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Dear Fellow Investor,
This CEO Just Bought $2 Million Worth of His Company’s Stock – Should You?
When company insiders put their own money on the line, investors should take notice.
Insider buying — especially large purchases from executives or board members — is often seen as a sign of confidence. After all, who knows the company better than someone running it? While it’s never a guarantee of future returns, insider activity can provide valuable insight into how leadership views the company’s prospects.
But not all insider buying is created equal. Context matters. A small purchase by a director isn’t the same as a CEO doubling down with millions. And that’s exactly what we’re seeing in some compelling names right now.
One of the most notable recent insider purchases came from Match Group (NASDAQ: MTCH) — but it wasn’t the only one. Executives at Nike and Advanced Micro Devices (AMD) also made significant buys.
Here’s a closer look at these three stocks — and why they might be worth a deeper dive.
Company: Match Group (SYM: MTCH)
A $4 Million Bet on the Future of Connection
Match Group — the parent company of popular dating apps like Tinder, Hinge, and Match.com — just received a bold vote of confidence from its CEO.
Spencer Rascoff, who took the helm at Match Group just 100 days ago, has now purchased $4 million worth of MTCH stock in just two quarters. His most recent buy: 70,885 shares for $2 million, split between an average price of $27.89 for 53,398 shares and $28.54 for the remainder. That’s on top of the $2 million he bought back in February at $34.41 per share.
That brings his total ownership to 137,478 shares.
As Rascoff stated in a post quoted by Barron’s:
“100 days in as CEO and more confident than ever in our team and Match Group’s future... Energized by the responsibility and privilege of defining the future of connections for this category.”
Match Group is also looking to reward shareholders in other ways. The company declared a quarterly dividend of 19 cents per share, payable on July 18 to shareholders of record as of July 3.
This marks a notable shift for Match, which had previously focused more on growth than shareholder returns. The introduction of a dividend suggests a maturing company, with leadership confident enough in its cash flow and long-term strategy to begin consistent payouts.
In short: a turnaround play led by a CEO who’s backing his conviction with serious cash.
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Company: Nike (SYM: NKE)
Insider Buy Meets Analyst Upgrade
It’s not every day you see a well-known retail stock trading near multi-year lows. But that’s the case with Nike (NYSE: NKE) — and at least one insider is taking advantage.
Director Robert Swan Holmes recently purchased $502,756 worth of shares at an average price of $58.46, a substantial buy for a company of Nike’s size.
Wall Street is starting to warm back up to the stock as well.
Jefferies recently upgraded Nike to a “Buy” rating and slapped a $115 price target on the stock — nearly double its current level. Their case is centered on a few key ideas:
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Valuation reset: The stock is now near what Jefferies calls a “valuation trough,” meaning expectations (and prices) are low enough to offer a good entry point.
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Product pipeline: Nike is “turning back on its innovation engine,” which could spark a fresh cycle of new product launches.
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Improved inventory position: With wholesale distribution expected to expand and inventories becoming more balanced, margins may improve as the company sells more products at full price.
With expectations low and both insiders and analysts showing renewed optimism, Nike might be primed for a rebound.
Company: Advanced Micro Devices (SYM: AMD)
A Big Bet on AI’s Future
The semiconductor industry has been front and center in the AI boom — and Advanced Micro Devices (SYM: AMD) is one of the most talked-about names in the space.
So when a top executive buys in, it’s worth paying attention.
On May 20, AMD’s Executive VP and Chief Commercial Officer Philip Guido bought 8,800 shares for just under $1 million. It’s a substantial show of confidence in the chipmaker’s long-term prospects — particularly in the AI space.
CEO Lisa Su recently revised AMD’s total addressable market (TAM) for AI chips to $500 billion by 2028 — a significant jump from her previous estimate of $400 billion by 2027. That would represent a massive expansion, equal to the entire semiconductor industry’s sales in 2023.
AMD’s newest product, the MI300, is its fastest-growing launch ever. The MI300X — a direct competitor to Nvidia’s H100 — is being positioned as “the most advanced AI accelerator in the industry,” according to Su.
The chip is already generating buzz as a viable alternative to Nvidia’s dominant position — and could provide AMD with a larger slice of the AI hardware market over the next few years.
For long-term investors betting on AI infrastructure growth, AMD remains a key player — and now, a freshly confident insider just reinforced that view.
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