CFOTL: What comes to mind when we ask for a finance strategic moment?

Friedman: MCI itself, during the ’90s, was a great place. I was there for just a little bit more than nine years. The opportunity within that organization to have different roles and different responsibilities that were all progressive, or progressing, was really key for me. When I had my first real corporate finance job at MCI, I literally was a direct report to the CFO. While I wasn’t going to show up on an org chart, it was kind of heavy for somebody who’ was in his late 20s at the time—to be able to have one-on-one conversations and have a real impact on decisions that were made and, toward the end of my tenure there, the direction that the company was taking.

I recall a time when I was working with the internal wireless strategy group. We went to Wall Street to talk to analysts about their views on the emerging wireless market. Keep in mind that this was 1997-ish, right? For CDMA, there were still five or six different providers. T-Mobile hadn’t come around yet. Nextel was still a viable player. Everybody had their projections for the adoption of wireless communications in terms of revenue, and all looked like reasonable growth curves—25%, 30% a year for the next X number of years. And then we met one analyst who said, “You know, they’re all wrong. This thing is going to explode. Every kid in the country is going to have one of these things. You’re going to be talking to your grandmother while you’re standing in line at Starbucks.” This one person had a different insight and a different view that proved to be correct. For me, this was the moment when I gained the realization that conventional wisdom can be stood on its head—that just because there’s a herd mentality around what the right answer is, you don’t necessarily have to go with it. That’s something that has stuck with me every day.