By Matt Villano, on October 31, 2014

Blogger spotlight: Spencer Spellman

It doesn’t matter how old Spencer Spellman really is. The truth: He’s one of those people who seems wise beyond his years.

I’m not talking book smarts, here (though the kid knows a ton about a lot of random stuff, and he majored in philosophy in college). I’m talking everyday smarts. People smarts. Life smarts. The kind of smarts that cause you to meet him, spend a few hours talking about baseball or travel or family, and leave thinking to yourself, “Wow, that guy really gets it.”

He’s no Doogie Howser, M.D. Spence will tell you himself that he’s worked hard for everything he’s learned, and that his journey has included debt, divorce, a few monumental moves, and the deaths of two of the most important people in his world.

The bottom line: Spencer Spellman, my colleague and friend, is a real philosopher.

Naturally, then, when he uprooted his life a few years ago and moved to Costa Rica with no subsequent plan, he titled his blog, The Traveling Philosopher. The rest, as they say, is history. Spencer’s travels led him to San Francisco, then to Seattle, and on to Los Angeles. Along the way, he happened to work with some folks on Expedia and start this incredible publishing platform for original travel content. Maybe you’ve heard of it. It’s called the Expedia Viewfinder. (Yes, really.)

Also along the way, Spencer became one of my closest pals. At first, it seemed weird to interview one of my best buddies about his career. Ultimately, the assignment turned out to be a real treat; an excuse to get my buddy talking philosophically about his journey as The Traveling Philosopher. Here are some of the highlights of our chat.

Matt Villano (MJV): Review for me the story of how you got into travel writing.

Spencer Spellman (SS): It’s been a trip, seriously. I was never really a great writer until my last year of college when a professor took me under his wing. The first writing post-college I submitted, I wrote just to get some feedback. The following week it was published in a magazine and it was on from there. A travel guide publisher where I was living at the time hired me as a writer (and then promoted to an associate editor my first day on the job), which I did for 1.5 years before going into freelancing.

MJV: And review for me how you ended up with the Expedia gig?

SS: It was love at first tweet. Really, could I be any cornier? Just prior to starting to work with Expedia I tweeted about this disconnect I saw between travel companies and travelers, and the illustrious Sarah Gavin, senior director of marketing at Expedia, saw my tweet and wanted to chat about collaborating. My original contract was just for two weeks. That was three years ago.

MJV: How would you describe your role with the Expedia Viewfinder to this point?

SS: It’s really been about combining my passions into one role: Travel, writing, and connecting with others. Such a role didn’t even exist just a few years ago. And no one day is the same. One day I’m looking at spreadsheets and presentations with travel industry professionals and another I’m snapping underwater photos of stingrays with a GoPro and writing about it. But I get it, I have it good. I have it real good.

Flying a jet over Las Vegas

MJV: Much fanfare was made over your “30 at 30” list. Explain what that was all about, and explain how the rest of us—perhaps those who don’t have the luxury or chutzpah to be so adventuresome—can internalize that process and try something similar in our own lives.

SS: Man, that was a ride. In short, on my thirtieth birthday, I wanted to do something new and big. I knew of lists like “40 by 40,” but I wanted something that gave life more urgency, as I viewed life/bucket lists as dynamic things. So I decided to do a “30 at 30 List,” in which I sought to do 30 things I had always said I wanted to do, but had never done before. I did 38 of them. And what has resulted is a new goal to do one new thing each month. Some people asked me if I would do a “400 by 40 List,” but I feel like at some point it becomes an end, rather than a means to an end. I highly recommend something similar for others, be it a month, six months, a year, or so on. It really challenges your predispositions and what you think is possible.

MJV: Your blog posts always are peppered with meaningful quotes. Where do you find them?

SS: That goes way back. When I was young, I used to either highlight or write down meaningful quotes, and then memorize them by heart. It’s stayed with me to this day. There are a ton of great, inspiring quotes (travel or otherwise), that have stuck with me that I’ve read over and over and committed to memory.

MJV: You’ve got 24 hours in a new city. What’s your plan of attack?

SS: Whenever I get to a new city, I try to find busy, hole-in-the-wall bar with locals and grab a seat at the bar. By the time I leave I’ve typically made a few friends, while getting a lay of the land from the people who live there and know it.

MJV: I know you love writing about booze. Why?

SS: Uh, why not? Booze has really had a colorful history in America. There was a time just decades ago when the laws were stiff against those who bought and sold booze. But look at it now and it’s a multi-billion dollar industry. And there’s a certain art to it. Many whiskeys, for example, have to sit for years. Years! I just have a great appreciation and interest in the history. That, and it’s just good. But people, drink responsibly.

MJV: Name one place you HAVEN’T visited in the United States, and tell us why you want to go there.

SS: Austin, Texas. My sister lived in Dallas for years and I never got to Austin. A travesty, I know. There just seems to be such a strong culture and soul there that you don’t see elsewhere. That and it’s contributed so much to music in America. And, of course, barbecue. Because barbecue.

MJV: Tell us about the most interesting person you’ve ever met on your travels. Why does this person hold this distinction for you?

SS: That would have to be karate Grand Master Kiichi Nakamoto, one of the first Okinawan to be recognized as 10th-Degree Karate Master by the Japanese Government, and the last living student of Mr. Miyagi. Yes, that Mr. Miyagi, as in the one who was portrayed in Karate Kid. I had the honor to take a class under him last year when visiting Okinawa and interview him afterward. Though he was 83 at the time, he was sharp, and didn’t miss a beat. He talked with such passion and earnestness of someone who had really lived a full life. It was inspiring.

MJV: Give us three examples of your travel rituals. Where on the plane do you like to sit? What do you like to eat on board? Do you like to engage your seatmates? Stuff like that.

SS: Always roll, never fold my clothes when packing. Always have headphones on my person when traveling.  Always carry on, unless it’s free to check.

Sailing Grand Caymans

MJV: Considering how much you have mastered the intersection of social media and travel, what do you think the next big innovation is at the confluence of these two worlds?

SS: Well I wouldn’t call myself a master. The thing about social media and travel is that it’s constantly evolving. What was a trend yesterday is gone today. I think the mobile space is only going to continue to innovate. And I think the travel companies that succeed are going to be the ones who are most connected and in tune with the travelers they serve. There are entire cities offering free WiFi, yet many hotels continue to charge. That should tell you something there.

MJV: With all of your travels all over the world, from which spot have you seen the most incredible sunset?

SS: What I love about capturing sunset photos from around the world is that there are no two that are the same. And it’s hard to narrow it down to one. But say what you will about Seattle, yet they have some of the most beautiful sunsets, when you combine the clouds, the color, the sound, and snowcapped mountains.

MJV: I know you’re on the cusp of some big personal and professional news. What’s next for Spencer Spellman?

SS: This Q&A actually serves as my last hoorah for Expedia. After making memories alongside Expedia in some capacity for the last three years, it’s time to make memories elsewhere. Because I like to make an exit, Halloween will be my last day. The last three years have been a part of the most formidable season of my life and it’s time for me to build and create memories elsewhere. In the near term, that’ll first look like a newly rebranded and redesigned website that shifts from just travel to travel, food, and drinks. Further afield, 2015 will see a shift toward working on some new projects beyond just travel.