Metromile

-100%

est. 2Y upside i

InsurTechSeries D+

Rank

#3841

Sector

Insurtech

Est. Liquidity

~2Y

Data Quality

Data: Low

Equity upside is effectively -100% given the $510M preference overhang dwarfing the $145M current valuation.

Last updated: July 3, 2026

Bull (10%)-100%

Even with a 3x revenue multiple (driven by telematics leadership), exit value of $330M falls below $510M preference stack, leaving common worthless.

Base (40%)-100%

Exit multiple converges to 2x, implying $220M exit, still below $510M preference stack; common equity receives nothing.

Bear (50%)-100%

Multiple compresses to 1x, exit value $110M far below $510M preference stack; common equity is wiped out.

Est. time to liquidity~2.0 years

Preference Stack Risk

severe

Funding Intensity

35170%

Total funding of $510M exceeds current $145M valuation by 352%, deeply underwater for common.

Dilution Risk

low

No further raises expected as subsidiary of Lemonade.

Secondary Liquidity

none

No secondary market exists; company is not independent.

Questions to Ask at the Interview

Strategic questions based on Metromile's data — designed to show you've done your homework.

1
“How will Metromile's telematics data be leveraged under Lemonade to drive growth?”
2
“What is the path to profitability given negative gross margins and low growth?”
3
“What is the expected timeline for an equity liquidity event, and how is the preference stack structured post-acquisition?”

Our model estimates -100% upside. What do you think?

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Disclaimer: This analysis is AI-generated and does not constitute financial or career advice. Always conduct your own due diligence.