Cloudflare (NYSE: NET) CEO’s trusts sell shares under 10b5-1 plan
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
Cloudflare, Inc. reported insider transactions involving trusts associated with CEO and Board Co-Chair Matthew Prince. On June 22–23, 2026, these trusts sold a net 104,768 shares of Class A Common Stock in open-market trades at weighted average prices spanning from about $212.43 to $230.04 per share.
The filing also shows that trusts converted a total of 79,218 shares of Class B Common Stock into an equal number of Class A shares, reflecting the one-to-one, no-expiration convertibility of Class B into Class A. One reported indirect account held 52,384 Class A shares after these transactions. The sales were executed under a pre-arranged Rule 10b5-1 trading plan adopted on February 11, 2025, indicating the timing was set in advance.
Positive
- None.
Negative
- None.
Insider Trade Summary 10b5-1
Net Seller: 104,768 shares ($23,221,887)
Net Sell
39 txns
Insider
Prince Matthew
Role
CEO & Board Co-Chair
Sold
104,768 shs ($23.22M)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Conversion | Class B Common Stock | 52,384 | $0.00 | -- |
| Conversion | Class A Common Stock | 52,384 | $0.00 | -- |
| Sale | Class A Common Stock | 395 | $216.2062 | $85K |
| Sale | Class A Common Stock | 483 | $217.2044 | $105K |
| Sale | Class A Common Stock | 370 | $218.2024 | $81K |
| Sale | Class A Common Stock | 825 | $219.3122 | $181K |
| Sale | Class A Common Stock | 1,030 | $220.5847 | $227K |
| Sale | Class A Common Stock | 3,339 | $221.3281 | $739K |
| Sale | Class A Common Stock | 5,522 | $222.4714 | $1.23M |
| Sale | Class A Common Stock | 2,134 | $223.2787 | $476K |
| Sale | Class A Common Stock | 5,459 | $224.6401 | $1.23M |
| Sale | Class A Common Stock | 10,478 | $225.3191 | $2.36M |
| Sale | Class A Common Stock | 5,059 | $226.251 | $1.14M |
| Sale | Class A Common Stock | 5,975 | $227.6067 | $1.36M |
| Sale | Class A Common Stock | 4,538 | $228.6522 | $1.04M |
| Sale | Class A Common Stock | 6,666 | $229.3658 | $1.53M |
| Sale | Class A Common Stock | 111 | $230.04 | $26K |
| Conversion | Class B Common Stock | 26,834 | $0.00 | -- |
| Conversion | Class A Common Stock | 26,834 | $0.00 | -- |
| Sale | Class A Common Stock | 3,990 | $212.9718 | $850K |
| Sale | Class A Common Stock | 2,543 | $213.9672 | $544K |
| Sale | Class A Common Stock | 4,560 | $214.9428 | $980K |
| Sale | Class A Common Stock | 6,268 | $216.069 | $1.35M |
| Sale | Class A Common Stock | 7,752 | $216.9738 | $1.68M |
| Sale | Class A Common Stock | 8,697 | $217.956 | $1.90M |
| Sale | Class A Common Stock | 2,834 | $218.7256 | $620K |
| Sale | Class A Common Stock | 4,915 | $220.1083 | $1.08M |
| Sale | Class A Common Stock | 3,583 | $220.9871 | $792K |
| Sale | Class A Common Stock | 2,258 | $222.0855 | $501K |
| Sale | Class A Common Stock | 2,868 | $223.0753 | $640K |
| Sale | Class A Common Stock | 1,818 | $223.9689 | $407K |
| Sale | Class A Common Stock | 298 | $225.0274 | $67K |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
Holdings After Transaction:
Class B Common Stock — 4,348,551 shares (Indirect, See footnote);
Class A Common Stock — 52,384 shares (Indirect, See footnote)
Footnotes (1)
- Each share of Class B Common Stock is convertible at any time into Class A Common Stock on a one-to-one basis at the reporting person's election and has no expiration date. The shares are held of record by The Matthew Prince Revocable Trust dated October 29, 2015, for which the reporting person serves as trustee. The sale reported in this Form 4 was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 11, 2025. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $212.43 to $213.42, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in footnotes (4) through (30) to this Form 4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $213.43 to $214.415, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $214.475 to $215.44, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $215.485 to $216.48, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $216.485 to $217.48, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $217.485 to $218.475, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $218.495 to $219.45, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $219.54 to $220.525, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $220.56 to $221.555, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $221.56 to $222.55, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $222.56 to $223.54, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $223.56 to $224.53, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $224.57 to $225.25, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $215.535 to $216.465, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $216.57 to $217.55, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $217.77 to $218.67, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $218.78 to $219.73, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $219.88 to $220.87, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $220.88 to $221.84, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $221.88 to $222.875, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $222.88 to $223.85, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $223.88 to $224.8775, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $224.88 to $225.865, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $225.90 to $226.895, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $227.03 to $228.02, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $228.04 to $229.03, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $229.04 to $230.025, inclusive. The shares are held of record by The Prince Family Nonexempt Irrevocable Trust dated March 29, 2016, for which the reporting person serves as an investment advisor. The shares are held of record by The Prince Family Exempt Irrevocable Trust dated March 29, 2016, for which the reporting person serves as an investment advisor. The shares are held of record by The Prince 2021 Remainder Trust dated September 23, 2021, for which the reporting person serves as an investment advisor. The shares are held of record by The Matthew Prince 2024 Grantor Retained Annuity Trust dated May 20, 2024, for which the reporting person serves as co-trustee and investment advisor. The shares are held of record by The Matthew Prince 2024 Grantor Retained Annuity Trust 2 dated August 20, 2024, for which the reporting person serves as co-trustee and investment advisor. The shares are held of record by The Matthew Prince 2025 Grantor Retained Annuity Trust dated May 10, 2025, for which the reporting person serves as an investment advisor. The shares are held of record by The Matthew Prince 2025 Grantor Retained Annuity Trust 2 dated August 11, 2025, for which the reporting person serves as co-trustee and investment advisor.
Key Figures
Net shares sold: 104,768 shares
Converted Class B shares: 79,218 shares
Post-transaction Class A in one account: 52,384 shares
+3 more
6 metrics
Net shares sold
104,768 shares
Net Class A open-market sales, June 22–23, 2026
Converted Class B shares
79,218 shares
Class B converted into Class A at one-to-one ratio
Post-transaction Class A in one account
52,384 shares
Indirect Class A holdings in a reported trust after trades
Highest reported sale price
$230.0400 per share
Class A open-market sale price on June 23, 2026
Lowest price range cited
$212.43 per share
Lower bound of a weighted average sale price range
10b5-1 plan adoption date
February 11, 2025
Date CEO adopted pre-arranged trading plan
Key Terms
Rule 10b5-1 trading plan, Class B Common Stock, weighted average price, Grantor Retained Annuity Trust
4 terms
Rule 10b5-1 trading plan regulatory
"The sale reported in this Form 4 was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 11, 2025."
A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.
Class B Common Stock financial
"Each share of Class B Common Stock is convertible at any time into Class A Common Stock on a one-to-one basis at the reporting person's election and has no expiration date."
A class B common stock is one of multiple types of a company’s ordinary shares that carries specific rights—often different voting power or dividend priority—compared with other classes. For investors it matters because those differences affect how much influence you have over company decisions, the income you might receive, and how freely the shares trade; think of it like owning a car with different keys: some keys let you start the engine and open the trunk, others only unlock the door.
weighted average price financial
"The price reported in Column 4 is a weighted average price."
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
Grantor Retained Annuity Trust financial
"The shares are held of record by The Matthew Prince 2024 Grantor Retained Annuity Trust dated May 20, 2024, for which the reporting person serves as co-trustee and investment advisor."
A grantor retained annuity trust (GRAT) is an estate-planning tool where the person who creates the trust transfers assets into it but receives fixed cash payments (an annuity) from the trust for a set number of years; whatever remains after that term passes to designated beneficiaries. It matters to investors because it can shift future appreciation of assets out of the creator’s taxable estate—like putting an asset into a timed vending machine that pays you fixed amounts while any extra value that grows inside the machine goes to heirs with reduced gift or estate tax consequences.
FAQ
What Cloudflare (NET) holdings remained after the reported transactions?
One reported indirect account held 52,384 Class A shares after the conversions and sales. The filing also lists several indirect Class B positions, each convertible one-for-one into Class A, giving ongoing exposure through multiple family and grantor retained annuity trusts tied to Matthew Prince.
Through what entities were the Cloudflare (NET) insider transactions made?
The transactions involved several trusts, including The Matthew Prince Revocable Trust and multiple Prince family and Grantor Retained Annuity Trusts. Matthew Prince is described as trustee, co-trustee, or investment advisor for these vehicles, which hold the shares of record for the reported transactions.