The former Wall Streeter turned "The Points Guy," travels the globe up to six months a year - and he does it for next to nothing, thanks to credit-card rewards and frequent-flyer miles.
When he's not jet setting, he's running his website, The Points Guy.
In an interview with Vice, Kelly shared the No. 1 card for those looking to maximize their
"It's got good earning and redeeming," he tells Vice.
"[With] most airline or hotel credit cards, you get two points for that airline or that hotel, but with the Sapphire, you get two times [back] on every single airline, hotel, car rental, and subways, parking, campgrounds, and amusement parks - it's this huge category."
Dining includes everything from Seamless to restaurants, and the card offers a sign-up bonus of 40,000 extra points if you spend $3,000 in the first three months. "Those 40,000 points, in my opinion, are worth about $800," says Kelly. "You're almost at a ticket to Europe just from getting the card."
The $95 annual fee is also waived the first year. "It's really just a no-brainer," he says.
Kelly's pick for second-best card is the Starwood Preferred Guest Card, which earns you one "point" for every dollar spent, and allows you to transfer points to 34 different airlines.
"Basically, travel and dining I put on the Sapphire because I'm getting double, but for everything else - clothing, and purchases where I'm not going to get a bonus - I put on the Starwood," Kelly explains.
In general, he says, don't rely too heavily on airline-specific cards.
"With airline credit cards, you're betting on that airline," he tells Vice. "Would you put your entire life savings into Apple stock? Just because it did great last year, it could tank this year, and then you'd be screwed."