Why I’m Betting on One Stock for 20 Years And Showing Every Step
- Silivere Bakomeza
- Apr 24
- 7 min read
Updated: 2 days ago
I do not time the market.
I do not chase trends.
I do not quit.
I show up 365 times a year.
For twenty years.
And I invite you to watch me do it.
The Challenge: One Stock, 50 Dollars a Day, 20 Years
I am not a trader.
I am not chasing alpha.
I am not juggling ten positions and calling it strategy.
I am building wealth the boring way.
Behavior first. Conviction only.
Every market day, I invest fifty dollars into one stock. Automatically.
No emotion. No second guessing.
That is 252 trading days per year. Over twenty years, that’s more than 5000 separate buy days.
But that’s not where the challenge ends.
Most investors take weekends and holidays off. I do not.
I invest on all 365 days.
Every Monday, I make a 100 dollar manual buy to cover Saturday and Sunday.
For federal holidays when the market closes, I buy manually. Every single time.
Because if Bitcoin trades 24/ 7, so can I.
The Winter Discipline Cap
Markets move in seasons. There are long green runs and there are brutal winters when everything looks frozen. Most investors disappear during the winters. They stop buying, they wait for the sun to come back, and they lose the most important advantage which is consistency.
That is where my system has a built in edge. Alongside my 365 days of daily investing, I have what I call a Winter Discipline Cap which is up to $18,250 set aside to deploy across any bear season.
It is not a requirement. Some winters I might use $2,000. Some winters I might use $10,000. Some winters, none at all. The point is not the money. The point is the identity. By committing a cap, I guarantee that when the market is coldest and fear is loudest, I am not running away. I am leaning in.
This keeps the 365 day system as the foundation, and the winter cap as the psychological reinforcement. It is my way of saying that no matter how long the winter lasts, my discipline will outlast it.
The Psychological Math Most People Miss
Here is what most daily investors do not realize:
252 trading days times 50 dollars equals 12,600 dollars per year
365 full days times 50 dollars equals 18,250 dollars per year
That is a 5,650 dollar gap most investors never cover.
They call it daily.
I actually mean daily.
Because discipline should not depend on a stock exchange calendar.
And wealth should not take weekends off.
No Diversification. No Distractions.
Wall Street sells complexity.
Mutual funds. Index rebalancing. Six different apps. Twenty seven tickers.
But complexity is a trap.
Clarity is the way out.
I picked one stock.
One amount.
One rule.
50 dollars a day into Strategy, formerly MicroStrategy. For 20 years publicly.
Not because it is easy.
But because it is impossible to hide from.
This challenge is not about MSTR.
It is about what happens when your system is so simple, it is impossible to cheat on.
Why I Chose Strategy
Strategy (MSTR) owns more than half a million Bitcoin.
It is not a proxy. It is a conviction amplifier.
I chose it because:
It gives me long-term Bitcoin exposure through a stock
It has a founder with skin in the game
It uses corporate leverage to amplify upside
It is volatile enough to scare traders but rewards patient builders
I do not want safe.
I want scalable.
And this is the system that delivers both.
The Public Rules
Yes, I have a private portfolio.
Yes, I have a family to protect.
But this is different.
This is my public proof of discipline.
The rules are simple:
One stock
Fifty dollars a day
No selling
No switching
No other positions shown
No quitting during red weeks
This is not content.
It is a conviction contract.
What 365 Days Really Means
Most people invest 252 times a year, when the market is open.
But what about the other 113 days?
That is where the real edge is.
I built a system that does not break when the market closes:
50 dollars automated every market day
100 dollars every automated every Monday to cover weekends
Manual 50 dollar buys for each market holiday
That is 50 dollars a day, 365 days a year.
No gaps. No skipped days. No emotional decisions.
Every weekday morning when I clock in as a bus driver, 35 percent of my paycheck is already spoken for. It does not go to bills or savings. It goes straight into my Robinhood account to buy Strategy (MSTR). I never wait to see what is left over. I fund my future first, so no matter what life throws at me, this streak never misses a day.
If the market closes, I still buy.
If it is a red week, I still show up.
Discipline is the asset. Not the stock.
My Investing Year Starts on April 21, 2025
I did not wait for January 1.
I did not need a new year, a new job, or a perfect setup.
I started on a random Monday.
April 21, 2025.
That is my day one.
That is why my investing year runs from April 21 to April 21.
If you are reading this in 2026 or 2030, your April 21 can start today.
Because discipline does not care what day it is.
It only cares that you show up.
Weekly Receipts. Real Proof.
Every Saturday, I publish a new update.
Not theories. Not predictions. Not recycled news.
Proof.
Each weekly receipt includes:
My total share count
My average cost per share
My MSTR versus Bitcoin, SPY, QQQ, and Gold comparison
One hard earned behavioral lesson
If I say I invest every day, you should be able to see it.
This is how you document a legacy.
Browse the Weekly Receipts
Scroll the streak.
Copy the system.
Build your own.
Week 1: April 21 to 25, 2025
Week 2: April 28 to May 2, 2025
Week 3: May 5 to 9, 2025
Week 4: May 12 to 16, 2025
Week 5: May 19 to 23, 2025
Week 6: May 27 to 30, 2025
Week 7: June 2 to 6, 2025
Week 8: June 9 to 13, 2025
Week 9: June 16 to 20, 2025
Week 10: June 24 to 28, 2025
Week 11: June 30 to July 5, 2025
Week 12: July 7 to 11, 2025
Week 13: July 14 to 18, 2025
Week 14: July 21 to 25, 2025
Week 15: July 28 to August 01, 2025
Week 16: August 04 to 08, 2025
Week 17: August 11 to 15, 2025
Week 18: August 18 to 22, 2025
Week 19: August 25 to 29, 2025
Week 20: Sept 1st to 5, 2025
Week 21: Sept 8 to 12, 2025
Week 22: Sept 15 to 19, 2025
Week 23: Sept 22 to 26, 2025
Week 24: Sept 29 to Oct 03, 2025
Week 25: Oct 06 to 10, 2025
Week 26: Oct 13 to 17, 2025
Week 27: Oct 20 to 24, 2025
Coming Soon
New update every Saturday.
This is my digital receipt. Come back to see it stack.
Why This System Is Duplicable
You do not need to copy MSTR.
But you should copy the structure:
Pick a high conviction asset
Automate buys on every market day
Cover weekends and holidays with discipline
Track your journey publicly even if only to yourself
Whether you start with 50 dollars a day or 5 dollars a day, the power is in the streak.
Do not chase return on investment.
Build repetition.
Final Word
This is not a meme.
This is not a hustle.
This is not content for clicks.
This is a system for legacy.
One stock.
Fifty dollars a day.
Twenty years.
And while most people wait for the perfect moment…
I already hit 365 perfect moments this year.
Because I created them.
I do not time the market.
I do not chase headlines.
I do not quit.
I show up.
And I build.
Every single day.
Want to Build Your Own
Choose your starting point below:
✅ Robinhood - Where I automate my daily MSTR buys (highly recommended)
✅ Acorns - Great for beginners investing in the background
✅ Webull - Best for trigger-based buys and lump sums
Your first ten dollars is not about money.
It is about momentum.
Start today. Build forever.
I started this challenge because most people wait for the perfect time to invest and never build momentum. For me, it is $50 a day into one conviction stock for 20 years. No timing. No guessing. Just proof of discipline. What challenge would you commit to if your only goal was to build wealth over decades, and what do you think of this 20 year challenge? Give me your honest take.