031: How To Create A Location Independent Business (Travis Sherry)

Travis Sherry

How many times have you thought or said you want to make travel a part of your everyday life? If you’re like most people, you’ve said it or thought about it quite a lot. And if you’re also like most people, you haven’t done much to make it happen.

Our guest for episode 31 wants to show you how to change that. Travis Sherry is the man behind the curtain at the Extra Pack of Peanuts web site and blog, where he shares travel tips, stories from successful travelers and ex-pats and strategies on how to make travel part of your life. Join us as we talk about all of that and more on the 31st episode of How’d You Get Into That?.


Like so many youngsters, Travis wanted to be a professional athlete when he was a kid. But by age 12, he realized it wasn’t in the cards for him. It wasn’t until his junior year of high school that he was struck with the idea for his next career path: teaching.

His mom was a teacher, he got on well with his teachers and it seemed like a fun job. So off he went to earn a degree and enter the teaching profession. With a bachelor’s degree in history, his first full-time teaching gig was in social studies.

He loved it but realized he didn’t want to be in a classroom for the next 30 years…but he wasn’t sure what was next.

Travis had traveled a bit and he enjoyed it, and he also understood he didn’t want to be in the same place for the rest of his life. He really wanted to explore. He landed a full scholarship to earn his master’s degree, so that was what he did next. He thought a professor position would give him more flexibility to travel.

While earning his master’s, he interned for the World Cup of Baseball. His position took him to Switzerland for four months and that’s when the travel bug really bit him. He wanted to work in international sports management and this was his ticket to do so. Until his boss was caught embezzling, it ruined all the hard work he had put into his role and squelched his chances. He went back to his hometown, with his tail between his legs.


  • Why you have to humble yourself if you aren’t sure what you want to do.
  • How to know when to pivot on your path.
  • What he discovered about himself while teaching overseas.
  • Why consulting wasn’t a primary focus for him.
  • How much did he lose when his biggest advertiser pulled the plug?
  • And so much more!

Travis spent a month or two in the doldrums, contemplating his next move. Over the next year, he took a few teaching gigs to pay bills while he sorted things out. He realized he could combine teaching and travel as his next move; he applied to teach in Japan and was accepted into the program six months later. A month after being accepted, he and his now-wife were wed. A month after that, they set off for Japan for two years.

He enjoyed it and was fully able to explore and travel to his heart’s content. By the second year, he had the itch again. He knew teaching wasn’t “it” but traveling was. So how to make a living by travel? He discovered the internet and airline companies frequent flyer miles programs; he combined the two at his web site. He knew nothing about building a site, but he figure it out as he went along.

After teaching all day, he came home and worked on his site for a few hours every night. In under a year, his hard work paid off and he was making enough money from his site to stop teaching in classrooms. He was making a few grand, primarily through affiliate sales and he was delighted to tell everyone he made his money from his web site.

Until his birthday the next year when one of his airline companies pulled the plug. He lost his largest advertiser and source of income that day and seriously considered giving up. It was a true low point for him, even lower than his post-Switzerland internship.

But his entrepreneurial spirit wouldn’t quit and he took up consulting and helping people figure out how to use their airline miles for free flights and travel. Though it was time-consuming work, he continued to do so for a few months until he developed his video course. And that course has been and continues to be a smashing success today.

Please join me in thanking Travis for sharing his knowledge biscuits on the show; he’s an awesome guest and it was great to chat with him. Leave him a comment below or send him a Tweet.

Tweetable: I wasn’t going to give up what I wanted – to live abroad – for stability.” Travis Sherry


Check Out Our Sponsor!

Your branding is the face of your business. Make a great impression with creative, professional designs from ninety nine designs. Visit www.99designs.com/grant and get a Power Pack Upgrade FREE!

Share this post!

Share on facebook
Share on twitter
Share on linkedin
Share on pinterest
Share on reddit

Join the Conversation

1 Comment

Leave a comment

Your email address will not be published. Required fields are marked *