#222, Living Life to the Fullest and Embracing Adventure with Dick Jackson

We continue our “legends” series with alpinist, pilot and entrepreneur Dick Jackson, founder of Aspen Expeditions (1977) and Aspen Paragliding (1989). Dick begins his amazing story with his journey into alpinism and paragliding, starting with his early expeditions to Denali and the Alps. He discusses the early days of paragliding in Aspen, where they used wings primarily as a descent tool. Dick talks about the lightweight gear and the evolution of paragliders, as well as the camaraderie and community that formed around the sport. He shares stories of flying off unclimbed peaks, hosting international trips, and even taking Maurice Herzog, the leader of the first Annapurna expedition, paragliding. Dick also reflects on the loss of his friend Dave Bridges and offers advice on dealing with grief and the pathway to compassion and impermanence because…what’s the alternative? Dick reflects on his experiences in the mountains and the impact they have had on his life. He discusses the thrill of flying and the incredible advancements in paragliding technology. He also shares a harrowing story of a dangerous gust front during a flying event in Aspen. Dick talks about selling his businesses and the changes in the paragliding industry. He mentions his daughter (Tashi Jangmo Sherpa) and her love for skiing. He also discusses a Buddhist ceremony he attended and the spiritual connection he feels to the mountains. Dick reflects on the fear factor in climbing and flying and the importance of living life to the fullest.

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Paragliding started as a descent tool for alpinists in Aspen, but quickly evolved into a soaring sport.
The early days of paragliding in Aspen were characterized by camaraderie and a close-knit community.
Dick Jackson shares stories of flying off unclimbed peaks and hosting international trips.
He reflects on the loss of his friend Dave Bridges and offers advice on dealing with grief. Advancements in paragliding technology have allowed for incredible flying experiences
The paragliding industry has undergone significant changes
The mountains and the sport of paragliding have had a profound impact on Dick’s life
The importance of living life to the fullest and embracing adventure
The spiritual connection and sense of peace that can be found in the mountains

Sound Bites

  • “These were the original speed wings, seven cells and two to one glide.”
  • “We did the first tandem off Aspen with Chris Blatchley. We both remember running about a third of the way down Walsh’s.”
  • “I had never done any hang gliding. My first exposure to it was when we went to Denali and some guys had just flown off Denali and landed at the airstrip.”
  • “Yeah, yeah, yeah, yeah. Yeah. Yeah. Yeah. Yeah. And wow, when Chris told me that, it’s like, you know, I don’t know the guy or anything, but man, that is serious, serious flying.”
  • “It was really serious. And I have to say that it’s just so fortunate that nobody was even hurt when you consider what the potential was for that one. It’s blowing all over the place. And that was kind of a wake-up call. It’s like, hmm, maybe we ought to pay a little more attention here.”
  • “No, no, no, that was an evening of flying and we had a bunch of visiting pilots around. It was mid, I don’t know, mid season. And, and it was just like, you know, where everybody was really excited about flying.”


00:00 Introduction and Background

03:02 The Evolution of Paragliding in Aspen

09:12 Adventures in Paragliding

14:31 Reflections on Grief

39:57 A Harrowing Experience with a Gust Front

43:22 The Impact of the Mountains on Dick’s Life

46:08 The Spiritual Connection and Sense of Peace in the Mountains

53:12 Living Life to the Fullest and Embracing Adventure

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