TIP783: What the Market Missed: Prem Watsa and One of the Greatest Records in Business w/ Kyle Grieve
We Study Billionaires - The Investor’s Podcast Network
Big long: buybacks and creative repurchases
Kyle outlines Watsa's 2020 purchases, TRS strategies, and selling minority stakes to fund large buybacks.
Kyle Grieve breaks down how Prem Watsa and Fairfax Financial compounded for decades through disciplined value investing, insurance float, and resilient capital allocation.
IN THIS EPISODE YOU’LL LEARN: 00:00:00 – Intro
00:03:29 – How Prem Watsa accidentally found investing and never looked back
00:07:48 – Why insurance float became Fairfax’s secret compounding weapon
00:09:43 – The exact thinking that shaped Fairfax’s long-term value discipline
00:10:02 – How Fairfax set bold targets and held itself publicly accountable
00:13:27 – Why cheap businesses taught painful but critical quality lessons
00:23:53 – How downturns and mistakes strengthened Fairfax’s balance sheet mindset
00:18:18 – What the short seller siege revealed about culture and conviction
00:24:47 – How crisis hedging created survival capital and massive opportunity
00:28:46 – Why overprotection hurt returns and forced strategic humility
00:37:25 – How culture decentralization and capital allocation became Fairfax’s moat
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
- Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
- Learn how to join us in Omaha for the Berkshire meeting here.
- Buy The Fairfax Way here.
- Listen to TIP772, How Great Compounders Turn Time Into A Superpower here.
- Follow Kyle on Twitter and LinkedIn.
- Related books mentioned in the podcast.
- Ad-free episodes on 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:
- HardBlock
- Human Rights Foundation
- Masterworks
- Linkedin Talent Solutions
- Simple Mining
- Plus500
- Netsuite
- Fundrise
References to any third-party products, services, or advertisers do not constitute endorsements, and The Investors Podcast Network is not responsible for any claims made by them.
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
