The Messy City Podcast

The Best Life Hack, Ever

March 17, 2026·50 min
Episode Description from the Publisher

We take a break from our routine conversations today to have some fun, and talk about the wonders of travel hacking with my sister, Cindy Weir. Cindy epitomizes how to really leverage having a system for travel hacking, as she made the most of her small business to rack up points. It’s paid off incredibly for her, as she’s traveled to 22 countries in just the last five years, in addition to doing so in style. We go over how she got there, some of the many little tips and tricks we’ve learned over the years, and even share insider knowledge on airline lounges, lodging, and more. Are you someone that loves to travel? Do you own a small business or have an active side hustle? If you can say yes to both of those, then you need to listen to how Cindy it, and you can as well. Find more content on The Messy City on Kevin’s Substack page. Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5. Intro: “Why Be Friends” Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe

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