Yesterday, a premium subscriber called with a question about the best way to plan his Hawaii trip. Since it was going to be a long/involved conversation, he agreed to do it on camera so others could “listen in” too. It turned out to be a pretty fun/productive one so I’m sharing it here.

No time to watch all 67 minutes? Highlights are listed below.

** If you’re not already a premium subscriber, click here for more tips/tricks like this AND 100 to 150 trip-alerts that are better deals than using frequent flyer points.

Chad, by the way, has a very unique business called “Your Family Bank”. He has a very unique way of getting people out of debt 10 times faster through subtle changes in your spending habits. Feel free to give him a call at 720-291-8602 to see if he can help you.  

  • 1:00: Planning a trip to Hawaii to visit daughter for birthday
  • 4:10: Value of points with specific airline vs with Chase, Citi, or Amex.
  • 6:10: Free resources to get the most out of your miles.
  • 7:20: Why points should always be as a last resort
  • 11:25: How Michelle & I flew to Hawaii for $22 and 25,000 points each (vs $51 and 50,000 points each)
  • 15:40: Finding deals so cheap you wouldn’t waste the points on them.
  • 17:00: Teaser about a hack to get the Southwest Companion pass
  • 17:40: Teaser about getting out of debt in a fraction of the time
  • 19:30: Deciding whether or not to keep a credit card after using the miles earned from it.
  • 21:30: Why cards from Chase bank should be among your first 5 credit cards.
  • 22:20: Why the $450/year Chase card is far better than the $95/year Chase card.
  • 24:00: Long demo of Award Hacker & how to use
  • 33:40: Discussion of RewardStock (and even better version of AwardHacker)
  • 36:00: backup plan #2 – finding trips that are better trips than redeeming points using your JGOOT subscription
  • 40:00: How to watch for good deals on your own without being a JGOOT premium subscribers
  • 43:05: Why you should bundle lodging/car reservations at same time you book the flight.
  • 45:00 – 52:00: Misc banter about navigating the JGOOT site. (Feel free to skip)
  • 52:30: Where to go & stay in Kauai (Including the only resort we would go back to in Kauai)
  • 55:50: Napali Coast Hike (an absolute must)
  • 57:00: Avoiding a disappointing boat ride (Do the Napali coast. don’t do the 90-minute each way island snorkel tour.)
  • 59:30: Misc things to do on the South side of the island
  • 1:02: Teaser about power of getting Southwest’s companion pass if you’re self-employed
  • 1:06:50 – Wrap-up with Chad’s thoughts on his JGOOT subscription and advice to future subscribers