The Future Investors

The Future Investors

Share this post

The Future Investors
The Future Investors
⚔️ 88: Oscar Health vs Lemonade
Stock Battle

⚔️ 88: Oscar Health vs Lemonade

The Stock Battle - Round 88: $OSCR vs $LMND

The Future Investors's avatar
The Future Investors
Jun 27, 2025
∙ Paid
5

Share this post

The Future Investors
The Future Investors
⚔️ 88: Oscar Health vs Lemonade
3
Share

Every three weeks, we host a Stock Battle on our X page between two competing companies. Which one is the favorite among our followers? And find out which one we believe has the stronger fundamentals.

This time, it’s Oscar Health vs. Lemonade — two insurtech disruptors fighting for investor attention. Which one stands out?

Subscribe for free to receive new posts and support our work

With 66% of the votes, you crowned Oscar Health the winner! 👑

Oscar Health and Lemonade are both innovative players in the insurance industry, but they operate in quite different niches. Oscar Health focuses on health insurance, while Lemonade offers property and casualty insurance — such as renters, homeowners, pet, car, and term life insurance.

Oscar Health was founded in 2012 in New York by Mario Schlosser, Josh Kushner, and Kevin Nazemi. The company wanted to make health insurance easier to use and more focused on the needs of consumers. Oscar mainly serves people buying insurance through the Affordable Care Act (ACA) in the U.S. Its platform offers a more transparent and digital-first experience, with features like telemedicine, personalized care teams, and an intuitive mobile app. Today, Oscar is active in over 20 states and has more than two million members.

Lemonade started in 2015, also in New York, and was founded by Daniel Schreiber and Shai Wininger. Their goal was to build a new kind of insurance company — fast, simple, and built for the digital age. Lemonade offers insurance for renters, homeowners, pets, cars, and term life. It is built as a fully digital and AI-driven company, using chatbots to automate everything from signing up to handling claims, making the process fast and easy for customers. The company is active in the U.S. and parts of Europe, and is especially popular with younger, tech-savvy customers. Notably, Co-founder Daniel Schreiber is still the CEO today.

View our Portfolios

They both serve insurance customers — but operate in different markets, each with its own strengths and challenges. Curious which of these companies we consider the best? Find out below, exclusively available to our paid members.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 The Future Investors
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share