Week 19 of My Strategy Investing Journey The Streak and the Shares Keep Building

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 18 of My 50 a Day Strategy Journey the Streak Is the Real Wealth.

The Market Was Rough but the Streak Lives On

This week was not friendly to the market. September historically has a reputation for red weeks, and Week 19 proved why. My portfolio closed more than 12 percent down, and for the first time in a while, I felt the tug of disappointment.

But here is the paradox: while the dollar value dipped, my shares kept growing.

That is the tradeoff every disciplined investor has to face. When prices drop, the portfolio looks worse on paper, but you are actually stacking ownership faster.

Week 19 of my $50 a day MSTR investing journey with 18.17 shares and $6,083 invested. The streak continues.

The Emotional Split

I will be honest: part of me was frustrated watching hundreds vanish in market value.

But the other part of me was excited because cheaper prices mean more shares.

And this is where discipline becomes more important than feelings.

You cannot have both emotions at once. You either cling to portfolio value and get anxious, or you focus on ownership and get stronger. I choose ownership.

Shares and Portfolio Value

By the close of Week 19, I now own 18.17 shares of Strategy with a portfolio value of $6,083.

Yes, that is down slightly from last week’s $6,110. But context matters:

• $6,000 invested already is further than most people ever get.

• This streak has been running for less than 5 months.

• Shares are compounding every week, regardless of price swings.

This system is not about chasing green weeks. It is about stacking ownership until the milestones pile up to 25 shares, $10,000 in value, and eventually six and seven figures over time.

Strategy journey progress from week 1 to week 19 showing total MSTR shares and portfolio value growth

The BakoBar Comparison

While Strategy took a hit, so did most of the market. The BakoBar is my weekly reminder that drawdowns are normal, and all assets go through them.

Week 19 BakoBar comparison of MSTR, Bitcoin, Gold, SPY and QQQ

The Discipline Behind the Streak

I do not skip days.

When the market closes for holidays like Labor Day, I buy $50 early to stay true to my 365-day system. Every Monday I add $100 to cover weekend days. Every holiday I make a manual $50 buy.

This is bigger than MSTR.

This is about proving that discipline works when emotions fail.

Start Your Journey

The streak begins with your first proof of discipline. Every platform below gives you a small nudge, so you have zero excuses not to start:

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

• Webull - advanced tools and multiple free stocks to kick off your account

• Acorns - invest your spare change automatically and they give you $5 to start

• Coinbase - buy fractional Bitcoin and earn up to $25 in crypto rewards

• Crypto.com - fast way to buy and stake altcoins

These offers are not the wealth. The wealth is in the streak you build after you take the first step.

Milestones Ahead

I see two clear checkpoints:

• 25 shares - a psychological milestone (a quarter of 100).

• $10,000 portfolio value - another big step in the compounding journey.

But here is the truth: milestones matter less than the streak itself.

The streak is the real wealth.

The Lesson for You

This journey is not about copying me.

It is about building your own system, one you can stick with through bear markets, dips, and boredom.

You could pick one stock.

You could build toward $1,000 in each of your five favorite assets.

You could do $5 a day instead of $50.

The ticker is optional. The discipline is not.

Posts You Might Like

• My Strategy DCA System for 20 Years

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

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

Final Word

Week 19 reminded me that this streak is not about dollar signs. It is about ownership, identity, and consistency.

When the market dips, I add.

When the market rises, I add.

Every week, I document.

The lesson is simple:

You escape the traps of average investing not by predicting, but by showing up.

Follow me

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🐦 Join the conversation on X @BakoExperience and share your own streak.