On this episode of Bootstrapped, we interviewed venture capitalist and UMD alumnus Gary Swart. Gary operates out of Silicon Valley as a general partner at Polaris Partners, a Boston VC firm that invests in technology and healthcare companies. Prior to his role at Polaris Partners, Gary was CEO of oDesk, a job-search platform that aimed to be the number one destination for job-seekers looking to work remotely. During his eight-year stint as CEO, Gary gained keen insights on customer acquisition, global expansion and staying ahead of competitors, lessons that as an investor he imparts to the entrepreneurs he works with. In this episode, Gary describes the challenges of being CEO, the key factors a startup needs before seeking investment and the differences between the startup ecosystems of Boston and Silicon Valley.