Gregg Bleakney: From Software Sales to Cycling Adventures


Gregg crossing from Argentina to Chile. Self portrait by Gregg.

In the early 2000s, Gregg Bleakney was on a strong path to (one type of) success. He was earning a six-figure salary as a software salesman, owned a house in Seattle, and was generally enjoying his career. Then Gregg and his best friend from college set out on a two-year bike tour from Prudhoe Bay, Alaska to Tierra del Fuego, Argentina to raise money for the American Diabetes Association. Towards the end of the ride, Gregg realized he couldn’t go back to his old life. He quit his job, sold his house and started making inroads to a new career as a self-described visual storyteller focused on adventure travel. Now he’s traveling around the world telling stories as a photographer and writer, often with a focus on bikes. I spoke to Gregg on a short break he was taking in the United States after covering the Tour de Langkawi in Malaysia. We talked about his Alaska to Argentina ride and its sea-change effect on him, his new career and world travels, and more.

I’ll start with the first trip that kick started your new path in life. What originally inspired you to take a leave of absence from work and ride from Alaska to Argentina?

I basically just wanted to take a one year sabbatical from my software job then come back with renewed energy and vigor for building my career. I’d worked in that career for a decent amount of time and was starting to work my way up the ranks pretty well, but I wanted a little break. So that was how it all started.

I had started riding my bike to rehab an injury I’d gotten from running track and field. I used to do the triple jump and I blew out my knee. I met some guy at a coffee shop on the coast who told me about someone who was riding down through Mexico on a bike. I didn’t even know anything like that was possible at the time. I found that bike tourist on the internet and followed some of his trip reports, I think on a Yahoo Groups message board. That all played into me deciding to do my trip.

I planned and began the trip with my best friend Brooks from college. We rode together all the way through Mexico. Then we were assaulted and nearly killed by some rebels down near the border, near Guatemala. He decided to call it quits after that. We both went through some pretty intense post-traumatic stress issues after that. Our families came down and met us. Brooks was engaged at that time and he decided the wiser move would be for him to go home and abandon the trip. I decided to keep going.

After Brooks left it became a solo trip and everything changed. I ended up taking two years to do the ride and realized towards the end that it wasn’t about trying to work my way back into my old job. I don’t think I could have gone back to my old nine to five technology career. After two years on the road it wouldn’t have fit well with my psychology.

Along the way, I bought a camera and made lots of pictures and met all these great photographers on the side of the road and in some of the spectacular locations where I’d stop. I started quizzing them on how to take pictures and what the photographer lifestyle is like. At the end of the trip I got a scholarship from a guy named Rich Clarkson, the former Director of Photography at National Geographic. He gave me a scholarship to come to a workshop. I got to meet a bunch of great National Geographic adventure photographers and that really encouraged me to keep going with a photo career instead of going back to my old job.

So that’s the two year trip in a nut shell.

You mentioned you were cycling to rehab your knee, but did you have any experience as a serious cyclist or bike tourist before you began your big tour?

It had been a few years since my injury and I started doing Team in Training century rides where you raise money for charity and ride a hundred miles. I did a few of those and got pretty into training. When I was running track I was training for the Olympics, so all I knew was high-intensity, competitive, winning-focused athletics. That summer I rode 20 or so weekend warrior type 100-mile endurance races all over California, where I was living at the time. I remember competing and just trying to beat everyone up every hill and always going all out.

Thank god for my friend Brooks. He was doing a longer distance, multi-day fundraising ride down the California coast to raise money for AIDS. I linked up with him and that ride is more about meeting people and enjoying yourself. He raised a bunch of money for the AIDS ride and later discovered that most of the money didn’t go to the charity, a lot of it went to event organizing costs. So we decided to do our own ride the next summer down the coast from Seattle, my home town, to San Francisco, his home town. We raised money on our own to give to the charity of our choice. His mom had recently passed away from diabetes, so we decided to give the money to the American Diabetes Association.

That was the first long-distance bike ride I did.

Later I went to a talk at REI by a guy who’d done the Alaska to Argentina ride over ten years in different bits. I got to be good friends with him. The last piece he hadn’t done was the very northern section from Prudhoe Bay down to Fairbanks. He invited me to join him on the trip and I did. He showed me how to camp out in the wild. I’d never even camped before that trip.

That was one or two years before starting my own ride, so I’ve actually done that section of it twice. It’s kind of funny. Not many people do the Prudhoe Bay road twice.


Photo from The Daily Randonneur.

Your new career has taken you all over the world covering bike races and various adventures, cycling and otherwise. Do you have some favorite assignments and places you’ve traveled?

I really love Colombia. Colombia is special to me because it’s the one place I skipped on my trip from Alaska to Argentina. That was in 2005 and it was a little questionable whether or not it was safe to ride a bike through the country at that time. But I met some Colombians later on in Peru and they invited me back to their country.

I just went for my fifth trip last month to Colombia. I’ve spent a lot of time with cycling teams there. It is one of the only developing countries that consistently produces world-class cyclists. These guys are coming out of nowhere and going to Europe and kicking ass.

I met one guy who was on the Café de Colombia national team. He bought his first bike by working in the coal mines in a small mining town in Colombia. I did a story for Bicycling Magazine and went with him to his hometown. We went down into the coal mines 600 meters below the surface in three or four foot tall mine shafts. All of his old coworkers and his old coach were still working the mines. The air was terrible, you could barely breathe. It was just a difficult space. A lot of the guys who work in the mines are competitive bike racers on the weekends. They have their own miners racing team. That was one of my favorite stories I’ve done.

Another, I just did recently. I got credentials to shoot photos from a helicopter at the Tour Down Under. It’s pretty rare to get credentialed to fly over the peloton in a helicopter to do aerial photos. Getting up and over the peloton and looking down helps put things in perspective and puts everything into place. It was a pretty amazing project to get to see the huge, amazing landscape of a bike race.

It seems like you’re doing really varied work, shooting commercial work, covering bike races, and otherwise. Do you have a particular sub-genre of adventure travel and photography that you like the most?

My first year or two, all my assignments had something to do with cycling. But I realized at the end of the day it was less about cycling and more about adventurous travel. The bicycle is just a tool to travel. I guess my sub-genre would be adventure travel with a bicycle. But I’m trying to do other things now as well and grow from that. I’ve been doing some investigative conservation work, which has been really fulfilling. That article will come out in the next month or two.

But, I always try to point this out. Cycling is the only major sport that really shows travel, whether through a landscape or a destination. There’s no arena. You’re out in the world, traveling through it. And that’s why I love covering professional cycling. And the only type of professional cycling I cover is stage racing that actually goes and travels through a place.

What’s on your short list of places left to go that you have not yet?

I’m really interested in Africa right now, especially when it comes to cycling. Green Edge, a pro cycling team out of Australia, just signed the first ever black African (Daniel Teklehaymanot from Eritrea) to a pro continental team. He says there are a ton of guys as good as him or better coming up through the ranks.

The UCI is trying to expand cycling to a more global sport by holding races in China, India and all through Asia. They’re also trying to recruit cyclists from Africa. I think next up for me, maybe even this year, I’m going to go to Africa and try to figure out what kind of talent pool there is and what the potential is for these guys adapting to be bicycle riders. With track and field, there’s no doubt that a lot of runners from Kenya and elsewhere have incredible cardio-vascular systems. They have an innate ability to run long distances at the highest level. But, running and cycling are total different animals, so we’ll see.


Gregg and Brooks on the “road.” Photo by Gregg.

Do you enjoy the nomadic lifestyle? Do you find it difficult to be away from home as often as not?

I just rented an apartment. I don’t have my bed yet, I’m sleeping on an air mattress. But I’ve been nomadic since 2005. I tried to count up the number of beds I’ve slept in and it’s well over 1000 beds in the last few years. There’s a thrill to being a nomad, but now with my career growing it’s become tough to execute everything I need to do on the road. There’s a lot of post assignment work, editing all your photos and writing a piece, doing interviews and references. You need a place to actually sit down and do all that.

In the first few years it was really what I needed to do. If you really want to be an adventure photographer and travel writer, you have to go out and do adventure travel. But I got to the point where I couldn’t be completely nomadic anymore. It’s kind of the latest phase of my life, where I really appreciate having an apartment. I probably won’t be there very much, but it’s nice to have a place to come back to.

Do you ever see yourself settling back in to a nine to five routine in one place?

I don’t know if I’ll ever do a nine to five. My goal right now is to continue building my career. I’ve stopped calling myself a photographer in the last year and started calling myself a visual story teller. I’ve been writing and doing video as well. I want to keep building that. I think there’s a lot of opportunity for that type of storytelling and people are actually starting to pay for it.

What do you have in the works for 2012?

It’s been a pretty amazing year so far for me. I actually had to make sure to take this month just to relax. I’ll be heading back to Europe soon and I’ll probably do something for the Giro d’Italia for the second year in a row. Then I’ll be back down in Colombia working on two different projects. Then towards the end of the year I’m probably going to go do some stuff in Africa. Those are some of the major projects I’m looking forward to, but I’m also looking forward to spending more time in the US this year. It sounds strange but I’m excited get my files organized. I have I don’t know how many terabytes of files stored and backed up on drives. Some are at my friends’ houses, some are at my parents house, so it’ll be nice to get that all in one place and in order.

Is there anything else you want to share with the world about your adventure life?

It’s been pretty amazing so far. It’s kind of a surreal experience to look back at what I was doing just a few years ago and what I’m doing now. It’s definitely a change of life.

I get emails from people all the time asking for help planning long bike rides or long trips. And the first thing most people ask me is “what kind of bike should I get” or “what kind of gear do I need?” But I tend to try and get people to look past the gear and think about how a year or two on the road will change their life. There’s a lot of things beyond equipment that mater. Being on the road for two years totally changed me. I try and encourage everyone to go out and do something like this and more Americans especially. A lot of people could benefit from leaving everything for a year or so and going out and traveling.

One Response to Gregg Bleakney: From Software Sales to Cycling Adventures

  1. Gregg – on of my sisters emailed me a link to your “Ex-Officio” underwear ad accompanied by these thoughts – “Don’t even pay attention to the underwear – you’ve got to see this guy and his adventure. It’s so you!”. I did love the “ad”!! That’s the coolest ad I’ve ever seen. I did a somewhat similar thing (not an ad) in quitting my great job at Intel in 2006, selling my home in Portland, and taking off on the road to camp and travel . I love “adventure” too and hence am intrigued by your “story” – as are many others no doubt. I am just wondering – if you ever have a chance to come through Bend, Oregon (Central Oregon) – it’s an amazing cycling town – among other things (I’m a big skier – and Mt. Bachelor is just 20 miles from town) – I would love to meet you! Cheers, Carol

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