A few months before I started Cedarcrest Capital LLC in 2004 I sat down for lunch with a college buddy who founded E-chalk, a company which supplies a technology platform for schools to link parents, students, and teachers online.

Eager to start my entrepreneurial career, I quizzed him about what founding a company felt like. I think I expected him to tell me about his then four-year venture using words like “Freedom!” “Excitement!”, “Satisfaction!”

Instead, the main word I recall from our lunch was “Ignorance.” Specifically, he related to me a cautionary tale: The best talk he’d heard at a conference on business start-ups he’d recently attended focused on ignorance as the key to entrepreneurship. What the conference speaker meant was that if the average entrepreneur truly knew how hard it would be to build a company, nobody would ever begin. It takes ignorance to want to start a company from scratch.

My friend’s weary look, four years after founding his company, told me he wasn’t kidding. In all my excitement to begin, I’m pretty sure I had no idea what he was talking about.

Shortly after that lunch, I walked into my attorney’s office to begin the process of creating Cedarcrest Capital LLC.

Before I even sat down, he commented to me: “You’ve got the grin of a guy who just quit his job and is starting his own company.”

“Yup!” I said, smiling widely.

He said, wisely I now understand, “You’re going to lose that grin. But hopefully, some day, you’ll be able to get it back.”

The optimism of that meeting has not left me in the subsequent years, but I have certainly had the smugness challenged. Four years since founding my own company, I’ve come to appreciate their thoughts even more.