Sean started his ballooning adventures on June 7, 1977, with his family in the Ohio Valley. His first flight was on his dad's second training flight to an altitude of 3000 ft., he was hooked from that day and knew that's what he always wanted to do.

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He bought his first balloon on Good Friday in 1986 and began to travel and participate in competitions. He ended up with sixteen top-ten finishes in sixteen events, including the True Value Cup in Lisle, Illinois,  and his home town event, The Great Zinzinnati Balloon Race in Cincinnati, Ohio. In 1987 he earned his commercial pilot certificate and set his sites on becoming a professional balloon pilot. In 1991 he did just that when he was hired to fly for Renaissance Balloons in Brighton, Michigan.

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In 2003 Sean started his own company,  Askren Air Balloon Team.

Sean has flown out of every Nascar track on the circuit, with over ninety mid-day flights,  over the Continental Divide two years in a row in,  operated the NFC balloon at Super Bowl XLV,  and the Coca Cola balloon for the Final Four. Sean has been an active participant in the Albuquerque International Balloon Fiesta for thirty years and was the assistant on Team Zvada at the  FAI World Hot Air Balloon Championship in Austria.