TIP741: The Intrinsic Value of Uber & Reddit w/ Shawn O'Malley
On today's episode, Clay is joined by Shawn O'Malley to discuss his work on The Intrinsic Value Podcast and two key holdings from The Intrinsic Value Portfolio.
Shawn recently launched The Intrinsic Value Podcast alongside co-host Daniel Mahncke, where they conduct weekly deep dives into companies while building their own concentrated portfolio of 20 holdings.
In this conversation, they explore Reddit's transformation from an unprofitable tech IPO to a rapidly growing, cash flow positive business, and examine Uber's dominant market position and diversified revenue streams.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
02:01 - Shawn's process for conducting weekly company deep dives on The Intrinsic Value Podcast.
16:14 - How Reddit transformed from an unprofitable IPO to a rapidly growing cash flow positive business.
29:27 - How Reddit’s user base presents unique challenges for its advertising business.
44:11 - Why Bill Ackman invested $2 billion in Uber’s stock.
52:29 - Why Uber is well-positioned to benefit from the trend to autonomous vehicles.
01:00:57 - An overview of Uber’s billion-dollar advertising business.
01:05:18 - Shawn’s intrinsic value target price for Uber.
And so much more!
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here.
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Check out The Intrinsic Value Podcast.
Check out The Intrinsic Value Newsletter.
Check out The Intrinsic Value Community.
Related Episode: TIVP014: Reddit (RDDT): Valuing the Front Page of the Internet Shawn O’Malley & Daniel Mahnke.
Related Episode: TIVP016: Uber (UBER): Cash Burner to Compounder? Shawn O’Malley and Daniel Mahnke.
Follow Clay on LinkedIn & X.
Follow Shawn on LinkedIn & X.
Check out all the books mentioned and discussed in our podcast episodes here.
Enjoy ad-free episodes when you subscribe to 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
AnchorWatch
Cape
Intuit
Shopify
Vanta
reMarkable
Abundant Mines
HELP US OUT!
Help us reach new listeners by leaving us a rating and review on Spotify! 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!
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
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Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
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1:21:56
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1:21:56
BTC245: The Next Metaplanet? (Smarter Web Company) w/ Jesse Myers and Andrew Webley
Andrew and Jesse join Preston to discuss Smarter Web’s transformation into a major Bitcoin Treasury firm, UK market dynamics, valuation strategies, and future growth plans, including preferred shares.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
14:02 - What is MNAV and why is it a crucial metric for valuing Bitcoin Treasury firms?
35:20 - How does Smarter Web plan to maintain its lead in the UK Bitcoin market amid rising competition?
49:52 - What are the benefits and risks of investing in a Bitcoin Treasury company versus Bitcoin directly?
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
Slides presented (Part 1).
Slides presented (Part 2).
Smarter Web Company's Website.
Smarter Web Company's X Account.
Andrew’s X Account.
Jesse's X Account.
Check out all the books mentioned and discussed in our podcast episodes here.
Enjoy ad-free episodes when you subscribe to our Premium Feed.
NEW TO THE SHOW?
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Follow our official social media accounts: X (Twitter) | LinkedIn | | Instagram | Facebook | TikTok.
Check out our Bitcoin Fundamentals Starter Packs.
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.
Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter.
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
AnchorWatch
Cape
Intuit
Shopify
Vanta
reMarkable
Abundant Mines
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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1:06:39
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1:06:39
TIP740: The Great Mental Models Part 1
On today’s episode, Kyle Grieve discusses the power of mental models, how they sharpen our thinking, and how they improve our decision-making in investing and everyday life. He explores various key concepts in general thinking, including the circle of competence, inversion, first-principles thinking, probabilistic thinking, and more.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
02:01 - What exactly are mental models?
04:37 - The three failures people have with interacting with reality.
08:43 - A simple 6-step framework for making mentals into a habit.
17:45 - How to utilize what you already know to gain an edge.
29:40 - The importance of thinking in first principles to improve your ability to innovate and simplify.
36:10 - How to use thought experiments to analyze a business.
41:14 - Why using second-order thinking can rapidly enhance your quality of thinking.
49:46 - How probabilistic thinking helps make sense of a dynamic world.
58:54 - Why spending time thinking about a problem backwards can improve your upside.
01:04:57 - Why you should focus on simple solutions over complex ones.
And so much more!
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here.
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Buy a copy of The Great Mental Models Vol. 1 here.
Read Shane Parrish’s blog here here.
Follow Kyle on X and LinkedIn.
Check out all the books mentioned and discussed in our podcast episodes here.
Enjoy ad-free episodes when you subscribe to 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
AnchorWatch
Cape
Intuit
Shopify
Vanta
reMarkable
Abundant Mines
HELP US OUT!
Help us reach new listeners by leaving us a rating and review on Spotify! 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!
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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1:15:07
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1:15:07
TIP739: The Psychology Of Human Misjudgement
On today’s episode, Kyle Grieve discusses Charlie Munger’s legendary speech, The Psychology of Human Misjudgment, and unpacks all 25 of his cognitive biases that often lead even the most intelligent people to make poor decisions. Drawing from Poor Charlie’s Almanack, Kyle explores how these psychological tendencies—like incentive-caused bias, social proof, and inconsistency avoidance—can distort our thinking in business, investing, and everyday life. He blends Munger’s timeless wisdom with real-world investing examples, personal experiences, and practical strategies to help listeners make better, more rational decisions.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
03:02 - Why incentives quietly override moral behavior.
06:32 - Why liking and disliking an investing thesis can distort reality.
09:54 - Why doubt avoidance cause investors to take significant risks in things like IPOs.
12:07 - How inconsistency avoidance causes a lazy creep into our thinking processes.
24:38 - How to avoid the destructive effects of reciprocation.
32:49 - The dangers of overestimating our abilities.
37:44 - Why jumping off a sinking ship beats trying to patch it up.
45:58 - Why contrasting stock prices in exuberant markets evaporates margins of safety.
59:41 - Why investors should choose simplicity > complexity.
01:01:43 - Why you should search for Lollapalooza effects in business.
And so much more!
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more here.
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Buy a copy of Poor Charlie’s Almanack here.
Read about Charlie’s Psychology of Human Misjudgement here.
Watch Charlie’s presentation on The Psychology of Human Misjudgement here.
Follow Kyle on X and LinkedIn.
Check out all the books mentioned and discussed in our podcast episodes here.
Enjoy ad-free episodes when you subscribe to 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
AnchorWatch
Cape
Intuit
Shopify
Vanta
reMarkable
Abundant Mines
HELP US OUT!
Help us reach new listeners by leaving us a rating and review on Spotify! 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!
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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1:09:28
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1:09:28
BTC244: Bitcoin Mastermind Discussion Q2 2025 w/ Joe Carlasare, HODL, and Jeff Ross (Bitcoin Podcast)
Bitcoin market insights, Treasury trends, stablecoin regulation, and bold predictions for Bitcoin's future.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
03:21 - How global liquidity and leverage affect Bitcoin's market performance
08:56 - The evolving role and risks of Bitcoin Treasury companies
17:26 - Why stablecoin regulations are reshaping digital finance
18:35 - What the Genius Act means for bank and non-bank stablecoin issuers
21:03 - How Tether and JPM are responding with gold tokens and Layer 2 solutions
24:50 - Why the Base network's centralization raises concerns
27:45 - Differing views on the US dollar's future amid AI-driven economic shifts
35:30 - Long-term predictions for Bitcoin and gold prices
40:33 - The strategic role of Bitcoin options trades
48:06 - Legal strategies for enforcing advertising contract disputes
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
Related Episode: Bitcoin Mastermind 1st Quarter 2025.
Related Episode: Bitcoin Mastermind 4th Quarter 2024.
American Hodl on Nostr.
Jeff Ross on Nostr.
Joe Carlasare on X (Twitter), Nostr.
Check out all the books mentioned and discussed in our podcast episodes here.
Enjoy ad-free episodes when you subscribe to our Premium Feed.
NEW TO THE SHOW?
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Follow our official social media accounts: X (Twitter) | LinkedIn | | Instagram | Facebook | TikTok.
Check out our Bitcoin Fundamentals Starter Packs.
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.
Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter.
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
AnchorWatch
Cape
Intuit
Shopify
Vanta
reMarkable
Abundant Mines
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
Acerca de We Study Billionaires - The Investor’s Podcast Network
We interview and study famous financial billionaires, including Warren Buffett, Ray Dalio, and Howard Marks, and teach you what we learn and how you can apply their investment strategies in the stock market.
We Study Billionaires is the largest stock investing podcast show in the world with 180,000,000+ downloads and is hosted by Stig Brodersen, Preston Pysh, William Green, Clay Finck, and Kyle Grieve.
This podcast also includes the Richer Wiser Happier series hosted by best-selling author William Green. William regularly interviews legendary investors such as Mohnish Pabrai and Guy Spier, exploring what they can teach us about how to succeed in markets and life.
And finally, our Bitcoin Fundamentals series is hosted by Preston Pysh, where he interviews prominent figures in the Bitcoin and macroeconomic space. To learn more about TIP, you can visit theinvestorspodcast.com or subscribe to our free daily newsletter here.
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
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