#179 - David Roshak, CEO at DMR Capital and Triathlete

In this episode, I sit down with David Roshak, CEO of DMR Capital, to trace a career that arcs from Big 4 accounting and Level 3 boardrooms to early-stage cyber investing, mentoring founders, and chasing Ironman finish lines. Dave shares candid stories—growing up near Warren Buffett in Omaha (yes, awkward restroom run-ins), a father who captained 747s, swapping a high-travel CFO life for a self-directed fund, and the hard reset that divorce forced on his priorities.They dig into what it means to trade control for influence as a board member, why time (not money) is the scarcest investment, and how to design goals you’ll actually live by. The conversation winds through mentorship, friendship, and community; the cultish joy of triathlon (and wearing too much swag); religious skepticism and mortality; new-dad advice; and learning to look up—from the Willamette River to Red Rock Canyon to the late-race finish chute.David’s IG: https://www.instagram.com/dmr2.0/SQ Socks: ⁠https://stupidquestions.show/pages/sq-merch⁠ SQ Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup⁠