After several seasons fishing, he moved to yachting in 1875, working initially for the Marquis of Ailsa aboard the Lady Evelyn.

Following early successes in the Babe, he rose rapidly to the top of his profession, and remained there until his death on 9 April 1930.

[31][32] At the outbreak of the First World War Isabella Alexandra and the Kaiser's yacht Meteor were being towed to Cowes by a torpedo boat.

[33][24] Sycamore joined the Royal Navy as a Lieutenant RNVR in May 1917,[34] aged nearly 62, and was appointed in command of ML 350 operating from the RNAS seaplane base at Newlyn.

[36] Sycamore had been suffering from the accidental breaking of multiple ribs as he had been racing Sir Thomas Lipton's Shamrock on the Clyde during 1929.