Entrepreneurial Selling

Because nothing happens until something gets sold, entrepreneurs must develop the knowledge, skill and discipline necessary to succeed in sales or that early momentum may never materialize.

Entrepreneurs face a lot of challenges. One of the first is selling. What’s your initial target market? How do you find the first customers in that market? What do you say once you’ve found them? And how do you get them to buy what you have to offer, and then stay loyal over time?

In this series, we explore a few of the critical skills and tools that entrepreneurs can use to succeed in selling. Our purpose is to help you become as efficient and effective as possible in the sales process, because you don’t have a minute to waste.


I’ve made lots of mistakes. I’ve had a few successes. And all along the way I’ve tried to understand what is it about the sales challenge that is unique to entrepreneurs. And what skill and discipline do they need to bring that idea that they’ve, that passion that they have to the market and win those most difficult set of customers which are the first customers. That’s what I spend my time thinking about.

I’m Craig Wortmann. And I’m a serial entrepreneur and a Clinical Professor of Entrepreneurship at the University of Chicago’s Booth School of Business. As an entrepreneur having sold software all the way to consulting services and run those businesses and then as a professional salesperson having sold multi‑million dollar consulting projects all the way down to $15 books and digital apps, I’ve seen this challenge from a bunch of angles early on in a business. The hardest customers you’re going to win are the first ones. When you don’t have a backstory to tell, you only have your backstory, your story. And how do you bring skill and discipline to the table such that you can succeed and replicate that enthusiasm and passion so it does good for people? That’s what’s exciting about it.

And so looking at this challenge of entrepreneurial selling is just fantastic because there are a whole host of skills and disciplines that we as entrepreneurs need to be successful, to be compelling, and to be magnetic such that we can grow this idea. And we can replicate this passion and enthusiasm for whatever we’re working on. That’s entrepreneurial selling and that’s what’s fun about it.

With this series we will give you the skill and discipline necessary to succeed at entrepreneurial selling because nothing happens ’til something gets sold.