OFF THE CUFF.

Bill O'Leary

Bill O'Leary is the President b CEO of the Alaska Railroad. The Fairbanks native has led the company at every level, from COO to CFO, eventually "ascending to the throne" back in 2013. O'Leary's leadership is rivaled only by his sense of humor--something that likely helped him through the brutal tourism season of 2020.

Despite seeing passenger levels decline a whopping 95 percent from the previous year, the new season has O'Leary optimistic.

"We're coming back," he says. "We've had strong bookings and a lot of it has really come in the last six weeks. Had you told me that in January, I would have said: 'Not happening.'" At the time of the interview, the Alaska Railroad's passenger season was set to kick off at the end of May, and O'Leary is looking forward to what's in store for 2021.

Alaska Business: What do you do in your free time? Bill O'Leary: Free time... Quite the concept [he laughs]. Oddly enough, I really enjoy cooking. I'm not great at it but it's fun and it's kind of rewarding to create something out of disparate ingredients. All that said, I have two vegetarians in the house, so it really is a challenge for a guy from Fairbanks who grew up eating roast beef all of the time... So it's interesting.

AB: Is there a skill you're currently developing or have always wanted to learn?

O'Leary: I've always wanted to learn how to skate ski. It just looks magnificent; very fluid, very rhythmic. But I haven't really done anything like that of late so as I continue to age less and less gracefully here, golf is certainly looking more appealing. One of my goals is to be able to hit a driver further than I can actually throw the ball.

AB: What's your favorite local restaurant? O'Leary: So here's the deal: It's a really small place out in the wilds off Dimond, near Anchorage Brewing. It's called Familia. They only work from...