Tag Archives: visual storytelling

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.

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