Matthew Prince April NET Sell: Class B Convert-Drip

Cloudflare CEO and board co-chair Matthew Prince filed Form 4s on April 7 and April 8 covering a now-familiar founder mechanic: convert one tranche of Class B super-voting stock to Class A, then drip-sell the resulting Class A position into the open market. The headline-grabbing number — total sale proceeds in the low single-digit millions on the day — undersells what the filing actually documents. The signal is in the cadence and the math underneath, not the dollar total of a single Form 4.

What the April filings show

Two Table II derivative lines, two days apart:

• 2026-04-07: 52,384 Class B shares converted to Class A. Post-conversion holding via derivative securities: 4,637,305 shares.
• 2026-04-08: 52,384 Class B shares converted to Class A. Post-conversion derivative holding: 4,584,921 shares.

And on the Class A side (Table I, non-derivative), April 8 carried fifteen separate execution lines at staggered prices between roughly $214.71 and $222.69. The largest single line was 4,588 shares at $214.71 — about $985,000. Total Class A position remaining after the April 8 prints: 659 shares.

Read literally, Prince's reportable Class A holding sits at 659 shares — a number you might think implies near-total exit. That reading is wrong, and it's the most important fact in this filing.

The 7.7% beneficial stake that doesn't show up on Table I

Per the February 13G/A on file with the SEC, Matthew Prince beneficially owns 26,338,507 shares of Cloudflare common stock — approximately 7.7% of the company. That holding is almost entirely the Class B super-voting block, which is what April's two conversions chipped 104,768 shares off of. At today's Class A market price near $215, the residual Class B-equivalent stake is worth on the order of $5.7 billion.

This is the multi-class founder structure working exactly as designed: economic exposure is concentrated in Class B, which carries 10 votes per share against Class A's one vote. Class A trades the public market; Class B trades almost never except through these conversion windows. Reporting that an insider on Form 4 "owns 659 shares" because Table I says so — and stopping there — is how journalism gets dual-class founders wrong.

The institutional book around Cloudflare

What gives this conversion-and-drip pattern its tension is the institutional book Prince is selling into. The recent 13G/A filings tell a coherent story about who the actively positioning holders are right now:

Two things stand out. First: Capital World Investors — the American Funds growth complex — is the single largest declared shareholder, ahead of the founder. That is unusual for a CEO-led tech name with super-voting Class B still active. Second: Baillie Gifford's stake has been on a one-way slide. From 8.9% in an April 2025 13G/A, to 7.0% by November 2025, to 5.3% by February 2026 — three sequential downshifts in under twelve months. That is a managed exit, not a rebalance.

Set against Baillie's drawdown, Prince's conversion-and-drip looks comparatively gentle: 104,768 shares against a 26.3M-share beneficial position is approximately 0.4% of the founder stake. The optics of a CEO trim are different from the substance.

The 10b5-1 question

Form 4 line 10 carries a footnote box for noting whether the transaction was executed under a 10b5-1 plan adopted in advance of the trading window — the standard structure that lets insiders trade through earnings blackouts without the appearance of acting on material non-public information. Prince's April filings include the relevant disclosure pointing to a 10b5-1 program; the daily-cadence executions on April 8 (fifteen lines, staggered prices, mechanical block structure) are consistent with a VWAP-style algorithmic execution under such a plan.

For investors trying to read intent: a 10b5-1 plan does not mean the founder has no view on the stock. It means the view, if any, was crystallized when the plan was filed — typically several quarters earlier — and the execution from that point on is automatic. April 2026's sales were almost certainly priced into Prince's intentions some time in late 2025 or early 2026, well before Q1 earnings.

What to watch from here

Three forward anchors:

• Q2 2026 Form 4 cadence: if Prince's 10b5-1 plan runs through a full year of monthly windows, expect similar two-day conversion-and-drip patterns to appear roughly monthly through mid-2026. Absence of those filings — particularly if Class A market price moves materially — would itself be the signal.
• Capital World Investors' next 13F (Q2 2026, due August 14): Capital World as the single largest declared holder is the institutional name worth tracking. Any meaningful trim from their book at 11.5% would change the institutional consensus picture for NET more than any founder sale would.
• Baillie Gifford's next 13G: the slide from 8.9% to 5.3% is approaching the reporting-threshold floor at 5.0%. If they cross under, the next 13G/A could be an exit filing — and exit filings from long-horizon growth holders usually price differently from passive-rebalancing exits.

The April 8 print is small. The pattern it documents — and the gap between Table I and the actual 7.7% beneficial stake — is the part to file away. See Cloudflare's full ownership profile for the institutional context, and Prince's full transaction history for the cumulative shape of the founder sell program.