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.

Through the first 41 trading days of 2026, the S&P 500 traded within a 2.7% range — the narrowest start to any year since 1928. The first 41 days of 2008 spanned roughly 35%. In 2020, the range ran near 15%. Even the placid 1950s never opened this tight…

Since the Iran attack began, global markets have been chaotic. Despite some wild intraday swings this week, the U.S. stock market has held up well. When bombs go flying, capital moves from frontier markets to safer shores. And even though the U.S. has been the one to aggressively move against Iran, capital that was going to foreign markets has shifted back to New York.

Ever since the re-election of Trump, the blue tribe has been searching for another event it could use to repeat its success with BLM. They thought they had finally found it with ICE (its enforcement actions produce numerous excesses it could exploit).

In normal times, the Chinese operate a quota system for refined product exports; this week, the throttle tightened. And even though they are Asia’s third-largest exporters of “energy,” the country still draws close to half its imported crude from the Gulf, including nearly all Iranian shipments.