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
First steps into insurance investing
Kyle describes Watsa's job choices, joining Confederation Life, and how insurance provided a formative, subsidized education.
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.
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