Jorge B. Macías had to figure out how to sell an AI product to medical offices from Puerto Rico, scale it to millions in ARR, and do it as the first founder from the island to take a company through YC—without a traditional sales background. The stakes were high: represent a whole ecosystem on the YC stage while carrying the pressure of proving a repeatable way to win B2B deals far from Silicon Valley.

You have to hear this one because Jorge breaks down how he turned industrial engineering tools into a “GTM engineering” system that took BrainHi from messy first calls to a structured sales engine. He talks about growing up trying to escape his family’s sales legacy, then realizing that process thinking—not charisma—is what closes and scales deals. Along the way, he unpacks the emotional hit of constant rejection, the mindset shift from fighting gatekeepers to winning them over, and the hidden differences between B2B and consumer selling that trip most founders up. This Year One episode also touches on YC expectations, Demo Day hindsight, and why his real career turned out to be building systems, not carrying a quota. Published June 11, 2026, it is especially relevant for early-stage B2B founders who know they need sales but do not yet have a sales engine.