2026 - Year of the Horse

The Year of the Horse symbolizes freedom, energy, and success - a lot of people have been telling me that lately. Horses are strong, fast, and beautiful and I spent a lot of my youth at race tracks with my Dad betting the ponies. I don’t exactly know what it all means but I like horses, so let’s fucking get it this year.

To those of you who read this every week in 2025, shared it with friends, and hit reply to tell us what moved you, thank you. This thing’s just getting started, and already you’ve helped us turn the corner on what it can become.

We’re proud to say we donated $4,000+ through The Fountain in 2025, including your recommendations on Thanksgiving to great organizations. (Including Helen’s Acres Community Farm, Chefs in the Classroom, Venice Family Clinic, Safe Place for Youth (LA), My Friend Dave YYC, CO Foodbank, Kelowna Women’s Shelter, Mamas for Mamas, and Childhood Connections.) And we helped fund the amazing Chris Koch’s participation in the Chicago Marathon!

Hope your year is off to a great start, pointed in a direction that matters to you.

Let’s keep sharpening our lens, together. Enjoy this week’s edition.

In 2026, the experimenting continues…

We will be digging a little deeper into policies and patterns that shape the world we live in, and the ones we’re trying to build.

We’ll try not to rant and we will aim to make you think. Sometimes the best way to sharpen your lens is to widen the frame. This is Potentially a “Drain” topic, but what we want to keep in mind is the positive outlook of public discourse, which we consider to be a “Fountain”.

This first piece in this series is on a theme I keep seeing and feeling along the lines of “Eating the Rich” and today we’re looking at Toronto’s new “Luxury Tax” and what happens when governments forget that capital — like people — moves fast.

Let’s make this a forum for open dialogue, learning and debate, share it with your friends, reply to this email let’s talk if you agree, disagree, or think we’re missing a piece.

This is a finance heavy week, but I am very interested in Tax and treating people equally, so we’re exploring our own interests along with the conversations we’ve had with all of you, enjoy!

⏳️ Estimated Read Time: 6 minutes

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Eat The Rich - Toronto’s ‘Luxury’ Tax: A Masterclass in Fiscal Deflection

In a 17-7 vote, Toronto City Council doubled down on its graduated Municipal Land Transfer Tax (MLTT), a levy the city has colloquially branded as a "Luxury Tax."

By drawing an arbitrary line at the $3 million mark, the city hopes to extract an additional $152 million in annual revenue.

But for anyone tracking the intersection of municipal bloat and capital flight, the "luxury" label looks less like a fiscal necessity and more like a political scapegoat.

To understand the "why," one must look at the "where it goes."

The City of Toronto now maintains a payroll of over 40,000 employees, with its 2025 "Sunshine List" (those earning over $100,000) representing over $1.3 billion in total compensation.

While the private sector grapples with productivity, the city’s largest unions—representing municipal workers—have secured annual wage increases ranging from 3.5% to 4.9% through 2027.

Leading this charge is Mayor Olivia Chow, whose own salary has climbed to approximately $225,300—making her one of the highest-paid municipal leaders in the country while she oversees the largest tax hikes in Toronto's history.

This isn't merely progressive taxation; it's an assault on capital mobility.

We aren't talking about a marginal increase in income tax—socially agreed-upon based on annual earnings.

We are talking about the "height of the hoop" changing mid-game for residents who bought into the market decades ago. A homeowner who purchased a modest property for $300,000 in the 1990s—which, through no fault of their own, is now a $3 million asset—finds themselves in the crosshairs of a tax rate that scales up to a staggering 8.6% for properties over $20 million.

When an individual is already taxed at a 52% top marginal rate, the government’s constant return to the "wealthy well" feels like a deflection from their own administrative ineptitude. It is easier to tax a $3 million home than it is to clear an encampment or solve a housing supply bottleneck caused by the city’s own bureaucracy.

History warns us that these "Eat the Rich" policies are often self-defeating.

The evidence is already appearing in the data: Canada’s net inflow of millionaires—long a reliable engine of investment—has cratered from 3,200 in 2024 to a projected 1,000 in 2025, the lowest level on record.

Domestically, the exodus is even more localized; Ontario saw a net loss of over 23,000 residents to other provinces in just the first quarter of 2025 alone. Wealthy residents are no longer just looking at other cities; they are looking at other jurisdictions entirely.

Look at Los Angeles’s "Measure ULA" (the so-called Mansion Tax) implemented in 2022. In the year following its adoption, high-end sales and investment plummeted by as much as 50% to 75% in certain tiers. Investment capital didn't just pay the tax; it evaporated, taking with it the very construction jobs and ancillary tax revenues the city claimed to protect.

Toronto’s leadership seems to believe that high-value residents are a captive audience. They are wrong. In a globalized economy, the "best players" don't have to play on an 11-foot hoop. They can take their talents, their capital, and their tax dollars to new leagues. If Mayor Chow continues to shoot at the city's most productive citizens, she may find herself on a very expensive court, playing a game with no one left to fund the lights.

Context

Circle Stock - Well sometimes your early and my decision to purchase circle stock for $130.00 was preceded by a decline in the stock over the next few months to a low of $76.00. approx a 50% loss.

Listening to the Earning Calls

I listen to the earnings calls of the companies I own. I love watching the Berkshire Hathaway AGM and so when the CRCL stock dropped - I listened to the call (you can listen here). All the numbers were great Revenue Growth, User Growth, Market Share, Yet the stock got halved. 

Dollar Cost Average

I invested approx $100,000 in the first purchase at $130. When you like a company and then the company value goes down, if you have the nuts, and more dry powder you can Dollar Cost Average.

What is Dollar Cost Average? Watch this great video walking down wall street.

So I decided to Dollar Cost Average Down and invest another $100,000 at $80.00, so now my total position is $200,000 with a dollar cost average of $100.00 which will help receiver the loss, and hopefully become a win. 

Circle is now trading today at $84.85.

So summary is get again seek your own financial advice, but I am still long Circle and doubled down.

Wishing you all the best in your investments and look forward to hearing from you what companies your investing in going into 2026.

My favorite financial publication, Barrons, also just shared their picks for 2026.  

Thanks for being here as part of the Community and wishing you and yours an incredible 2026 of health, happiness, and abundance.

Please let us know what topics or questions you want to see on the fountain and be a fountain this week. All love.