We Study Billionaires - The Investor’s Podcast Network

Kyle discusses Stock Market Maestros, revealing that elite fund managers succeed not by picking winners the majority of the time, but by making dramatically more on their wins than they lose on their losses. Through profiling world-class fund managers, the book proves that disciplined execution, such as how you size, hold, and exit positions, ultimately matters more than stock selection itself.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:03:43 - The five investor archetypes and why behavior determines investing success
00:06:37 - How three key metrics identify truly skilled investors from lucky ones
00:09:36 - Why a 49% hit rate can still massively outperform the market
00:10:01 - How the best investors make 1.87x more on winners than losers
00:11:06 - Why riding winners longer matters more than finding the next great idea
00:12:59 - How different selling strategies suit different investing styles and timeframes
00:18:20 - Why losers consume disproportionate mental energy relative to portfolio weight
00:32:28 - How small position sizes allow larger losses without destroying overall returns
00:53:04 - Why changing your thesis to fit reality is a major red flag
01:07:40 - Why execution and position sizing matter as much as stock selection

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

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On today's episode, Clay is joined by Daniel Mahncke to break down Kinsale Capital. Kinsale is a specialty insurer that has quietly become one of the most exceptional businesses in the financial sector by dominating the Excess & Surplus insurance market.

Clay and Daniel break down the DNA of this wonderful business, and if the recent drawdown in the stock is a compelling opportunity for value investors.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:03:32 - An overview of the insurance industry and how Kinsale fits into the bigger picture
00:17:32 - The durable competitive advantages that Kinsale has built
00:20:19 - The advantages of keeping underwriting in-house in the Excess & Surplus market
00:35:04 - What is driving Kinsale’s incredibly low combined ratio
00:39:29 - Why it’s focus on the E&S market and smaller accounts is a moat in itself
01:07:25 - Kinsale’s valuation and primary risks to monitor for investors

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

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

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Kyle Grieve discusses key mental models from economics and art and how they apply to investing and decision-making. He explores economic concepts such as scarcity, supply and demand, optimization, specialization, efficiency, competition, and bubbles, illustrating them with real-world business examples. Then he shifts gears to art, examining things such as audience, contrast, framing, and narrative, emphasizing how they shape investor behaviour and decision-making.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro

00:03:22 - How scarcity drives value and luxury brands engineer demand

00:07:40 - Why Costco wins by reducing scarcity and leveraging scale

00:09:03 - How supply and demand influence stock prices and volatility

00:10:53 - Why economic cycles impact nearly all businesses over time

00:12:38 - How COVID reshaped demand across industries and markets

00:14:19 - The risks of cyclical investing and the benefits of steady compounders

00:15:34 - How optimization can backfire in business and biology

00:19:49 - Why specialization has trade-offs and why investing legends often stay generalists

00:29:58 - The tension between competition, monopolies, and market structure

00:35:14 - How bubbles form through demand surges and investor psychology

00:38:45 - Why great management teams leverage audience building to build the right type of shareholder base

00:43:34 - How contrast framing and narrative shape investor decisions

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

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In today’s episode, Kyle Grieve discusses the speculative boom of the 1960s “Go-Go Years” as presented in John Brooks’ book, highlighting the dangers of euphoria, leverage, and financial engineering. He explores case studies like Ross Perot, Edward Gilbert, Atlantic Acceptance, and Gerry Tsai to reveal how incentives, momentum, and fraud can distort markets. The episode ultimately emphasizes timeless investing lessons around valuation discipline, skepticism, and aligning incentives with long-term outcomes.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:02:02 - About the Nifty Fifty’s rise and the dangers of extreme valuation multiples
00:03:34 - Why great businesses can still be poor investments at high prices
00:05:07 - About Ross Perot’s EDS and the psychology of ignoring market volatility
00:09:45 - The dangers of leverage through Edward Gilbert’s collapse
00:16:13 - Why sharing stock ideas can create unintended consequences
00:19:32 - How fraud fueled Atlantic Acceptance’s explosive growth
00:29:17 - Why rapid growth without explanation signals potential risk
00:33:28 - Gerry Tsai’s momentum strategy and performance-chasing cycles
00:42:07 - How conglomerates used financial engineering to create illusory value

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

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In today’s episode, Kyle Grieve discusses lessons from venture capital that long-term value investors can apply to improve decision-making. He explores concepts such as power laws, network effects, de-risking investments, and the importance of holding high-potential businesses.

IN THIS EPISODE YOU’LL LEARN:
00:00:00 - Intro
00:03:23 - How venture capital power laws shape investing returns and portfolio outcomes
00:06:19 - Why a tiny number of winners dominate most long-term investing results
00:08:41 - Why selling potential power-law winners early can severely damage portfolio performance
00:08:41 - How modest portfolio contributors can evolve into massive long-term winners
00:09:21 - Why accepting losses is the cost of capturing outsized investing returns
00:11:25 - How Moore’s Law and Metcalfe’s Law create powerful technology-driven investment opportunities
00:13:34 - Why investors should scale positions as businesses become progressively de-risked
00:25:41 - How unpopular or overlooked businesses can generate exceptional long-term investment returns
00:32:24 - Why averaging up in strong businesses can outperform traditional value strategies
00:57:06 - How long-horizon arbitrage allows investors to benefit from fundamental business improvement

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

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