Andrew Boos - Darwinian Ventures

Episode Stack: https://stackl.ist/4sSOZBB Andrew Boos is the founder of Darwinian Ventures, a fractional sales advisory firm that builds go-to-market teams for early-stage B2B startups. He's also quietly investing in his own clients from profit, not a fund. Before Darwinian, Andrew had a profitable exit at 24 from a startup that began as an ad exchange for China (yes, really), fell into post-exit depression nobody wanted to hear about, learned enterprise sales under a CRO with a $4.2 billion annual quota at a Sutter Hill incubation, blew his exit money trying to launch a quantitative hedge fund, and started freelancing to pay rent when law firms came knocking. We talk about why a linear path to entrepreneurship is a privilege, what happens when your North Star disappears after an exit, how he built Darwinian from a solo 1099 gig into an embedded sales team that's worked with 100+ startups, and why he's now writing small checks into companies where he can see product-market fit before the founders do.