Quietly Crushing 3,714 Miles with Bob Jesernik

Today we’re going to talk about another small team that just quietly went out and crushed it every single day, Bob Jesernik.

Bob rolled up to the start line without a chase truck and without a full support crew. It was just Bob and Dylan Jesernik (Dylan was riding a Moto Guzzi from stop to stop.) If you know anything about running a 100 year old motorcycle across the country, you know that not having a vehicle leapfrogging you with tools, parts, and backup plans can make things interesting real fast. But you honestly never would have known it watching these two operate.

Bob always looked like he was having a great time. His bike was consistently in tip top shape, and he made it from stop to stop with seemingly zero drama. No panic repairs, no big roadside scrambles, just steady miles and a big smile at the finish each day. Any onlooker could tell that Bob’s knowledge of his J model runs deep. He knows that bike inside and out, and it showed in how confidently and smoothly the whole week unfolded. Of course, he got help getting his things from here to there from Monica Olson, who was such an integral part of many pieces of the race!

Dylan was right there alongside him the whole way. While Bob was out on the road each day, Dylan would enjoy the ride to the next stop and then jump in to help our staff with whatever needed doing. Whether it was moving bikes, helping riders find what they needed, or just being an extra set of hands, Dylan was always willing to pitch in. Having that kind of positive, helpful energy at the stops makes a big difference during a long event like this.

Bob was riding a 1925 Harley Davidson JE, and he made those 3,714 miles look easy. Bob’s from the Midwest, and that crafty, problem solving mindset showed through the race. The bike ran strong, the routine stayed simple, and the miles just kept stacking up day after day. It was a great example of how preparation, experience, and a calm approach can make even a massive endurance ride feel manageable.

We absolutely loved having Bob and Dylan as part of the TransAm family, and we already can’t wait to see Bob back on the start line in 2027.

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Photos by: Olivier Touron, Kazuo Matsumoto, Ed Harriger

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