TIP742: Invest like a Business Owner w/ David Fagan
We Study Billionaires - The Investor’s Podcast Network
Building Meaningful Connections
This chapter explores the dynamics of relationships and personal growth, emphasizing the importance of vulnerability and listening. It also addresses innovative investment strategies and practical tools for enhancing productivity in the entrepreneurial journey.
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.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
05:35 – Why some business owners often become better investors through firsthand experience with risk, volatility, and capital allocation.
14:57 – The blind spots business owners have when they enter the world of investing.
23:09 – Why you might shift your attitude toward dividends after experiencing firsthand how brutal capitalism is.
28:30 – David shares the daily habits that help him stay grounded, including exercise, reading, and reflection.
35:49 – 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.
37:51 – Why financial independence raises deeper questions about purpose, relationships, and long-term alignment in life and work.
59:06 – When (and how) to go into business with friends: lessons from real stories about incentives, equity splits, and mutual expectations.
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
- Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here.
- Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
- Listen to our interview with David Fagan about Buffett’s favorite business book.
- Check out all the books mentioned and discussed in our podcast episodes here.
- Enjoy ad-free episodes when you subscribe to our Premium Feed.
NEW TO THE SHOW?
- Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter.
- Check out our We Study Billionaires Starter Packs.
- Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok.
- Browse through all our episodes (complete with transcripts) here.
- Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool.
- Enjoy exclusive perks from our favorite Apps and Services.
- Learn how to better start, manage, and grow your business with the best business podcasts.
SPONSORS Support our free podcast by supporting our sponsors:
- SimpleMining
- Hardblock
- AnchorWatch
- Human Rights Foundation
- Cape
- Unchained
- Vanta
- Shopify
- Onramp
- Abundant Mines
HELP US OUT!
Help us reach new listeners by leaving us a rating and review on Spotify! 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!
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Learn more about your ad choices. Visit megaphone.fm/adchoices
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
The AI-powered Podcast Player
