Venu Shamapant's path into venture was unusual—he started as a software engineer, moved through Harvard Business School and McKinsey, led a startup, and only got into venture capital after an interviewer turned out to be a partner at Austin Ventures; he's also been candid about just how hard fundraising was, noting it took over 18 months, 46 road trips, and nearly 200 in-person meetings to get LiveOak's first fund off the ground. That fundraising experience left him with a strong sense of empathy for founders asking for money, shaping how he evaluates pitches today: he says the first meeting is less about a polished business plan and more about whether someone has lived through a real problem and found a genuine way to solve it.