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Defining Creativity Podcast       [September 13, 2022]

S1E11: A Financial Advisor-Civil Air Patrol Pilot's
                     Definition of Creativity with:

Malcolm Webb

“I thrive in circumstances where there’s a set of constraints and the creativity is in adapting to those constraints to come up with something.”

    —Malcolm Webb

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A tribute to the relationship of Malcolm's family with Leonard Bernstein can be found in the movement VII of Bernstein's "Arias and Barcarolles" entitled "Mr. and Mrs. Webb Say Goodnight" in which Malcolm and his brother, Kent, are part of the dialogue as the soprano sings: "Boys! Stop that noise! Malcolm, Kent, cut the noise!"

Listen to a recording by the San Francisco Symphony here.

Sharing an example of how his, as he calls it "Batman job" with Civil Air Patrol informs imaginative interactions in his profession job as an investment advisor, Malcolm relates:


“I’ll give you one analogy that I use, and some of this has to do with the client relationship. I will ask a client, ‘Are you looking for a pilot or are you looking for a co-pilot?’ I don’t ask that as much because the nature of our specialization has driven me more towards being the pilot for people who are looking for a pilot rather than a co-pilot. I did have this conversation with a client once who said, “Co-Pilot? Pilot? I’m a passenger! I’m way back in row 38. I don’t wanna… I don’t wanna even see what’s going on in the cockpit!”

Malcolm Webb embraces creativity in a variety of ways. Acknowledging that creativity in his profession of investment advisor can be problematic, Malcolm channels his creativity into understanding and communicating with his clients. Similarly, being a pilot and much of his Civil Air Patrol duties do not lend themselves to creative manipulation, but he finds a creative outlet in the instruction of cadets.

Malcolm discusses the impact of his interior designer mother and musician father in his cultivation of creativity:

“I became fascinated with the process [interior decorating] and [my mom’s] ability to see something in her mind that we didn’t see, and I tried to develop that...”


Another impactful personality with whom he interacted growing up was Leonard Bernstein. One remembrance Malcolm shares is the following:

“Charlie [Malcolm’s brother] was listening to Earth, Wind, and Fire, and he said to Mr. Bernstein, ‘It’s just rock music’ and I’ll never forget, Leonard Bernstein looked at him and said, ‘Yes, but is it good rock music?’ Now, that question expanded my thinking in a way that had not been done before, because I was young and I had not thought of rock music in terms of quality and now I did. With that one question, I did. Charlie’s answer, incidentally, was, ‘Well, it’s Earth Wind, and Fire,’ and he said, ‘That is good rock music.’”

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