My Biggest Investing Regret in 2025 Was Buying This Stock

Regret shows up when you replay 2025 with today’s prices, but the useful question stays simple: Did you buy a business or did you buy a story? Regret can teach you more than wins if you let it right now. High rates, headline swings, and quick “policy pivot” rumours made it easy to chase momentum and call it conviction. When you look back, separate bad process from bad luck. Write down what you thought would happen, what had to be true, and how long you planned to wait. Then check whether you followed your own rules on position size, diversification, and risk. Do you need an example? Let’s look at mine.

WEED

Yep, I invested in Canopy Growth (TSX:WEED) back in the day and certainly got some wins. It sits near the centre of Canada’s cannabis boom-and-bust story. The cannabis stock sells marijuana in Canada across adult-use and medical channels, and it also sells vaporizers through Storz & Bickel. It brands its products with names many investors recognize, like Tweed and 7ACRES. The stock still attracts attention as it feels like a “one headline away” name, for better or worse.

Over the last year, Canopy’s news flow looked like a mix of hope and hard reality. Traders chased U.S. policy headlines, especially the push to move marijuana to a less restrictive federal schedule, as that idea can change taxes and financing for the industry. The headlines sparked sharp moves, but the follow-through stayed uncertain, and investors kept pricing in delays. That gap between hype and timelines punished anyone who bought the pop and forgot the calendar.

Canopy also kept trying to reshape its balance sheet and its path into the United States. In January 2026, it announced recapitalization transactions and plans to refinance and extend maturities, with proceeds aimed at paying down existing secured debt and funding general corporate needs. That sort of move can buy time, but it also reminds you that WEED stock still needs financial engineering alongside operational improvement.

Looking at earnings

Now for the numbers that mattered most. In its second quarter of fiscal 2026, WEED stock reported consolidated net revenue of $67 million, up 6% year over year. It generated cannabis net revenue of $51 million, with $24 million from Canadian adult-use and $22 million from Canadian medical. The company also reported $298 million of cash and cash equivalents, and it said that cash exceeded debt balances by about $70 million at quarter’s end.

Those results showed real progress in a few places. Canopy cut selling, general, and administrative expenses by 13% year over year, and it said it captured $21 million of annualized savings since Mar. 1, 2025. It also narrowed its adjusted earnings before interest, taxes, depreciation, and amortization (EBITDA) loss to $3 million from $6 million a year earlier. Investors should like that direction, as cost control can create breathing room when pricing pressure hits, and consumers trade down.

However, valuation tells a harsher story, and it explains a lot of the regret. On recent quotes, WEED stock traded around $1.50 per share with a market cap near $602 million, and it showed a deeply negative trailing earnings per share of $2.67. The stock also sat way down from 52-week highs, down 48% at writing, which signals how quickly sentiment can flip in this space. Even a decent quarter can’t fix a broken long-term chart on its own.

Bottom line

Looking ahead, WEED stock’s bull case needs more than a single catalyst. It needs sustained share gains in Canada, continued expense discipline, and a clearer route to value from its U.S. interests, including brands like Wana Brands and Jetty Extracts under the Canopy USA umbrella. The bear case still looks familiar: ongoing losses, dilution risk if capital needs return, and regulatory timelines that move at political speed, not market speed. That’s why I decided to cut my losses into something more stable.

For today’s investor, set triggers. A string of quarters with shrinking losses, cash strength, and guidance you can trust. If a U.S. policy shift arrives, assume volatility, not certainty. Decide where you take profits or cut losses, then stick to it.

The post My Biggest Investing Regret in 2025 Was Buying This Stock appeared first on The Motley Fool Canada.

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More reading

• 2 Popular Stocks That Could Wipe Out a $100,000 Nest Egg
• 3 Risky Stocks That Could Send Your $100,000 Investment to $0
• Here’s Why I Wouldn’t Touch Canopy Growth Stock With a 10-Foot Pole
• 3 Overhyped Stocks to Leave Behind in the New Year
• 2 Stocks That Could Turn $100,000 Into $0 Faster Than You Think

Fool contributor Amy Legate-Wolfe has positions in Canopy Growth. The Motley Fool has no position in any of the stocks mentioned. The Motley Fool has a disclosure policy.