MI345: A DECADE OUTPERFORMING THE NASDAQ

W/ BRIAN STOFFEL

16 April 2024

Kyle Grieve chats with Brian Stofell about the crucial role of being transparent with your track record, how to score anti-fragility, managing risk in a portfolio where evaluation isn’t critical, the interplay of narrative and investor sentiment, how to utilize a reverse DCF to find the market’s assumptions on growth, investment lessons from Nassim Nicholas Taleb, how to weight probabilities for analyzing the outcome of a stock, and a whole lot more!

Brian Stoffel is an investment educator. He’s the co-founder and Chief Content Officer of Long-term Mindset. He started his career as a middle school teacher in Washington, D.C., and then transitioned to work for The Motley Fool, where he has written more than 4,000 articles. He’s been investing for over a decade and has a track record that most fund managers would be jealous of!

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IN THIS EPISODE, YOU’LL LEARN:

  • The significance of track record in decision-making processes.
  • The crucial role of having “skin in the game” in various ventures.
  • Insights into Brian’s transition towards tech-oriented businesses.
  • Exploring the anti-fragility inherent in specific tech sectors.
  • The importance of free cash flow when looking at loss-making businesses.
  • How Brian enters a position and how he allows it to earn its way to a higher allocation.
  • Why Brian adds a stock at any price, regardless of valuation, if the business is anti-fragile.
  • Why switching costs are so easily identifiable.
  • How to use RDCF to help you better understand the assumptions made about a business.
  • The importance of understanding the relationship between narratives and price.
  • And much, much more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

[00:00:03] Brian Stoffel: There’s two types of risks. One type of risk is that I’m significantly overpaying for it, which is basically every day that you wake up and you don’t sell a stock, you’re basically buying it, which I think is a really important idea that a lot of people miss. They’re like, yeah, you got in at Shopify at $4 a share, but what should I do today?

[00:00:23] Brian Stoffel: And I’m like, look, I’m not selling. So that’s the same as buying to me. And the first risk is that you overpay. And that’s what happened to Shopify for me, even though I wasn’t paying, I was paying. The other risk is that I look at a company and I say, it’s got a PE of 200. I got to sell. And then it just continues to go up and up and up.

[00:00:45] Brian Stoffel: And the reason for that is that people don’t understand what happens to profits or free cash flows when you’re going through operating leverage. I try and assume, say, when I’m looking at CrowdStrike, I try and assume that today they’ve reached that free cash flow margin. So I don’t have the numbers in front of me, but let’s say they’ve got $10 billion in sales and they’ve got a 38 percent free cash flow margin.

[00:01:11] Brian Stoffel: Then I say, okay, I’m going to put myself in a world where they have $3.8 billion in free cash flow, 38 percent margin. How much does that have to grow to justify today’s stock price?

[00:01:27] Kyle Grieve: Brian Stoffel is an investor with one heck of a track record. From December 31st, 2014 to December 31st, 2023, his portfolio has compounded at 17.7 percent per annum. Over the same time period, the S&P 500 has done 11.3%. The Nasdaq Composite Index has done 15%. So his strategy has been crushing the market now for a decade, and it’s a lot different than most strategies you’ll come across.

[00:01:50] Kyle Grieve: One of the things that Brian shared with me on this chat that was a real eye opener was that valuation does not play a part in whether he’ll buy a stock or not. Essentially, he just tries to find businesses that are as anti fragile as possible, then buys them without factoring in evaluation, then adds to it as the business proves itself.

[00:02:07] Kyle Grieve: In this episode, we’ll chat about the crucial role of being transparent with your track record, how to score anti fragility, managing risk in a portfolio where evaluation isn’t critical, the interplay of narratives and investor sentiment, how to utilize the reverse discounted cash flow to find the market’s assumptions on growth, investment lessons from Nassim Nicholas Taleb, how to weigh the probabilities for analyzing the potential outcomes of a stock hypothesis. And a whole lot more. If you want to learn some very unique strategies that Brian has used to beat the market, you won’t want to miss this episode. Now, without further delay, let’s jump right into this week’s episode with Brian Stoffel.

[00:02:46] Intro: Celebrating 10 years. You are listening to Millennial Investing by The Investor’s Podcast Network. Since 2014, we interviewed successful entrepreneurs, business leaders, and investors to help educate and inspire the millennial generation. Now for your host, Kyle Grieve.

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