As the Year of the Retail Investor comes to a close, one of the biggest battleground stocks emerging is a tiny insurance company: newly public Lemonade (LMND -2.73%). After reaching all-time highs in July, the stock is down over 40%. Does that make now the optimal time to buy?

Motley Fool contributors Brian Stoffel and Brian Feroldi believe that's the wrong question to ask. Instead of trying to time the market -- or even attempt a precise valuation of a business that's trying something relatively new to the industry -- it's important to evaluate whether the business itself is very high quality. Indeed, there are a lot of moving parts. And because Lemonade is focused on landing younger customers and getting them to expand over time, it will take time before we know if the company's thesis can play out in the real world.

In this Oct. 8 video, Stoffel and Feroldi summarize an hour-long deep dive into Lemonade all the way down to five minutes. They'll also reveal how the stock performed on their respective investing frameworks.