Montgomery County Leadership: Brian Kelly, Founder and Former CEO of The Points Guy

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Brian Kelly, Founder & CEO of The Points Guy

Brian Kelly, the founder and former CEO of The Points Guy, a popular travel website, spoke with MONTCO Today about being born on Long Island and moving to Jamison near Doylestown when he was seven years old; his jobs as a teenager and the lessons he learned from them; serving in student government in both high school and college, and his choice to attend the University of Pittsburgh.

Kelly also discussed moving to New York after he graduated; working at Lord and Taylor, where he worked hard to impress his boss, who ended up becoming his biggest advocate and close friend; buying a 30-acre equestrian farm in Solebury; and what lies on the horizon for him personally and professionally.

Where were you born, and where did you grow up?

I was born the third of four children on Long Island, in Manhasset, New York, in 1983. In 1990, when I was 7 years old, we moved to Jamison, a small village in Warwick Township, Bucks County, when my father started a new job for a company in Blue Bell. My parents realized they wanted to live in Bucks County and found an affordable house in a Toll Brothers community.

What did your parents do?

My dad worked in pharmaceutical marketing for a hospital purchasing group, and my mom was a legal secretary for Bill Goldman, a lawyer in Doylestown.

What memories do you have growing up in Jamison?

Jamison was up and coming when we moved in 1990. We were on the earlier end of Jamison’s growth, and it began to increase in development in the mid-1990s.

I like to consider myself the last of the free-range kids. We grew up in a nice neighborhood with a big park and a lake in the middle of it. There were no cellphones. In the summertime, my friends would pick me up on their bikes at 8:00 a.m., and we would be outside playing until dinner time. It was also a very safe time to grow up.

Did jobs did you have growing up?

When I was fourteen years old, I started working at Madeleine Wolcott Imports in Plumstead, which imported upscale children’s clothing. My brother worked there and told me they were short-staffed. I asked my mom if I was old enough to fill one of their many vacancies, and she decided I was old enough to have a job. After that, I worked at Thompson Toyota as one of my first jobs.

I am grateful she agreed because it allowed me to learn the lesson to work hard for what I wanted.

Of those jobs, what lessons say with you today?

Working in the warehouse, I learned to work hard for my money. I remember that amazing feeling when I got my first printed pay stub. I was able to save up for things, which made me appreciate them so much more.

I learned to hustle from a young age. There’s a gene that some of us have more than others, and I definitely honed my hustle factor early on. Even as I’ve gotten successful in my career, I will never forget that.

Did you play any sports in high school?

I always played intramural basketball, but my sport has always been student politics. I caught the bug at CB East and served as the senior class Vice President and Treasurer junior year. That’s where I put a lot of my time and effort in high school.

What kind of music were you listening to back then?

I grew up in the pop boy band era of the 1990s. Backstreet Boys were my jam. I still listen to 90s music on XM radio today. I’ve always been a fun, pop music guy. I live in New Hope and am still driving on the same roads and listening to the same tunes! It always brings back so many fun memories.

Where did you go to college?

I followed my two older brothers to the University of Pittsburgh. When I went there, I said, “I’m going to become student body president,” and that’s what I did. I was elected in 2003 and became the first person to serve two terms in a row.

Why Pitt? Did you look at any other schools?

I was choosing between American University and Pitt. The price difference was staggering. My parents offered to help me with the tuition at Pitt, but because American was a private school and they had four other children, they couldn’t provide as much financial assistance there. I mistakenly thought the more expensive the school, the better the education. I somewhat begrudgingly went to Pitt because, in my head, I thought, the more expensive, the better.

Looking back, was Pitt a good choice?

Definitely! All my friends went to Penn State, and I looked there briefly, but I’m so happy I went to Pitt. At Pitt, I experienced a big city college campus while still at a small school. When I graduated, I worked at Lord and Taylor in New York City, and so many of my coworkers who went to private school were saddled with so much debt, and I graduated pretty much debt-free. I was getting paid the same amount as everyone who was $200,000 in debt. I had that hustle factor back then. It was more challenging to break into that “elite” world at the time, but it can certainly be done.

When you look back on your career, who opened up doors?

When I graduated from Pitt and moved to New York for work, I was a frat boy and not cosmopolitan! I was working in fashion on 5th avenue in the cosmetics buying office at Lord and Taylor. I knew very little about fashion and thought I would be in the men’s fashion buying office, but I was assigned to the cosmetics team.

My first boss, Sally Shaw, was a pit bull and one of the top buyers at the company. She had several assistants, all women and beautiful, and I was one of the only men in the office. Even though I didn’t know anything, she taught me so much, and I realized that I needed to work hard to impress her. It was very much The Devil Wears Prada. Often, we want the easy boss who is nice and flexible, but that’s not always good for development. She was laser-focused on the business and pushed me to up my game.

What do you think Sally saw in you?

That’s a great question, and I ask her that often. She’s a great friend today. I recently brought her into a charity that I was on the board of, and she’s now the chair.

I had to wear a suit and tie every day to work, and Sally noticed my suits were getting a little ragged. She went to bat for me in HR and got me a $5,000 raise and told me I couldn’t spend it on anything other than dry cleaning. She believed in me and didn’t want people to see me as anything less because of my suits.

I bring positivity wherever I go, and she liked that. She wanted to see me succeed. She saw that I had the people skills. Being an assistant buyer, it’s a lot of paperwork, but my talent was becoming friends with the women who worked at the brands. I was able to go to the ladies at Chanel, and as an openly gay 6′ 7″, 22-year-old man, they loved me.

Chanel would come out with a new lipstick line, and Lord and Taylor would compete with Saks or Neiman Marcus to get Chanel’s one lipstick sample for the marketing shoot. I was Sally’s assassin because I could connect with people quickly. A piece of that is my height. You know, when you walk into a room, and you’re 6′ 7″, you make an impression. I created deep connections with the women and men I worked with very quickly, and Sally really saw that in me and used it to our ability.

Who else saw your potential?

My parents. I was in a mood about going to Pitt because I thought it was below what I deserved, and she told me to go be a big fish in a small pond. She knew I was going to run that school.

Another person was my boss at Morgan Stanley. When I was thinking about quitting to start The Points Guy, Jane Hong, my boss, was very supportive. She told me, ‘I was waiting for you to see your own potential, and if you ever come back, we have an open door.’ That gave me confidence and allowed me to stop focusing on the negative “what ifs” and just channel the positivity.

When did you realize that you could ‘run the room,’ as you called it?

I’ve always had it in my head that I would live an extraordinary life. I didn’t know how I was going to do it, but I knew I was going to do it.

Growing up in Jamison, we would use my dad’s Marriott points to go to New York and stay for a weekend. I remember looking at the Manhattan skyline and thinking, “this is where I belong, and I’m going to be fabulous.”

What are the opportunities you’re focused on at the start of 2022, Brian Kelly?

Personally, I’ve always known I wanted to be a father. What I am most excited about this year is that I’m in the process of using a surrogate to have a child!

I just bought a farm in Solebury, a 30-acre equestrian farm. It’s a magical place. I’m working on renovating that barn, having horses, and have rescued several dogs and cats. I am turning my farm into a sanctuary for the animals and my kids.

Professionally, for The Points Guy, I am excited to transition my career away from daily management to focus on bringing our message to millions of more people via TV, podcasts, books, and more. As we see the light at the end of the tunnel with the Omicron variant, I am very optimistic about the future of travel and connecting with one another again in person.

What do you do with your free time?

I love horseback riding. I started over the pandemic. I have 11 nieces and nephews, and I was worried about them being stuck at home during pandemic learning. They were taking riding lessons, and I asked if I could join them someday. The instructor they were using is now the managing director of my farm! He helps with horse boarding and lessons.

I’m a river rat and just bought a plot of land on the Delaware River in Point Pleasant. I have my own beach and have kayaks to use on the water. I love to watch the bald eagles. The Delaware River from New Hope up to Frenchtown is just amazing. Getting on my kayak and taking in the beautiful nature of Bucks County brings me lots of joy.

Do you read much, Brian?

I read voraciously travel and finance blogs every day, but usually from my phone. One of my biggest resolutions for 2022 is to read more paper books. I was a voracious reader growing up. I’m reading a lot of great news on my phone, but I’m not reading enough good books.

What gives you hope, Brian Kelly?

Being around and empowering young people. I work a lot with an organization called Peace Jam. We engage with Noble Peace Prize winners and connect them with young people around the world. If we just listen to young people, they will solve many of the world’s problems. There are a lot of great people in this world, and that’s why I love travel. You meet so many authentic people on the ground, and they are not what the media or their government say they are.

Finally, Brian, what’s the best piece of advice you’ve ever received?

I go back to what my mom said when I went to Pitt. She said, “believe in yourself and be the big fish in the small pond. The rest will follow.”

My mom’s advice meant to stop trying to solve world hunger today and focus on what’s in your circle of influence. Many young people get overwhelmed with everything they have in front of them. You need to believe in yourself and work within your framework.

I’ve learned from working with the Noble Peace Prize winners that they didn’t get that accolade overnight; they started by helping people in their local community. It’s easy to be overwhelmed and feel like you’re not good enough when you compare yourself to the world.

Focus on where you can have an impact and push yourself little by little. You’ll be shocked by how much you surprise yourself, says Brian Kelly.

Brian Kelly
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