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.’”
An 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.