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.

Copper and resources are sending us a cleaner market signal than AI stocks.

Channeling Ludwig von Mises, we observe this morning that price is not just a number; it’s information. Price reflects what buyers and sellers collectively believe: demand, scarcity, fear, speculation, disappointment, future expectations and available supply.

When prices rise, and inventories fall at the same time, the message is usually straightforward: buyers need the stuff, and there is not enough of it.

A low VIX does not predict disaster. It measures complacency. A serial skeptic will read it as the calm before a storm. We shook off that feeling this morning and opted to pursue an opportunity instead.

Here goes:

A VIX reading below 15 means the market is not pricing in much near-term trouble, even though there are obvious risks still sitting in the room: Iran, oil prices, memory chip speculation, circular financing, high valuations, epic high concentrations, spiking long-term interest rates, a regime change at the Fed, a meltdown in Japan and a historic deficit and rising national debt.

Money is not flowing in a clean, straight line from outside investors to productive businesses. The firms at the top are investing in and buying from each other.

Microsoft and OpenAI are the easiest examples to follow.

Microsoft says OpenAI has contracted to purchase an additional $250 billion in Azure services, while Microsoft continues to account for $13 billion in funding commitments to OpenAI as an investment.

At this stage, it’s a stock picker’s market.

We expect space, robotics and some more visible tech startups to remain sources of speculation. After weakness in the first half of 2026, we’re also due for a strong rotation of capital into natural resources, precious metals, critical minerals and energy.

Copper and resources are sending us a cleaner market signal than AI stocks.

When prices rise, and inventories fall at the same time, the message is usually straightforward: buyers need the stuff, and there is not enough of it.

Here goes:

Money is not flowing in a clean, straight line from outside investors to productive businesses. The firms at the top are investing in and buying from each other.

Microsoft and OpenAI are the easiest examples to follow.

Microsoft says OpenAI has contracted to purchase an additional $250 billion in Azure services, while Microsoft continues to account for $13 billion in funding commitments to OpenAI as an investment.

At this stage, it’s a stock picker’s market.