Own Less, Know More with Jeremy Kokemor, Founder and Portfolio Manager at Right Tail Capital

In this episode of the Planet MicroCap Podcast, I spoke with Jeremy Kokemor, Founder and Portfolio Manager at Right Tail Capital, to dig into how two decades inside institutional investing shaped a concentrated, quality-focused approach he now runs on his own terms.

We break down his framework for owning roughly fifteen high quality businesses at a time, why returns on capital are central to how he evaluates businesses, how he’s thinking about AI both as a research tool and as a threat to the companies he owns, and what covering small cap metals and mining at T. Rowe Price taught him about the wide quality spectrum in public markets. We also get into his process for knowing when a thesis has broken - being patient when the thesis is intact, but moving on the underlying thesis has genuinely broken.

For more information about Jeremy Kokemor and Right Tail Capital, please visit: https://www.righttailcapital.com/

Chapters:

00:00 Introduction to Jeremy Kokemor and Right Tail Capital 02:06 Jeremy’s background and early influences in investing 04:50 Jeremy discusses his transition from institutional to independent investing 11:00 Starting Right Tail Capital: motivations and timing 16:46 Defining quality and evaluating distressed assets 22:24 Research process and team building at Right Tail 24:31 The role of AI in research and decision-making 26:50 AI’s potential to disrupt or enhance current holdings 33:58 Portfolio construction and new investment evaluation 36:39 Lessons from past investment mistakes and exits 41:04 Jeremy’s best decision and personal stories 44:00 Influence of poker on investment strategy 46:39 Future outlook on AI and investment opportunities 48:28 Where to follow Jeremy and learn more

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