Sales in Context

Entrepreneurial Selling is a contact sport. It can’t be done sitting behind a computer screen. Whether you have a B2C or a B2B company, you have to sell. Topline revenue earns you the right to worry about product development, operations and finance. Without it, you have nothing.


Let’s talk about selling. And let’s talk about a specific form of selling that I like to call entrepreneurial selling. I like to refer to this as the toughest best job there is. Because both of these things are challenging. Entrepreneurship, of course, is challenging and difficult. And so is selling. But we have to do both. We have to get good at both.

Think about our ability to communicate all over the world. Well telecommunications companies, of course, they lay the fiber optic cable across the ocean. They put in the substation and they put in the boxes and infrastructure near our neighborhoods and our businesses. But then think about it, what gives us the ability to actually communicate? It’s what they call the last mile. It’s the last, that wire or wireless signal to the house or the business that gives us the ability to communicate. That’s what’s important. And I think many of us as entrepreneurs, we lose sight of that sometimes with the sales challenge because we think well look, I’ve laid‑‑ I built product, I’ve laid the fiber optic cable. It’s fantastic. It’s fast. It’s beautiful, right? But guess who the last mile is? You are the last mile.

We as entrepreneurs are that last mile that connect to customers because that’s where the market is. One of the things I love to talk just about is just think about the world’s most boring income statement, right? You’ve got an income statement. You’ve got you know, revenue at the top, you’ve got gross margins, operating expenses, marketing expenses, cost of goods sold. You got your bottom line down here. Now think about it for a second, what’s the most important line on that income statement? And most people say, well, Craig, it’s the bottom line, of course. Well, the bottom line is hugely important but guess what? Nothing happens until there’s a top line. We spent a lot of time as entrepreneurs thinking about how to build financial statements and how to run those income statements and looking at all the lines. It’s the top line that counts. It is your ability to sell and make a market that’s absolutely critical to driving that top line growth.

Suggested Readings

Founders School || Entrepreneurial Selling || Sales in Context || Impact Guide (PDF).

Deutsch, Waverly & Craig Wortmann. Entrepreneurial Selling (PDF). Chicago, IL: Polsky Center for Entrepreneurship, 2011.

Stevens, Samantha & Craig Wortmann. InvoiceMe (PDF). Chicago, IL: University of Chicago Booth School of Business, 2011.

Pink, Daniel. To Sell is Human: The Surprising Truth About Moving Others. Edinburgh, Great Britain: Canongate Books, 2012.

Allen, David. Getting Things Done: The Art of Stress-free Productivity. New York: Penguin Books, 2002. Chapters 1-2.

Duhigg, Charles. The Power of Habit: Why We Do What We Do in Life and Business. New York City, NY: Random House Publishing Group, 2012. Chapters 1-3.

Koch, Jim. “Portrait of the CEO as Salesman“. Inc. March 1, 2000.

Sarasvathy, Saras D. “What Makes Entrepreneurs Entrepreneurial?” (PDF) Vol., pp. 1-9, Available at SSRN.

Questions for You

Knowing a lot about your product doesn’t guarantee that you have the skills and discipline to get out and sell it. In fact, that knowledge can get in your way.

What skills do you already have?

Do you know what objections you’ll face and how to handle them?

Do you know the first few things you will say when you walk up to a prospect?

Do you know when and how to qualify a prospect in the first conversation?

Do you know how to handle the pricing conversation?

These are just a few of the skills (and disciplines) required for success in selling.

What skills do you lack? How can you work on these? How much time will you devote to selling on a weekly basis?

How will you balance the need to sell vs. product development, operations, finance, hiring, and doing the dishes?

Tools and exercises

Go out and get rejected! Here’s an exercise to toughen you up: Get Rejected (PDF)