In 1960 at the age of 17, Stroud won the Mākaha Junior Championship, and placed fourth overall in the Duke Kahanamoku International event.

[2] After jobs parking cars, bouncing, and eventually managing at the Whisky A Go-Go in Hollywood, he received advice on getting a start as an actor from Sidney Poitier, who frequented the club.

Poitier set Stroud up with Dick Clayton, who was also an agent for such actors as James Dean, Michael Douglas, Al Pacino and Burt Reynolds, among others.

Garrison taught Stroud the rudiments of flying so that he could manage to take off and land the aircraft, making some of the footage more realistic.

Stroud and Robert Conrad performed in the speedboat chase through Fort Lauderdale in the film Murph the Surf (1975).

Being under contract at Universal, Stroud appeared in Barnaby Jones, Cannon, Charlie's Angels, Ironside, Hawaii Five-O, Marcus Welby, M.D., Starsky & Hutch, and The Streets of San Francisco, among others.

Stroud played a bartender in the second season's fourth episode, "Mea Makamae" (meaning "Treasure" in Hawaiian).

On September 16, 1970, during a low-level sequence flying a two-seat SV.4C Stampe biplane across Lake Weston, a duck flew through the propeller's arc, striking the pilot Garrison in the face, knocking him unconscious.

The aircraft flew into five power lines, snap rolled and plunged inverted into Ireland's large Liffey River.