The Biggest Outbound Sales Mistakes Founders Make, Episode 8


Founders are a rare breed. 

They’ve set out to put their dents in the universe.

And they are willing to take large risks to get there. The odds of making it are long, and the hours brutal. 

It’s also very lonely. 

Not everyone is willing to sacrifice it all to make the world better. Because founders are no ordinary people, they usually gravitate to one another and bond when they first meet. 

Game recognizes game. Cut from the same cloth, they sniff each other out as members of this rarified air. 

And yet, founders forgo leaning on this commonality.


In the last 8 years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. I’ve done my best to help. And in doing so, I’ve spotted patterns: those costly outbound sales mistakes that keep occurring, and that prevent startups from growing to their full potential. Over 10 weeks, we’ll examine each of these very closely: at the pace of one per week. Consider this your mini-series on the biggest outbound sales follies founders make. And here’s your 8th installment. Read on.

Founders forget to leverage one of their main strengths: founder-to-founder kinship.

One of the ways founders can leverage this kinship with fellow founders is by introducing themselves properly and asking other founders for feedback. The founder on the receiving end usually sees themselves in the outbounding founder and feels obliged to respond. 

After all, they’ve been in those shoes and have trekked that solitary, treacherous path. Yet very few founders think to leverage this advantage they have over others. 

There’s even a bonus corollary to this maxim. Prospects – even non-founders – would rather talk and interact with founders than coin-operated salespeople. This translates to higher response rates and more introductory calls booked. 

It makes complete sense. If you’re a prospect who suffers from a pain point that was mentioned in an outbound email, you’re more enthused to talk to the person who has studied the problem intensely and crafted a solution over the past two-plus years, than a salesperson whose sole goal is fattening their next commission check. 

Who could blame you? Empathy for your problem is going to overflow from the founder. They’ve gotten so close to the issue you’re facing they can taste it. Even if they didn’t directly suffer from it. Knowing this founder has invested great chunks of their existence making something that will enhance your life has you leaning in. “You understand me!”, is the overwhelming feeling you get when thinking about the founder’s dedication to your cause.  

This is such a powerful force in go-to-market, that we often recommend that hired sales reps impersonate their bosses – the founders – in their outbound messages. It’s a shrewd tactic known and widely used in sales circles. The delta in difficulty between breaking into accounts as a founder and doing the same as a salesperson is a major reason why going from founder-led sales to salesperson-led sales feels like an arduous transition for most startups. But more on that in future writings.


Next week, we’ll expose a founder faux pas that turns off a sizeable portion of folks out in the market. Perceived as a “power move” by some, it can ruin your chances of garnering interest from prospects.