For Ian Fitzsimmons, there was that chance to invest in sports apparel giant Under Armour before anyone knew its name. And the time he sold his bar, only to see it grow to a thriving chain of six.
Then there's his father-in-law, who was offered a ground-level opportunity with Chili's restaurants but declined.
Were there other missed chances?
"How many more do you want?" laughs Fitzsimmons. "If you have a great business idea, come to me, because it will definitely fly, as long as I turn it down or sell it."
As rocker Rod Stewart sang, some guys have all the luck.
Before feeling too sorry for Fitzsimmons, you should know he actually has been lucky. He has a high-profile job in a sports-crazy market.
The former 1320-KFAN radio host now works on-air at WJOX 100.5-FM in Birmingham, Ala. That means he's up to his chin strap in college football, which happens to be his passion.
Not only is he in the heart of Dixie, he's in the heart of the Southeastern Conference.
"To borrow a phrase from Bear Bryant, 'Mama called,"' says Fitzsimmons.
Alabama's gain is Utah's loss. When he breezed through Salt Lake in 2004-06, he brought a big-picture, national sports perspective, having already previously worked in Birmingham, as well as at ESPN. Yet Fitzsimmons was never too cool for the Mountain West and the WAC. He quickly educated himself on Utah State, Utah and BYU go ahead, ask him the Cougars' quarterback lineage even though he couldn't have been blamed for acting snobby.
"It's still great Division I college football," he says.
It didn't hurt that he arrived just when Urban Meyer was making the Utes famous.
No, the MWC isn't the SEC, but who is? Nobody does college football better than Dixie.
You can't put a price on a job covering that.
Still, at one time he had the chance to try. A high school friend named Kevin Plank approached him in the late 1990s, wondering if he would invest $10,000 in a venture. Plank, a former University of Maryland football player, had developed a skin tight, synthetic fabric sports undershirt. As a special teams captain, he had grown weary of changing sweaty cotton tees. He wanted something sleeker; something you might see on X-Men or the Fantastic Four.
"Cotton," says one of Under Armour's slogans, "is the enemy."
Fitzsimmons didn't have the capital to invest, but his mom did. But when her son asked about it, she said, to his recollection, "I'm not going to give $10,000 to the Kevin Plank you knew in high school."
Now Plank keeps that much in his pajama pockets.
Under Armour not only makes gear for virtually any activity, but also outfits college teams. The University of Utah announced in March it had switched from Nike to Under Armour as its supplier. Utah is the seventh football program to sign with the company, along with Auburn, Maryland, South Carolina, Texas Tech, Hawaii and South Florida.
"Kevin has never failed," says Fitzsimmons.
His friend "used to take the Metro to RFK Stadium for Grateful Dead concerts and cook grilled cheese sandwiches on a hibachi and sell peace shells."
He also sold roses by the roadside during prom week.
That was when he was 15.
"Everything this guy has done has turned to gold, from his playing career to his entrepreneurship at 15 to Under Armour. It doesn't rain on Kevin unless he wants it to," continues Fitzsimmons.
Rather than give Plank the 10 grand, Fitzsimmons' mom gave her son the money to start a bar. He ended up selling to other investors, who then turned it into a thriving, multi-location enterprise. Then there was the Chili's opportunity his father-in-law ignored. For a $25,000 investment, he could have helped launch one of America's most successful restaurant chains.
Still, you won't find Fitzsimmons complaining. Even before landing at Football Central, he loved where he worked, including the stop in Salt Lake.
"I never wanted to leave," he says. "The mountains, the fly-fishing, I still get chills thinking about it."
But KFAN decided to change directions, so Fitzsimmons moved on to Dallas, then back to Birmingham, where he has Alabama and Auburn in his backyard. He and his wife, Katherine, are expecting their second child.
Meanwhile, the Crimson Tide is on its way back, and Auburn never left.
"We're in heaven," says Fitzsimmons. "The SEC is college football Mecca, the best conference in the country, and my passion is college athletics."
His hobby?That seems to be watching others get their start.