Don't Hire a Salesperson Until You've Done This First — Collin Stewart
Summary
*Bring your team to StartWell in Toronto for meetings and events: https://startwell.co
Most founders think they have a sales problem.
Collin Stewart thinks they’re wrong.
In this conversation, the Predictable Revenue founder unpacks why product-market fit strength - not better scripts, not more SDRs, not fancier tools - is the real multiplier behind growth.
We start with the book he almost didn’t write - and the uncomfortable truth behind going from 0 to $1M ARR… only to not have the breakout outcome people assume follows.
Then we dig into the mistake nearly every founder makes: mistaking “That’s cool” for “I’ll pay.” Collin shares the hard lesson that changed his entire approach to customer development.
From there, we hit the inflection point: a campaign that booked 327 meetings from 1,000 emails. The takeaway? When demand is real, selling feels easy. When it isn’t, no tactic saves you.
We unpack why product-market fit isn’t binary - it’s a spectrum - and why so many startups stall because they found a customer, not a market.
Then we zoom into modern selling: de-risking deals, buyer-verified pipeline stages, MEDDPICC-style thinking, and how AI should actually be used in go-to-market (hint: not spam).
Finally, Collin leaves founders with a rule most VCs won’t say out loud:
Don’t hire sales until you’ve sold $500K yourself.
If you’re building, scaling, or stuck - this is a masterclass in sequence.
Chapters:
0:00 - The Book He Almost Didn’t Write 6:54 - “Everyone Said It Was Cool”… Then Nobody Paid 8:45 - The Uber Moment: 327 Meetings From 1,000 Emails 14:42 - Product-Market Fit Isn’t Binary 26:39 - Why Sales Feels Terrifying 1:14:30 - The $500K Rule: Don’t Hire Sales Yet