During the same period, Richmond's friend, conductor Arthur Fiedler, was forced to cancel a series of bookings on the Chautauqua circuit.

[2] An onstage lapse of memory during Richmond's Boston debut caused him to reevaluate his professional goals and led him to a career in music management.

Pianist Ignace Jan Paderewski was quoted as saying of Richmond, "[He was] perhaps the only manager I have ever known to whom the word 'suite' has meant a musical composition and not a set of furniture for a room.

"[2] Aaron Richmond Concert Management's roster for the 1920–21 season included pianist Felix Fox, cellist Jean Bedetti, soprano Laura Littlefield, flutist Georges Laurent, the American String Quartette, the Smalley Trio, the operatic duo of Mr. and Mrs. George Mager and the Boston Symphony Ensemble, under the direction of Augusto Vannini.

In this role, Richmond was the New England artist representative for Sergei Rachmaninoff, Mischa Levitski, Kirsten Flagstad, Fritz Kreisler, Monte Carlo Ballet Russe and the Vienna Choir Boys, among many others.

The new venture, called the Wolfsohn Series, included sopranos Katherine Palmer, Kathleen McAlister, Suzanne Dabney, Mildred Cobb and Laura Littlefield; contraltos Abbie Conley Rice, Betty Gray and Rose Zulalian; mezzo-soprano Elena Gerhardt; baritones, Parish Williams, William Richardson, Wellington Smith, and Ernest Lamoureaux; pianists Winifred Byrd, Moriz Rosenthal, Cyrus Ullian, Hyman Rovinsky, Alexander Brailowsky, George Smith, Harold Morris, Harrison Potter, Grace Cronin, Guiomar Novaes, Alfredo Oswald, and Alberto Sciarretti; the Kibalchich Russian Symphonic Choir and The Roman Choir; the Fox-Burgin-Bedetti Trio; cellist Felix Salmond and violinists Joseph Coleman, Harry Farbman, and Paul Cherkassky.

Over the next several years, Richmond also presented such noted artists as pianist and composer Sergei Rachmaninoff, singer and composer J. Rosamond Johnson, pianist Harold Samuel, contralto Margarete Matzenauer, the Fisk Jubilee Singers, Harrison Keller, Denoe Leedy, violinist Albert Spalding, the People's Symphony Orchestra and the Cleveland Orchestra.

"[10] In 1951, Richmond was elected vice president of the National Association of Concert Managers,[11] which later became the International Society for the Performing Arts (ISPA).

Richmond took over direction of the Castle Hill Festival in Ipswich, Massachusetts, in 1964 where he organized the New England debut of violinist Itzhak Perlman and a concert by an eighteen-year-old Peter Serkin.