I’m Brian Kelly, the Glasses Guy, and This Is How I Work

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You wouldn’t think a guy who named his whole company after himself would be so nice. But when Brian Kelly started his travel and deals site The Points Guy, he didn’t know he would lead a large team writing a multi-section site for more than 10 million monthly readers. We talked to him about how to run a company, the gadgets he wears everywhere, and how he uses his travel knowledge to help nonprofits.

Name: Brian Kelly Location: New York Current Place of Work: Founder & CEO, The Points Guy Current Computer: iMac Pro 2017 Current Mobile Device: iPhone 11 One word that best describes how you work: passionate

First of all, tell us a little about your past and how you got where you are now.

The Points Guy really started in the 90’s when I figured out how to use my dad’s glasses to give us a “free” family vacation. While I was at Morgan Stanley, I traveled a lot, and that’s when points and miles really started to accumulate. I would use those points to go on a cool vacation and fly first class and it caught the attention of my colleagues. They started lining up at my desk to ask my advice on managing their miles / points, and that’s when I realized I had pushed something.

The Points Guy Blog started shortly thereafter as a passionate project, and nearly 10 years later, we have grown our community to over 10 million worldwide.

What are your job responsibilities?

My main role as CEO is to chart the future of the brand. I am currently working to help us transform from a content platform into a technology solution that will help people travel better. We are currently working on launching an application and tools on the site that will revolutionize the way people move.

Tell us about a recent work day.

  • Film the holiday tour live with Kelly and Ryan.
  • Visit our new office for a stroll
  • Lunch with a Fast Co. reporter.
  • Discuss 2020 partnerships with credit card issuers
  • Meeting with my subordinates
  • TPG Awards meeting
  • Drinking with Red Ventures CEO Rick Elias who visits New York

What apps, gadgets or tools can’t you live without?

  • Bose QC35 Headphones
  • iPad Pro: especially when traveling
  • Insight Timer : Meditation App
  • Slack: How We Communicate as a Company
  • Zoom: for business meetings
  • Parse.ly : for TPG traffic statistics
  • Instagram: When I Need Travel Inspiration

How is your workplace arranged?

You can call me old school, but I still value my own office. My door is always open and we usually have daily meetings in my office.

I always have fresh flowers from the Union Square farmers market in my office (my favorite part of Monday morning), healthy snacks (lots of La Croix and cheese for more stressful times), souvenirs from my travels around the world and of course The Points Puppies !

What’s your favorite shortcut or hack?

Record my blog posts with voice memos so they can be decrypted later.

Tell us about an interesting, unusual, or challenging process you have at work.

At TPG, we take inclusion and impact very seriously. As an open and proud CEO and business founder, I have made it my mission to make sure that I always return to the LGBT community and that every employee can support issues and funds that matter to them.

Giving is a huge part of my life and an integral part of The Points Guy. Throughout the year, I am honored to participate in a number of conferences with PeaceJam , a non-profit organization that brings together Nobel laureates and youth around the world, throughout the year with some of my staff. The TPG team has grown so much over the past few years that traveling with my co-workers, for such an incredible reason, allows me to spend time with them profitably, doing good deeds in the world.

Who are the people who help you achieve results, and how do you rely on them?

Christy, my wonderful executive assistant, prepares and manages all of my appointments. She is the one who manages my schedule and ensures that I have everything I need when I go to meetings one by one.

Our new travel analyst, Zach, is truly gaining points at TPG. He is always exploring and coming up with new ways to earn points!

Nathan, our new CMO, plays a critical role in brand / company strategy and is my go-to when I need to share ideas from someone.

What’s the biggest mistake you made at work and how did you deal with it?

I wish we had hired more people sooner. I never really wanted to run a big company, but TPG grew rapidly and we didn’t expand our team to fit our needs. Our workforce has doubled over the past year, and now that we are part of Red Ventures, we are paying more attention to human capital.

How do you keep track of what you need to do?

I never stop thinking about the key things I need to do, and luckily I have a wonderful assistant to help me manage my schedule and make a list when I run to appointments or interviews. I still manage my inbox and go through all my emails, but I tried to delegate more. Lately, I have focused on the top level and determined who I need to meet and learn from.

How to recharge or relax?

I’m going to my country home in Bucks County and spending time with my 11 nieces and nephews. I also remember to plan one or two solo trips a year in which I take time for myself and reflect – usually while scuba diving.

What’s your favorite side project?

I always do things that I care about. We work closely with Rainbow Railroad (as a result of our fundraising and mile donation efforts, 50 LGBTQ lives have been saved and successfully resettled with a shelter). I am the Global Ambassador for PeaceJam, where I help advise on travel and fundraising for the organization.

I’m also an advisor to Morning Brew and it was great to see how popular they really are.

What are you reading now or what do you recommend?

Who else would you like to see to answer these questions?

  • Richard Branson
  • Claudia Oshri (Girl out of work)
  • Celine Dion

What’s the best advice you’ve ever received?

Do not feed the trolls! There will always be people who are negative by default. At the beginning of my career, I used to hang out with them and they let me down, but once you get rid of the fact that there are negative people, you can really free yourself creatively.

What problem are you still trying to solve?

We are working on an application that will truly change the game! We are focused on creating a platform where earning and burning points will take place in one place.

Our ultimate goal is to empower people to travel more. I would like to partner with more hotels and airlines so they can integrate to help achieve the mission of getting more people to explore the globe.

This interview has been lightly edited for clarity.

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