Today’s episode features the one, the only Lindsay Shepard. I met Lindsay in 2021 while riding together during the Arkansaw High Country Race. Since then Lindsay has been one of the most inspiring and most influential members of the bikepacking community that I’ve had the opportunity to follow and become friends with.

Lindsay is no stranger to hard things. She’s been adventuring on her bike since 2014, having completed the Tour Divide, the French Divide, and the American Trail Race. Most recently Lindsay set sail on what we’ll call the Arkansaw Singlespeed Yo-Yo Extravaganza which consisted of Ozark Gravel DOOM, the Quachita Triple Crown, and the Arkansaw High Country Race. A 'Yo-Yo' is when a rider or racer completes the course in one direction and then turns around to finish the course in the opposite direction. Altogether, Lindsay racked up an estimated 3,200 miles and 280,000 feet of elevation gain before it was all said and done.

During our conversation, Lindsay and I touch on how she was introduced to riding a bike, her entrance into ultra-distance bikepacking, why she chooses to tackle such difficult events, and what she discovers about herself in the process.