My cousin Jared Pot is a family legend for all kinds of reasons, the main one being that you can't listen to FM radio in the greater Toronto area without hearing him win a contest. I'm only barely exaggerating: The man routinely wins three to four prizes a week. Everyone in my family has a story where they were listening to the radio only to hear Jared winning some prize or another, usually while also making the host laugh. There’s a familiarity—they’ll ask how his daughter is doing, for example, or joke that they've heard his voice somewhere before.

A lot of these prizes aren't huge—a $50 gift card, say, or a trip to African Lion Safari. But some of them are big—he went to the Grammys in 2012, for example, and once got a check for $1,200.

You might be thinking of Canada as a series of small towns, and the radio stations in question as only having a few thousand listeners. That's not the case: Ontario, where Jared lives, is home to over 14 million people, which is more than all but four US states. He is calling into some of the most-listened-to radio stations in North America and routinely winning. How does he do it?

I asked him what advice he would give to someone hoping to win. “Rub my head for good luck,” he said, grinning. And that's Jared: a slightly off-kilter sense of humor that's a little confusing but ultimately charming. It's no wonder Jared is known, by name, by seemingly all of the DJs in the province. One I reached out to declined to comment but knew exactly who I was talking about.

Now, I have a job to do—I'm a serious journalist—so I followed up. Seriously, though, Jared: How do you win this consistently? Here's the advice I got.

You might think the best way to win radio contests is to listen to a single radio station all day and call in when the prompt happens. Jared doesn't do that. Most radio contests happen at a set time every week, and Jared says a rough time is generally listed online.

“I go to each radio station's website and I see what the contests they're doing this week are,” he says. He then compiles all of the contests for the coming week into a spreadsheet, noting what time the contest will happen, the name of the station, and what he needs to do when the time comes—generally either call in, text in, or fill out a form online. This spreadsheet, which is meticulously crafted, allows him to block out his week of listening and calling.

Most of the contests Jared enters require calling into the station, the classic radio giveaway format. Typically you need to be among the first, but not the first, callers in—the ninth caller, for example. It's essential, given the format, that you don't waste any time actually dialing the number on your phone.

“If you really want to get into it, put all the phone numbers for the stations in your phone,” Jared says. His Contacts app is full of radio stations, so he's ready to hit the call button right when the contest starts.

Speaking of: If you're listening to the station online, there's going to be some lag between the terrestrial broadcast and the digital stream, meaning you won't be hearing the station in real time and as such will be way behind when it's time to call in. Jared's answer to this: Call early, call often. “Most stations will make the line busy so that no one can call in until the contest starts,” he says. “So I just keep dialing until the phone rings.”