Investing Strategies: Bet Sizing and Market Dynamics

This chapter explores the critical rules of bet sizing in investing, using poker as a metaphor to illustrate key concepts. It highlights the importance of strategic investment checks in early-stage ventures and how industry dynamics shape investment decisions.

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Brought to you by Protekt's REST sleep supplement, Athletic Greens's AG1 all-in-one nutritional supplement, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business.

Bill Gurley (@bgurley) has spent more than 20 years as a general partner at Benchmark. Before entering the venture capital business, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at Credit Suisse First Boston.

Bill also maintains a blog on the evolution and economics of high technology businesses called Above the Crowd.

Over his venture career, he has worked with such companies as GrubHub, Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow.

Bill has a BS in computer science from the University of Florida and an MBA from the University of Texas. He is also a chartered financial analyst. Bill is a board trustee at the Santa Fe Institute, a research and education center focused on the study and understanding of complex adaptive systems.

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[05:51] The book Bill calls "the most efficient short-form MBA one can find."

[07:31] Sell-side analysts vs. buy-side analysts.

[09:45] Financial models, rules of thumb, and making (sometimes wrong) decisions.

[17:28] Howard Marks and Stan Druckenmiller.

[19:26] Micro vs. macro investing.

[20:40] Institutional Investor's All-America Research Team.

[24:16] Expanding distribution.

[27:04] Return On Invested Capital (ROIC).

[33:10] Repurposing good ideas for alternative applications.

[37:01] The conviction of network effects.

[38:58] SaaS and open source.

[42:40] Bet sizing.