Gutter Capital is a venture fund co-founded by a former WeWork executive who sold his company for $220M and a computer scientist turned professional gambler who built software to predict athlete performance, with both partners having invested their own exit proceeds and gambling winnings into over 100 angel investments before raising their institutional fund. The fund focuses on "advancing the American experiment" through investments in affordability, economic mobility, and sustainability, while operating with an unusually hands-on, blue-collar approach that treats portfolio support—especially recruiting—as a core systematized product rather than occasional help.