The Sure Shot Entrepreneur · 2026-05-05 · 38 min
Ian Sandler, COO of Insight Partners and co-founder of Riley’s Way Foundation, engages in a deeply personal and wide-ranging conversation on leadership, venture capital, and building meaningful impact. Ian reflects on his unconventional career path, his philosophy on building organizations, and how a personal tragedy shaped his mission to empower the next generation of kind leaders. He also shares practical advice for founders and young leaders on dreaming big, understanding themselves, and building networks that matter. In this episode: [ 00:58 ] Ian Sandler’s background and upbringing [ 03:59 ] From law to “wimpy entrepreneur” [ 06:05 ] Building and scaling at Insight Partners [ 09:27 ] Balancing venture capital with purpose [ 12:35 ] What makes great investors today [ 17:12 ] The story behind Riley’s Way Foundation [ 31:33 ] Advice for young leaders: dream big, self-care, network [ 36:17 ] The future of Riley’s Way Foundation The nonprofit organization Ian is passionate about: Riley’s Way Foundation About Ian Sandler Ian Sandler is the Chief Operating Officer at Insight Partners, where he oversees the firm’s non-investment operations and helps scale new strategic initiatives.
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