E. TIMOTHY BIXBY - 18 Jul 2025 Form 4 Insider Report for Lemonade, Inc. (LMND)

Signature
/s/ Timothy Bixby
Issuer symbol
LMND
Transactions as of
18 Jul 2025
Transactions value $
-$297,700
Form type
4
Filing time
22 Jul 2025, 16:22:10 UTC
Previous filing
16 Jul 2025
Next filing
25 Aug 2025

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
BIXBY TIMOTHY E Chief Financial Officer C/O LEMONADE, INC., 5 CROSBY STREET, 3RD FLOOR, NEW YORK /s/ Timothy Bixby 22 Jul 2025 0001232142

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction LMND COMMON STOCK Options Exercise $142,140 +6,000 +2.28% $23.69 269,393 18 Jul 2025 Direct
transaction LMND COMMON STOCK Sale -$255,000 -6,000 -2.23% $42.5 263,393 18 Jul 2025 Direct F1
transaction LMND COMMON STOCK Options Exercise $23,690 +1,000 +0.38% $23.69 264,393 21 Jul 2025 Direct
transaction LMND COMMON STOCK Sale -$42,700 -1,000 -0.38% $42.7 263,393 21 Jul 2025 Direct F1
holding LMND COMMON STOCK 30,000 18 Jul 2025 Held by Timothy E Bixby Family Trust F2

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction LMND STOCK OPTION Options Exercise -$142,140 -6,000 -2.11% $23.69 278,300 18 Jul 2025 COMMON STOCK 6,000 $23.69 Direct F3
transaction LMND STOCK OPTION Options Exercise -$23,690 -1,000 -0.36% $23.69 277,300 21 Jul 2025 COMMON STOCK 1,000 $23.69 Direct F3
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Buy Plan / Sale Plan: These are also open market purchases/sales of shares, but in this case the transaction is part of a trading plan. Rule 10b5-1 allows insiders to setup a trading plan to buy/sell stocks over a certain period of time. Since the purchases/sales are predetermined, this protects the insiders from violating insider trading law.

Transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).

Explanation of Responses:

Id Content
F1 Represents sale pursuant to a Rule 10b5-1 trading plan adopted December 12, 2024.
F2 The Reporting Person is Co-Trustee of Timothy E. Bixby Family Trust ("Trust") and has voting and dispositive control over the shares held by Trust.
F3 The stock option is fully vested.