Lemonade’s Path to 6x Again: Why Its Future is Clearer Than Ever

Since my original Lemonade writeup two years ago, its stock is up 6x. I think its next 6x is more likely and less risky than the last 6x. When Lemonade’s stock was in the teens throughout 2023 and most of 2024, there were legitimate questions about the company’s long-term potential. To me, the biggest question was whether Lemonade could extend its success in pet and renters insurance to the more complex and competitive markets of home and auto. Today, I don’t have any major concerns about Lemonade, and I am far more confident in their future than I was two years ago.

Lemonade is going through a major multi-year transition. They are evolving from a niche insurer to—what I believe—a serious player in the consumer insurance industry. In my December 2024 writeup I called out 2025 as being critical for Lemonade to become a serious contender to the likes of Allstate, GEICO, and Progressive. Below is exactly what I said.

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Why I Invested in Lemonade Over Root: Branding, Culture, and the Long Game

During my initial Lemonade research in 2021 I looked into Root as well. I was not overly impressed with Root as its own potential investment or as a Lemonade threat, so I moved on and only loosely followed it for the next few years. Throughout 2024 as I made Lemonade a significantly larger investment, I spent a lot of time researching any potential risks. And Root was part of that. This time I did a much deeper dive on Root… and more or less came to the same conclusion.

With that being said, I do think Root will be successful. Consumer insurance is not a winner-takes-all market, and Root has a great deal with Carvana. I think there is plenty of room for two tech savvy insurers to make space for themselves in this industry. But I think Lemonade is a better long-term investment than Root. As to why, I’ll start high-level and then zoom in.

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Lemonade: 2024 Review and 2025 Preview

In October 2023 I published a 12-page writeup titled “Lemonade: Short-Term Headwinds Will Soon be Tailwinds.” Fourteen months later, it looks like that title is turning out to be quite prescient. My last paragraph in that writeup was the following:

As inflation inevitably slows down and Lemonade’s rate increases get approved, their loss ratios should come down. This will also allow them to turn marketing back on and thus growth will accelerate. As their heavy investments to build out their three new lines of insurance are mostly complete, I expect [2024’s] growth to have high incremental margins and prove once more the operating leverage Lemonade has. Reaccelerating to 20-30%+ growth while loss ratios decrease and margins increase should result in a significant sentiment shift in Lemonade’s stock.

In summary, I predicted four things:

  1. Loss ratios would decrease
  2. Growth would accelerate
  3. Margins would increase
  4. Sentiment would improve

All four of those things happened in 2024, but more importantly, I expect 2025 to be the real inflection. I predict all of those same four things will happen again in 2025. Let’s walk through why.

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Lemonade: Short-Term Headwinds Will Soon be Tailwinds

Lemonade is a consumer insurance company that currently offers renter, condo, home, auto, pet, and life insurance. While most insurance companies that consumers are familiar with—Progressive, GEICO, State Farm, Nationwide—were founded 80+ years ago, Lemonade was started in 2015 by the current CEO, Daniel Schreiber, and COO, Shai Wininger.

Not surprisingly given that timeline, Lemonade is a much more tech-oriented company than their larger competitors. Lemonade does not sell its insurance via agents and brokers, instead focusing on online ads, fun social media presences, and word-of-mouth that comes from their high net promoter scores. Lemonade insurance can be purchased in just a couple of minutes from their bot, AI Maya, and one-third of claims are handled entirely by AI Jim—with zero human interaction. This tech advantage is obvious by simply using the product. I have now switched all of my insurance from Progressive and GEICO to Lemonade due to their tech and app being so much better.

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