Ask Me Anything: Points & Miles Travel Edition

December 3, 2025

This episode pulls back the curtain on the real-life systems we use as a family to earn, manage, and stretch our points. It’s full of practical answers, honest numbers, and lessons learned the hard way—so you can shortcut your own strategy.

In today’s episode, we’re chatting about

  • How many personal and business credit cards I actively keep open
  • Why my credit score stays above 800—even with frequent applications
  • What I do with cards after the first year (your 4 options)
  • The real (and shocking) number I pay in annual fees each year
  • The always “annual spend” question debunked
  • How I think about using points vs cash for flights and hotels
  • The #1 item I will not travel without
  • The biggest mistake I made when I started—and how it held us back for years

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