- Playing For Doubles
- Posts
- Down -50% To Up +80%
Down -50% To Up +80%
The Power of Doing Nothing
If this resonates with you, please click the ❤️. Thanks!
If you’re new here, I share “buy-and-hold portfolios” that I think can double in 3-5 years. My investment philosophy is simple: Try to find the best stocks you can and let them sit for years. You incur no costs with such a portfolio, and it is simple to manage.
Below is the performance of our currently active portfolios:

The Power of Doing Nothing

In August 2025, an investor messaged me about our shared investment in $DIBS.
He was down 50%.
He had spent more than a year watching the stock decline, while the broader market had ripped higher.
His every instinct was screaming “sell”!
That’s when I decided to double down.
Three months later, he was saying “I nailed it.”
But here’s the thing: I didn’t nail anything.
I had simply decided that I didn’t want to sell.
This is a story about why patience is the most underrated edge in investing.
The 3-5 Year Commitment
When I buy a Maverick in a Coffee Can portfolio, my intention is to hold it for the full duration of our 3-5 year holding period.
This is something I pre-commit to when buying.
This leads me to invest primarily in good assets, because when one is planning to hold for that long, one isn’t engaging in short-term market speculation.
Why 3-5 Years?
I’ve learned from tracking my own investments that when I sell a Maverick before the 3-year mark, I’m usually wrong.
Not sometimes. Usually.
Because it takes time:
For business fundamentals to compound
For market sentiment to catch up to value
For management strategies to play out
For my own emotional biases to fade
And the 3-5 year window isn’t arbitrary.
It’s long enough to let the business prove itself, but also short enough to stay accountable and reassess.
I’ve realized from past experiences that in aggregate, if I don’t hold for at least 3-5 years, I am leaving money on the table.
The 16-Month Journey: From -50% to +80%
Let me show you what patience actually looks like.
Not in theory, but in practice.
The Timeline
July 12, 2024 - I purchased $DIBS at $4.54/share in Coffee Can 13.
April 10, 2025 - Nine months later, the stock traded down to $2.30/share. A 50% decline.
June 5, 2025 - I doubled down, buying more at $2.75/share in Coffee Can 15. Subscribers on my Alerts Waitlist saw this firsthand.

November 14, 2025 - Sixteen months after the original purchase, the stock closed at $4.96/share. We’re now up 9% on the original purchase and a whopping +80% on the second purchase.

What Holding Actually Feels Like
A lot happened during these 16 months.
Let me show you what it actually felt like.
Here’s a conversation I had with a DIBS 0.00%↑ investor over the past several months.
I’m sharing this, not to put him down in any way, but to highlight a common experience that perfectly captures why patience is so hard, and why it can be such an important edge in the market.
May 28, 2025: 10 months in, “Getting harder and harder”
Here is what the investor wrote to me:

This is the voice of every investor who’s ever held a stock that isn’t working. The doubt. The second-guessing. The search for reasons to sell.
My response:

His concerns about SBC were legitimate.
But here’s what experience has taught me: when a stock is down 50% and trading at absurd valuations, the “problems” investors fixate on are usually justifications, not causes.
The cause is usually, that nobody’s paying attention.
And when attention returns, whether through earnings, catalysts, or just market rotation, those same “problems” suddenly don’t matter as much.
On June 5, I Doubled Down:


Want to see these decisions in real-time?
I share every Coffee Can purchase, including the uncomfortable ones, with my Alerts subscribers. You’ll see the thinking, the timing, and yes, the drawdowns too.
August 6, 2025: 13 months in, The Depths of Despair

My response:

Notice that I was frustrated too.
The difference wasn’t superior conviction.
It was a pre-commitment to a timeframe.
There was no decision to be made yet.
August 22, 2025 : The Moment of Capitulation

Read that last line again. “People have completely given up on it.”
This is the moment when most investors sell.
When the pain becomes unbearable.
When you feel like the only one still holding.
October 13, 2025: 15 Months in, Even Good News Doesn’t Help

Every sentence reveals the psychological torture:
Wants to add more
But fears it could go lower
Worries about macro conditions
Paralyzed by uncertainty
A week later:

Pessimism has set in.
This is the day-to-day emotional grind of holding a position that isn’t working.
October 24, 2025: A Glimmer of Hope

The relief is palpable.
October 27, 2025: Finally Some Validation

October 28, 2025: The Congratulations

Look At What We Went Through
16 months of doubt
A 50% drawdown
Watching the broader market rip while our investment languished
Questioning management, the business model, our judgment
The torture of day-to-day volatility
And yet, we held.
The business didn’t fundamentally change between August (when people had “completely given up on it”) and now.
What changed? Market sentiment. Investor attention. The narrative.
Here’s the critical insight: You cannot control when that shift happens. You can only control whether you’re still holding when it does.
The System That Keeps You In The Game
When I bought $DIBS at $4.54 in July 2024, I committed to holding it through this entire Coffee Can period.
When I doubled down at $2.75 in June 2025, I made the same commitment.
Not because I knew it would work out.
But because I know that selling early tends to be premature.
That’s a pattern I’ve seen repeatedly in my own investing history.
And I’ve learned, painfully, through experience, that my track record is better when I simply hold through the noise.
So I try to give my former self, the person who made the original buy decision, the benefit of the doubt, and honor his original plan to hold for 3-5 years.
Patience Is The Competitive Advantage Nobody Wants
Most investors can’t handle being wrong for 16 months.
They can’t endure:
A 50% drawdown while the S&P hits new highs
Friends asking “you still holding that?”
The voice in their head saying “just cut the loss”
The FOMO of watching other stocks rip while theirs flatlines
The daily psychological grind of holding something “people have completely given up on”
The opportunity cost of capital tied up in a non-performer
This is human nature.
Of course, not every stock rebounds.
But here’s what I’ve learned: most of the time, when I’m tempted to sell, it’s not because the thesis broke. It’s because I’m uncomfortable.
But if you can build a system, not willpower, a system, that keeps you in the investment long enough, you can capture the returns that impatient capital leaves behind.
That system, for me, is the Coffee Can Commitment.
That’s the edge.
Not superior stock picking.
Not better analysis.
Just being there when it finally works.
It’s not sexy. It’s not exciting. It won’t make for good cocktail party conversation.
But it works.
Not always, but in aggregate.
Kudos to the above investor for hanging on to his investment despite his doubts!
Have you held through a harsh drawdown only to see it pay off?
Or sold too early and regretted it?
Let me know.
