Why Y Combinator warns that automation ruins your early sales

This article summarizes an episode of Y Combinator’s video series featuring its partner, Max Kolysh.

Y Combinator partner Max Kolysh / Photo credit: Y Combinator

Building an early customer base requires more than an internet connection and automated outreach.

Max Kolysh, a visiting partner at Y Combinator, observes that startup leaders hurt their sales by prioritizing automation before understanding their customers.

Relying on bulk messaging before understanding a target audience obscures true demand, delays trust building, and stalls the acquisition of those crucial first ten customers.

Founders pick the wrong ways to reach buyers

Many founders choose communication channels based on convenience rather than customer behavior.

That creates misleading feedback. When outreach fails, founders often assume the product lacks demand when the real issue is that they are using channels their buyers rarely check.

Understanding where customers spend their time, what information sources they trust, and how they make decisions should come before scaling outreach efforts.

“You can blast them with cold email all you want,” Kolysh warns, “and you’re just going to conclude that outbound sales doesn’t work for you.”

Showing up in person proves commitment
Leaving the laptop behind to find buyers in their natural environments reveals a secondary hurdle: early prospects need to trust an entrepreneur before testing an unproven product.

Kolysh recalls the story of one founder who endured months of digital silence before realizing his target market simply did not conduct business over email.

Kolysh explains, “When he finally decided to actually go to an industry trade show and walk the floor, he closed more in three days than he had in three months of sending cold emails.”

Founders must earn trust before buying software

Transforming physical interactions from formal pitches into trusted relationships happens in distinct stages.

Entrepreneurs must adapt their approach as their customer base grows, proving their credibility first, validating the product second, and demonstrating repeatable sales third.

Asking for help works better than pitching

Buyers ignore long messages and unclear demands