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Perhaps the easiest, most profitable strategy in investing is to simply follow the smart money.

Smart money can be corporate insiders: the people who actively run a company and know more about its operations than anyone.

And smart money can also be investing legends: the people who are in the top 0.01% of investors.

But in the case of Under Armour (UA) today, it’s both.

Under Armour is a global designer and retailer of performance-oriented athletic apparel, footwear, and accessories. The company operates a dual-channel business model, selling products both through major wholesale partners and its own direct-to-consumer platforms.

And business has been struggling to say the least.

UA went public in its current iteration in 2016. At their peak UA shares traded $45 per share and the company was valued at $19 billion. It has since lost $17 BILLION of that value as revenues declined along with profitability.

UA missed the “athleisure” boom that ignited in 2017, choosing to focus on sports-related apparel while other companies like Athletica acquired market share.

UA also struggled to pivot towards female apparel, while other female centric companies like Lulu Lemon (LULU) rode that wave to tens of billions of dollars.

And it failed to fend off competition from shoe rivals Hoka, On Running, and Brooks.

Revenues have stagnated and profitability has disappeared: profit margins have recently dipped into negative territory, a sharp reversal from the healthier 6%–7% margins seen just a few years ago.

Who would buy such a company?

Glad you asked.

While Wall Street believes UA is doomed, corporate insiders are loading up.

On August 13th 2025, Director Dawn Fitzpatrick bought $493,000 worth of UA stock.

A week later, another Director Mohammed El-Erian bought $519,000 worth of UA stock.

Three days later, a 3rd Director Robert Sweeney bought $488,000 worth of UA stock.

And then came the investing legends.

Prem Watsa is widely considered to be the “Warren Buffett” of Canada. As CEO of FairFax Financial, Watsa has maintained average annual gains of ~18% since 1985. He did this following the same principles Warren Buffett used: taking highly concentrated bets on undervalued stocks.

Today, Watsa is taking a MASSIVE stake in UA stock. In the last month, he’s bought over $200 MILLION worth of a company or a little under 10% of the shares outstanding.

Something BIG is brewing here. High level corporate insiders only load up on their company’s shares when they KNOW major gains are coming. But to see corporate insiders AND one of the greatest investors of the last 50 years buying a stock to the tune of hundreds of millions?

This is the kind of set up where fortunes are made.

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