Insider transaction reports made between May 21 and May 27, 2026, show a mix of confidence-driven purchases and planned or large-scale disposals across a range of U.S.-listed companies. The disclosures include private placement participation, open-market buying by an institutional holder, director purchases executed over multiple days, and large sales tied to option exercises, indirect holdings or Rule 10b5-1 plans. Below is a company-by-company accounting of the most significant moves disclosed over the period.
Top insider buys
HCW Biologics Inc. recorded meaningful insider participation in a private placement conducted on May 22, 2026. Hing C. Wong, who serves as Chief Executive Officer, a director, and a 10 percent owner, purchased 113,879 shares of common stock at $1.405 per share for an aggregate of $159,999. These shares were acquired directly from the issuer at a price below the security's then-current trading level of $1.95. The filing notes that HCW Biologics has returned 99.88% year-to-date, though it trades with high volatility. The disclosure also reports a second board-level purchase that same day: director Scott T. Garrett purchased 177,936 common shares at $1.405 per share for a total of $250,000. In addition to the equity purchase, Mr. Garrett acquired 177,936 common stock purchase warrants with an exercise price of $1.28 per share and an expiration date of November 22, 2031. Each warrant conveys the holder the right to acquire one share of common stock.
BOSTON OMAHA Corp. saw a concentrated buying program by director Jeffrey C. Royal across a six-day span. Between May 22 and May 27, 2026, Mr. Royal accumulated shares valued at $520,983 via multiple transactions executed at prices ranging from $12.40 to $12.82 per share. The company's share price was trading at $12.59 at the time of reporting, reflecting a 16% decline over the past 12 months, and InvestingPro analysis indicated the stock is modestly overvalued relative to a Fair Value of $12.33. On May 27, Mr. Royal recorded a direct purchase of 10,000 shares of Class A common stock at $12.72 per share.
TWFG, Inc. reported the largest single insider purchase by dollar amount for the week. Director Michael Doak disclosed purchases of Class A common stock totaling $882,585, executed over three transactions filed with the SEC on May 27, 2026. The purchases took place between May 22 and May 27, 2026, at per-share prices ranging from $18.62 to $19.23. The filing details the individual trades: 11,000 shares acquired on May 22 at $18.89 each; 11,000 shares on May 26 at $19.23 each; and 24,880 shares on May 27 at $18.62 each, for a cumulative total of 46,880 shares. TWFG's share price was reported at $18.57, a drop of 35% over the previous six months and approximately half of its 52-week high of $36.85. InvestingPro analysis included in the reporting suggested the stock appears undervalued with a Fair Value estimate of $32.43.
GameSquare Holdings, Inc. drew material purchases from an institutional investor rather than a company insider. Blue & Silver Ventures, Ltd. disclosed open market purchases of GameSquare ordinary shares amounting to roughly $328,873. The Form 4 reported that on May 26, 2026, the investor bought 620,100 shares at $0.4331 per share. On May 27, 2026, the same entity purchased another 144,346 shares at a weighted average price of $0.4178, with the series of trades recorded at individual prices between $0.40 and $0.4327.
Top insider sells
Infleqtion, Inc. disclosed two of the more sizable insider sales during the filing window. CEO and director Matthew John Kinsella sold common stock totaling approximately $13.1 million across multiple transactions on May 22 and May 26, 2026. Those sales followed an exercise of fully vested stock options: on May 22 Mr. Kinsella exercised options to acquire 545,824 shares at $0.90 per share, representing a purchase cost of $491,241 prior to the subsequent dispositions. In a separate and much larger set of transactions, director David B. Singer completed sales amounting to about $181.6 million over two days in May. The SEC filing shows that on May 21 Mr. Singer sold 6,369,163 shares of Infleqtion common stock at a price of $14.6934 per share; additional sales took place on May 22, with executed prices ranging up to $17.0408 per share. The company was trading at $15.46 at the time of reporting, up 51% over the prior year but still below a 52-week high of $27.50. The filing specifies that Mr. Singer sold shares held indirectly through several entities, including Maverick Long Fund, Ltd.; Maverick Fund II, Ltd.; Maverick Advisors Fund, L.P.; Maverick Designated Investments Fund, L.P.; Maverick Ventures Investment Fund, L.P.; and Maverick Silicon Fund, L.P. The disclosure states Mr. Singer is connected to these entities either through a limited partner interest or as a managing partner.
Twilio Inc. registered a very large sale from entities affiliated with Sachem Head Capital Management LP, including the investment adviser Sachem Head Capital Management LP and Twilio director Andrew J. Stafman. These reporting persons sold 1,000,000 shares of Class A common stock on May 27, 2026, at a per-share price of $184.14, totaling $184,140,000. After these transactions, the filings indicate the indirectly held shares by these reporting persons total 620,000 shares of Class A common stock. Twilio's market price at reporting was $181.57, a 55% gain over the last year, and InvestingPro analysis in the filings noted that the shares may be overvalued at current levels. The disclosures further note that 18 analysts had raised earnings estimates for an upcoming period, according to InvestingPro Tips. The filings also show that Andrew J. Stafman directly holds 13,492 shares of Class A common stock but has granted all ownership interests in those shares to Sachem Head for no consideration pursuant to an arrangement.
Cloudflare, Inc. saw planned disposals under a pre-established trading plan. Michelle Zatlyn, President and Board Co-Chair, sold 86,362 shares of Class A common stock between May 22 and May 27, 2026. The transactions were executed under a Rule 10b5-1 trading plan adopted on February 14, 2025. The sale activity spanned multiple days: May 22, May 26, and May 27, with share prices ranging from $208.45 to $216.24 per share, and the aggregate proceeds reported to be approximately $18.3 million. Cloudflare's trading price at the time of the filing was $209.22, with a 12-month return of 29% noted in the disclosure. The filing also indicates all sold shares were held indirectly through The Sutherland/Zatlyn Revocable Trust dated November 17, 2016, for which Ms. Zatlyn serves as co-trustee.
AppLovin Corp. recorded a sizable Rule 10b5-1 sale executed by its Chief Technology Officer, Vasily Shikin. On May 22, 2026, Mr. Shikin sold 70,316 shares of Class A common stock under a trading plan adopted on December 9, 2025. The collective proceeds from those transactions were reported as approximately $34,346,827, with sale prices ranging from $477.71 to $493.66 per share. The filing specifies that 62,204 of the sold shares were held directly by Mr. Shikin. After the transactions he remained a direct holder of 3,189,739 shares of AppLovin Class A common stock, some of which are represented by Restricted Stock Units. AppLovin's reported market price at the time of filing was $568.01, and the company had posted a roughly 50% gain over the past year. The filing also included an InvestingPro assessment indicating the shares may be overvalued versus the firm's Fair Value estimate and placed the company among highly valued market equities.
What the filings collectively indicate
The set of filings for the week highlights a split picture: insiders and related parties at smaller or mid-cap issuers participated in private placements and staged purchases, while executives, directors and affiliated entities at larger growth names executed substantial sales for a variety of stated or disclosed reasons. The filings include option exercises followed by sales, sales under Rule 10b5-1 plans, transactions by indirect holders, and open-market accumulation by an institutional investor. Details in the filings emphasize that sales do not, by themselves, equate to a negative forecast by insiders, as dispositions can follow option exercises or trading plans adopted months prior; conversely, purchases by insiders and institutional buyers can reflect a vote of confidence or a strategic allocation. Investors should consider the mix of motivations for these trades when weighing them alongside other fundamental and market data.
Notable patterns by sector and market cap
- Smaller-cap, high-volatility issuers such as HCW Biologics and GameSquare attracted purchases that were executed either via private placement or open-market accumulation.
- Insurance and financial services names, represented here by BOSTON OMAHA and TWFG, featured director-level purchases executed across multiple days.
- Large-cap technology and software companies including Twilio, Cloudflare, and AppLovin disclosed substantial planned or affiliated sales, including Rule 10b5-1 activity and indirect transfers tied to institutional arrangements.
Takeaways for market observers
Monitoring insider filings offers a window into the transactions of those closest to company operations and ownership, but interpretation requires context. Purchases may indicate confidence or opportunistic accumulation at lower prices, while sales can stem from financial planning, option exercises or pre-planned strategies. The filings in this reporting period illustrate both ends of that spectrum: director and CEO purchases in smaller, more volatile names on the one hand, and very large disposals tied to indirect holdings or structured plans at larger growth companies on the other.
For investors focused on fundamentals and product-market fit, these filings are one input among many. They signal where insiders and affiliated institutional holders are deploying or extracting capital, but they do not provide a definitive statement on future operational performance. Incorporating insider activity into a wider analysis that includes revenue, margins, user metrics and valuation can help place these disclosures in a constructive decision-making framework.
Detailed list of tickers mentioned
- GAME - GameSquare Holdings, Inc.
- TWLO - Twilio Inc.
- NET - Cloudflare, Inc.
- INFQ - Infleqtion, Inc.
- APP - AppLovin Corp.
- HCWB - HCW Biologics Inc.
- BOC - BOSTON OMAHA Corp.
- TWFG - TWFG, Inc.
Investors and observers should treat these filings as factual disclosures of completed transactions and structured plans. The filings record dates, quantities, prices and the nature of holdings or plans where specified. They do not, on their own, explain the broader strategy or longer-term intentions of each insider or affiliated institution beyond the documented transactions.
Disclosure: The article reflects reported SEC filings and InvestingPro analyses as presented in the filings; it does not provide investment advice and is intended as a factual summary of disclosed insider activity.