“Winners Take None:” Coworking, Self Storage, Scooters Have Burned Billions of Investor Dollars and Maybe Were Never ‘Tech Companies’

Hunter Walk
2 min readAug 8, 2023

The historical dynamic for software markets was one of ‘winner take all/most.’ Economies of scale, network effects, soft monopolies/bundling, patent moats: there are many reasons why. Putting your money into one of these leading companies could produce incredible returns over time for venture, institutional, and retail investors. In some twisted way then, the opposite of these companies (Oracle, Google, Meta, Microsoft, Apple, Salesforce for example) would be ‘winner take none’ outcomes. Verticals where an incredible amount of investor capital was committed and even the ‘best/surviving’ companies ended up consuming a tremendous amount of dollars.

Sometimes a winner take none market can emerge when a technology breakthrough just didn’t pan out, or there’s a dramatic change in customer needs/expectations. But other times, and through the most recent cycle, it seems like some of the most dramatic ones were just blitzscaling aimed the wrong target. Narratives and spreadsheets which somehow would take low margin, high fixed cost businesses and transform them into technology companies.

Self-storage on Demand. Winner take none.

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Hunter Walk

You’ll find me @homebrew , Seed Stage Venture Fund w @satyap . Previously made products at YouTube, Google & SecondLife. Married to @cbarlerin .