I do think it’s important to be able to feel passion. I have a lot in my life for which I am passionate. I just don’t let passion run my business. That’s a revelation that has come to me over the past couple of years, mostly as I’ve been building Trajectify and able to look at many companies from the outside-in and work with dozens of entrepreneurs. Two years ago, I was likely quoted as saying that passion is the first thing I look at when evaluating an entrepreneur’s business. I was wrong. The way to grow a business is through being practical, measurable, and grounded, not by being “barely controllable.”

We spend a lot of time in the office - working with our team, on our projects, with our money (investments, revenues). We see our business through the eyes of those who know us well - employees, investors, family. It’s a very narrow perspective that we get when we only interact a typically homogeneous and friendly population. Every week, I drag entrepreneurs out of the office nearly kicking and screaming - they say they have too much work to do! - in order to me to help them view their business by talking with customers, competitors, partners and their market. Here are three stories to show how some of my clients and I did millions of dollars in deals by following an outside in approach.