Lemonade, Inc. filings document operating results, governance, and capital-structure matters for its digital insurance business. Form 8-K reports furnish shareholder letters covering insurance operating metrics, financial condition, underwriting performance, profitability measures, and cash-flow disclosures.
The company's proxy materials address board and executive compensation matters, including equity-award and pay-versus-performance disclosures. Its SEC record also includes capital-structure and security-status filings related to warrants to purchase common stock, including exchange suspension, expiration, and Form 25 removal from listing and registration on NYSE American.
Lemonade insider Adina Eckstein filed a Form 144 notifying a proposed sale of 5,000 common shares to be executed through Oppenheimer & Co. on 08/11/2025 with an aggregate market value of $244,900. The shares were acquired on 06/07/2020 under an employee stock option plan and will be paid in cash upon exercise. The filing lists 73,886,417 shares outstanding, making the proposed block about 0.0068% of outstanding stock. The filer disclosed two recent sales in the past three months totaling 10,000 shares for $470,000 in gross proceeds. The notice includes the standard representation that the filer is not aware of any undisclosed material adverse information.
Form 144 filed for Lemonade, Inc. (LMND) notifying a proposed sale of common stock and disclosure of recent related transactions.
- Proposed sale: 5,000 common shares via Oppenheimer & Co.; aggregate market value $239,650; approximate sale date 08/05/2025; exchange: NYSE.
- Outstanding shares: 73,886,417.
- Acquisition details: 1,250 shares acquired 12/24/2019 (Employee Stock Option Plan); 3,750 shares acquired 06/07/2020 (Employee Stock Option Plan).
- Recent sale (past 3 months): Adina Eckstein sold 5,000 shares on 06/23/2025 for gross proceeds $225,000.
The filer represents no undisclosed material adverse information and includes standard signature/attestation language required by Form 144.
Lemonade (LMND) delivered Q2-25 top-line growth but remains unprofitable. Total revenue rose 34% YoY to $164.1 million, driven by a 26% increase in net earned premium (to $112.5 million) and higher ceding-commission income. Loss and LAE grew more slowly, improving the loss ratio to ~69% (vs. ~79% a year ago). Sales & marketing spend jumped 62% to $59.6 million as the company pursues expansion. Net loss narrowed to $43.9 million (-$0.60 per share) from $57.2 million (-$0.81), while weighted shares rose 3.8% to 73.4 million.
Operating cash outflow was $41.7 million for H1-25, in line with H1-24, and cash/equivalents held steady at $386 million. Borrowings under the General Catalyst marketing-finance facility increased to $123.5 million (from $83.4 million), boosting leverage but providing growth capital. Stock-based compensation fell to $25.7 million (H1-24: $30.3 million). Book value declined to $527.1 million as the accumulated deficit widened to $1.41 billion.
The reinsurance program was renewed on 1 Jul 25 with a sharply lower cession rate (~20% vs. ~55%), increasing Lemonade’s retained risk from Q3 onward. Q2 results include $16.9 million of California wildfire losses and a $6.9 million FAIR Plan assessment, partially offset by an $11.7 million Employee Retention Credit refund. Termination of the Chewy warrant agreement removed 3.17 million potential shares and reversed $5.2 million of previously accrued expense.