Lemonade just did something most insurtechs never live long enough to see: it made money. After years of burning cash that gave WeWork a run for its money, the AI-powered insurer has finally posted its first full year of positive free cash flow—a phrase that used to sound about as realistic as “profitable Uber.” But here we are. 

(Source: Giphy) 

In short, the company pulled in $48 million in adjusted free cash flow for 2024, with $27 million in Q4 alone. Meaning, due to the fact this is actual money staying inside the company instead of vanishing into the abyss—Investors, who have spent years treating Lemonade like a toy company with good branding, took notice. Shares are absolutely mooning today as bulls have pumped prices nearly 17%. 

Adding to the party, Lemonade’s in-force premium hit $944 million, up 26% year-over-year, and revenue climbed 29% in the same period. More importantly, the company’s gross loss ratio dropped to 63% in Q4, its lowest ever, while the trailing twelve-month loss ratio improved to 73%. In plain English: the company is finally figuring out how to price risk like an actual insurance business instead of a friggin’ experiment. 

(Source: Insurance Business Mag) 

On the other hand though, no good news doesn’t come without a punch in the face. In Lemonade’s case, that came in the form of the California wildfires in January 2025. The company expects $45 million in gross losses, with a $20 million EBITDA hit. But here’s the thing: without its new catastrophe risk management strategy, the damage could have been five times worse. So kudos to management for estimating a “Black Swan” event. 

But, but, but… even still, Lemonade’s stock has been ripping over the past six months, up 102%, though it’s been mostly flat year-to-date—until today’s 17% move. Which is why, at this moment, investors are wondering if we’ll see another six month run of this magnitude, or whether we’ll see the stock flatline the rest of the year. 

(Source: Giphy) 

My take? The fact that they’ve just clinched massive cash flow, could ignite some bigger moves ahead. For years, Lemonade has been the insurtech world’s problem child: cool branding, slick AI promises, but zero proof it could ever make money. Now, the numbers are starting to tell a different story, and if this momentum keeps up, it won’t just be the stock that’s unrecognizable—it’ll be the entire way Wall Street views this company.

Which means, you better keep your eyes on Lemonade, because it’s looking like the market is about to hand out a massive pile of lemons disguised as bigly returns. Now obviously, don’t quote me on that or take that as scripture, so please do your due diligence. In the meantime though, place your bets accordingly and as always—stay safe and stay frosty, friends! Until next time… 

P.S. My buddy Jared is sharp as hell—probably one of the smartest guys I know. But when it comes to investing? An absolute clown. Why? Because he doesn’t grasp the one thing that separates winners from losers in the market: information. And not just any information—I’m talking about the kind of intel that Wall Street hoards like the FBI hoards Hunter Biden's laptop—because the second retail traders get their hands on it, their edge starts to disappear.

Moral of the story here? Don’t be a Jared. Get access to the real market-moving data, the stuff hidden behind paywalls and institutional gatekeeping by joining Stocks.News premium. At the end of the day, the market isn’t playing fair—so why should you? 

Stocks.News holds positions in Uber as mentioned in the article.