We’ve Changed Our Investing Strategy 4 Times (Here’s Why)

I used to think that people who invested successfully were wealthy and had it all figured out.

That they had a strategy they were crystal clear on.
That they executed flawlessly.
That they always knew what they were doing.
And that they got it right the first time.

But here we are, entering our 7th year as investors and we’re changing our strategy again.

We’re now in our fourth season of investing, and I can finally see the pattern: it’s an ever-evolving strategy.

So why am I writing this today?

To give you a gentle nudge if you’re still waiting for the ‘perfect’ moment to start investing.

I hope this shows you that there’s no perfect moment, only an evolving process.

Today I’d love to pull back the curtain and walk you through the four ‘seasons’ our portfolio has lived through over the past six years.

Because the strategy we use today looks nothing like the one we started with in early 2020.

Want to watch it evolve? Let’s jump in.

(And as always, this is not financial advice. I’m just a person on the internet sharing what worked for us. Do your own research.)

My husband and I were in bed in March 2020 with our brand-new baby, cuddled up while the world shut down outside.

Boredom hit, so we started learning about investing.

Between a book he was reading and a YouTube video I found showing a detailed walk through on how to buy dividend stocks, we entered season one.

We threw money at big Canadian banks and anything that paid a dividend.

Just “buy stuff we’ve heard of that sends us cash.”

Why was it an accidental win? Because we bought our first dividend stocks in April 2020 — right at the bottom of the COVID crash (pure, dumb luck).

Those stocks soared 40–50 % in the next year and paid us $150–$200/month on average in dividends.

Accidental win achieved.

We aggressively dumped every extra dollar from work into dividend-paying Canadian stocks with no real plan.

Not until we entered season 2.

Then, in March 2021, one YouTube video sent us down a new rabbit hole: investing for cash flow.

Mind. Blown.

This became the bedrock of our strategy — the one that let us reach financial independence in our early 30s, quit working, and take a multi-year sabbatical in our mid-30s.

The idea? Invest in funds that focussed on cash flow instead of capital growth as the primary return mechanism.

I’ve written about this strategy. You can catch-up here:

This strategy worked so well that we sold our townhouse and rental property in 2021 and went all in on cash-flowing ETFs.

We started season 2 with ~$3,000 in monthly cash flow from our portfolio.

We reinvested every dollar we earned in dividends in addition to a few thousand a month that we saved.

And every month, our portfolio compounded.

We stayed in this season of focused investing from March 2021 to July 2024.

Three years of ruthless consistency later, we reached $7,000+/month.

Then, in mid-2024, life threw us a curveball.

That curve ball set in motion the third phase of our journey.

It was a late summer evening in June 2024 when our landlord showed up at our door and served us eviction papers.

She sold the house and we had exactly 2 months to vacate.

We made the bold decision to sell most of our stuff, put the rest in a storage locker and become nomads.

With the support of our monthly income from the portfolio, I made the decision to unwind my decade-long health consulting business and stop working.

There was no more fresh capital going in and we lived off ~60 % of dividends, only reinvesting the Tax Free Savings Account distributions.

Compounding slowed… but life didn’t.

We spent a fun-filled year in Bali, the Dominican Republic, and Vancouver, chasing sun and slow mornings.

Income still crept from $7,084 → $8,100/month through TFSA reinvestment + fund distribution increases.

Same strategy as Season 2, just a different use of the cash.

With expenses fully covered and a rock-solid income base, we asked new questions:

“How do we accelerate growth?”
”Was there a bigger swing we could be taking?”
”What if we could make a move NOW to set us up five years from now?”

This foundational thinking set us up for season 4.

Before we dive in, one piece of clarity: we only made this “big swing” decision because we had full stability with our monthly income. (Our November 2025 portfolio income was $8,498).

Anything invested from here on out in the new strategy we could afford to lose.

The two biggest opportunities right now? The biggest disruption plays we could go all in on: Bitcoin and AI.

We cleaned up our portfolio and maintained our monthly cashflow with only 80% of our invested capital.

With the remaining 20%? We split it between Bitcoin and Tesla.

Bitcoin is a hard asset that offsets our dollar that is devaluing every year due to money printing and inflation.

Tesla is a vertically integrated AI play that is well diversified — robotaxis and fully self-driving vehicles, energy and data centres, investment into xAI, and the development of the Optimus robot.

The compound annual growth rate (CAGR) of these two assets is above 30% annually, averaged over a four-year cycle.

If we could even get 25% CAGR, we would be way ahead of the 14.26% return of our cash-flowing portfolio.

The only trade-off: we had to take on the risk that at any time, bitcoin or Tesla could go to zero.

Once we reallocated 20% of our portfolio to those two assets, the path forward was relatively simple and boring.

Every month, we reinvest our TFSA distributions and buy Bitcoin or Tesla on dips.

Our income stays flat(ish) at ~$8,500/month, but the growth side is now on rocket fuel.

In November, our confidence in our new strategy (income stability + big swings in disruptive assets) felt locked in.

We see it working with a clear path forward, our time horizon set to 5-7 years out.

What if every dollar we invested NOW could create exponentially more wealth in the future?

We wanted to throw some fuel on this fire.

With big dreams for our future, we made the decision to buckle down and start a new business.

The goal? Build our agency to $20,000/month gross revenue by month six and funnel 90% of net profits into building this portfolio.

With AI advancing quickly and jobs being wiped out daily, I believe the world is going to change fast and most people won’t be ready for it.

And it’s easy to say it won’t come that fast or it won’t affect my job… but what if it does?

Amazon laid off nearly 14,000 people last month and replaced them with AI.

Walmart is warning of massive job cuts and these companies aren’t the only ones.

My husband and I are hyper-focussed on building a moat around our family, a safety net that provides stability in an uncertain future.

I never want to put myself in a position where we need to rely on government handouts or universal basic income to live a barely comfortable life.

We’ve got the shovels in hand. We’re digging the moat.

If we don’t need it? Great.

If we do? We’ll be glad we started digging now.

It hasn’t been linear or smooth.

We couldn’t have built today’s strategy in 2020 because we weren’t ready.

We couldn’t have predicted the turns we would take.

We had to live the dips, make the mistakes, and let the vision evolve, one decision at a time.

So if you’re at the beginning, the middle, or anywhere in between…

maybe it’s time to throw some gasoline on your own fire.

What’s your family’s priority right now?

Hyper-growth? Stability? Safety?

Begin with the end in mind and build toward your version of freedom.

Let this letter be the gasoline you pour on your own fire.

I’ll be over here throwing gas on mine.

Let’s GO.