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In this week’s episode, I am joined by Alison Kinsey; relocation expert and a proud serial mover. Alison quit her job 4 years ago, said goodbye to a nice salary with all the perks, and took leap of faith in freelancing. Not ignoring her entrepreneurial spirit that fuels her (she launched her first eBay business at 16!), she went to work and created a business that could be as mobile as she was.

Having moved 9 times in the span of 6 years, and through her extensive experience in relocation, she gave birth to Cityleaper, designed for people who crave adventure, movement and new beginnings. It is a fiercely comprehensive moving resource and digital community cultivating inspiring stories and tactical tips – everything from savvy budgeting, expanding your social circle, apartment hunting, decorating and road trip planning.


Episode 5 | Alison Kinsey from Cityleaper

In this episode:

  • Alison’s journey on screwing the cubicle and leaving a cushy job and salary behind to start Cityleaper
  • How she came up with the idea for Cityleaper
  • Her entrepreneurial spirit and career path
  • Her own experience with moving cities throughout her life and seeing a need for this type of community
  • How Alison overcame her own hurdles and fears about moving and starting her own business
  • Her tools and resources for creating your own website


Memorable Podcast Snippets:

“I am 28 years old and 4 years ago, I said goodbye to my cubicle lifestyle permanently. It was a feel-good moment. I traded a very cushy salary and 100% employer paid benefits for a pass into the freelance world and never looked back. That was it for me. And since my foray into this world of freelance, I’ve learned that it’s very challenging. It can be rocky and complicated but I truly wouldn’t trade it for anything. It’s been such an exciting experience. It feels like you’re trading two lifestyles for another. You’re trading the security and comfort of a job full-time and going into something freelance and something that’s more scary and it could be temporary and you don’t know what’s going to happen.”



“I feel like millennials especially they move around a lot. They move around either for that dream job they just got at that really cool, techy start-up or they’re just eager to chase an adventure. Maybe they’re just tired of their life living in the same way. Maybe they lived in their hometown their entire life. I was just at a point where I needed to change the scenery and do something new. What I’ve cultivated is a place where you can really read and see really inspiring moving stories of people who have done things in their new cities. And it’s also a place you can go to get tips.”




“I feel like my best and brightest ideas come to me either on an airplane or while on a business trip. Coming up with the idea for Cityleaper fit right into that picture. So, I was at this really boring conference surrounded by executives and people just all wearing the same black suit and I was the black sheep in this crowd thinking, “Why am I even here? I’m not passionate about this.” It just shed to light that this wasn’t the path that I should be on. So I started just thinking about business ideas, and I think about ideas all the time. I fill notebooks with them and you have to always think about is what’s that one idea thats going to be it that i should go with and put all my time into.”


Resources from this episode:

Alison’s website: Cityleaper: https://www.cityleaper.com

Help with branding yourself online – ByRegina: https://byregina.com

A community of other entrepreneurs to bounce ideas off of: Join Uncaged Lifers: https://www.theuncagedlife.com/community

Resources for building your own website:

Blogger: https://www.blogger.com

WordPress: https://id.wordpress.com

Squarespace: https://squarespace.com

Smart Passive Income Podcast by Pat Flynn


Contact Alison:

Twitter: @alisonkinseym
Instagram: @cityleaper
Facebook: https://www.facebook.com/cityleaper


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