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