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Mike started Vagabond Heart in 2017. They detail the beginnings of their company in their Starter Story interview: 
Q: How did you get started on Vagabond Heart?
As I mentioned above, I’m a serial entrepreneur, and a lifelong maker. I’ve been selling online since the early 2000’s, well before Shopify made it easy, even before Amazon existed. In the past I’ve designed typefaces, ran a literary magazine, published books, sold vintage menswear, and even built and sold wooden furniture online.
The idea for Vagabond Heart came to me three years ago when I was on a winter-long vacation in a small town in Mexico, which I loved, except for the fact that I didn’t really have anything to do with my time. I thought to myself, “If i’m going to come down here every winter, I need a project to keep me busy.”
The idea was a combination of my interest in vintage clothing, style, and old movies, with my love of menswear and fashion, and of course, travel. What I wanted was a way to make my normal looking duffel bag look like an updated version of the luggage you’d see on a trans-Atlantic crossing in the 1920’s, or on the runway in Casablanca.
I wanted to have patches from Paris and Rome and Cuba plastered all over, but I didn’t want the readily available (and boring) flag patches, and I didn’t want something too retro and costumey.