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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: Ad
02:59: Starting The Points Guy as a side hustle
07:28: Why the points game isn't dead
08:09: How points really drive US airlines
12:59: How to get started in the points game
18:09: Selling The Points Guy
19:53: Advice to other entrepreneurs on building a brand
24:55: Stepping down as CEO and being honest about your own strengths
25:58: When should we expect airfares to come down, if at all?
26:53: Industry consolidation — outlook for United, American, Delta, Spirit andJetBlue
28:07: 'Debundling' of airline prices and how carriers are working to 'maximize every single square centimeter on the plane'
30:47: With current volatility, should we be booking all our flights ahead now?
32:01: Creating a 'couch' in economy: Brian's take on airlines' new cabin concepts
34:43: 5-star hotels, cruises and yachts: Where Brian sees the best value in luxury travel right now
36:41: Tips and tricks to make the most of your trip
40:02: Brian's biggest travel recommendation this summer
41:24: How US airlines compare to those abroad
43:35: How Brian's son Cooper became the youngest person to ever visit all 7 continents
46:38: Long-term view: Brian's end game
48:32: 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.
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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
#Travel #Blogger #Entrepreneur #Startup #Founder #CEO #Leadership #CareerStory #CreatorEconomy #BusinessPodcast 
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