# Lemonade, Inc. (LMND)

> Source: Nexqual · https://nexqual.com/LMND · data as of 2026-10-22 20:00 UTC · cite as "Nexqual, Lemonade, Inc. (LMND), nexqual.com/LMND" · informational, not investment advice.

**Price:** USD 45.41 (+0.29% on the day) · last close of Oct 22, 2026; US market pre market, not a live price. Prev close 45.28 · day 44.42–46.24 · 52w 42.7–99.9 · market cap $3.51B · NYQ

## Key facts
- Last four reported quarters (through Jun 30, 2026): revenue $975M, net income -$138M (-14.2% margin), free cash flow $8.1M (SEC filings).
- Insider open-market sales, last ~7 months: 9 Form 4 filings, $7.4M; 5 not under a Rule 10b5-1 plan ($922K); 0 by opportunistic insiders, 7 by routine insiders (three-year test, Cohen, Malloy & Pomorski 2012).
- Analysts: Hold (mean 2.82 on a 1–5 scale) (11 analysts), mean target USD 58.44 (range 38–92).
- Total return with dividends: 1Y -11.6% vs S&P 500 +14.9%; 5Y -28.4% vs S&P 500 +80.3%.
- Next earnings: 2026-11-05, EPS estimate USD -0.58, revenue estimate $322M.

## Financials (SEC 10-K; TTM = last four 10-Q/10-K quarters)
| USD | FY2021 | FY2022 | FY2023 | FY2024 | FY2025 | TTM |
|---|---|---|---|---|---|---|
| Revenue | $128M | $257M | $430M | $527M | $738M | $975M |
| Net income | -$241M | -$298M | -$237M | -$202M | -$166M | -$138M |
| EPS (diluted) | -$3.94 | -$4.59 | -$3.40 | -$2.85 | -$2.24 | — |
| Free cash flow | -$154M | -$173M | -$128M | -$20.8M | -$25.9M | $8.1M |
| Net margin | -187.9% | -116.0% | -55.1% | -38.4% | -22.4% | -14.2% |
| Revenue growth | +36.0% | +99.9% | +67.4% | +22.5% | +40.2% | — |
| Cash + short-term investments | $381M | $382M | $310M | $404M | $399M | — |
Fiscal years end Dec. EPS is split-adjusted.

## Valuation (price ÷ last four quarters, through Jun 30, 2026)
P/S 3.6x · P/FCF 433.9x · P/B 7.0x · FCF yield 0.23% · Earnings yield -3.94%

## Insider sales (SEC Form 4, open-market, last ~7 months)
4 of 9 under a Rule 10b5-1 trading plan (scheduled in advance). Unplanned sales were timed by the insider.
| Trade date | Insider | Role | Shares | Value | % of holdings sold | 10b5-1 plan | Insider type |
|---|---|---|---|---|---|---|---|
| 2026-09-03…2026-09-04 | Peters John Sheldon | Chief Insurance Officer | 3,108 | $169K | 4% | Yes | Routine (sold in Mar & Jun & Sep & Dec each year 2023–2025) |
| 2026-09-03 | Prosor Maya | Chief Business Officer | 1,040 | $57K | 0.5% | No | Too little history (no open-market trades in 2023) |
| 2026-09-03 | Bixby Timothy E | Chief Financial Officer | 1,893 | $103K | 1.1% | No | Routine (sold in Mar & Jun & Sep each year 2023–2025) |
| 2026-08-13 | Peters John Sheldon | Chief Insurance Officer | 11,000 | $578K | 12.5% | No | Routine (sold in Mar & Jun & Sep & Dec each year 2023–2025; this trade is outside those months) |
| 2026-07-07 | Bixby Timothy E | Chief Financial Officer | 73,000 | $5.8M | 29.5% | Yes (adopted March 13, 2026) | Routine (sold in Mar & Jun & Sep each year 2023–2025; this trade is outside those months) |
| 2026-07-06 | Peters John Sheldon | Chief Insurance Officer | 3,444 | $272K | 4.2% | Yes (adopted March 11, 2026) | Routine (sold in Mar & Jun & Sep & Dec each year 2023–2025; this trade is outside those months) |
| 2026-06-03…2026-06-04 | Peters John Sheldon | Chief Insurance Officer | 5,343 | $283K | 6.2% | Yes | Routine (sold in Mar & Jun & Sep & Dec each year 2023–2025) |
| 2026-06-03 | Bixby Timothy E | Chief Financial Officer | 2,227 | $118K | 0.9% | No | Routine (sold in Mar & Jun & Sep each year 2023–2025) |
| 2026-06-03 | Prosor Maya | Chief Business Officer | 1,220 | $65K | 0.6% | No | Too little history (no open-market trades in 2023) |
% of holdings sold = shares sold ÷ (shares sold + all holdings the insider reported on that Form 4, direct and through trusts).
Insider type follows Cohen, Malloy & Pomorski (Journal of Finance, 2012). An insider who traded the stock in the same calendar month in each of the past three years is a routine trader; one who traded in each of those years without such a pattern is an opportunistic trader. In their study, trades by opportunistic insiders predicted future returns and trades by routine insiders did not. Counts open-market purchases and sales only (SEC Form 4 codes P and S) by that insider in that company. Not investment advice.

## Analysts
Consensus Hold (mean 2.82 on a 1–5 scale), 11 analysts; mean target USD 58.44 (low 38, high 92).
Rating changes, last 120 days:
| Date | Firm | Action | Rating | Price target |
|---|---|---|---|---|
| 2026-10-06 | Morgan Stanley | Target lowered | Equal-Weight | $56 → $48 |
| 2026-08-19 | Morgan Stanley | Target lowered | Equal-Weight | $65 → $56 |
| 2026-07-30 | Piper Sandler | Target lowered | Neutral | $75 → $51 |
| 2026-07-30 | Keefe, Bruyette & Woods | Upgrade | Underperform → Market Perform | $48 |
| 2026-07-15 | Piper Sandler | Target raised | Neutral | $62 → $75 |
| 2026-07-08 | Keefe, Bruyette & Woods | Target raised | Underperform | $44 → $48 |
| 2026-07-08 | Morgan Stanley | Downgrade | Overweight → Equal-Weight | $75 |

## Total return (dividends reinvested)
|  | 1Y (from 2025-10-23) | 5Y (from 2021-10-18) |
|---|---|---|
| Total return | -11.6% | -28.4% |
| S&P 500 (SPY) | +14.9% | +80.3% |
| Per year | -11.7% | -6.5% |
| Volatility (annualized) | 78.2% | 79.0% |
| Max drawdown | -55.3% (Jan 2026→Oct 2026) | -84.8% (Nov 2021→Oct 2023) |

## Peers (Insurance - Property & Casualty)
SLDE (Slide Insurance Holdings, Inc.) USD 27.75 +2.36% · PLMR (Palomar Holdings, Inc.) USD 144.53 +3.85% · SKWD (Skyward Specialty Insurance Gro) USD 62.16 +1.24% · HCI (HCI Group, Inc.) USD 206.68 +1.11% · WTM (White Mountains Insurance Group) USD 2,247.52 +1.70% · SIGI (Selective Insurance Group, Inc.) USD 91.74 +0.72%

## More
Full page: https://nexqual.com/LMND · Free keyless MCP server with the same data and citations: https://mcp.nexqual.com/mcp · Guide for agents: https://nexqual.com/agents · https://nexqual.com/llms.txt

## Supply chain and relationships (SEC annual reports)

Named in LMND's own 10-K filed 2026-02-25 (https://www.sec.gov/Archives/edgar/data/1691421/000169142126000016/lmnd-20251231.htm):

| Relationship | Company | Sentence in the filing |
|---|---|---|
| Customer | GC Customer Value Arranger | "On June 28, 2023, we entered into a Customer Investment Agreement (the "Agreement"), with GC Customer Value Arranger, LLC (a General Catalyst company) ("GC") under which GC agreed to provide up to $150 million of financi…" |
| Customer | SAP (SAP) | "In developing SAP, insurance regulators were primarily concerned with evaluating an insurer's ability to pay all its current and future obligations to customers." |
| Customer | Amazon (AMZN) | "AWS's facilities are vulnerable to damage or interruption from human error, intentional bad acts, earthquakes, floods, fires, severe storms, war, terrorist attacks, power losses, hardware failures, systems failures, tele…" |
| Customer | Apple (AAPL) | "Our ability to market and distribute our insurance products depends on maintaining cost-effective, satisfactory relationships with Apple and Google, as most of our customers access our services exclusively through their …" |
| Customer | Alphabet (Google) (GOOGL) | "Our ability to market and distribute our insurance products depends on maintaining cost-effective, satisfactory relationships with Apple and Google, as most of our customers access our services exclusively through their …" |
| Customer | Demotech | "While our Demotech, Inc. rating has proved satisfactory to date, we cannot assure that this rating will remain at its current level and it is possible that some prospective customers may be reluctant to do business with …" |

## Company outlook (8-K filed 2026-07-29)

- "Below is our view of how we expect the third quarter and full year 2026 to shape up."

## Analyst estimates and revisions

| Period | EPS est. | 90d ago | Change | Revenue est. | Analysts |
|---|---|---|---|---|---|
| Current quarter (ends 2026-09-30) | $-0.58 | $-0.53 | +9.4% | $322.3M | 10 |
| Next quarter (ends 2026-12-31) | $-0.24 | $-0.18 | +28.0% | $340.4M | 10 |
| Current fiscal year (ends 2026-12-31) | $-1.85 | $-1.73 | +7.3% | $1.22B | 11 |
| Next fiscal year (ends 2027-12-31) | $-1.10 | $-0.82 | +33.8% | $1.64B | 12 |

## Options: expected move (Cboe, 15-min delayed)

Expected move by 2026-11-06 (includes earnings 2026-11-05): ±16.9%; earnings reaction alone ±14.2%; last 8 reports averaged ±19.7%.

| Expiration | Days | ATM IV | Expected move |
|---|---|---|---|
| 2026-10-30 | 7 | 55.6% | ±6.6% |
| 2026-11-06 | 14 | 104.5% | ±16.9% |
| 2026-11-13 | 21 | 83.3% | ±16.3% |
| 2026-11-20 | 28 | 84.6% | ±19.0% |
| 2026-11-27 | 35 | 79.8% | ±19.9% |
| 2026-12-04 | 42 | 75.8% | ±20.7% |
| 2026-12-18 | 56 | 70.8% | ±22.2% |
| 2027-01-15 | 84 | 66.1% | ±25.2% |