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Retail investors hold 0% of the company behind ChatGPT.
The rest of the cap table breaks down this way: Microsoft holds roughly 27%, the nonprofit parent holds 26%, and employees hold about 25%. For most readers, that breakdown is where interest in the story typically ends — there's no share class available to buy.
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3 Stocks Under the Microscope After Large Insider Sales
Author: Leo Miller. Article Published: 9/28/2026.
Key Points
- Seagate Technology, Adobe, and Chime Financial have all seen notable insider selling recently, but the reasons behind those transactions differ substantially.
- Seagate’s insider activity comes after a massive AI-driven rally, while Adobe’s sales stand out because they came from CEO Shantanu Narayen during a period of weak share-price performance.
- Chime Financial has also seen heavy selling following strong earnings and a sharp rebound, although major insiders and early investors still retain sizable positions.
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Insiders are selling shares of one of the top beneficiaries of the AI boom, a software behemoth facing a wave of negative sentiment and an up-and-coming fintech name. Not only does the recent performance of these companies differ significantly, but so do the details of their recent insider sales. As a result, closely examining each set of insider moves is necessary to understand how strong a bearish signal the sales actually send.
Seagate Sales Spike in Q3 With Shares Up Over 200% in 2026
Despite many AI-related stocks soaring in 2026, few have achieved gains as impressive as those of Seagate Technology (NASDAQ: STX), with shares up well over 200%. The company’s primary product is hard-disk drives (HDDs), which have seen a resurgence in demand amid the AI boom. This comes as hyperscalers look for high-capacity and economical storage products to house the immense amount of data generated and used by AI. This helped sales increase by 48.5% year over year (YOY) last quarter, marking some of Seagate’s fastest growth in more than a decade.
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Watch Whitney Tilson's urgent briefing and prepare your portfolio nowHowever, the company has also seen a significant amount of insider selling recently. In Q3, insider sales totaled $379 million, more than triple the $107 million recorded in Q2. This raises questions about whether Seagate insiders believe the stock’s impressive run is coming to an end. However, insiders made at least $125 million of these Q3 sales to satisfy tax-withholding requirements upon the vesting of employee stock units. Because these sales are not discretionary, they do not constitute negative signals.
Still, many sales, including Teh Ban Seng’s large $41.2 million sale, were not attributable to tax withholdings. Additionally, most sales occurred at prices considerably below Seagate’s recent levels. Overall, Seagate’s recent sales provide a mildly bearish signal, but investors should recognize that nondiscretionary sales contributed substantially to the spike.
Adobe CEO Initiates Large Sales With Shares Deeply in the Red
Software giant Adobe (NASDAQ: ADBE) has lost approximately $50 billion in market capitalization in 2026, with shares down around 30% on the year. Still, the company has generally maintained strong financial performance. It currently expects to generate adjusted earnings per share (EPS) of $24.45 to $24.50 in fiscal 2026, which would represent a nearly 17% YOY increase at the midpoint. That would be a notable acceleration from the 13.7% YOY EPS growth recorded in fiscal 2025. Still, sentiment around the company remains weak, primarily because investors fear AI tools will damage long-term demand for Adobe products.
Amid the stock’s poor performance, it is concerning that CEO Shantanu Narayen recently sold more than $31 million worth of the company’s shares. This equates to Narayen selling more than one-third of his holdings, a very significant percentage. It is not exactly a confidence-inspiring signal from Adobe’s top executive. However, the Form 4 filing notes that the sales were “primarily made for the reporting person's tax and estate planning purposes.” Nonetheless, the size of the sales is difficult to ignore.
Narayen will step down as CEO in December, which somewhat limits the negative signal as he moves away from day-to-day management. However, he will continue to hold a prominent role as Adobe’s executive chair. Overall, it is difficult not to view the sale as a bearish indicator, especially with Adobe shares down so significantly.
Chime’s Insider Sales Balloon After Blowout Earnings
Chime Financial (NASDAQ: CHYM) is an approximately $10 billion fintech company that provides consumer banking and payment solutions. The stock has soared recently, rising approximately 50% in the last six months. This is largely the result of Chime’s latest earnings report, which caused shares to rise more than 20% in one day. The company posted strong growth and profitability improvements, with revenue rising 27% YOY and its second consecutive quarter of positive GAAP EPS. Its adjusted earnings before interest, taxes, depreciation and amortization margin also expanded by 12 percentage points YOY to 15%.
However, since Chime’s report, the company has seen around $618 million worth of insider selling. For a company with a market capitalization of only $10 billion, that is a significant amount. It appears that insiders are taking substantial profits after the stock’s strong performance.
Still, it is important to note that many insiders continue to hold massive positions in the company. This includes DST Global Advisors, which still holds more than 35 million shares through several funds. Many sales also came at well above $30 per share, substantially higher than Chime’s recent levels. Overall, the sales are mildly bearish and may indicate that insiders see limited near-term upside above the mid-$30 range.
Not All Insider Sales Send the Same Signal
While none of these sales are positive signals for the companies involved, their circumstances differ enough that the raw dollar totals should not be viewed equally. Narayen’s Adobe sale stands out because of its size relative to his prior holdings, but the filing explicitly ties it primarily to tax and estate planning. Looking ahead, it will be worth monitoring whether Narayen continues to significantly reduce his position. If the sales prove to be an isolated incident, they would align with the tax and estate-planning rationale rather than signal a broader lack of confidence.
Akamai’s Anthropic Deal Puts $5.5 Billion Behind Its Edge AI Pivot
Reported by Jeffrey Neal Johnson. Publication Date: 9/28/2026.
Key Points
- Akamai secured a firm $11.6 billion, seven-year cloud infrastructure deal with Anthropic that could grow to roughly $20 billion in total value.
- The company plans $5.5 billion in capital expenditures to support the contract, which will compress operating margins and pressure near-term profitability.
- Anthropic received warrants for up to 5% of Akamai's shares, creating equity dilution risk while Akamai also paused its buyback program.
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Akamai Technologies (NASDAQ: AKAM) recently secured a $11.6 billion cloud infrastructure commitment from AI developer Anthropic. The agreement accelerates Akamai's evolution from a legacy content delivery network into a distributed compute operator.
Capitalizing on this structural shift requires significant infrastructure investment. Management projects $5.5 billion in capital expenditures (CapEx) to support the contract, including approximately $1.7 billion in additional CapEx during 2026 to secure critical components such as memory. That spending will pressure free cash flow in the near term, while the warrants issued to Anthropic create potential equity dilution as the relationship expands. Investors evaluating the transition must weigh the long-term value of anchoring a premier AI tenant against the near-term financial costs of deploying the necessary hardware.
Zoning for AI: $11.6 Billion in Edge Compute
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See what's next for SAGA Metals before the deadline hitsThe seven-year agreement marks a clear pivot in Akamai's network utility. The $11.6 billion figure represents a firm commitment. Contract parameters allow for up to $9 billion in additional spending, bringing the maximum potential transaction value to approximately $20 billion. Recognizing this distinction is important when valuing the forward revenue pipeline, as the remaining $9 billion depends entirely on Anthropic expanding its usage.
Beyond the dollar amounts, the arrangement's technical specifics point to a broader shift in artificial intelligence (AI) infrastructure. Anthropic specifically requires distributed CPU environments rather than the centralized GPU clusters typically associated with large language model development. While foundational model training demands concentrated GPU power, large-scale model execution, often referred to as inference, can benefit from distributed, low-latency CPU networks positioned closer to the edge.
By catering to this CPU demand, Akamai is positioning its cloud platform as a scalable AI inference network. Processing data closer to the end user can reduce latency and bandwidth costs, which are critical factors for AI agents performing real-time tasks. This supports the view that some inference workloads could eventually migrate away from expensive, centralized data centers and toward distributed edge environments. Akamai is adding this deal to the more than $2.8 billion in multi-year cloud infrastructure commitments across its customer base that it announced earlier this year, demonstrating momentum in its compute segment.
The Price of Construction: $5.5 Billion in Capital Costs
Supporting these enterprise workloads demands a substantial upfront investment. Akamai estimates total related CapEx of $5.5 billion over the life of the contract. Approximately $1.7 billion of that total is scheduled for 2026 to secure critical supply chain components, particularly memory. Because management maintained its 2026 revenue guidance, this accelerated spending will weigh on near-term free cash flow and capital efficiency before the full revenue contribution develops.
The legacy content delivery network business continues to contract, with delivery revenue down roughly 6% year over year in Akamai's most recent quarter. The Anthropic partnership is an important part of Akamai's effort to offset this legacy decline as it shifts its revenue mix increasingly toward security and compute.
This transition materially alters the shareholder return profile. Akamai traditionally pays no dividend and recently paused its share buyback program during the second quarter of 2026 to reallocate capital toward cloud infrastructure expansion. By halting buybacks, Akamai removed a consistent buyer from the market, eliminating a mechanism that can often provide a floor for the stock price. Shareholders now rely primarily on capital appreciation during a high-CapEx cycle, magnifying the risk if margin compression lasts longer than expected.
Paying the Contractors: The Equity Cost of Anchor Tenants
Securing an anchor AI tenant required structural concessions that directly affect Akamai's capital structure. Anthropic received a warrant to purchase non-voting convertible Series B preferred stock representing up to 7.7 million shares, or roughly 5% of Akamai's outstanding common stock. The strike price is $111.33.
A 2% tranche of the warrant vests immediately based on the initial $11.6 billion commitment. This creates a quantifiable baseline for potential equity dilution associated with finalizing the partnership. The remaining 3% vests in 1% increments for every $3 billion in additional cloud services purchased during the seven-year term.
With a strike price near current trading levels, these warrants are essentially at the money, introducing tangible dilution risk. If the cloud migration is successful and Akamai's valuation climbs, Anthropic will likely exercise the warrants and capture a portion of the upside. Presenting the $20 billion maximum transaction size as guaranteed revenue would misrepresent the deal structure. The additional equity issuance remains contingent on client expansion, aligning Anthropic's upside with Akamai's performance while diluting existing shareholders.
Checking the Foundation
Wall Street's reaction suggests a polarized view of the deal's capital intensity. Institutional ownership stands at approximately 94%, heavily concentrated among major asset managers. This high level of institutional ownership may help explain the rapid retracement of the post-announcement price spike, as institutions assess the multi-year timeline required for free cash flow to normalize.
Akamai currently trades at a price-to-earnings multiple near 41.10x, while return on equity is approximately 8.92% and its weighted average cost of capital is 5.04%. Compared with growth-oriented cloud operators, these figures suggest a business in transition rather than a fully optimized cloud platform.
Short interest currently represents about 13% to 14% of the outstanding float, with a short ratio nearing six days to cover. This elevated short positioning reflects skepticism regarding operating margins and near-term CapEx burdens. Options data also skews defensive, with near-term expirations showing a higher put-to-call ratio and signaling active hedging against post-catalyst drawdowns.
The broader market currently applies a legacy content delivery discount to Akamai. The company trades at a compressed multiple compared with pure-play edge network peers such as Cloudflare (NYSE: NET). If the CPU-heavy inference strategy succeeds and compute revenue outpaces the decline in legacy delivery, a realistic path to multiple expansion exists. Bridging the gap between current capital outflows and future profitability, however, will require flawless execution.
Tracking the AI Infrastructure Pivot
Investors tracking this transition should monitor several fundamental indicators to gauge execution. The most immediate metric is sequential quarterly operating margins, which will reveal the financial impact of the $1.7 billion capital outlay. Comparing actual capital expenditures with projections will clarify the cash burn rate and its effect on Akamai's balance sheet.
Onboarding additional enterprise AI clients will show whether the distributed CPU model can attract a broader customer base. Relying heavily on Anthropic introduces single-customer concentration risk. Securing additional tenants would validate the edge computing architecture and diversify revenue. Conservative investors evaluating a position may prefer to watch upcoming earnings cycles to assess how the infrastructure buildout affects free cash flow generation before committing capital to the transition.
Investors with a higher risk tolerance might view the current CapEx-driven cash flow pressure as a temporary discount and initiate a position to capture potential multiple expansion before AI inference revenue fully materializes. Entering the stock during this foundational phase offers an opportunity to anticipate the institutional capital that could rotate back in once free cash flow begins to normalize.
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