The Roundabout Entrepreneur

What does it mean to be roundabout and in what contexts can this strategy apply?

Jackson Kelley
5 min readApr 18, 2020

Lately, three materials have been filling my free time. These three materials have one theme tying them together, although ironically, for some of the materials, in a roundabout way. This theme is the idea of the roundabout as Mark Spitznagel calls it in The Dao of Capital.

The gospel of this book, which should be obvious by now, is the strategic advantage gained in the roundabout way

The Berkshire Hathaway Annual Letters

I spent the last few months reading every annual letter Warren Buffett wrote for Berkshire Hathaway going back to 1965. The reasons I did this were two-fold.

The first is that there is a lot of talk surrounding what Warren Buffett did, does, says, and said in investment circles, and I figured I’d get it straight from the horse’s mouth given how often his verbiage is quoted. I’d also been watching all the previous annual meetings that had been recorded on YouTube so I was already a follower and to some mild extent a practitioner.

While I’m on this point, I’ll mention that since reading his letters I’ve seen a great deal of…

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Jackson Kelley

crypto @robinhoodapp | ex-@amazon | @yAcademyDAO resident | whitehat @securityoak | built & sold @ConsoleWeekly