He was working in Moncton, New Brunswick when he met Kingman and was invited to train at his Kardinal Sinners Wrestling School with himself and co-owner "Kowboy" Mike Hughes.
Having a lifelong interest in weightlifting and bodybuilding, Jessome accepted and they soon began traveling to the Johnstons River area in Prince Edward Island where he and Kingman worked out in a barn while Mike Hughes taught him ring psychology and technical ability.
He suffered numerous injuries during his time at the Kardinal Sinners "boot camp" including a concussion, whiplash, bruised kidneys, heels and tail bone.
[3] He made his debut match in Hughes' Real Action Wrestling against fellow student and training partner Downtown Ray Brown[1] in Charlottetown, Prince Edward Island on February 27, 2001.
In April, Jessome joined one of the promotion's earliest Maritime tours which included Kingman, Mike Hughes, Larry Destiny, Bill Skullion, Notorious T.I.D., Rogue, Buddy Lane, Bobby Rude and Kurrgan.
[5] Two weeks later, he joined his rival Custom Made Man in a tag team match to defeat his former trainers Mike Hughes & Kingman in Sydney, Nova Scotia on September 16.
He once joked during an interview about learning "a great deal of invaluable lessons while on the road with them, things like don't trust Duke MacIsaac with a sharpie if you pass out in Mike Hughes’ van.
He lost to Gary Williams in a "street fight" match in Louisdale three days later, and on several other occasions as well, but did score impressive victories over Mike Hughes; one of these occurred on the promotion's first television taping in Halifax on June 17.
He would also defeat Hughes in subsequent rematches during the next two days as well as picking up wins against Remington Steen and Vance Nevada before losing to Bobby Rude in a table match in Charlottetown, Prince Edward Island on July 23.
The event, which featured Bobby Roode, Lincoln Steen, Scott Savage, Gary Williams, Sonny Roselli and "The Future" Tony Armstrong, was a huge success and later released on VHS/DVD.
[12] Earlier that year, they had met Sarah Dunsworth, star of the TV comedy Trailer Park Boys, at her Barrington Street store Junk and Foibles which was a popular spot for local wrestler to purchase costumes and similar items.
He also took part in a three-day tour of Eastern Canada with Grand Prix Wrestling visiting Petit Rocher, New Brunswick, New Carlisle, Quebec and Borden, Prince Edward Island.
[15] On November 26, 2005 in Canning, Nova Scotia, Jessome appeared in the main event in a best 2 out of 3 falls match with Lincoln Steen against Brody Steele and Gary Williams.
[17] Although not featured in the tournament itself, Jessome took part in the semi-main event pitting he and Trash Canyon in a tag team elimination match against Gary Williams & Bobby Roode.
[21] Following a television taping during the tour, Jessome appeared with Kingman, Trash Canyon and others at an afterparty celebration at the Dresden Row nightclub, The Speakeasy, which also featured rock band Dogbite and performances by Pink Velvet Burlesque.
[22] In late 2006, Jessome joined Brody Steele, Chad Collyer and Gangrel and other Canadian wrestlers for a three-month tour of the United Kingdom with All Star Wrestling.