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Make Me Smart with Kai and Molly
The Big Book

Running an online retail business in rural America

Kai Ryssdal and Maria Hollenhorst Mar 11, 2019
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Online retailer Cheekys offers a monthly subscription service called "Chicks Fix" to their online customers.
Audrey Austin/Cheekys

The 2010 census put the population of New Plymouth, Idaho — a small town about an hour from Boise — at 1,538. New Plymouth, and rural towns like it, are not places you normally hear about as prime locations for new businesses. And yet, for a particular slice of the market in this digital age of retail, they can be.

In New Plymouth, in 2011, Jessi Roberts founded online apparel and accessories brand Cheekys. Cheekys, which is geared at rural women, is now a multi-million dollar enterprise. Roberts talked with Marketplace host Kai Ryssdal about her new book on life and business in rural America, “Backroads Boss Lady.” The following is an edited transcript of their conversation.

Jessi Roberts in the apparel section of Cheekys’ warehouse.

Kai Ryssdal: When you started in New Plymouth, and you set up that boutique, what were you setting out to do?

Jessi Roberts: Well, I think there are a lot of people have these super inspirational “why” stories, and what their “why” is, but the truth is that I wanted to feed four kids. Like, that was why I started the business. I had kids to feed, and I had a very small amount of money. I didn’t want to sell cars anymore. I didn’t want to own a laundromat but, whether I enjoyed it or not, I was there to pay the bills.

Ryssdal: This store is originally handbags, accessories, clothing for rural women. Do me a favor, for those who are listening to this (and, honestly, me included) who might not understand that market segment, what was your business?

Roberts: Well, originally, I actually started — don’t judge me — a tanning salon.

Ryssdal: Well, right. I was going to get there. But, yeah.

Roberts: Yeah, I thought that people would want that. And I bought a handful of handbags and some jewelry. And the first thing that sold was all of that, and no one was tanning. So I was like, all right, well, we’re going to sell these tanning beds and buy some more stuff. And then it just got to the point where I wanted to have something different, and I started to realize that the majority of the items that were sold to women who lived in the country — you know, farm girls, ranchers, just anyone who lived a more outdoor, down-to-earth kind of lifestyle. All of those items were being designed in Asia, so they didn’t, sometimes, make sense. I wanted to figure out how can I make these products more authentic. So I started designing my own products.

Ryssdal: And you have become, now, a woman running a plus-minus $10 million enterprise, right? You have an international supply chain.

Roberts: We do. We’re working on a distribution center in Australia.

Ryssdal: I know. So, holy cow.

Roberts: Literally [laughter].

Ryssdal: Well, yeah, I guess the question is: When did you make that transition — from selling things in a little rural boutique in New Plymouth, Idaho — to a brand and an enterprise?

Roberts: You know, every day I had to grow just a little bit. We very quickly outgrew the infrastructure that our town could handle. We outgrew the electricity, the phones, the cable … the weight of our product, actually, and our equipment, was too heavy for most of the late-1800s buildings. We’ve had to replace floors, air conditioning, I mean, like, everything, you name it. So, I just let it grow naturally and stayed content in where I was.

Ryssdal: Could you take a minute and explain what it’s like to try to compete, from rural America, with a lot of the big urban brands who, in a lot of ways, don’t … aren’t … they don’t have your best interests at heart?

Roberts: I think that that is a struggle that I have every day. Not only in the business, but personally. You know, I’m oftentimes told “you’re not big enough, you’re not small enough, you’re not country enough.” I have this saying, that is: if you want to get paid white-collar wages, then you better be prepared to work like a blue-collar worker. And so, I had to be willing to do what other people wouldn’t. And that, that was working.

Ryssdal: Are you getting the white-collar wages now?

Roberts: I am providing white-collar wages for a lot of other people, and that’s what’s really important to me.

Click here to read an excerpt from Roberts’ book “Backroads Boss Lady.”

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