I’ve changed since I started TPG — but here’s 1 thing that has remained a constant in my life
As we approach the 15th anniversary of The Points Guy, I look back at how far the business has come since I started it as a side hustle while working on Wall Street. So much has changed in the last 15 years, but one thing remains constant: the power of points and miles to transform travel experiences.
Related: Getting started with points, miles and credit cards to travel
Before I became "The Points Guy," I really was a Points Kid — and my first job was booking travel for my dad. Travelocity had just launched, and while he thought using it was a long and complicated process, I thought it was a simple task. I handled all of his bookings and only charged him $10 each.
By the time I was 12, my dad had accumulated so many frequent flyer miles from his work travel that he challenged me to book a trip for our family of six using only airline miles and credit card points. Challenge accepted. I went big and decided on Grand Cayman. (I may have had a little inspiration from the John Grisham novel, "The Firm.") The whole time, my dad thought I was planning a trip to the Grand Canyon, so he was surprised to discover I had planned a trip to the Caribbean.
While he and my siblings flew on a nonstop flight, I booked my mom and me on a flight through Miami International Airport (MIA). I was panicked, thinking this would either be an epic win or an epic fail. If it were the latter, I could be grounded for a very long time. But when we landed, my dad met us at the plane with the biggest smile and assured me that I knocked it out of the park.
This was the trip that sparked my love of travel planning — and points and miles.
After college, when I went to work as a corporate recruiter for Morgan Stanley, I traveled all over the country racking up credit card points and frequent flyer miles while trying to convince college students to work in technology. This was during The Great Recession, and I was points-rich but cash-poor. (My boss used to joke that my bonus was not getting fired.) It was actually cheaper for me to fly first class, stay at a hotel and enjoy the perks of free breakfast than to go grocery shopping or eat out in New York City.
In 2010, my then-boyfriend encouraged me to turn my passion for travel and points and miles into a business. I originally started TPG as an online form where people could submit information about their points and where they wanted to travel. For just a $50 fee, I would then give them personalized advice and help them book a trip using points.
I started blogging about travel and points and miles that same year, with my first-ever story publishing on June 7, 2010. The site really took off after an interview (that almost didn't happen) with Seth Kugel, the "Frugal Travel" columnist at The New York Times.
I actually found an email from him in my spam folder requesting an interview with me, but it was a month old. He was a staunch opponent of frequent flyer miles and credit cards, even going as far as referring to them as "useless" in his original email. I emailed him back and asked to take him to lunch so I could change his mind. During that lunch, I actually helped him book a trip to Brazil to see his long-distance girlfriend. His eyes lit up, and I knew that his entire outlook on points and miles might have changed in that instant.
After his trip to Brazil, Seth wrote an article about how reading TPG should be a key step for anyone who wants to get into the points and miles game. He linked directly to the TPG website (which temporarily crashed it!) and gave the website valuable credibility in the eyes of Google.
His endorsement of me, "The Points Guy," as a travel expert forever changed the trajectory of the site. Nine months later, I quit my job at Morgan Stanley and became "The Points Guy" full-time.
Today, TPG has a headquarters in New York City and nearly 150 employees worldwide. They bring you the latest news in loyalty programs, points and miles, travel and more.
Looking back over the past 15 years, many things have changed in the travel and credit card industries. Today, I have credit cards that didn't exist in 2010. New loyalty programs have been created, and new airlines have taken to the skies. I've also gone through changes in my personal life. I'm now the father of two boys, Dean and Cooper, and it's been such a thrill to begin showing them the world.
I really think we are in the "platinum age of travel" — not only from an elite status and credit cards point of view, but also because of how airlines continue to innovate. The race to create the best airport lounges and most luxurious inflight experiences continues, but these products (and travel in general) are very accessible — especially if you take advantage of the loyalty ecosystem. And that's something with staying power.
Throughout my career (and really my entire life), points and miles have been there, allowing me to make memories with my family, build a successful business and share my passion with millions of TPG readers across the globe. I wouldn't be where I am today without them.
My biggest piece of advice is simple: Find value in your everyday spending, no matter whether it's cash back in your pocket or transferable rewards to unlock luxury travel. Points are built into virtually everything we do, so if you're not getting a return on every dollar you spend, you're missing out.
Thank you for helping make The Points Guy what it is today — and here's to the next 15 years!
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