Prince Matthew, CEO and Board Co-Chair of Cloudflare (NET), has demonstrated a consistent and pronounced selling bias in his insider transactions, with no recorded purchases across 254 filings. His total sell activity amounts to $293.7 million, all concentrated in NET shares. The most recent transactions, executed on March 17–18, 2026, involved 24 separate sales totaling over $19.3 million, with individual transactions ranging from $24,624 to $5.96 million. The largest single sale occurred on March 17 ($5.96 million), followed by a $3.44 million disposal the same day. March 18 saw multiple mid-sized sales, including a $1.93 million transaction and two others exceeding $1 million.
The pattern suggests ongoing, structured divestment rather than isolated liquidity events. Notably, all transactions occurred within a two-day window, with no offsetting buys—a continuation of Matthew’s historical activity. The absence of purchases, coupled with the scale and frequency of sales, underscores a one-directional approach to his holdings in Cloudflare. While the filings do not indicate whether these sales were prearranged (e.g., 10b5-1 plans), the consistency and concentration in a single ticker highlight a deliberate reduction in exposure to NET. The transactions represent a small fraction of his total sales history but reinforce the broader trend of monetizing his equity position in the company.
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