Week 20 of My Strategy Investing Journey Discipline and Share Growth

This post is part of my ongoing twenty year fifty dollars a day investing series in Strategy (MSTR). Each week I document the streak, the share growth, the portfolio value, and the discipline behind the system. You can read last week’s update here: Week 19 of My Strategy Investing Journey the Streak and the Shares Keep Building.

How I Felt in Week 20

MSTR dipped for the third week in a row. That means my portfolio value slid deeper into the red, and yes that stings.

But here is the other side: my shares grew faster, and my average cost dropped dramatically. That is the quiet advantage of sticking with the system.

I could buy more if I wanted to. But I don’t.

Because my system says 50 dollars a day, $100 on Mondays, and $50 on holidays. Nothing more. Nothing less.

👉 If you want to build your own investing streak, here are the same platforms I use:

• Robinhood - easy daily automation, plus free stock when you sign up

• Webull - great for research, plus free stocks when you join

• Acorns - invests your spare change automatically, $5 to start

• Coinbase - buy Bitcoin fractionally, get a $35 bonus

• Crypto.com - fast access to altcoins and staking options

The Mental Game of Money

This week taught me again that making money is not only math. It is a mental game.

If you don’t gamify your system, you will burn out.

If you don’t enjoy the streak, you will break it.

My game is simple: 20 years, one share at a time.

Sometimes it feels lonely. I don’t know anyone else playing this game at this scale or with this discipline. But that is also what makes it powerful, the identity you build by doing what most won’t.

Week 20 Progress

Week 20 portfolio snapshot of my Strategy (MSTR) journey

By the numbers:

• Shares: 19.06

• Portfolio value: $6,217.12

• Average cost: dropping fast, even in red weeks

Week 1 to 20 shares and portfolio value growth in my Strategy journey

Even though the portfolio is down, the streak is alive. And more importantly, the system is working exactly as designed: accumulating ownership at cheaper prices.

The BakoBar

BakoBar Week 20 shows MSTR down 3.40 percent while Bitcoin and Gold closed strong

The BakoBar keeps me grounded. Every asset goes through drawdowns. This week, everything looked shaky. But that’s exactly when streaks pay off.

Looking Ahead

The next milestones are clear:

• 25 shares - a quarter of 100

• $10,000 portfolio value - the first real five-figure checkpoint

I know both are coming. I don’t know when. But the streak guarantees I’ll get there.

And when the comeback happens? The math of cheap accumulation will make it look explosive.

Final Lesson

If you take one thing from Week 20, let it be this:

You don’t need to chase every stock or every coin. You need a system you can repeat without breaking.

Mine is simple. Yours can be too.

Stick with it. Stack ownership. Let time do the work.

Posts You Might Like

• How Dollar Cost Averaging Builds Wealth Even When Markets Crash

• The First 10 Shares Are the Hardest That Is Why They Matter Most

• Most People Quit Investing in 3 Months I Am Going 20 Years

PS

Your streak does not have to look like mine. But it does have to start.

👉 Grab your free stock with Robinhood or Webull,

👉 Start investing automatically with Acorns,

👉 Or stack Bitcoin with Coinbase ($35 bonus) and Crypto.com.

The system you commit to is more important than the dollar amount you start with.

This journey is for the underdogs and 9-to-5 workers who are told wealth is out of reach. It is not about timing the market, it is about proving that discipline beats emotion. Every $50 buy is a receipt of ownership, a brick in the foundation of long-term wealth. If you want to follow along, subscribe to my weekly updates and join me as I build this position one share at a time.

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