Darwinian in Conversation

B2B buyers vet vendors with AI before any human conversation happens. Spray-and-pray outbound is finished. Andrew Boos on why your first sales hire needs curiosity over quota and why brand credibility is now a frontline sales weapon.

Kyle sits down with Andrew Boos to trace the real Darwinian origin, a profitable exit at 24, enterprise sales training under a $4.2B quota CRO, freelancing to pay rent, and how that path built a GTM firm behind 100+ B2B revenue launches. The lesson: GTM expertise built solo, under real quota pressure, transfers better to client work than theory does.

Post-exit depression. Building through failure. Writing checks into his own clients instead of raising a fund. The unedited Andrew Boos: for founders who want the full story behind how Darwinian operates, not the polished version. The lesson: GTM expertise built solo, under real quota pressure, transfers better to client work than theory does.

The GTM motion that worked in 2019 doesn't work now. Andrew Boos on how AI, market compression, and the rise of the GTM Engineer are reshaping how B2B revenue teams are built, staffed, and run and what founders and revenue leaders need to do differently as a result.

Most startups don't fail because of product. Andrew Boos and an investor go on record about what actually breaks when you scale to $100M: where the revenue motion cracks, where hiring goes wrong, and what neither side usually says out loud.

170+ rejections before closing a $4M seed round. Andrew Boos on what changed, how he reframed the pitch, and what founders consistently get wrong when they walk into a VC meeting. Unfiltered and specific.