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Upgrading Reimagined: How to Fly First and Business Class for Little or No More than Coach

Matt Bennett, aka “Mr. Upgrade”
Matt Bennett, aka “Mr. Upgrade”

Take a look at the passengers departing a plane and you can get a pretty good idea of who flew in First Class and who didn’t. The long-haul First Class and Business Class passengers have that well-rested, satisfied look, while the economy passengers tend to have the crumpled appearance of someone who slept sitting upright. After decades of flying extensively for business and personal travel, I can tell you which passenger I would rather be. 


But flying First and Business Class exclusively can be tremendously expensive, and the pricing structures are wildly confusing – you just know the person sitting next to you paid a different fare than you did, (which can be either wonderful or disheartening depending on where your fare compares.)


When I met Matt Bennett, aka “Mr. Upgrade,” of FirstClassFlyer.com and learned that there are ways to buck the traditional airline ticketing system, I was all in. Having published a travel industry newsletter for 26 years, Bennett has helped millions of travelers, including actors, heads of state, professionals and athletes, save money on First Class airline travel. When he talks, people lean in.


“You’ve got to have a certain mindset,” he says. “We believe that anyone can beat the airline system, take advantage of loopholes and create dream vacations without paying $30,000 for a First Class ticket. We try to get those for three grand or less.”


I love Bennett’s origin story because it’s so directly tied to his skill set. He grew up with an entrepreneurial father who bought and sold surplus goods; his motto was “Bennetts don’t pay retail.” As a 17 year old with a 92 mph fastball pitch, Bennett signed a minor league contract with the Kansas City Royals. When the Royals gave him $650 for a one-way ticket to spring training, Bennett remembered his father’s adage. He found a sweet airline deal and pocketed the change. Three years and six spring trainings later, he made thousands from his savings, had figured out a lot about the airline industry and the concept of surplus tickets. When the Royals released him due to an arm injury, he went right into a career of helping people fly in style for less.


Bennett taught me a wealth of techniques and strategies for finding travel deals, but more importantly he has taught me that flying First Class is more about mindset shifts than tactics. Do any of these traditional travel thought patterns ring a bell with you?


Traditional Thinking: Airline miles are the best way to purchase tickets or to upgrade to First or Business Class.

Mindset Shift: Credit card points are more valuable because you can transfer them to airline loyalty programs that offer Business and First Class flights on major airlines for 70% fewer miles.


Traditional Thinking: Miles and points are exchanged by dollars spent or miles flown.

Mindset Shift: Airline miles frequently go on sale. If you purchase miles when they are below the standard rate, you can redeem them for otherwise $30,000 First Class tickets that cost you just $2,800 round-trip.


Traditional Thinking: Select the location and travel dates that work best for you and then start searching for the plane tickets.

Mindset Shift: Look for airline deals and plan your travels around them. Take advantage of airline surplus seats when business traveler demand is low. Sign up for fare deals and alerts from the airlines and from a trusted third-party travel advisor like FirstClassFlyer.com. If you can be flexible, you can find last-minute premium flash fares. You can also freeze flash fares for free or a small fee, on most airlines, for a day or week while you solidify your plans.


Traditional Thinking: Getting your heart set on visiting a specific location.

Mindset Shift: Have a long bucket list of locations that you can cross off as the deals pop up, and be open to accidental bucket list vacations. If First-Class fares to your preferred destination are too expensive, are there nearby destinations you could visit? If there is a flash sale to a nearby location, check into it. I’m going to employ this strategy in my quest to see old school rock stars. I’ll see them where the flights are the least expensive and make a vacation out of it.


Traditional Thinking: The flight is booked, it says so on the website.

Mindset Shift: Pick up the phone and call. Some airlines, including Emirates, have a waitlist which you can get on for the flights you want and about 50 percent of the time, a date will open up at a reduced rate close to departure.


Traditional Thinking: Business trips and vacations require separate bookings.
Mindset Shift: Combine business with pleasure. When booking your business destination, look for a leisure fare that allows stopovers. Let’s say you’re headed to Miami for business. Book a flight to St. Thomas with a stopover in Miami, get your business done and then head off to the islands on vacation. This can get you free side trips or even lower the cost of the one-destination fare.


Traditional Thinking: I have two options: spend hours on the computer searching for flights or hire a travel agent.
Mindset Shift: The average person researches a flight 38 times before booking. This is not necessary. FirstClassFlyer.com is simple and brilliant and offers many ways to find the best airline deals without all the extra work. 


In my experience with Bennett, I have learned that booking airline travel does not have to be a bank-breaking and time-consuming endeavor. A few mindset shifts and the assistance of skilled professionals who study travel around the clock can change the way you travel for the better. Make sure to watch the podcast interview for all of the details. 

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