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An index-beating stock picker shares 3 under-the-radar AI trades he's betting on

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Kilito Chan
  • The Osterweis Opportunity Fund beat the Russell 2000 in 2024 by finding overlooked tech stocks.
  • Small-cap software stocks will benefit from the next wave of AI, says Bryan Wong, a PM of the fund.
  • Here are 3 of his high-conviction AI stock picks.

The so-called "AI trade" has become almost synonymous with either Big Tech or utilities companies over the last two years. Now, Wall Street is expecting the scope of AI investment opportunities to widen into beneficiaries of the technology.

Bryan Wong, a portfolio manager of the small-cap Osterweis Opportunity Fund (OSTGX) with James Callinan and Matt Unger, has already been ahead of the curve.

Based in San Francisco, Wong has used his expertise in the technology industry and meticulous stock-picking process to find overlooked opportunities in the market, especially ones using AI to grow their margins. It's paid off: in 2024, the fund returned 22%, beating the Russell 2000 index's 15% return for the same period.

In an interview with Business Insider, Wong shared what's led to his success — and what he's betting on going forward.

The small-cap AI advantage

Most investors have gained exposure to the AI trade just by buying the S&P 500. After all, Apple, Microsoft, Amazon, Nvidia, and Alphabet make up roughly a third of the index's total capitalization.

But to capitalize on up-and-coming AI opportunities, investors need to do some more digging. There are a lot of AI winners in the small-cap space for those who take the time to look for them, Wong said.

As the AI trade matures, banks like Goldman Sachs are recommending investing in "Phase 3" stocks, or companies directly using AI to enhance their revenues, such as software companies.

Small-cap software companies are especially well-positioned to take advantage of this next wave of AI investing, according to Wong. He's particularly bullish on vertical software. Unlike horizontal software companies like Salesforce or Microsoft, which provide general-purpose solutions for many industries, vertical software companies are designed to address specific needs for a singular market.

Small caps have a competitive advantage when it comes to vertical software, according to Wong.

"If you're a vertical-specific company, you own the distribution, you own the data, you have relationships with the customers. You can be more efficient on sales and marketing as well because you're focused on one vertical," Wong said.

It's much easier for a smaller company to develop a specialized niche with stickier revenue streams. In contrast, a company like Salesforce has to spread its sales and marketing across hundreds of verticals, making it difficult to create a competitive advantage, Wong added.

Under this strategy, several of Wong's picks have expanded rapidly and outgrown the small-cap categorization. Below, Wong identified three software AI beneficiaries that he's bullish on going forward. They are all constituents of the Osterweis Opportunity Fund.

3 software AI trades

Guidewire Software

Guidewire Software one year stock performance
Markets Insider

Ticker: GWRE

Market Cap: $14.4 billion

Company description: Guidewire provides software solutions for property and casualty insurers, including policy, billing, and claims management systems.

Commentary: "Guidewire is the 800-pound gorilla of insurance property and casualty insurance. Companies like Geico, State Farm, and Allstate use Guidewire for their mission-critical claims filing and processing," Wong said.

Axon Enterprise

Axon Enterprise one year stock performance
Markets Insider

Ticker: AXON

Market Cap: $44.2 billion

Company description: Axon is a public safety company that develops technology and equipment for the military and law enforcement, including TASER devices.

Commentary: "[Axon] was founded originally on Tasers, so they dominate that market, then they add it on body cameras," Wong said. These hardware products also serve as data collection points, which integrate directly with Axon's cloud-based software. For example, body camera footage can be wirelessly uploaded, timestamped, and transcribed.

Duolingo

Duolingo one year stock performance
Markets Insider

Ticker: DUOL

Market Cap: $13.7 billion

Company description: Duolingo is a gamified language-learning platform.

Commentary: "This is a stock that I think very few people were following and paying attention to, but it's outperformed in video lessons," Wong said.

To Wong, the expertise of the management team is also a plus. "One of the things we look for is real technical jobs and founders," Wong said. Duolingo co-founder and CEO Luis von Ahn is a professor at Carnegie Mellon and previously sold his company reCAPTCHA to Google in 2009.

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