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Lemonade: Reasons to Buy and Reasons to Sell

There's a lot to like about the insurance disruptor, but there are some reasons to be cautious.

By Matt Frankel, CFP and Tyler Crowe – Mar 4, 2026 at 11:12AM EST

Lemonade (LMND 1.77%) is a fast-growing company that revolutionizes the customer experience of buying insurance, making claims, and the rest of the insurance process. In this video, Lemonade shareholder and Motley Fool analyst Matt Frankel makes the bull case for the stock, while colleague Tyler Crowe discusses why he's not convinced.

*Stock prices used were the morning prices of Feb. 26, 2026. The video was published on March 4, 2026.

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About the Author

Matt Frankel, CFP
Matt Frankel, CFP, is a contributing Motley Fool stock market analyst and personal finance expert covering financial stocks, REITs, SPACs, and personal finance. Prior to The Motley Fool, Matt taught high school and college mathematics. He holds a bachelor’s degree in physics from the University of South Carolina, a master’s degree in mathematics from Nova Southeastern University, and a graduate certificate in financial planning from Florida State University. He won a SABEW award for coverage of the 2017 Tax Cuts and Jobs Act. He is also regularly interviewed by Cheddar, The National Desk, and other TV networks and publications for his financial, stock market, and investing expertise.
TMFMattFrankel
X@MattFrankelCFP

Matt Frankel, CFP has positions in Lemonade and has the following options: short September 2026 $140 calls on Lemonade. Tyler Crowe has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Lemonade. The Motley Fool has a disclosure policy.

Matthew Frankel is an affiliate of The Motley Fool and may be compensated for promoting its services. If you choose to subscribe through their link they will earn some extra money that supports their channel. Their opinions remain their own and are unaffected by The Motley Fool.

Stocks Mentioned

Lemonade Stock Quote
Lemonade
NYSE: LMND
$53.00
(-2.00%)-$1.08

*Average returns of all recommendations since inception. Cost basis and return based on previous market day close.

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