A Lone Insider Joins the Crowd

Early February brought a sharp sell-off in SaaS and AI infrastructure names. Some high-growth software stocks fell as much as 80% from prior peaks.

Retail investors, duly trained by Wall Street’s sell-side, stepped in “buy the dip” in “software as a service” (SaaS).

According to JPMorgan data, after dip-buying hit a year-to-date low on February 5, 2026, retail flows surged, particularly into high-quality names like Microsoft.

John Stanton, a Microsoft director, stood out as the lone insider. Stanton bought nearly $2 million in shares, right as the tech giant hit its 200-week moving average:

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A Microsoft insider makes a $2 million share buy. (Source: TrendSpider)

The last insider buy at Microsoft? April 4, 2025, amid the tariff tantrum market lows.

While the broad S&P 500 is down 2%, Microsoft has gotten whacked… down over 20% from last year’s peak.

Most insider sales are simply noise. Insiders have many reasons to sell shares – especially as stock options tend to be a big part of compensation.

Insider buying is a strong indicator that a bottom may be settling in. A company’s executive – presumably a full-time expert on the company and its operating environment – sees value with upside.

One buyer doesn’t make a trend. But insider buying around these levels in software stocks may be an indicator that the worst has passed… for now.

~ Addison

P.S. Yesterday on Grey Swan Live! did a deep dive into stocks that are several steps removed from bear market trends on the Wall Street indexes. Matt Milner, Private Market Profits, gave us a tour of – and a strategy for – investing in the massive private capital markets usually reserved for well-connected investors: the pre-IPO space.

Elong Musk’s SpaceX and Palmer Luckey’s Anduril have grabbed headlines this year as their unicorn giants approach their very public launch into the AI stock market.

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Matt Milner created a way to get access to these companies before they go public.

Early February brought a sharp sell-off in SaaS and AI infrastructure names. Some high-growth software stocks fell as much as 80% from prior peaks.

Retail investors, duly trained by Wall Street’s sell-side, stepped in “buy the dip” in “software as a service” (SaaS).

According to JPMorgan data, after dip-buying hit a year-to-date low on February 5, 2026, retail flows surged, particularly into high-quality names like Microsoft.

John Stanton, a Microsoft director, stood out as the lone insider. Stanton bought nearly $2 million in shares, right as the tech giant hit its 200-week moving average:

Turn Your Images On

A Microsoft insider makes a $2 million share buy. (Source: TrendSpider)

The last insider buy at Microsoft? April 4, 2025, amid the tariff tantrum market lows.

While the broad S&P 500 is down 2%, Microsoft has gotten whacked… down over 20% from last year’s peak.

Most insider sales are simply noise. Insiders have many reasons to sell shares – especially as stock options tend to be a big part of compensation.

One buyer doesn’t make a trend. But insider buying around these levels in software stocks may be an indicator that the worst has passed… for now.

~ Addison

Elong Musk’s SpaceX and Palmer Luckey’s Anduril have grabbed headlines this year as their unicorn giants approach their very public launch into the AI stock market.

Turn Your Images On

Matt Milner created a way to get access to these companies before they go public.

SpaceX is the most valuable private startup in history — and if its success continues, it might become the most valuable public company in history.

After all, as Musk famously said in 2023, “I have never lost money for those who invest in me and I am not starting now.”

For investors, SpaceX has been a wild, joyful ride — and now the journey continues!

The Supreme Court voted 6–3 to block President Trump’s use of the International Emergency Economic Powers Act to impose his “Liberation Day” tariffs.

Chief Justice John Roberts wrote that the Constitution grants tariff authority to Congress alone. Justices Thomas, Alito, and Kavanaugh dissented.

The case centered on Trump’s 10% global tariff and the higher reciprocal tariffs layered on select trading partners. Oral arguments were heard in November. The Court concluded that IEEPA did not authorize such broad tariff power.

A concurrent research paper from the New York Fed concluded that American consumers bear most of the tariff cost.

According to Global Markets Investor, U.S. dominance peaked in late 2024. The relative line has trended downward for fifteen months. Leadership has dispersed. Even though we’ve been writing about the alarming, historic, high concentration in the Mag 7 at the very top of the indexes, large amounts of capital moved before the financial media headlines caught up.

The “real” annual return on bonds – net of inflation – is 2%. That’s before high transaction costs to buy and sell bonds or paying taxes on your bond income.

The return for investors, even for a safe-haven investment, is too low. Bonds will only assert their vestigial “safe-haven” status if there’s a stock market crash. (At that point, trust in everything else will have disappeared.)

SpaceX is the most valuable private startup in history — and if its success continues, it might become the most valuable public company in history.

After all, as Musk famously said in 2023, “I have never lost money for those who invest in me and I am not starting now.”

For investors, SpaceX has been a wild, joyful ride — and now the journey continues!

The Supreme Court voted 6–3 to block President Trump’s use of the International Emergency Economic Powers Act to impose his “Liberation Day” tariffs.

Chief Justice John Roberts wrote that the Constitution grants tariff authority to Congress alone. Justices Thomas, Alito, and Kavanaugh dissented.

A concurrent research paper from the New York Fed concluded that American consumers bear most of the tariff cost.

The “real” annual return on bonds – net of inflation – is 2%. That’s before high transaction costs to buy and sell bonds or paying taxes on your bond income.