TIP783: WHAT THE MARKET MISSED: PREM WATSA AND ONE OF THE GREATEST RECORDS IN BUSINESS

W/ KYLE GRIEVE

TIP783: WHAT THE MARKET MISSED: PREM WATSA AND ONE OF THE GREATEST RECORDS IN BUSINESS W/ KYLE GRIEVE

10 January 2026

On today’s episode, Kyle Grieve discusses the remarkable rise of Fairfax Financial and its founder-led CEO, Prem Watsa. He’ll explore how disciplined value investing and insurance float fueled decades of compounding, and created a resilient business that withstood short sellers, the tech bubble, and the GFC. Kyle will also share key lessons on capital allocation, culture, and business legacy.

SUBSCRIBE

IN THIS EPISODE, YOU’LL LEARN:

  • How Prem Watsa accidentally found investing and never looked back 
  • Why insurance float became Fairfax’s secret compounding weapon
  • The exact thinking that shaped Fairfax’s long-term value discipline
  • How Fairfax set bold targets and held itself publicly accountable
  • Why cheap businesses taught painful but critical quality lessons
  • How downturns and mistakes strengthened Fairfax’s balance sheet mindset
  • What the short seller siege revealed about culture and conviction
  • How crisis hedging created survival capital and massive opportunity
  • Why overprotection hurt returns and forced strategic humility
  • How culture decentralization and capital allocation became Fairfax’s moat
  • And so much more!

Disclosure: This episode and the resources on this page are for informational and educational purposes only and do not constitute financial, investment, tax, or legal advice. For full disclosures, see link.

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] Kyle Grieve: The company and founder-led CEO that I’ll be discussing today has one of the most remarkable track records in modern business since 1985. It has compounded capital at over 19%, placing it firmly in the top 1% of all companies in America. And here’s a twist, it isn’t even American.

[00:00:19] Kyle Grieve: It’s a Canadian insurance conglomerate called Fairfax Financial, led by Prem Watsa. Today, we’re going to unpack just how that happened. We’ll break down Fairfax’s playbook from the ground up. We’ll explore how Prem Watsa used insurance float as an investment jet fuel, why his deep value investing roots mattered, and how culture and patience became just as important as financial returns.

[00:00:41] Kyle Grieve: We’ll also examine how Fairfax survived a brutal multi-year short seller attack that would’ve just crushed most companies. And what that period revealed about conviction, transparency, and leadership under pressure. Then we’ll turn to the global financial crisis. We’ll explore Fairfax’s massive windfall from one bold and widely misunderstood decision, the lessons that came out of that success, and how those same lessons later slowed the company’s growth.

[00:01:05] Kyle Grieve: From there, we’ll look at how Fairfax course corrected and why its best years may still be ahead. We’ll close out the episode by diving into Fairfax’s culture and what makes it resemble the world’s greatest compounding machines. We’ll walk through a few pivotal case studies from its history, including wins, painful mistakes, and decisions that ultimately shaped a business designed to outlast its founder.

[00:01:25] Kyle Grieve: So if you’re an investor or business owner who cares more about durability than narratives, enjoys thinking deeply about capital allocation, and is curious about how culture quietly drives long-term results. This episode is just for you. Now, let’s dive right into Prem Watsa and the Fairfax Way.

[00:01:44] Intro: Since 2014 and through more than 190 million downloads, we break down the principles of value investing and sit down with some of the world’s best asset managers. We uncover potential opportunities in the market and explore the intersection between money, happiness, and the art of living a good life. This show is not investment advice. It’s intended for informational and entertainment purposes only. All opinions expressed by hosts and guests are solely their own, and they may have investments in the securities discussed. Now for your host, Kyle Grieve.

[00:02:27] Kyle Grieve: Welcome to The Investor’s Podcast. I’m your host, Kyle Grieve, and today we’re going to discuss a highly underrated insurance-like conglomerate, and it’s outsider type CEO. Don’t worry, it’s not Berkshire Hathaway. It’s a lot more unknown. The company is Fairfax Financial Holdings, and the CEO is Prem Watsa. So Prem Watsa today, I think, is an investing legend.

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

Some of the links on this page are affiliate links or relate to partners who support our show. If you choose to sign up or make a purchase through them, we may receive compensation at no additional cost to you.

NEW TO THE SHOW?

SPONSORS

Support our free podcast by supporting our sponsors:

References to any third-party products, services, or advertisers do not constitute endorsements, and The Investor’s Podcast Network is not responsible for any claims made by them.

CONNECT WITH KYLE

PROMOTIONS

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

WSB + BFF + RWH Promotions

The Intrinsic Value Newsletter