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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Carvana’s Moat is Very Wide and Nearly Unassailable

Carvana is the fastest growing used car dealer in the US while also having the industry’s best margins. That rare combination comes from having more vertical integration and scale advantages than any of their competitors. Traditional used car dealers have more local, outsourced, and variable expense business models.

Historically, the used car market has been extremely fragmented because no competitors benefit from economies of scale—especially on a national level. Today, CarMax is the industry leader, and they only have around 2% of the market. I think Carvana can change this market share dynamic though.

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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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Olympus is Creating the Most Well-Designed Currency in the World

Olympus wants to create the best currency in the world. It has been designed very well over the past four years to incentivize good behavior from investors and guarantee purchasing power via long-term price predictability. Its north star is to be fully decentralized, programmatic, and codified on public blockchains—a true cryptocurrency in every sense of the original term, and unlike any other “cryptocurrency” that exists. OHM is the token, and Olympus is the protocol behind OHM.

Olympus has seven mechanisms in place to achieve this goal. I will walk through all seven, and then I will explain how they interact and reinforce each other. All in all, these seven mechanisms have been designed to create a flywheel that I believe is going to be difficult to stop.

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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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My Ethereum Investment Thesis: Fundamentals and Flows

I am invested in Ethereum for similar reasons that I am invested in Amazon Web Services, Microsoft Azure, and Shopify. I want to own the platforms that internet businesses are built on top of. One of the reasons I am attracted to these types of platforms is that customer stickiness is very high. When a company has built their business on Amazon Web Services, switching to a competitor is risky, time consuming, and expensive.

Just as important though, the businesses built on Shopify have a vested interest in making Shopify better and more successful. And this same dynamic is seen with Ethereum. Ethereum is by far the most popular blockchain in the crypto economy, and thus has the most projects and people working to make it successful.

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Burford Capital is By Far the Most Undervalued Company I Know Of

Burford Capital is the largest legal finance company in the world. While Burford is mostly known for funding lawsuits, they provide legal capital in a variety of ways. In the simplest example though, Burford funds a plaintiff’s lawsuit by paying their legal expenses. If the case is lost, Burford loses their entire investment. If the case is won, the plaintiff pays Burford a share of the winnings. I believe there are numerous benefits for plaintiffs to get funding from a company like Burford.

At a high-level, litigation funding can flatten the legal playing field. Lawsuits are expensive. Many legitimate lawsuits are never filed because the potential plaintiff cannot—or does not want to—pay for the legal expenses. Plaintiffs often do not like the traditional hourly billing model that many law firms operate on. But working with a litigation funder allows a plaintiff to exchange having to pay their own legal expenses for a percentage of their winnings if the case is victorious. To date, many plaintiffs have welcomed this trade-off of less downside, less upside, and more flexibility.

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Shopify and its Strong Competitive Advantages Continue to Take Market Share

Shopify is a commerce platform that helps merchants sell across all their sales channels: online, physical retail, social media, and marketplaces such as Amazon and eBay. In 2004, Shopify was founded as an e-commerce platform for new entrepreneurs and small businesses. While that is still a meaningful part of their business, they have moved upmarket via Shopify Plus, which is a higher-end platform that starts at $2,000 per month and manages commerce for brands doing up to around $1 billion in revenue per year.

Tobi Lütke, founder and CEO, has made the comparison that Shopify is like an operating system for retailers. I think this is a good analogy. The platform that runs a merchant’s sales is arguably the most mission-critical system that company has. Like the Windows operating system, once a merchant runs their business on Shopify, they are unlikely to switch to a competitor.

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Spotify’s Moats, Management, and Unit Economics

Spotify has the most global market share of any music streaming service. In 2018, Spotify accounted for roughly 70% of global streaming revenue and 33% of all recorded music industry revenue. Given there are only two other sizable music streaming services, this is a hint that there are large barriers to entry in this industry.

The only three companies with meaningful market share are Spotify, Apple and Amazon: one dedicated streaming service founded in 2006 and two tech giants. Spotify has the benefit of brand name, reputation, network effects, and being synonymous with online music. Apple and Amazon have the benefit of hundreds of millions of users they can cross-sell music to. It would be much more difficult to start a dedicated streaming service today now that Spotify already exists and has scaled globally to over 200 million users.

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