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:
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🎙️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
longtime reporter at CNN. She's covered top stories in global business,
including the chip and trade wars, world-leading IPOs, the corporate
response to Russia's invasion of Ukraine, Europe's energy crisis and
China's property problems. Previously, she was with FORTUNE. She has
reported for The New York Times, TIME and South China Morning Post.
Find her on Instagram: / bymichelletoh
TikTok: / behindthebusinessshow
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