RWH032: The Vigilant Investor w/ Chris Bloomstran

RWH032: The Vigilant Investor w/ Chris Bloomstran

In this episode, William Green chats with Chris Bloomstran, President & Chief Investment Officer of Semper Augustus. This conversation is so rich that it’s been divided into two episodes. Here, in Part 1, Chris explains how to achieve long-term success by seeking a “dual margin of safety” that comes from owning high-quality businesses at attractive prices. He also warns about the perennial dangers of irrational exuberance, which he now sees in hot stocks like Tesla & Nvidia. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 04:45 - What Chris Bloomstran learned from his brilliant mentor, Robert Smith. 08:17 - How Chris & Robert skillfully sidestepped the dotcom bubble & crash. 10:00 - What lessons Chris drew from an early investment that fell to zero. 35:17 - Why Chris named his investment firm after a crazily overvalued tulip. 44:53 - What Sir John Templeton saw as the best antidote to financial insanity. 55:38 - How to succeed in stocks by seeking a “dual margin of safety.” 56:51 - How his definition of a quality business has evolved. 1:07:01 - Why he’s skeptical about Cathie Wood’s ARK portfolio. 1:09:02 - Why hot tech stocks like Nvidia are likely to disappoint for many years. 1:11:32 - Why he’s wary of hype & “puffery” about Tesla’s glorious future. 1:17:49 - Why he’s trimmed great but pricey holdings like Costco & Nike. 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, and the other community members. Chris Bloomstran’s firm Semper Augustus Investments Group “Extraordinary Popular Delusions & The Madness of Crowds” by Charles Mackay “The Rise & Fall of American Growth” by Robert Gordon William Green’s book, “Richer, Wiser, Happier” – read the reviews of this book Listen to Stig Brodersen’s April 2023 interview with Chris Bloomstran, or watch the video. Follow Chris Bloomstran on X (AKA Twitter) Follow William Green on X (AKA Twitter) SPONSORS Support our free podcast by supporting our sponsors: River Toyota Range Rover Sun Life SimpleMining The Bitcoin Way Onramp Briggs & Riley Public Shopify Meyka Fundrise AT&T iFlex Stretch Studios 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 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 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 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 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 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

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TIP785: My Reflections on Money, Life, and Happiness w/ Stig Brodersen

TIP785: My Reflections on Money, Life, and Happiness w/ Stig Brodersen

In this episode, Stig Brodersen shares personal reflections on money, life, and happiness. He explores how money magnifies who we already are, why lifestyle creep can quietly erode happiness, and how ...

18 Tammi 59min

TIP784: History's Biggest Market Bubbles w/ Clay Finck

TIP784: History's Biggest Market Bubbles w/ Clay Finck

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BTC257: Bitcoin Mastermind Q1 2026 w/ Jeff Ross, Joe Carlasare, and American HODL (Bitcoin Podcast)

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The Bitcoin mastermind group explores geopolitical tensions, including a potential U.S. response to Taiwan's defense and Venezuela’s strategic oil reserves. They analyze the revolutionary impact of AI...

14 Tammi 1h 20min

TIP783: What the Market Missed: Prem Watsa and One of the Greatest Records in Business w/ Kyle Grieve

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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 LEA...

11 Tammi 1h 8min

TIP782: The Search for Mispriced Stocks w/ Clay Finck

TIP782: The Search for Mispriced Stocks w/ Clay Finck

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9 Tammi 1h 1min

TECH012: Monthly Tech Roundup – Data Centers in Space, AI5 Chip, Tesla vs. Waymo w/ Seb Bunney (Tech Podcast)

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Preston and Seb unpack AI’s implications for safety, governance, and economics. They debate AGI risks, corporate centralization, Bitcoin's regulatory role, and Elon Musk’s ventures in space and autono...

7 Tammi 1h 10min

TIP781: My Portfolio & Current Market Conditions w/ Clay Finck & Stig Brodersen

TIP781: My Portfolio & Current Market Conditions w/ Clay Finck & Stig Brodersen

In this episode, Stig Brodersen sits down with Clay Finck to reflect on Clay’s portfolio decisions, investment philosophy, and personal evolution as an investor. Clay walks through the rationale behin...

4 Tammi 1h 27min

TIP780: Top Stocks for 2026 w/ Shawn O'Malley, Daniel Mahncke, & Clay Finck

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Clay is joined by Shawn O’Malley and Daniel Mahncke to share their top stock ideas for 2026. Shawn is pitching Exor N.V. ($EXO), Daniel is pitching Mercado Libre ($MELI), and Clay is pitching Meta ($M...

2 Tammi 1h 32min

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