Toronto hedge fund manager hunts for stocks that could rise 100x in value — here’s how hunting for 100-baggers shaped his career

According to a report by Jon Erlichman published on BNN Bloomberg’s Ticker Take, Jackson sets a minimum threshold of a 50-fold return over a five-year horizon for any new stock position, with his ultimate sight fixed on a 100-fold gain.

Jackson explained that the thrill of finding massive multi-baggers drives his investment process, attracting retail investors who are seeking life-changing wealth creation rather than modest incremental gains.

High concentration and heavy drawdowns

To execute his strategy, Jackson maintains a highly concentrated portfolio — holding only 10 to 12 equities rather than spreading capital thinly across broad indexes.

“I’d rather have some diversification through those names,” Jackson told BNN Bloomberg, “rather than only plowing my money into one Carvana and having the rest of the portfolio in a bunch of indexes.”

But to achieve his outsized returns, Jackson admits that the portfolio has to endure severe volatility. Highlighting online auto retailer Carvana Co. (NYSE: CVNA) as an example, Jackson pointed out that the stock suffered five or six drops ranging between 30% and 40%, along with a single plunge of 62%.

“You feel really stupid,” Jackson remarked regarding watching unrealized wealth evaporate during pullbacks, adding that significant drawdowns are simply the necessary price of entry for outsized long-term upside.

The screening mechanism and pattern recognition

Jackson uses artificial intelligence (AI) tools to scan the broader market for potential investment targets, likening AI screening to a watering hole where key investment ideas naturally gather. However, he emphasizes that algorithmic filters only serve as an initial starting point, with final decisions hinging entirely on human judgment and corporate pattern recognition.

Instead of searching for conventional value metrics, Jackson looks for companies the market has fundamentally mischaracterized. His framework focuses on identifying specific operational triggers before mainstream Wall Street analysts react, such as:

• Executive leadership turnarounds: Jackson targets underperforming companies undergoing major management changes, such as real estate platform Opendoor Technologies Inc. (NYSE: OPEN) hiring former Shopify Inc. executive Kaz Nejatian to overhaul operations, or social network Nextdoor Holdings Inc. (NYSE: NXDR) bringing back founder Nirav Tolia.

• Corporate insider buying: Tracking executive behaviour provides critical timing cues, such as watching Carvana leadership aggressively purchase company shares a full year before the online auto retailer began its major market rebound.

• Underappreciated infrastructure assets: Jackson seeks out companies whose physical or technological assets are mispriced by the market. This includes digital asset miners like IREN Ltd. (NASDAQ: IREN), Cipher Mining Inc. (STU: 3A9.SG) and Hut 8 Corp. (NASDAQ: NMS) that possess land and power infrastructure suitable for high-demand AI data centres, as well as post-quantum cybersecurity developers like BTQ Technologies Corp. (NASDAQ: BTQ)

• Catalysts in unloved or polarizing sectors: He actively hunts in out-of-favour corners of the market, targeting heavily discounted turnaround stories like fitness firm Peloton Interactive Inc. (NASDAQ: PTON), mortgage lender Better Home & Finance Holding Co. (NASDAQ: BETR), or fintech lender Dave Inc. (NASDAQ: DAVE)

Navigating the high-stakes trade-off

Ultimately, Jackson’s strategy highlights the calculated trade-off required when attempting to generate better-than-market investment returns. None of his portfolio entries represent safe, predictable holdings; each relies on taking positions before public sentiment catches up — positions that require taking on risk. While substantial losses on wrong calls is an inevitable part of operating on the market’s fringes, Jackson maintains that for investors willing to endure sharp paper losses, the ability to capture even a single 100x winner can swing the strategy in the investor’s favour — and redefine long-term financial outcomes.