You wouldn’t think a guy who named his whole company after himself would be this nice. But when Brian Kelly started his travel and deals site The Points Guy, he didn’t know he’d be leading a large team writing a multi-section site for over 10 million readers a month. We talked to him about running the company, the gadgets he takes everywhere, and how he uses his travel knowledge to help non-profits.
Name: Brian Kelly
Location: New York City
Current gig: Founder & CEO, The Points Guy
Current computer: iMac Pro 2017
Current mobile device: iPhone 11
One word that best describes how you work: Passionately
First of all, tell us a little about your background and how you got to where you are today.
“The Points Guy” really started in the 90s, when I figured out how to use my dad’s points to get us on a “free” family vacation. While I was working at Morgan Stanley, I ended up travelling a lot and that’s when the points and miles really started racking up. I would use these points to go on cool vacations and fly first class and that got the attention of my coworkers. They started lining up at my desk to ask my advice on managing their miles/points and that’s when I knew I was onto something.
The Points Guy blog started shortly after as a passion project and almost 10 years later, we’ve grown our community to over 10 million strong around the world.
What are your job responsibilities?
As CEO, my main role is to chart the future of the brand. I’m currently working to help us expand from a content platform into a technological solution to help people travel better. We’re currently working towards launching an app and tools on the site that will revolutionise the way people travel.
Take us through a recent workday.
Film a holiday travel segment on LIVE with Kelly and Ryan
Visit our new office for a walk through
Lunch with a Fast Co. reporter
Discuss 2020 partnerships with credit card issuers
Meeting with my direct reports
TPG Awards meeting
Drinks with Red Ventures CEO Ric Elias, who is visiting NYC
What apps, gadgets, or tools can’t you live without?
Bose headphones QC35
iPad Pro: especially when travelling
Insight Timer: meditation app
Slack: how we communicate as a company
Zoom: for company meetings
Parse.ly: for TPG traffic stats
Instagram: for when I need travel inspiration
What’s your workspace setup like?
Call me old school, but I still value having my own office. My door is always open and usually we have our daily meetings in my office.
My office always has fresh flowers from the Union Square Farmers Market (my favourite part of Monday mornings), healthy snacks (lots of La Croix and cheese for the more stressful times), mementos from my travels around the world, and of course The Points Pups!
What’s your favourite shortcut or hack?
Recording my blog posts via voice notes so that they can be transcribed later.
Take us through an interesting, unusual, or finicky process you have in place at work.
At TPG, we take inclusivity and giving back very seriously. As an out and proud CEO and business founder, I have made it my mission to make sure that I’m always giving back to the LGBTQ community and to make sure that every employee can support issues and foundations important to them.
Giving back is a huge part of my life and is an integral part of The Points Guy. Throughout the year, I have the honour of attending a number of conferences with PeaceJam, a nonprofit that connects Nobel Laureates to youth around the globe, throughout the year with a few of my staff. The TPG team has grown so much over the last few years so travelling with my employees for such an incredible cause allows me to spend quality time with them while doing good in the world.
Who are the people who help you get things done, and how do you rely on them?
Christie, my amazing executive assistant, preps and manages all my meetings. She’s the one who handles my schedule and ensures that I have everything I need when I’m going to back to back meetings.
Our new travel analyst, Zach, is the real points guy at TPG. He’s always doing research and strategising new ways to maximise points!
Nathan, our new CMO, is crucial in brand/company strategy and is my go-to when I need to bounce ideas off of someone.
What’s the biggest mistake you’ve made at work, and how did you deal with it?
I wish we had hired more people earlier on. I never really wanted to run a large company, but TPG grew rapidly and we didn’t expand our team in a way that matched our needs. Over the last year, our staff has doubled in size and now that we are a part of Red Ventures, we have more of a focus on human capital.
How do you keep track of what you have to do?
I never really stop thinking about the key things I have to do and luckily, I have an amazing assistant who helps manage my schedule and to do list when I’m running to meetings or interviews. I still manage my own inbox and go through all my emails, but I have been trying to delegate more. Recently, I’ve been focusing on the highest level and identifying who I need to meet with and learn from.
How do you recharge or take a break?
My getaway is going to my country house in Bucks County and spending quality time with my 11 nieces and nephews. I also make sure to plan one or two solo trips a year, where I take time for myself and reflect—usually while scuba diving.
What’s your favourite side project?
I’m always getting involved with causes I care about. We work closely with Rainbow Railroad (as a result of our fundraising efforts and mile donations, 50 LGBTQ lives have been saved and successfully relocated with asylum). I am the Global Ambassador for PeaceJam where I help advise on travel and raise funds for the organisation.
I’m also an advisor to the Morning Brew, and it has been awesome to see how they’ve really taken off.
What are you currently reading, or what do you recommend?
Mighty Be Our Powers: How Sisterhood, Prayer, and Sex Changed a Nation at War by Leymah Gbowee. We work with her for PeaceJam.
Super Pumped: The Battle for Uber by Mike Isaac, which taught me how to not lead a company
Who else would you like to see answer these questions?
Claudia Oshry (Girl With No Job)
What’s the best advice you’ve ever received?
Don’t feed the trolls! There will always be people whose default is negativity. Early in my career I used to engage with them and they would bring me down, but once you get passed the fact there are negative people you can really free yourself up creatively.
What’s a problem you’re still trying to solve?
We’re working on an app that will really change the game! We’re focused on building a platform where the earning and burning of points will exist in one place.
Our ultimate goal is to provide people with the ability to travel more. I’d like to work with more hotels and airline companies to integrate to help further the mission of getting more people to explore the globe.
This interview has been lightly edited for clarity.