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Morgan O’Brien gets called lots of things. On April 17, as he spoke at the School as the final participant in the Bloomberg Leadership Series, the Nextel founder had already been pilloried in that morning’s Wall Street Journal. The paper’s editorial pages are stout opponents of O’Brien’s current, controversial campaign to hold a prime chunk of broadband spectrum in trust for public safety communications. But, as O’Brien told his audience at Feinstone Hall, he is equally bothered by another, far kinder term often attached to his name in the media. 

“The press always has to label me ‘visionary,’” said O’Brien. “I think that term is slightly pejorative; it implies the fuzzy, the soft, the vague. I think being a visionary is precisely the opposite of that. I can’t think of anything that’s more hard, or more real.”

This was a recurring theme in O’Brien’s lunchtime talk, in which he outlined the leadership principles that helped a former lawyer build a wireless industry giant worth $36 billion. O’Brien, who left Nextel after a merger with Sprint in 2005, used the firm’s bumpy 18-year ride to the top as something of a cautionary tale for would-be entrepreneurs. “I could tell you that story and make you laugh—or I can make you cry,” he promised. “I have so many people who come up to me and say, ‘I would so much like to do what you did.’ And I say, ‘Is that really what you mean, or would you just like to have what I have? Because I don’t think you really want to do what I did. And you wouldn’t if you knew what I had to do.’”

O’Brien detailed several lessons of his life on the wireless frontier, including some counterintuitive management strategies. First: Embrace failure. “Highly motivated people are usually approval junkies,” he said. “But there are times when your addiction to success and your exaggerated fear of failure is holding you back. During the process of building Nextel, we talked about failure a lot. So we learned how to exorcise the demon by talking about it. We couldn’t wait to talk about some horrendous mistake we’d made.”

There was no shortage of material to discuss: Nextel endured several management shakeups, stock freefalls, and assorted technical crises during O’Brien’s tenure. The experience shaped his approach to decision making, he says. “Action and decisiveness is almost always better than paralysis. There’s no such thing as perfect information.” O’Brien also advocates a hard-nosed realism when faced with difficult choices. “One of the things you have to get out of your head as an entrepreneur is that there’s some great virtue in optimism. Optimistic people sometimes ignore very real, harsh things that are going to cause them to stumble.”

His present venture, , is proving to be no less a challenge. Inspired by the communications breakdowns that occurred in the immediate aftermaths of the 9/11 and Katrina disasters, O’Brien is lobbying to build a next-generation broadband network for use by emergency responders in a 30 mHz block of wireless spectrum due to be auctioned by the FCC in 2009. It’s a prime frequency also coveted by commercial carriers, and while Cyren is backed by public safety organizations, the idea is bitterly opposed by rival companies such as Verizon.

Hopes for success may be dim, but that’s the way O’Brien prefers it. “Professionally, you always have to be moving from the merely happy to the truly satisfied. I had many sleepless nights before I jumped off the cliff that became Cyren. I tried to tell myself: Don’t do that. Do something easier. But doing the thing that most suited me—the thing that, if I didn’t do it, it wouldn’t get done—that’s where true satisfaction comes from. I’ve got to pick something with heft, so that when I fail—if I fail—it will have been worth it.” —David Dudley