Do you have friends or family who pay cash for flights? Are you manually searching and comparing award prices? This episode dives deep into my award booking workflow and compares new tools like PointsYeah and and why they have become an essential part of the process.

Corrections: Virgin Atlantic is actually part of SkyTeam, not Star Alliance. But they do partner directly with ANA for awards. Also, PointsYeah requires a free account to view search results

Show Notes

SHUT UP AND TAKE MY MONE... oh it's free?

Mentioned in episode

🤖 AI Episode Highlights

The following highlights were generated entirely by AI, with no editing from me... let me know what you think 😬

Travel Hacking Concerns: "And the common concern I heard from friends and family when I asked them what's holding you back from booking award flights for everything is that it's just really overwhelming. It's a lot if you're not familiar with it, there's a lot of carriers, there's a lot of point options, a lot of loyalty programs, carriers, credit cards."

— Kai [00:01:10 → 00:01:29]

The Efficiency of Award Travel Planning: "But I also plan to visit a lot of other destinations that I haven't been to before. And for those, it's more useful to have a general workflow that you can follow that can help you quickly answer questions that you have and also tools that can make that whole process easier."

— Kai [00:03:26 → 00:03:43]

Decoding Award Booking Strategies: "I'll cover new services like PointsYeah and and how they fit into my workflow and why PointsYeah is my new absolute favorite award booking tool, how it compares to some of the other services out there, like and when to use PointsYeah versus versus the old school ExpertFlyer, and why."

— Kai [00:05:49 → 00:06:13]

Maximizing Credit Card Rewards for Travel: "A lot of these kinds of considerations are where I think a lot of people stop and give up because it feels like there's a lot of different rules and options and permutations, and they're not sure, like what credit card to open in order to transfer where and which option is the best option."

— Kai [00:14:09 → 00:14:10]

Maximizing Travel Savings: "But the main thing I want to impart is just being clear about your travel goals. Like, if you tally up all of your travel expenses, how much are flights costing you each year? And if you're not tracking your expenses to that granularity, definitely check out Episode 36 - Simplifi, which is an app that imports all of your data, transactional data, financial data, automatically, and sums it up into categories, and you can see everything."

— Kai [00:17:13 → 00:17:42]

Navigating Airline Alliances for Award Travel: "And that's when things like knowledge and experience and research and planning and time spent doing it comes into play. Because things like airline alliances come into play and exponentially increase the amount of permutations that are possible with your award booking."

— Kai [00:21:23 → 00:21:42]

Travel Service Criticism: "There's just no reason to pay for that service versus even just using directly and spending the 20 minutes instead of spending $200. That coupled with just this constant trying to get you to buy that service and then not letting you even search without an account and then giving you only three searches, I mean, everything feels a little slimy."

— Kai [00:49:24 → 00:49:48]

Maximizing Travel Booking Efficiency: "I believe they pay for specific licenses that give them access to instant, top level data on seat availability and fare classes and all that stuff. No one else, I think, does it quite as well."

— Kai [00:54:48 → 00:55:01]

Travel Subscription Costs: "The other downside, other than it just being like a really old interface that looks like it's from 1995, is that it also costs $5 a month. And because you're setting up these alerts for flights that you're flying 9, 10, 11, 12 months in the future, you're most likely going to have to keep that subscription active so that you keep getting alerts. So you're potentially paying for like 9-10 months worth of that $5 subscription up until your trip is done."

— Kai [00:56:03 → 00:56:31]

Maximizing Award Travel Efficiency: "these tools can save you a ton of time and will often get you 80% of the way to the finish line. With only 20% of the work, which is ideal, and whether you want to dedicate another 80% effort just to optimize everything all the way up to the max, that's up to you."

— Kai [00:59:53 → 01:00:11]