Diane Ballweg, introduced by John Olsen. The Pink Pilot: Diane Ballweg can be identified by a number of interests and titles. She’s a business owner, a teacher, a criminal justice reformer, a philanthropist, a patron of the arts, and a licensed pilot. The latter has not only given her an amusing moniker — The Pink Pilot — it has prompted her to write a new book about the joy of flying: Into the Wind, Above the Clouds: Love at First Flight. Introduced by John Olsen.