Episode Details

Do you ever see all those Instagram influencers flying business class using miles and points and think, “How TF do they do that?” 

Well… we sat down with points and miles expert Ross Alcorn, CEO and founder of Itinerary Boss, to figure it out.

Ross has helped thousands of people turn their everyday spending into five-star luxury travel — and honestly? It's probably more attainable than you might think. We're breaking down how to choose the right credit cards for your lifestyle, why transferring points is a game changer, and how to stretch your miles further than you ever thought possible.

Whether you're a total beginner or you've been sitting on points for years without knowing how to use them, this conversation will change the way you think about travel rewards. Plus, Ross shares his all-time favorite trip and his take on whether learning points and miles is always worth your time. (Spoiler: it is — even if you're not a constant traveler.)

⏰ Timestamps

[3:00] Ross's origin story — how he discovered travel rewards

[5:00] Building your foundation: Why budgeting comes first

[8:00] Choosing your first credit card & debunking the annual fee myth

[14:00] Cash back vs. points: Why points absolutely win for travel

[17:00] Transferring points 101

[25:00] Is learning points and miles worth it if you don't travel constantly?

[28:00] Planning ahead: how to strategize big purchases for bonus points

[35:00] Stretching your points for maximum flexibility

[38:00] Ross's dream honeymoon in Thailand & Bali 

Resources & Links

Free Points & Miles Cheat Sheet 

Capital One Venture X — Recommended starter card

Chase Sapphire Preferred — Another great entry point

Rakuten — Earn extra points on everyday shopping

Rove Miles — Find award availability and book flexible flights

Bilt Card — Bilt 2.0 coming Feb 7

Mesa Card — Earn on mortgage, daycare, and other homeowner expenses

Follow Ross: @itineraryboss on all socials

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