How to travel for less: The Points Guy takes 3 Pressing Questions

August 6, 2026

AI Summary

5 min read

In 2010, Brian Kelly was a 28-year-old HR professional at Morgan Stanley, points-rich and cash-poor, living paycheck to paycheck in New York City. He had been obsessed with travel rewards since he was 12 years old, when he helped his family book a free trip to the Cayman Islands. At Morgan Stanley, he put all his department's expenses on his personal credit card, earning millions of points while his colleagues hated doing expense reports. He started a side hustle called The Points Guy, charging $50 to help people use their miles. A friend set him up with a WordPress blog and told him to post every day at the same time. Within six months, the blog was making a million dollars. Two years later, a publicly traded company offered him $28 million for it. He took the deal. "People today will be like, well do you regret it? And I'm like, no."

The game is not over — it has always changed

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What you'll learn

1 (01:04) **Origin Story: From HR to Points Guy** – Brian Kelly explains how a childhood trip booked with points led to a side hustle at Morgan Stanley that became a multi-million dollar media brand.
2 (07:05) **The Game Is Not Over** – Kelly debunks the recurring myth that points are dying, explaining why loyalty programs are more entrenched than ever.
3 (09:42) **The Platinum Age of Travel** – A battle is emerging between airline co-brand cards and general travel rewards cards, with airlines restricting award access.
4 (12:44) **Getting Started for Expats and Novices** – Practical steps for those new to the U.S. credit system or the points game.
5 (16:01) **Transferable Points vs. Co-Brand Cards** – Why general rewards currencies hedge against devaluation and how to value them.
6 (18:56) **The $28 Million Sale and Building a Brand** – Kelly reflects on selling his two-year-old blog to Bankrate and how media training became his competitive advantage.
7 (25:35) **Stepping Down as CEO** – Kelly explains why he stepped away from day-to-day management in 2020.

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Guests on this episode

Brian Kelly

Show Notes

Joining us this week is The Points Guy founder Brian Kelly. He turned what started as a personal blog while working at Morgan Stanley into one of the world’s leading travel media platforms — shaping how millions of consumers spend, earn and think about travel. In our special new segment, “3 Pressing Questions,” Brian weighs in on hot topics shaping travel today, and explains how he built a top creator business that sold for tens of millions of dollars. From why flights feel so expensive right now, to how industry shifts could affect your wallet, to common mistakes to avoid when booking a trip, Brian breaks down what’s worth paying for today. In this conversation, we dive into: 00:00: Introduction 01:28: Starting The Points Guy as a side hustle 05:57: Why the points game isn't dead 06:38: How points really drive US airlines 11:28: How to get started in the points game 16:38: Selling The Points Guy 18:22: Advice to other entrepreneurs on building a brand 23:24: Stepping down as CEO and being honest about your own strengths 24:27: When should we expect airfares to come down, if at all? 25:22: Industry consolidation — outlook for United, American, Delta, Spirit and JetBlue 26:36: 'Debundling' of airline prices and how carriers are working to 'maximize every single square centimeter on the plane' 29:16: With current volatility, should we be booking all our flights ahead now? 30:30: Creating a 'couch' in economy: Brian's take on airlines' new cabin concepts 33:12: 5-star hotels, cruises and yachts: Where Brian sees the best value in luxury travel right now 35:10: Tips and tricks to make the most of your trip 38:31: Brian's biggest travel recommendation this summer 39:53: How US airlines compare to those abroad 42:04: How Brian's son Cooper became the youngest person to ever visit all 7 continents 45:07: Long-term view: Brian's end game 47:01: Rapid-fire round 🚀 Season 2 of Behind the Business is here, featuring the leaders of brands including Airbnb, Rivian, NYSE, Canva, Samsung, Poppi, Peloton, Revolve, Lucid Motors, PHLUR, The Points Guy and Away. New episodes Thursdays. 👇🏼 SUBSCRIBE + FOLLOW: YouTube: https://bit.ly/YTBTB Apple Podcasts: http://bit.ly/3IFGuIA Spotify: https://bit.ly/SpotiBTB Amazon Music: http://bit.ly/4pPZZPp 🎙️About Behind the Business Behind the Business is a Webby Award-winning, thoughtfully produced video podcast grounded in the belief that business is in fact personal. This is not a fawning interview show. We pair deep research with thorough interviews — asking the real questions and avoiding fluff, while keeping it fun! What’s the toughest day you’ve ever had at work? How do you mentally prep for a big event? Or what’s a pinch-me moment you’ll never forget? In each episode, guests get into it all. Each episode also connects guests with audience members who send in a question. New episodes every Thursday. About Michelle Toh Michelle is an award-winning international journalist, most recently a longtim