Before becoming an investor, Troy Henikoff built and ran several companies himself, including co-founding SurePayroll, one of the first online payroll companies in the U.S., and he later helped start Excelerate Labs, which grew into Techstars Chicago, partly to keep promising local startups from leaving the city. That operating background shapes how he invests and teaches today: he's known for genuine generosity with founders as part of Chicago's Give First culture, teaches financial modeling in real depth, tells founders to spend most of their pitch on where the company is headed since investors are really backing its future, looks for founders who combine drive with real openness to feedback, and favors opportunities that offer big upside alongside a low-risk way to get there.