At a Glance
The only thing on my nightstand is dust. That said, currently in the queue is a book called Thug Kitchen.
Both my wife and I are big supporters of public radio and public television.
That’s in the crosshairs right now, but I really want to do one of those longer rafting trips through the Colorado River on the Grand Canyon.
At a Glance
The only thing on my nightstand is dust. That said, currently in the queue is a book called Thug Kitchen.
Both my wife and I are big supporters of public radio and public television.
That’s in the crosshairs right now, but I really want to do one of those longer rafting trips through the Colorado River on the Grand Canyon.
Off the Cuff
ill O’Leary is the President & 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.
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 Thursday through Saturday and it almost like a little pop-up thing. They usually only serve one meatless entre and one other type of entre. And it’s just fantastic. It’s nothing fancy but it’s just really fresh and amazingly inventive.
AB: Other than your current career, if you were a kid today, what would your dream job be?
O’Leary: Doesn’t every kid want to be an actuary looking at mortality tables? [he laughs]. I actually like project type work with a really defined scope and a schedule. So probably some type of project management or consulting type work would be kind of appealing. One way or the other, it would have to involve transportation.
O’Leary: Springsteen. But only on the River or Born in the USA tour (not that I’m stuck in the ‘80s or anything).
AB: What’s your greatest extravagance?
O’Leary: I’m a certified public accountant: there’s no room for extravagance.
AB: What is your best attribute and your worst attribute?
O’Leary: I think I’m good at not making snap judgements about issues. I really do like to hear both sides to a story before any decisions are made. And I think that’s something that has served me well over the years. The worst attribute—there’s a really good chance that at times I’ll give people more chances than I probably should about certain things. And I think that sometimes can be problematic. 
