Grit #151 CEO Outreach, Manny Medina: 10M or Die
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Aug 14, 2023 
Manny Medina traces his move from Ecuador to the US and the winding road to building Outreach. He talks startup survival, crossing the chasm from early adopters to the mainstream, and the race to give sales reps AI assistants. Along the way: imposter syndrome, “10 million or die,” CEO sacrifices, and why hiring someone who’s simply “been there, done that” may be the wrong move.
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The Outage That Proved Product-Market Fit
- Outreach discovered product-market fit when a customer panicked after an outage because its sales team could not work without the platform.
- Medina’s co-founder recognized that losing the product, rather than gaining a paying customer, provided the decisive validation.
New Categories Face A Double Chasm
- New categories face a double chasm because buyers must first accept a new way of working and then believe a particular vendor will win.
- Established categories cross more easily because pragmatists already understand the problem and only compare solutions.
Scaling Can Strip Away Customer Context
- Scaling introduces tightly defined roles that can strip employees of the context and urgency founders once held naturally.
- Leaders must repeatedly explain purpose, structure, and accountability, while accepting that not everyone will share startup-level existential urgency.