He thought Ten Most Wanted could win the Kentucky Derby in 2003, only to see the horse bumped out of contention at the starting gate and finish ninth.
Ten Most Wanted, in which the Canadian had a minority stake, went on to finish second to Empire Maker in the Preakness but the dream was over.
"Since then I learned you go in with low expectations and be surprised," he said Wednesday. "And right now I'm surprised — which is a good thing."
The unassuming Reddam is also in the spotlight with his horse I'll Have Another on the verge of joining the select club of Triple Crown winners.
"I want to maintain low expectations," he added. "They're probably not — under hot lights — really low. But I just know in a horse race, a lot of things can go wrong, so I'm just hoping that they all go right one more time."
I'll Have Another has yet to disappoint.
"It's a little bit of a fantasy ride," Reddam said ahead of Saturday's Belmont Stakes, "because I've actually had to watch the Derby and the Preakness a few times to see 'Oh that really happened.'"
A former philosophy and logistics professor at California State University, the 56-year-old native of Windsor, Ont., is president of CashCall, a California-based company that offers short-term, high-interest consumer loans.
"So you can get the money you need, when you need it, even if you don't have perfect credit," the CashCall pitch goes.
"No one else would lend me money," said the late child star Gary Coleman, who was signed up as a pitchman after going to CashCall for a loan. "Not even my relatives."
Jockey Mario Gutierrez, a Mexican who calls Vancouver his second home after riding there, wore the CashCall logo on a plain white top when he attended Wednesday's Belmont draw.
The low-key Reddam opted for a dress shirt with open neck.
Reddam founded Ditech.com, a mortgage loan company known for its use of TV and billboard advertising to show current rates, before selling it to General Motors in 1999 for a reported US$240 million.
He got into standardbred racing through a friend, turning to thoroughbred racing in 1988. Reddam currently owns 35 thoroughbred horses and looks to add to his stable.
"Always. Because you just never know where your next horse is going to come from," he said.
He bought I'll Have Another as a two-year-old for US$35,000 on the advice of trainer Doug O'Neill's brother Dennis at the Ocala Breeders Sales.
At the time, Reddam did not expect much.
"Not really special in that any horse that he buys he always says 'Oh this is the one.' So he bought six and somehow they were all the one at the particular sale. And I'm thinking 'Well, OK, the one you just said this was the champion and I said OK. And now three minutes later, now this other one's the champion.'
"So to me, to be honest, he was another one of a group of horses. Before they run, you think they all have that potential but generally that doesn't pan out."
I'll Have Another got Reddam's attention in his maiden race last July at Hollywood Park when he won a 5.5-furlong race.
"Pretty impressive," he said. ''We thought he was stakes calibre at that point."
I'll Have Another won his next race in August, then finished sixth on a sloppy track in September.
Reddam and Doug O'Neill then spotted little-known jockey Gutierrez at Santa Anita and put the Mexican aboard for the Grade 2 Robert Lewis Stakes in February.
Gutierrez, who got his start at Vancouver's Hastings Racecourse, won that race as a 43-1 longshot and three since, including the Kentucky Derby and Preakness.
"He is absolutely terrific," said Reddam. "It may be if the horse wins and they do a movie about him like Seabiscuit or something 30 years from now that the jockey character will be the lead role because he's absolutely genuine and humble, thoughtful, intelligent.
"And he obviously has what we would call very light hands with the horse. He's kind of got magic in the way he communicates with the horse."
I'll Have Another went off at 15-1 in the Derby, but Reddam had a good feeling.
"I know I was in the minority but I actually really liked his chances because I thought the outside draw, despite what everyone else said, was a good thing for him because he would avoid traffic.
"And the main thing was coming up to the Derby he was training very well, hadn't missed a beat, had no physical issues. The Derby requires a lot of luck to win because there's 20 horses in it. I thought if we get lucky, we definitely have a good chance."
Reddam placed a six-figure bet on his horse — his largest to date, he said — and won a seven-figure return.
The owner says he was more nervous for the Preakness.
"I just thought now we're under the microscope and we don't know exactly how everyone's going to react to the pressure," he said. "But they pulled it off flawlessly I thought."
O'Neill credits Reddam for ensuring that the team around the horse has everything it needs.
Said Reddam: "Our philosophy has been 'Look, this is for all the marbles so let's leave no stone unturned.' So he's got more assistants on his horse than I think probably any horse in racing history."
"He is great," said O'Neill, a huge fan. "He is such a cool guy and very giving, very generous."
Reddam calls racing "somewhat of a business" for him although not on the level of his day job.
"I try to treat it more as fun but there is a dollars and cents perspective of it too," he said. "Certainly most horse owners will lose money because most horses don't fulfil their promise.
"Every once in a while you'll have a good one that you hope will make up for the losses. This horse will make up for a lot of losses."
He has had success before.
Wilko won the 2004 Breeders' Cup Juvenile and Red Rocks took the 2006 Breeders' Cup Turf.
But the 11-member Triple Crown club conjures up legendary horses such as Secretariat, Seattle Slew and Affirmed.
Reddam lives in California but his father and brother still live in Windsor so he does return home "here and there."
His California home is about 40 minutes from both Hollywood Park and Santa Anita.
He reckons he gets to the track once or twice on weekends, when he's running horses. A weekday visit is rare "because I work."
The Belmont Park notes say I'll Have Another is named for Reddam's fondness for wife Zillah's homemade cookies.
Reddam offers a slight correction, however.
"Not necessarily her cookies. It could be any cookies. People have said 'Well, what kind of cookies?' No, any cookies.
"Even stale cookies. I have a weakness that way."