d absorbed from:
Warren Buffett's discipline, and
the authors of "Chicks Laying Nest Eggs", who hammered home the power of steady, rational investing
And I swooped in like a vulture at a fire sale.
I still had a TD Ameritrade account — the successor to my old Scottrade days — and I started buying the mega‑dips. Not recklessly. Not emotionally. But with intention.
Little by little, I rebuilt my portfolio.
The Chase Experiment: Setting Up My Baseline Competitor
Later that same year, I kept hearing rumors about Chase's conservative performance. Some people defended them. Some shrugged. Some said they were "fine."
"Fine isn't good enough. Let's see what they can actually do."
So I transferred one of my old IRAs from Invesco to Chase — not because I expected brilliance, but because I wanted a baseline. A benchmark. A competitor.
Same starting point. Same market. Same timeframe.
And that's when the real comparison began.
The Setup: My "Managed" IRA That Wasn't Built for My Goals
In December 2020, I opened the managed IRA with Chase. In January 2021, I funded it with $23,903.16.
To be clear, Chase didn't "fail." Their managed portfolio did exactly what it was designed to do:
deliver steady, conservative returns
especially for people nearing retirement
It just wasn't aligned with my goals.
I'm comfortable with volatility. I'm comfortable with long‑term bets. I'm comfortable taking responsibility for my own decisions.
That's why my self‑directed strategy outperformed — not because they were wrong, but because we were playing different games.
Fast‑forward to December 2025 — five full years later:
Final value before I transferred it to my self‑directed IRA:
👉 $31,659.03
Note: This IRA was just one slice of my broader portfolio — the point isn't the size, but the difference in strategy and outcome.
Not terrible. Not amazing. Just… fine.
And "fine" is the most expensive word in investing.
Meanwhile, My Personal Portfolio Was Doing This…
At the same time, using the same starting point, my personal portfolio — the one I actually researched, managed, and adjusted myself — hit:
Same timeframe. Same market. Same starting point.
The difference? Turns out I was the edge all along.
Oh, and One More Thing: My Strategy Outperformed Theirs Three Years Straight
This wasn't a one‑off. It wasn't luck. It wasn't a fluke.
My self‑directed portfolio outperformed Chase's managed allocation three years in a row, including 2025.
But here's the important part:
We weren't playing the same game.
They were operating within a framework built for stability:
and the freedom to adapt quickly
So yes — my approach outperformed theirs. Not because they were wrong, but because I wasn't bound by the constraints that define a managed portfolio.
Bonus Chapter: The "Dip Buying" Mistakes That Taught Me More Than Any Win
Let's sprinkle a little salt on my own wounds too.
Back in 2020, I bought American Airlines (AAL) and Canada Goose (GOOS) because they were "cheap."
Cheap is not a strategy. Cheap is a trap.
And I fell right into it.
American Airlines: The Reverse‑Split Mirage
AAL had years — literal years — to recover. But the fundamentals were never there:
A business model that struggles even in good times
Then came the reverse split — a cosmetic price boost that didn't change the underlying reality.
I held it too long. In December 2025, I finally said: "Enough. I'm done."
Canada Goose: The Goose That Cooked Itself
GOOS was another lesson wrapped in a parka.
The brand had global momentum — especially in Asia — until a series of missteps cracked the growth story. The fundamentals softened. The stock reflected that.
I waited for a turnaround that never came.
This month, I sold it too. Bu‑bye.
The Lesson These Trades Taught Me
Buying during a dip is not a thesis. A dip only matters if the company underneath it is strong enough to rise again.
AAL and GOOS weren't. And holding them taught me more than any winner ever did.
December 31, 2025: The Day I Finally Folded the Losers
New Year's Eve 2025, I did what I should've done years ago:
And when I say "dead weight," here's what I mean — this is the actual lineup Chase had me holding:
CGLBX, BNDX, BND, GOVT, BBJP, VCIT, CRDOX, BBCA, BBEU, MBB, BBAX, PIMIX, CUSDX
A greatest‑hits compilation of:
and positions that barely moved for years
Basically, the financial equivalent of a beige waiting room.
And here's what I kept — the only things in that entire portfolio that actually aligned with my strategy:
Everything else? Gone. Folded. Cleared out like a garage sale.
And because this is a self‑directed IRA, I didn't owe a single penny in taxes for rotating out of them.
I freed up $14,857.91 in clean, tax‑sheltered capital.
That's not a setback. That's opportunity.
The Future: Redirecting Into What I Actually Believe In
With that capital freed up, I finally had the chance to put it into something that actually fits my long‑term strategy.
Not because it was "on sale." Not because I was trying to time anything. But because ASML sits at the center of one of the most important technological bottlenecks in the world — advanced semiconductor manufacturing. Their moat isn't just deep; it's structural. There is no substitute for what they build.
Even if the price moved a bit before settlement, I'll live. This wasn't about catching the perfect moment. It was about aligning my capital with conviction.
And that's exactly what I did.
Final Thought: This Is the End of My Training Arc
My journey didn't start ten years ago. It started with a Paris Hilton penny stock that wiped out my dignity.
But everything since then — the comeback, the discipline, the wins, the losses, the lessons — built the investor I am today.
I'm not the rookie anymore. I'm not the student. I'm not the guy chasing hype.
And the numbers speak for themselves.
If my journey helps you make sense of your own, then every mistake I made was worth it.
