You’re Doing Points and Miles All Wrong, Says Barbara Corcoran

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By Margie Goldsmith 

At Bloomberg Pursuits, we love to travel. And we always want to make sure we’re doing it right. So we’re talking to road warriors to learn about their high-end hacks, tips, and off-the-wall experiences. These are the Distinguished Travel Hackers.

Barbara Corcoran is a true rags-to-riches legend. In college, she had straight D’s, and by the time she turned 23, she’d been through 20 jobs. Undeterred, she borrowed $1,000 and started a minuscule New York City real estate company, the Corcoran Group, which she eventually sold in 2001 for $66 million. “All my best successes come on the heels of failure,” she says.

These days, Corcoran is best known as the most amiable investor on “Shark Tank,” though she is also the author of the best-selling memoir “Shark Tales, How I Turned $1,000 into a Billion Dollar Business,” and host of the podcast Business Unusual with Barbara Corcoran. She’s also the co-founder of Barbara Corcoran Investment Partners, which invests in an array of industries far beyond real estate.

This month, Corcoran teamed up with Trey Zoeller, founder of Jefferson’s Bourbon, to create the Marian McClain Entrepreneurial Fund, which aims to kick-start innovative business ideas with grants of up to $20,000. “People need help,” says Corcoran. “If I didn’t get that $1,000 loan, I never could have started.”

Now she’s practically unstoppable, especially where travel is concerned. Although it only takes two trips to Los Angeles a year to tape each season of “Shark Tank” – “the least of my travels,” she says – Corcoran accumulates hundreds of thousands of miles, typically taking from 30 to 40 trips a year. And shockingly, she does almost all of it in coach. Here’s why – plus a slew of other tips.

There’s something better than first class.

I never fly first class except once in a while when the client books. Usually, I’m a coach traveler. I feel pretentious in first class, and I can’t justify the additional costs. As for the miles, I never use them for an upgrade – I’d rather fly my family all over the country. I have nine brothers and sisters, 32 nieces and nephews, and then there’s my husband Bill’s side of the family. It makes all the difference for them to take that vacation and go somewhere they haven’t seen before. That’s my greatest joy.

You can fly like royalty in economy – as long as you pack a few small luxuries.

I always do the same routine [when I fly]. I bring my own delicious food: a couple of cheeses, usually hard salami, and really nice artisan crackers that aren’t soggy. I always bring two very pretty napkins – one as a tablecloth on my tray and the other for my lap – and a real wine glass. Then I buy a bottle of Sauvignon Blanc at the airport, and I eat lunch like I’m a queen in my coach seat. For dessert I bring an orange, and when I break it open, that aroma shoots out and everybody gets jealous. [Editor’s note: airline regulations vary by country and region, and consuming alcohol you’ve brought on board is generally not allowed, unless a flight attendant agrees to serve it to you.]

The one thing you should pack to pass time in the airport – it works even better if you’re delayed.

I don’t hang out in the lounges even though one of my cards allows me to – I’m a daydreamer, so I miss a lot of flights. Instead, I always go right to the gate and set an alarm. I also bring a portable Scrabble board and just ask the two people around me, “Hey, do you play Scrabble?” There’s always a Scrabble player, and they’re delighted to pass the time that way. When you’re playing Scrabble, people inevitably walk around or look at your words and you might even end up playing with them next.

Don’t get settled into a beach resort without doing these two things first.

My hairdresser told me that when I go on a beach vacation, I should scout out the bar facing the sunset and find the best seat. Then I give a $100 bill to the bartender and say I want to sit there every night. Same thing for the beach. Two-thirds of my vacations are water-associated and not everybody gets up early to attack the beach loungers. I give the beach boy a $100 bill and ask him to please reserve a particular lounger for me. Very often I’m traveling with friends, so he reserves all the loungers [I need] for me. I do it all the time. It takes the stress out of travel.

If you want to fit two weeks’ worth of clothes in a carry-on, go bottom up.

Unless I’m in L.A. for “Shark Tank,” which requires lots of different outfits, I travel carry-on – checked luggage gets lost. I generally pack a neutral pair of shoes and wear sneakers, so, I only have two pairs of shoes with me. Then, I pack everything from the shoes up. I’ll pick the pants and skirt that go with the shoes and the top that goes with the skirt, making sure that everything is interchangeable. I really get double the outfits. Leave room for a steamer, too. It’s fast and you always look fresh.

You’re probably throwing away the best packing accessory.

Plastic dry-cleaning bags are the secret to creaseless clothing. When you pack your suitcase, you put one inside the garment bag and one outside, then roll it up. Even a tailored jacket comes out of your suitcase as though it just came from the dry cleaner. It makes it impossible for the clothing to wrinkle.

It’s not where you go, but who you go with, that matters.

Carefully planning everything takes the spirit and heart out of things. So I usually plan my hotel and leave everything else open except for one or two activities. Really that’s how you have the most fun – spur-of-the-moment things have become my absolute best memories.

As for where I want to go, I don’t have places on my bucket list, I have people on my bucket list. I’ve been talking to my brother and my youngest sister for over a year trying to plan something exciting – maybe a bike trip. But whatever that trip will be, it’s got to be with them.

(c) 2023, Bloomberg · Margie Goldsmith 


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