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
Quality lessons from Odyssey and Crum & Forrester
Kyle recounts turning around Odyssey and Crum & Forrester, highlighting patience, management and rebuilding underwriting quality.
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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