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Rule Breaker Investing

Calculating Risk Foolishly, Vol. 4: ETSY v. DUOL

Rule Breaker Investing

The Motley Fool

Business, Investing

4.4 • 959 Ratings

🗓️ 21 January 2026

⏱️ 84 minutes

🧾️ Download transcript

Summary

Risk gets talked about a lot in investing—and often defined poorly. This week on Rule Breaker Investing, David is joined by Motley Fool analysts Alicia Alfiere and Yasser El-Shimy to walk through his full 25-point risk rating system, a framework he’s used for more than a decade to replace vague labels like “medium risk” with something concrete and measurable. Using Etsy and Duolingo as live 2026 case studies, the trio scores each company question by question—covering the business, financials, competition, leadership, and the investor’s own willingness to dig deeper. Along the way, listeners get a deeper look at how studying risk is really about studying quality—and how seeing risk clearly with a number is just another way Rule Breaker investors can learn to break the rules…. Companies mentioned: DUOL, ETSY Host: David GardnerGuests: Alicia Alfiere, Yasser El-ShimyProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Risk. A lot of people talk about it, but especially in the investment world, I've never found

0:05.6

that talk very satisfying. First of all, how do you, how do I, how do they define risk? What does it

0:15.0

mean even to say that's a risky stock? The definitions are often unclear. Then some professional analysts in the risk section

0:23.6

of their stock research will say stuff like medium. As in this is a medium risk stock. What does

0:30.9

that mean? Well, more than a decade ago, I developed a 25 point risk rating system that I've used as a

0:37.4

rule breaker investor ever since. First off, I developed a 25 point risk rating system that I've used as a rule breaker investor ever since.

0:39.7

First off, I defined risk. Well, at least what that word means to me as an investor.

0:45.7

And then we went on not just to put a word to the riskiness of the stock, not just a word like medium,

0:52.9

but to go on to put a number on that stock's risk, a number to give you a

0:58.1

much more specific understanding, and that number is itself based on 25 questions asked of each

1:05.1

stock. You know what? We're going to cover the whole thing this week, joined by my two motley

1:10.3

fool friends, Alicia Alfieri and Yasser al-Shimi, we three are going to cover the whole thing this week. Join by my two Motley Fool friends, Alicia Alfieri and Yasser al-Shimi,

1:13.5

we three are going to teach you the entire system,

1:17.0

help you raid stocks yourself along this very important dynamic of risk.

1:25.0

Only on this week's Rule Breaker Investing.

1:28.8

It's the Rule Breaker Investing podcast with Motley Fool co-founder, David Gardner.

1:37.0

Welcome back to Rule Breaker Investing. This week, joined by two Motley Fool experts, two friends

1:42.8

for diving into assessing investment risk. my 25 point risk rating system.

1:49.8

Now, risk in equity investing, as I define it, is the potential loss of a substantial portion of capital over a significant period, like, let's say, three years.

2:05.4

Understanding this risk at both an individual stock level and also a portfolio level is crucial.

2:12.3

And my framework, which was created to provide clarity in risk assessment, moves away from

2:17.4

vague terms like medium risk.

...

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