We had the good fortune of connecting with Rick Crandall and we’ve shared our conversation below.

Hi Rick, what role has risk played in your life or career?
My whole business career has been about taking a risk – starting a tech company, breaking new ground, helping over a dozen other venture CEO’s get past their challenges – and helping companies navigate the risk of a strategic transformation to a digital future. In few words, I say: 1: pick and attract the best possible team, do not settle for “OK”, 2: infect them with your enthusiasm for the mission; 3) proceed into the unknown with a strategy and focus as though you know for sure it’s going to work – your team wants to believe you have all the answers even when you don’t., and 4) believe in your heart that there is a way to succeed and get past the risks. The secret here is if you see an element of the plan or a team member not working – change them early and then proceed with the same belief and confidence and passion. Later in life I met a completely different kind of risk – climbing mountains. My dog got me going, hiking higher and higher (she insisted) until we got to summit of a 13,000′ peak – and the feeling took me over – I had a new passion in life – a pretty strange one given that I was 64. I found subsequently such joy, beauty, connection with nature and relationships deepening with the younger climber friends who became my team – that I did the work it took to move up the scale of difficulty and risk to master the more difficult mountains. I went on to climb all 58 mountains in the Rockies over 14,000 feet. My attitude towards risk was really not unlike business risk -the difference being risk on the mountains means you could die. But the whole idea of taking a big problem (e.g. reaching a summit) and breaking it down into smaller more achievable pieces, where each one can be solved more easily and with less risk. In each crux move I assumed I would get past it and that confidence is critical to the momentum needed to master the physics of the move.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?

Right out of graduating University of Michigan with a Masters, I founded one of the very first timesharing companies called Comshare, in Ann Arbor, Michigan. That was an early success, many challenges to overcome (that was the cloud before cloud computing), was one of the first software public offerings in 1970. By end of 70’s timesharing was in decline so had to execute a complete strategic transformation to enterprise software and by mid-1980’s was back on growth path. By early 90’s I sold the company and used my tech and management background (26 years as CEO) to form the roundtable of the ceo’s of the 50 larger of enterprise software companies which has been meeting in person for 25 years. I have also served on many company boards, some as Chairman. Most recently I chair the Cyber Committee of the National Cybersecurity Center working to research and educate better cyber-health. This past year I published a memoir (HCI and Simon & Schuster) called The Dog Who Took Me Up a Mountain released last October which is a memoir about “Never Too Late to Find a New Passion in LIfe – the story of my climbing all 58 fourteeners in the Rocky Mountains starting at age 64 and finishing the hard ones in my early 70’s.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Are you talking about Aspen where I live? I would probably take them on an amazing hike with views beyond belief, then perhaps to the Pine Creek Cookhouse for great food and another heart-arresting view of the mountains. Hanging out in summer would be anywhere in the center of the town and in winter, take a break from skiing with a coffee and famous oatmeal pancakes at Bonnies on-mountain restaurant ,

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
My wife, Pamela Levy who supported me pursuing my late-in-life passion for mountain climbing The incredible management team of Comshare, Inc.one of the very first computer timesharing companies I founded in 1966 at the beginning of Silicon Valley. My amazing dog Emme, an Australian terrier who led me up the first 16 of the fourteeners helping me to discover that “it’s never too late to find a new passion in life”.

Website: www.RickCrandallBooks.com and www.RickCrandall.net
Linkedin: www.linkedin.com/in/rlcrandall
Facebook: https://www.facebook.com/RickCrandallBooks/

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