Cloudflare (NET) CEO Matthew Prince sells 157,152 shares in 10b5-1 plan
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
Cloudflare, Inc.’s CEO and Board Co-Chair Matthew Prince reported a series of pre-planned share sales and conversions involving family trusts. Trusts for which he serves as trustee or investment advisor converted 157,152 shares of Class B Common Stock into Class A Common Stock on a one-to-one basis and sold 157,152 Class A shares in open-market transactions at weighted average prices generally in the low $200s per share. The filing states these sales were made under a Rule 10b5-1 trading plan adopted on February 11, 2025. Prince continues to hold 360,807 Class A shares directly as of May 19, 2026, along with several large indirect Class B positions through various family trusts that are each convertible into Class A stock.
Positive
- None.
Negative
- None.
Insights
Prince’s trades show a planned convert-and-sell program while retaining large positions.
The filing shows trusts associated with Matthew Prince converting 157,152 Class B shares into Class A and selling the same number of Class A shares in open-market transactions. This is a classic convert-and-sell pattern rather than an open-market purchase.
The sales were executed under a Rule 10b5-1 trading plan adopted on February 11, 2025, indicating the timing was pre-scheduled. Prince still holds 360,807 Class A shares directly and multiple large Class B positions indirectly, each convertible 1:1 into Class A. Overall, this looks like structured diversification from a sizable continued stake, so the informational signal for investors is moderate and context-dependent.
Insider Trade Summary 10b5-1
Net Seller: 157,152 shares ($32,606,962)
Net Sell
38 txns
Insider
Prince Matthew
Role
CEO & Board Co-Chair
Sold
157,152 shs ($32.61M)
| 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 | 1,827 | $207.4011 | $379K |
| Sale | Class A Common Stock | 4,227 | $208.3131 | $881K |
| Sale | Class A Common Stock | 5,568 | $209.3099 | $1.17M |
| Sale | Class A Common Stock | 15,667 | $210.3768 | $3.30M |
| Sale | Class A Common Stock | 13,362 | $211.3315 | $2.82M |
| Sale | Class A Common Stock | 10,845 | $212.1929 | $2.30M |
| Sale | Class A Common Stock | 888 | $213.1844 | $189K |
| Conversion | Class B Common Stock | 52,384 | $0.00 | -- |
| Conversion | Class A Common Stock | 52,384 | $0.00 | -- |
| Sale | Class A Common Stock | 1,876 | $202.964 | $381K |
| Sale | Class A Common Stock | 3,602 | $203.9052 | $734K |
| Sale | Class A Common Stock | 1,651 | $204.8158 | $338K |
| Sale | Class A Common Stock | 2,545 | $206.1717 | $525K |
| Sale | Class A Common Stock | 8,576 | $207.0909 | $1.78M |
| Sale | Class A Common Stock | 15,825 | $207.9378 | $3.29M |
| Sale | Class A Common Stock | 11,147 | $208.999 | $2.33M |
| Sale | Class A Common Stock | 7,085 | $209.8339 | $1.49M |
| Sale | Class A Common Stock | 77 | $210.7213 | $16K |
| Conversion | Class B Common Stock | 52,384 | $0.00 | -- |
| Conversion | Class A Common Stock | 52,384 | $0.00 | -- |
| Sale | Class A Common Stock | 3,062 | $201.1709 | $616K |
| Sale | Class A Common Stock | 7,910 | $202.0596 | $1.60M |
| Sale | Class A Common Stock | 13,694 | $203.037 | $2.78M |
| Sale | Class A Common Stock | 6,923 | $203.9778 | $1.41M |
| Sale | Class A Common Stock | 6,160 | $205.0473 | $1.26M |
| Sale | Class A Common Stock | 6,127 | $206.0396 | $1.26M |
| Sale | Class A Common Stock | 6,485 | $206.9029 | $1.34M |
| Sale | Class A Common Stock | 2,023 | $207.7857 | $420K |
| 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 | -- | -- | -- |
| holding | Class A Common Stock | -- | -- | -- |
Holdings After Transaction:
Class B Common Stock — 4,427,769 shares (Indirect, See footnote);
Class A Common Stock — 77,934 shares (Indirect, See footnote);
Class A Common Stock — 360,807 shares (Direct, null)
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 $200.505 to $201.49, inclusive. The reporting person undertakes to provide 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 (27) 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 $201.54 to $202.535, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $202.545 to $203.54, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $203.55 to $204.545, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $204.55 to $205.535, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $205.56 to $206.55, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $206.56 to $207.44, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $207.575 to $208.265, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $202.41 to $203.355, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $203.43 to $204.33, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $204.48 to $205.47, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $205.505 to $206.475, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $206.51 to $207.50, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $207.51 to $208.505, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $208.51 to $209.505, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $209.51 to $210.49, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $210.63 to $210.815, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $206.77 to $207.755, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $207.81 to $208.78, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $208.81 to $209.805, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $209.815 to $210.805, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $210.825 to $211.82, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $211.825 to $212.795, inclusive. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $212.83 to $213.645, 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: 157,152 shares
Shares converted: 157,152 shares
Direct Class A holding: 360,807 shares
+3 more
6 metrics
Net shares sold
157,152 shares
Net non-derivative sell transactions reported in Form 4
Shares converted
157,152 shares
Class B converted into Class A via derivative conversions
Direct Class A holding
360,807 shares
Class A Common Stock held directly as of May 19, 2026
Large Class B block
6,928,408 underlying shares
One indirect Class B position, convertible 1:1 into Class A
Rule 10b5-1 plan adoption date
February 11, 2025
Date Prince adopted trading plan governing reported sales
Sale price range example
$200.505–$201.49
Weighted-average price range for one sale tranche
Key Terms
Rule 10b5-1 trading plan, Class B Common Stock, weighted average price, Grantor Retained Annuity Trust, +1 more
5 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"
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"
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. These shares were sold in multiple transactions"
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"
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.
Revocable Trust financial
"The shares are held of record by The Matthew Prince Revocable Trust dated October 29, 2015"
A revocable trust is a legal arrangement where the person who creates it keeps control and can change or cancel the trust at any time, while naming who will manage and receive the assets later. Think of it like a flexible folder for your investments and property that can be relabeled or reworked as circumstances change; it matters to investors because it determines how ownership is recorded, how easily assets transfer on incapacity or death, and whether holdings bypass public probate proceedings.
FAQ
What insider transactions did Cloudflare (NET) CEO Matthew Prince report in this Form 4?
Matthew Prince reported that family-related trusts converted 157,152 shares of Class B Common Stock into Class A and sold 157,152 Class A shares in open-market trades at weighted average prices in the low $200s, as part of a structured trading program.
What Cloudflare (NET) holdings does Matthew Prince report after these transactions?
After the reported trades, Matthew Prince holds 360,807 Class A Common Stock shares directly as of May 19, 2026, plus several large indirect Class B positions through multiple family trusts. Each Class B share is convertible into one Class A share with no expiration date.
What is the significance of Cloudflare (NET) Class B Common Stock in this filing?
The filing shows Class B Common Stock held indirectly through trusts, each convertible one-for-one into Class A Common Stock with no expiration. Several large Class B blocks were partially converted into Class A and then sold, illustrating how dual-class structures can be used for liquidity without immediately relinquishing all control-related holdings.
Does Matthew Prince still have substantial exposure to Cloudflare (NET) after these sales?
Yes. Despite net sales of 157,152 Class A shares, the data show he retains 360,807 Class A shares directly and multiple large Class B positions through family trusts. Because each Class B share converts 1:1 into Class A, this represents ongoing significant economic exposure.