TIP742: INVEST LIKE A BUSINESS OWNER

W/ DAVID FAGAN

TIP742: INVEST LIKE A BUSINESS OWNER W/ DAVID FAGAN

02 August 2025

In this episode, Stig Brodersen speaks with David Fagan, a successful entrepreneur and investor, about the powerful overlap between building businesses and investing in public markets. They explore why business owners often think differently about diversification, dividends, and risk—and how habits, friendships, and clarity of purpose shape long-term success in both business and life.

SUBSCRIBE

IN THIS EPISODE, YOU’LL LEARN:

  • Why some business owners often become better investors through firsthand experience with risk, volatility, and capital allocation.
  • The blind spots business owners have when they enter the world of investing.
  • Why you might shift your attitude toward dividends after experiencing firsthand how brutal capitalism is
  • David shares the daily habits that help him stay grounded, including exercise, reading, and reflection.
  • A different take on “you are the average of the five people you spend the most time with”—and the tradeoffs of seeking higher-caliber peers.
  • Why financial independence raises deeper questions about purpose, relationships, and long-term alignment in life and work.
  • When (and how) to go into business with friends: lessons from real stories about incentives, equity splits, and mutual expectations.

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] Stig Brodersen: In today’s episode, I’m having a conversation with our recurring guest, David Fagan, a seasoned entrepreneur, thoughtful investor, and someone I’m fortunate to call a close friend. In this discussion, we examine the intersection between being a business owner and public market investing.

[00:00:18] Stig Brodersen: We explore how operating a company influences one’s views on portfolio concentration, risk, dividends, and management quality, and how those insights can both be an asset and a liability in public equities. Then we talk about what happens after you reach financial independence and how finding your why becomes the next big challenge.

[00:00:40] Intro: Since 2014 and through more than 180 million downloads, we’ve studied the financial markets and read the books that influenced self-made billionaires the most. We keep you informed and prepared for the unexpected. Now for your host Stig Brodersen.

[00:01:04] Stig Brodersen: You are listening to The Investor’s Podcast. I’m your host Stig Brodersen, and I am joined by David Fagan today. And some of you might know David from episode 639, where he covered Buffett’s favorite investment book together with Clay, others as a thought leader of business. And to me he’s all of that. But first and foremost, he’s just my friend David. So David, how are you today?

[00:01:27] David Fagan: I’m doing great. Thank you for having me on today, Stig.

[00:01:31] Stig Brodersen: You bet. And let’s just dive right into the first segment here, because David, here on the show, as you know, we discuss and interact with a lot of investors, and in this episode we want to turn the tables and focus on investing, but from the perspective of being a businessman or businesswoman, and you know, I can’t help myself but say the Buffett’s family just said, I’m a better businessman because I’m an investor and I’m a better investor because I’m a businessman.

[00:01:55] Stig Brodersen: And so that is our first segment here. And you know, I like to think that we use the same part of the brain whenever it comes to investing, whenever it comes to business, which generally is to our advantage as businessmen, but probably sometimes not. We’re going to talk a bit more about that. And we have a lot of these conversations here in our mastermind community, and I kind of felt we should open it up here to the entire TIP community because.

[00:02:24] Stig Brodersen: One thing I very much appreciate about our community is that there’s a lot of business owners in the community, and I really hope this doesn’t come across as if you don’t own your own business, it’s you’re not a good investor or anything like that. That’s the very opposite. But I think I want to mention is that there’s a lot of investing pundits out there and most often haven’t run their own business.

[00:02:42] Stig Brodersen: And I would argue that once you have the opportunity to do that, you might see investing a little bit differently. And then at the same time, because I know there are a lot of businesspeople out there who run their own business in the audience, you probably also need to unlearn a thing or two. If you run your own business and you’re like, oh my God, I’m good at this.

HELP US OUT!

Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it!

BOOKS AND RESOURCES

NEW TO THE SHOW?

SPONSORS

Support our free podcast by supporting our sponsors

 

CONNECT WITH STIG

CONNECT WITH DAVID

PROMOTIONS

Check out our latest offer for all The Investor’s Podcast Network listeners!

WSB + BFF + RWH Promotions

The Intrinsic Value Newsletter