BootsnAll: The Early Days

As part of the 10th Anniversary celebrations last week, former BootsnAll employee and wordsmith extraordinaire from the Eugene days, Anthony St. Clair was in Portland and had penned a reflection on his time with BnA. He was due to read it to the large audience at the Wonder Ballroom, but given the ambient noise and mood of the crowd we decided it was best saved for the after-after party.

It was a more intimate setting, and in the end probably more appropriate. Ant kindly agreed to let us share his words with the interwebs:

When you’re young, you do some crazy stuff - such as moving from where you grew up to a different country. Even crazier, is when you move from that different country, to a different part of your home country, to take a job where you know you won’t be getting paid, at a company where the full-time staff - all three of them - work part-time jobs to pay the bills.

When you’re young, that can seem pretty crazy. But when you’re older, you learn that the crazy stuff isn’t always as crazy as it seems. Sometimes it is, sure. But usually, what you learn, what you come to understand, is that the crazy stuff is just you following your heart, just you acknowledging that sometimes you have to do something a little different, a little nuts, something completely beyond your control - because if you don’t, you’ll always know you missed out, and you’ll regret it.

I became part of BootsnAll in 2000, after meeting Sean Keener at a travel exhibition in Edinburgh, Scotland. I was nearing the end of a UK work visa, and was looking for what to do next. I’d first come to Scotland as a college student, leaving my native Virginia and my collegiate Tennessee to learn that beer could actually taste good; that not everyone believed in shotguns and Confederate flags; and that Glaswegian accents, drunk or sober, are completely mind-bogglingly incomprehensible. I needed to see the world, and here I was, twenty-two-years-old, amazed at this new, unknown vastness and variety.

A beer with Sean led to writing opportunities. Later, when he learned I was planning to move to Oregon after completing a four-month Irish work visa, he offered me a job. Sean made it clear that the pay would be, well, there wouldn’t be any pay. He made it clear that quarters would be tight, or, well, that quarters would be four guys, four desks, and four big desktop computers - complete with those huge, console-TV-sized old-fangled CRT monitors - crammed into a dining room in the oldest still-standing house in Eugene, Oregon.

I accepted.

For nearly three years I worked side-by-side, literally, with Sean, Chris Heidrich, and Nick O’Neill. The company was by no means a shoe-in for success. BootsnAll wasn’t hatched in a Silicon Valley happy-hour bar. We weren’t backed by heavy venture capital. We were considered so unlikely a viable company, that one business consultant even called BootsnAll “a bad idea, based on a mix of ignorance and innocence.”

But we were determined, and we believed that, succeed or fail, we would give Boots our all. To pay the bills, Sean and Chris biked around town, at ungodly hours and in all weather, to deliver newspapers. I temped and hawked cutlery. Nick folded towels while averting his eyes from fat naked men at a local health club. By and large, things went well. We didn’t always agree. We didn’t always understand each other. But we were building a business, a company, based out of a shared passion and a common goal: to one day quit our part-time jobs.

The first time someone bought me a beer because I was one of the “BootsnAll Guys”, I could hardly believe it. When the four of us drove to Portland for the first BootsnAll party, a summertime shindig at Ringlers Annex, we were stunned to see 30 people turn up. And yes, it was incredible to have our hands shook and shoulders clapped, and for people to tell us how cool it was, what we did, and how hard they knew we worked. But what really floored us, was watching these 30 strangers talk with each other. People who had chatted endlessly on the BootBoards were meeting face-to-face for the first time. Three women had traveled to the party just to meet their favorite BootsnAll writer. All around the bar that night were stories of confidence found and dreams realized, in part because of how us four crazy guys in Eugene were building something that helped all of us and all of them come together, out of a shared passion and a common goal: to travel, to authentically experience our crazy, profane, profound, beautiful, beastly, amazing and always-beyond-our-comprehension world.

They were drawn to BootsnAll, as you are, because they wanted to see the world. At BootsnAll they found people whose reaction wasn’t, “Are you crazy?” but was instead, “Rock on, mate! You’re gonna love it! Where do you want to go first?”

When I left BootsnAll in 2003, I could feel the company’s momentum increasing. Leaving was not an easy decision, but just like leaving my hometown and moving abroad when I was younger, I knew it was the right thing to do. I also knew that the work I’d done, the hours and sweat equity I’d put in, had gone to build something bigger and better than me, bigger and better than all us four guys combined.

It’s been a long time since I posted an author’s new travelogue, or explained “Thorntree Refugee” status on the message boards, or wished Keener would be quiet for five minutes so I could concentrate on the new massive section of “content, commerce and community” that I was supposed to be building. But I’ve always known where BootsnAll was going, and tonight, I see that I was right.

BootsnAll is more than Sean, Chris, Nick and I ever could have imagined. Everyone here tonight is here out of a common dream and a common love - to see the world, and to share with like-minded people that passion not just for travel, but for a life fully lived. I am honored to see you and meet you here tonight, to see how far BootsnAll has come, and to have been part of something that, no matter how crazy it might have seemed at the time, has helped people’s dreams come true. Thank you.

Thanks again, Ant. Very meaningful to Sean and I and it was great to see you again.