Kimberly Crupi Dobbins, SIMPLE Squares
Kimberly Crupi Dobbins, SIMPLE Squares

How one woman turned a corporate sabbatical and a kitchen dream into a snack company that let her quit her day job. Follow Kimberly Crupi Dobbins’ of SIMPLE Squares journey from big-company employee to founder of Simple Squares, healthy snack bars that are now sold everywhere.

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Kimberly Dobbins: I came up with idea for Simple Squares as this healthy snack that tasted delicious, um, but was also good for you. And I thought, well, maybe there’s an idea there.

Colleen DeBaise: Welcome to The Story Exchange, featuring the stories and strategies of entrepreneurial women around the world. I’m Colleen DeBaise, an editor at The Story Exchange, and we’ll be joined later by our co-founder, Sue Williams. Today’s podcast is for all of our listeners with entrepreneurial aspirations. What do I mean by that? Let me paint a picture for you, and see if this sounds at all familiar. Say you have a really great idea for a new product or service -- something completely different than what’s already out there. Something you think could change the world. Something you think could be worth millions maybe even billions of dollars. But of course, here’s the big problem. You’ve got this great idea -- but if you’re like most of us, you have a day job. You’re probably working for someone else. And you’re quite possibly in a line of work that has, well, nothing at all to do with your great idea. do you turn this dream you have into a reality? How do you even start? We asked Kimberly Dobbins of Chicago this very same question. Now, you probably have never heard of Kimberly, but you might have heard of her product. She’s the inventor of Simple Squares, which you can find now in Whole Foods, Fairway, and a lot of stores you see in the airport. They’re snack bars -- healthy snack bars, not candy bars -- and they stand out because they are square-shaped, unlike your average granola bar that looks like a rectangle. And they’re very healthy and as the name suggests, very simple. They come in flavors like cinnamon, or more savory ones like sage and rosemary. Here’s how Kimberly describes Simple Squares:

Kimberly Dobbins: They are all natural whole food ingredient snack bars. They are organic. They’re composed of nuts, honey, vanilla, sea salt - a pinch of sea salt - and herbs or spices.

Colleen DeBaise: What makes Kimberly’s story interesting is that just a few years ago, she was doing something completely different…she was working in Corporate America, at Morningstar, which is a big investment-research firm that has this shiny office tower in downtown Chicago. She was making a very comfortable salary as director of global recruiting. But she decided to leave all that behind and now, she is successfully making and selling Simple Squares, despite having zero experience -- zero -- in the food industry. A while back….we headed to the Windy City to ask Kimberly exactly how she did it. If you go to our website,, you can watch a video we produced on Kimberly, telling her complete story. Today, we are going share to snippets from that conversation, so you can get a sense of how she got her product on the market…

This is a story you should listen to if you’ve ever dreamed of turning your idea into a business, especially in a field where you have little to no experience. It’s filled with tips, advice, not to mention a few mistakes. You can hopefully avoid those as you begin your own entrepreneurial journey.

The story starts over 7 years ago, when Kimberly was still working at Morningstar. She liked her job well enough, but something was missing.

Kimberly Dobbins: I was looking, um, for something more in my personal life. I was looking into volunteer opportunities, I was looking at resurrecting the acting career, library sciences. I mean, it was really varied.

Colleen DeBaise: So Kimberly decided to do a little soul-searching. She was lucky that Morningstar offers a pretty nice perk to its employees: a 6-week paid sabbatical.

Kimberly Dobbins: So on my sabbatical, I decided to travel. I purchased an around the world ticket and I made my way from East to West. So I visited….13 cities, 11 countries and traveled the whole 42 days. And part of the goal of this trip was really to focus on what I wanted to do in my personal life, um, and all roads pointed to health and wellness.

Colleen DeBaise: Now, Kimberly is a marathon runner and triathlete, so she naturally has an interest in fitness. She says in her 30s, she started to become more aware of what she was putting into her body.

Kimberly Dobbins: So along the trip, it was so fascinating and interesting to see what individuals were doing across the world that were either, you know, worse than what Americans were following in their dietary lives or, in a lot of cases, better. So when I returned, I decided to focus on health and wellness, and I enrolled in the Institute for Integrative Nutrition in New York City. And that is a program that allows you to study all the different dietary theories around the world and use those to help counsel clients in a holistic health counseling session.

Colleen DeBaise: Kimberly continued her day job, but would fly to New York one weekend a month to take classes. She graduated a year later, in 2008. Right around that time, she started having a chronic skin problem.

Kimberly Dobbins: I was having really just these very large cystic bumps that would appear on my face and would last for six months and not go away. So I was really curious, ‘What is the root of the problem?” I didn’t want to take antibiotics.

Colleen DeBaise: Kimberly went to see an Eastern medicine practitioner.

Kimberly Dobbins: She recommended that I go on an elimination diet. And essentially that was a diet that was eliminating wheat, gluten, dairy, soy and refined sugars from my diet. I am a self-professed lover of snacks and desserts and at the time had to eliminate all of that, so what I found myself doing was eating bananas with maple syrup every day, which...I didn’t think that was necessarily good for me as well.

Colleen DeBaise: So, still with bumps on her face, Kimberly began working in her own kitchen, trying different concoctions and finally coming up with a winner.

Kimberly Dobbins: I came up with this idea for Simple Squares as this healthy snack that tasted delicious, um, but was also good for you, at the end of 2008. My husband, very stereotypical Midwest eating habits, very meat and potatoes, I gave him some for him to try and he liked them. And I thought, “Well, maybe there’s an idea there.”

Colleen DeBaise: Her original goal was to sell Simple Squares at farmers’ markets on weekends, and start a little side business that would become her personal passion -- a pet project, if you will. But that actually wasn’t as easy as it sounds. Farmers market can be hard to get into and if you do, some require attendance, with penalties for no-shows.

Kimberly Dobbins: So I decided to go to Plan B, which was the mass distribution. And that, in turn, led to 2009, when I incorporated and began the work to find a co-manufacturer.

Colleen DeBaise: So that’s the first part of Kimberly’s story, and we’ll continue in just a bit with how she got Simple Squares from her kitchen into more than 2,500 stores, including Whole Foods and Fairway. But first, let’s take a step back, and look at Kimberly’s background. At The Story Exchange, we like to show how women from all different walks of life can become entrepreneurs. If you’ve never checked our site, please do so, it’s We’re a nonprofit media company and we do articles and videos about women business owners. I’m being joined now by Sue Williams, co-founder of The Story Exchange, who spent a day with Kimberly in Chicago and produced a video profile of her for our site. Sue, welcome.

Sue Williams: Thank you.

Colleen DeBaise: So, tell me a little bit about Kimberly and what she wanted to be when she was younger. I understand “entrepreneur” was not what she said.

Sue Williams: No, it wasn’t. So, we met at her apartment, which is in this really nice modern high rise in downtown Chicago and my first impression of Kimberly is she’s very kind of typically midwestern. You know, she’s tall and blonde and she smiles very easily. And she has a certain presence. But you also get the sense that she’s very focused on the job at hand. We chatted about what she wanted to be when she was young and, no, there was nothing entrepreneurial. Like many kids, she wanted to be an actress. Here’s what she told me.

Kimberly Dobbins: I loved singing, I loved dancing, um, I loved acting but I did get the stage fright. And I remember in second grade we had a production of The Wizard of Oz and I, of course, thought I would go out and audition for Dorothy. Not only did I not get Dorothy, I did not get the part of a munchkin, but I was cast as part of the yellow brick road. So that was my first failure in life. But it turned out great. I was a proud brick.

Colleen DeBaise: She’s got a good attitude.

Sue Williams: I know, she’s funny. And she still acts today. In fact, right before her sabbatical with Morningstar, she signed up with an acting agency in Chicago. And she told me she had more recently auditioned for a commercial, playing a hockey mom for a local meat agency.

Colleen DeBaise: Well that sounds smart. It’s a little bit of extra income as she grows her company?

Sue Williams: Yeah, plus she loves to act.

Colleen DeBaise: So, tell me about Kimberly’s background, especially education wise...did she study business?

Sue Williams: Nope, no, not at all. Um, she loves history. Especially East Asian history and that’s what she studied at Wake Forest and after that she went and got a master’s in elementary education at Boston College. And for years-- actually for most of the 1990s’ she taught kindergarten through fourth grade and then decided to try something new. Let’s listen to a bit of what we talked about.

Kimberly Dobbins: And when I moved to Chicago, I was really interested in working with people my own age, try something different. I was in my late 20s and a friend of a friend had turned my resume into Goldman Sachs. Goldman, I think is a really interesting company where they focus on hiring people with core skills, so it seemed a natural fit.

Sue Williams: So you go from teaching elementary school to Goldman Sachs. That’s not an obvious career move.

Kimberly Dobbins: No, it was interesting. I became a generalist so I was focusing in the HR realm on everything from benefits, to talent acquisition, to compensation… and as the years went on I really found myself interested in working with people, and talking to people every day. And I always circle it back to wanting to be an actress. You know, I think most actors, they always need to be on, and as a teacher, you always need to be on for the children. And in, um, recruiting, you always need to be on.

Sue Williams: And so Kimberly stayed in recruiting for a long time…eventually going to Morningstar. And the common thread of all her jobs -- including what she’s doing today -- is this concept of being “on.”

Colleen DeBaise: Yeah, yeah. Right, and in entrepreneurship, you always need to be “on,” particularly if you are trying to sell a product like she is. Uh, so, Sue - any last thoughts about Kimberly’s personality -- was there anything that struck you?

Sue Williams: Yeah, you know, I think she has this incredible passion for her product. Like it’s her baby and she’s protective about it and she has this passion that all entrepreneurs need if they’re gonna be successful because it’s just such a tough road.

Colleen DeBaise: Yeah it is. And you definitely have to have passion, especially in the early days when there are a lot of naysayers too. Well, Sue, thanks for sharing Kimberly’s background.

Sue Williams: Oh, that’s a pleasure.

Kimberly Dobbins: My original goal was just to sell at farmers markets and have a great side business. But it turned into a career and lifestyle change.

Colleen DeBaise: We’ve been looking at Kimberly Dobbins, who several years ago, came up with the idea for healthy snack bars called Simple Squares, and decided to mass distribute them. Now, when you don’t know anything about the food industry, learning how to manufacture a snack bar while maintaining a corporate job that requires travel to Britain and Australia is not the easiest feat.

Kimberly Dobbins: A steep learning curve. I have learned more about a lot of things that I never thought I would learn about it, things I had no interest in learning about. Um, and I’m sure, as most of the folks you speak with can attest, being an entrepreneur, you wear every hat, so learning legal, learning R & D, learning marketing and sales. Uh, so it’s been an interesting road and again, a path I thought I would never would be on but I’m thrilled that it happened.

Colleen DeBaise: To figure out distribution, Kimberly did a little research. She found a food-processing plant run by Land O’Lakes, you know, the big dairy company -- they were very nice, but they told her “we don’t normally work companies unless they have a million in sales.” But they put her in touch with a consultant. So that consultant was very useful to Kimberly. She paid him $1,200 -- and keep in mind, she still had her day job, so she had extra income for things like this -- and he flew to Chicago and spent time with Kimberly at a place called Kitchen Chicago. It’s sort of a shared commercial kitchen, that rents space to people by the hour. Kimberly brought her food processor, and her pots and pans so he could see exactly how she made her Simple Squares. So that way, he would know what sort of manufacturer she needed. So then he connected her to a manufacturer that was a family-run business in Oregon, which was actually willing to work with a startup. In early 2010, Kimberly spent about $2,500 on a pilot run, producing a whole batch of Simple Squares in individually wrapped plain packs. She had to put stickers with the brand name on herself. She had them shipped to a hotel in Anaheim, California, in preparation for her first trade show. This was a big moment for her.

Kimberly Dobbins: I left for the Natural Products Expo Show West in Anaheim, and we had our first debut into Simple Squares, which was both exciting and, you know, a little bit scary but it went very well. Well, you know it...I guess it wasn’t as seamless as it sounds.

Colleen DeBaise: I’ve been interviewing business owners for many years, and most have a picture-perfect story about how they started. Kimberly was honest enough to tell us about what went wrong with her big launch. So at the trade show, she took a ton of orders for Simple Squares - that’s the good part. But a short time later, there was -- let’s just say a major snafu.

Kimberly Dobbins: So about six weeks into receiving our first set of bars, we noticed that they were starting to leak oil. So we needed to go back to the drawing board and that took about eight months to really reformulate the commercial formula and get it right so that we were not having this issue.

Colleen DeBaise: So 8 months -- that’s a big setback -- she basically had to start over. It was tough to lose momentum from that first expo. But Kimberly said actually, most of her customers were patient. She called them up, explained the reason for the delay, and they waited. By that end of that year, with all its ups and downs, she was ready to take a 3-month leave of absence from Morningstar. And even though her friends told her she was crazy, she decided during that time to quit her corporate job and focus on growing Simple Squares.

Kimberly Dobbins: Would you like to try some coconut goodness here? We’ll fire you up a piece of square.

Kimberly Dobbins: I always want to be a part of going out and selling the product. It’s my baby. It’s my passion.

Colleen DeBaise: We’ve been talking with KImberly Dobbins, who made a giant career switch a few years ago. So now, we want to take a look at whether that leap into entrepreneurship has been worth it for Kimberly. The short answer is yes.

In 2011, the year Kimberly left Morningstar, she sold 50,000 bars of her Simple Sqaures -- that’s a pretty impressive number. But in 2013, sales jumped to 450,000 bars. That's because Kimberly started building relationships with regional distributors. Then she identified the big players -- the national distributors that got brands into stores -- and she targeted them at trade shows. She hired a broker to negotiate with them and get her deals. That’s really driven growth.
She’s now in health-food stores and gyms, Whole Foods and Fairway, not to mention a number of airports. She’s even won a silver medal from the Specialty Food Association for “outstanding snack.”

Kimberly Dobbins: We wanted to be the big fish in a small pond, the small pond being the celiacs that could also not do dairy. But we found was that we really had a much larger breadth. So our target audiences right now are primarily individuals who are gluten-free, people that are focusing on raw and paleo diet, as well as individuals that are road warriors -- people on the go, people that are looking for that healthy snack that they’re not able to find otherwise.

Colleen DeBaise: Paleo by the way, is the popular diet where you eat like a caveman -- lots of lean proteins, lots of nuts and seeds, not so much carbs or refined sugars. Simple Squares are definitely on the paleo diet. For Kimberly -- that’s the best part of being an entrepreneur: She’s created a healthy alternative to a lot of the unhealthy snacks that are out there on the market. That’s not something she could do at her old job.

But, even with all this success, it takes a lot of time for a company to make money. And in case you’re wondering, Kimberly spent about $50,000 of her own funds to get Simple Squares up and running. She’s supported herself with savings from her corporate career.

Kimberly Dobbins: I was able to take my bonuses and really put them away for a rainy day, which I have done and that’s primarily how Simple Squares has been able to sustain itself over the last few years, funding-wise. People say you need a lot of passion, but passion can only take you so far. I think it’s a nice underlying item to have, but you really need the perseverance and the tenacity to move forward.

Colleen DeBaise: When I spoke to Kimberly recently, she told me: “Entrepreneurship is about 5,000 times more challenging than I thought it would be.” But she’s more than content with the choices she’s made. And by the way, that skin condition we told you about earlier? Maybe it’s Simple Squares, or maybe it’s her new lifestyle, but it’s cleared up. And her company’s future looks promising, too. At the end of 2014, she turned a profit for the very first time.

Kimberly Dobbins: I would like to definitely reach the five million mark in sales. Now, since we’re into distribution, the goal is to grow the company and eventually sell. However, I may decide, ‘Hey, I wanna keep this growing. I wanna keep it under my wing.” We’ll see where the road takes us.

Colleen DeBaise: Join us next time to hear more stories about innovative and inspirational women doing the things you’d never dream of. Or…maybe you would. This has been The Story Exchange. If you like what you’ve heard, visit our website at, where you’ll find news, videos and tips for women entrepreneurs. I’m Colleen DeBaise. Editing help provided by Michelle Ciotta and Nusha Balyan. Interview recorded by Sam Shinn. Executive producers are Sue Williams and Victoria Wang.


Related Article: The Long Journey to Market for an All-Natural Snack Bar