How Entrepreneurs Who Hate Selling Close Sales

Or: How startups sell accidentally on purpose

Joe Procopio
6 min readAug 13, 2020


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Do you enjoy the sales process? The cold calls? The awkward pauses? The millions of different ways to hear the word NO?

For many entrepreneurs, myself included, we’d rather have a series of root canals than pick up the phone and face the possibility of someone we don’t know laughing or swearing at us.

Yeah. I’ve had nightmares like that.

In building and selling products for over 20 years, one thing Ive learned about startup sales: There are several misconceptions about what a sales call should be — from first contact to closing the deal.

Here’s how to avoid the myths and start selling accidentally on purpose.

It’s not a job, it’s a game.

As a founder or leader, forget everything you’ve learned about sales. A colleague of mine, Ricky Spero, co-founder and CEO of Redbud Labs, puts it like this:

“I didn’t get or enjoy sales until I understood how structured and gamified it is.”

Don’t look at sales as your job. For you, it’s a game. And the game comes down to two basic strategies: Play the right competition and come prepared.

For the former, that means you’ll need to stop practicing. In other words, avoid these two major mistakes most entrepreneurs make:

  1. Don’t sell to friends, sell to strangers: A lot of entrepreneurs will try to sell in a comfort zone, calling on people they know in order to get a few suspected easy wins under their belt. Friends, family, and associates aren’t customers, even when they buy. In fact, I don’t even practice my pitch on people I know, because the feedback they give me will always be skewed.
  2. Don’t sell to fans: Using that same comfort strategy, entrepreneurs will usually pick target customers who they believe give them the best chance at a positive response. Most of the time, this isn’t the customer who can make a difference to your top line.

So don’t play unless there’s a chance to win.

It’s not a cold call, it’s an exploration



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at