The Rise of the Chicago Entrepreneur

Yes, we get it. The economy is still bleak. Competition for jobs is as fierce as ever and technology is rapidly restructuring every industry from agriculture to the arts. Many are struggling to find their way, while others—like Jess Burley, Jodie Deschler, Danny Loiacono and Zachary Sutter—are paving a new way and inspiring others to follow suit. This is the rise of the entrepreneur. Innovative and agile, these individuals are trailblazing down the road less traveled to turn their raw passions into full-fledged businesses. And they’re all under 30.

Work Hard, Play Hard—Work Harder

While most of their friends were out celebrating the end of the workweek, Danny Loiacono and Zachary Sutter spread out stacks of business strategy notes and inspiring art and design books, like the minimalism bible, “Less and More: The Design Ethos of Dieter Rams” and “Sparks of Genius: The Thirteen Tools of the World’s Most Creative People,” across a mock granite countertop in the model kitchen of Tolo Designs—the interior design business Loiacono runs with his brother Anthony—in preparation for another Friday night work session.

When a meeting with their web developer got pushed back to the following day, the online lifestyle magazine and fashion ecommerce site moguls-in-the-making turned their attention to curating content for the Departure website that was set to launch the previous week.

“We don’t want to put it out until it’s really ready,” said Sutter, 24. “You don’t want to show off your brand new car with no wheels and old paint. You want to roll up in your new Ferrari and be like, ‘What’s up?’”

For three years, these long-time friends from the ‘burbs have been working tirelessly to turn Departure, or DPTR for short, into a fully functioning online clothing store and accompanying digital publication with the latest in lifestyle, fashion, design and music for creative types. The apparel itself, which includes everything from hoodies to t-shirts to hats and accessories, is also designed to support those who constantly strive to better themselves, pushing them to feel confident in all their pursuits. “Look good, feel good, do good,” said Loiacono, 25.

The "Bootlegger" Beanie by DPTR. Photo by Amanda Boleman.

The “Bootlegger” Beanie by DPTR. [Photo by Amanda Boleman]

Minimal in presentation, each piece is thoughtfully crafted with a heavy emphasis on fabric contrast, texture and hue, making sure to keep each look feeling modern, yet timeless. Think American Apparel with slight decoration—like a small leather label with the DPTR namesake–that sets Departure’s apparel apart from AA’s signature basics. With the site now set to launch with their Spring/Summer collection, these guys have become familiar with odd working hours and late nights. “I don’t sleep!” shouted Loiacono from the Tolo office.

But that’s what happens when you’re building your own business.

Others like to spend their Saturdays running their weekly errands or catching up with friends over lunch. For Jodie Deschler, it’s just another day to build on marketing strategies for her arts and crafts storefront Sew Crafty Studios. On this uncharacteristically warm Saturday in February, she had the chance to mix business with pleasure as she photographed her friends cutting out patterns and experimenting on the sewing machines spread around the intricately decorated studio with its adorable round tables disguised as spools and frames of all shapes and sizes holding unexpected objects like paint bottles, brushes and even a glue gun. “All you have to do is hold the fabric in place and push down on the foot pedal to make a stitch,” she demonstrated on the already threaded machine and pinned fabric. “Play around for as long as you’d like!”

As she snapped photos for the Sew Crafty website that launched on Monday, March 18, a curly-haired woman walked in with her two young daughters to inquire about hosting her 5-year-old’s birthday at the studio. Their presence transformed Deschler, 30, from a sweet blonde goofing around with her friends to a savvy businesswoman showing the little girls examples of crafts hung on the bright turquoise walls and getting them excited about all the fun projects, such as homemade necklaces and uniquely designed t-shirts, that they would get to do during their own party. “While I may not always be behind a desk or in the studio, it’s impossible for me to turn off that part of my brain,” she said. “My business is such a large part of who I am.”

Said pretty much every successful entrepreneur ever.

Decor around Sew Crafty studio. [Photo by Amanda Boleman]

Decor around Sew Crafty Studio. [Photo by Amanda Boleman]

With a social painting class company that expanded from one city to 11 in just over a year and a half (and plans for eight more in 2013), Colors & Bottles founder Jessica Burley is also accustomed to non-stop work hours. When she first started out back in October 2011, the 27-year-old Columbus, Ohio native spent many sleepless nights teaching herself web development and design to gain attention for the group art class event she was planning for her hometown. “You should have seen that first site,” she said with a laugh. “It was seriously hillbilly.” But her nights of no sleep and persistence paid off to the tune of over 1 million hits and an average of 800 to 5,000+ daily unique visitors to the once “hillbilly” site. “You will work harder than you’ve ever worked and no one will understand unless they are entrepreneurs too,” said Burley. “I love talking to people who have started up other companies because they get it. It’s like a bond.”

After graduating from Ohio University with a background in environmental science and industrial engineering, Burley found herself working in Chicago as a federal investigator for the US Public Health Service. Although she “can’t paint to save her life,” the self-proclaimed science geek spent a lot of her free time attending art classes in the city, but never felt like she fit in with the arrogant artistic types at many of the studios. “One day I was painting some horrible ballerina in class and started thinking, “This would be way more fun if I could do this in a different location—like with friends at a bar,” recalled Burley. She also couldn’t get over the $350 she had just dropped on pottery classes and wanted to find a way to make art more accessible.

As a “pretty conservative” person, she started thinking about how her affordable art classes could get people to work and stir up the economy. Rather than setting up an art studio, Burley had the idea to host painting classes at local small businesses, saving her expensive overhead costs and differentiating her brand from other painting studios. “It not only promotes businesses by upping their marketing and bringing in extra money, but it’s also much more fun than just going to a studio,” she said.

Fed up with the corporate culture, Burley quit her job and decided to turn Colors & Bottles into a reality. With years of experience investigating and writing extensive reports on multi-million-dollarcompanies for the FDA, she thought to herself, “If I can do that, I can do anything.”

You’ve Gotta Start Somewhere

Having worked in experience-based retail and training program development for children’s retailer Club Libby Lu, Deschler also found herself prepared for entrepreneurship in thanks to her former work experience. “I always felt like I was essentially running a business already,” she said. “Between the creation of new ideas and the responsibilities of day-to-day business practices, I felt like I had what it took to start a business of my own by taking the knowledge I had acquired and applying it to something I was really passionate about.”

While pushing to create a crafting section within Libby Lu back in 2008, Deschler received a call explaining that the company would be closing down all 100 of its nationwide stores in a matter of four short months. Rather than find work at another retail job, she and a coworker envisioned starting their own experience-based company for young girls. Instead of styling them up in fancy costumes and makeup like at Libby Lu, Deschler and her former partner decided to focus on empowering these girls to celebrate their creativity through arts and crafts. “Whether it would be cooking brownies at the age of 7 or doing funny hairstyles at the age of 8 when most other kids don’t even like combing their hair at that age, I was always super into crafting,” she explained. “Both my partner and I were pretty kooky and creative so we thought, ‘Why not do what we like to do?’” Driven by the D.I.Y. ethos, the girls started hosting crafting classes and parties at local community centers and customer’s homes under the name the Glitter Girlz.

The Glitter Girlz weren’t the only ones who could get a little crafty.

Before they graduated to creating stylish beanies and cardigans, the DPTR guys got a taste for fashion design back in high school, making bracelets made from materials they picked up from their local Hobby Lobby. “We’d go to the mall and see these bracelets selling for so much money and we thought, ‘We can make our own that are so much cooler,’” said Sutter. With stretchy string bracelets and glue scattered across the floor in his basement, the boys went to work making their own designs, which proved to be popular with the kids at school. “We’d wear these bracelets and everyone would be like, ‘Can I get one of those?’” Back then they had no idea that their future would look quite similar.

DPTR was still just a pattern waiting to be sewed. The beginnings of a novel idea were there and the guys had upped their game from bracelets to having a small t-shirt order placed, but there was no set plan of action as to how the brand would grow. Lucky for them, they had someone to help right under the same roof. During one of the many work sessions at the Loiacono household, Danny’s sister Mariella, who worked in fashion, came downstairs and asked if the guys would like to set up a booth at the 3rd Annual Mo’Rockin Fashion Fest. “Oh my God. Fashion show. Sign us up,” said Sutter. With no time to waste, they scrambled to produce enough products to make a good showing, expanding beyond just apparel and adding posters and water bottles to the mix. “We just bought em’ and did it,” said Sutter.

And did it well.

Take a Risk; Take a Chance

The DPTR booth sold more products than any other booth that day. “Towards the end of the show, they were kind of impressed by how we did,” said Loiacono modestly. “And the people who were running it said if we grabbed some friends and put them in our stuff, they could model it off. There were definitely some clowns up there.” The Fashion Fest may not have been the most perfectly planned debut, but it definitely taught the guys the first lesson in entrepreneurship: It’s all about taking a chance and learning through trial and error.

Just ask Jess Burley. She didn’t even attend the first-ever Colors & Bottles event.

When only two friends signed up for her first attempt at an event in Chicago, she decided to return to her roots and start the company back in Columbus. “I hadn’t been living in Chicago very long so I didn’t know a lot of people,” she explained. “I thought I would have more success if I started where I’m from and had a larger base of friends and family.” Working out of her home in Chicago, Burley managed to find her first Columbus-based artist, Quinn Kellogg, on Craigslist and coordinated and ran an event from over 300 miles away.

On October 2, 2011, 24 people arrived at Bar Louie in downtown Columbus ready to paint and ready to drink. Jess Burley was not one of them. “It was so weird not being there! I kept calling my parents asking, ‘Is it real?’ ‘Are they painting?’” she said. Kellogg also received quite a few calls that week. “Since I do everything over the phone or Internet, my biggest fear is that the artists and coordinators won’t show up,” she explained. “I called Quinn like five times a day for a week to remind him.”

Although Burley can’t be in every city for every Colors & Bottles event, her spirit is felt through the artists, event coordinators, and even attendees who uphold the ideal that every painting class should be open to everyone regardless of talent or skill. From the South African couple that were as immersed in one another as they were in their paintings to the row of chatty gay men experimenting with new brush techniques along the bar, the feelings of openness and approachability were definitely in the air at a Colors & Bottles event at Revolver (3759 N. Damen Ave) on Thursday, Feb. 28. Maybe it was just all the glasses of flowing red wine that were almost as common of a fixture on every table as the canvas and paintbrushes that were there upon arrival. Or maybe it was artist and event coordinator Sara Renae Jones’ step-by-step breakdown of Picasso’s Jacqueline with Flowers that made painting seem simple to even the most clueless of beginners.“Start thinking about what you want your figure to look like,” she said. “I like to start with the neck and break it into geometric shapes.” Her words of encouragement perfectly matched how Burley described the classes would be. “There are 17 people here tonight,” said Jones. “If we had 17 identical paintings, it would be weird. We want everyone’s to be different.”

Event Coordinator and Artist Sara Renae Jones poses with her rendition of Picasso’s Jaqueline with Flowers at Revolver (3759 N. Damen Ave) on Thursday, Feb. 28. [Photo by Amanda Boleman]

Event Coordinator and Artist Sara Renae Jones poses with her rendition of Picasso’s Jaqueline with Flowers at Revolver (3759 N. Damen Ave) on Thursday, Feb. 28. [Photo by Amanda Boleman]

To this day, Burley still hasn’t met nearly 80% of her staff—not including Jones or Kellogg who she met in Chicago and Columbus respectively. From the start, Kellogg worked closely with Burley to transform Colors & Bottles into what it is today. “We really changed and tweaked pretty much everything about it in those first few months,” said Kellogg. “It really stuck with me that Jess chose to try something new because she wasn’t happy before, and we both worked hard to find good people to work with.” The only hiring criteria? People who were down to roll with the punches, like Jones, who was first drawn to Colors & Bottles for their wide range of painting styles and techniques. “I needed people who weren’t obsessing over the details,” said Burley. “I didn’t pass out an employee handbook. If they had the entrepreneur, gung-ho attitude, I was down to give them a shot.”

If At First You Don’t Succeed…

As Burley was beginning to find success with the help of people she had never met in late 2011, Deschler was in the process of starting over with a total rebrand of the Glitter Girlz after her partner and co-worker of nearly seven years abruptly moved back to Michigan to deal with personal matters. Deschler was left to deal with the legal issues of continuing the company of just over two years on her own, which proved to be tricky as the Glitter Girlz brand was connected to both her and her ex-partner’s name. “It was best and advised by a lawyer to start fresh where everything was connected to me,” she explained. The sudden change left Deschler feeling panicked at first, but after a few months of nannying, she knew she needed to get back to what she truly loved. “There was just such a huge gap from what I had been doing and I know that I needed to challenge myself,” she said.

So she saved up her nannying money and started Sew Crafty Studio.

After a jam-packed afternoon of crafts and cake, Jodie Deschler had a hard time rounding up the crowd of seven-year-old girls to get a photo in the homemade puppy shirts they had just made. “I want to see your best poses!” shouted Deschler, 30, who has been working to empower young girls through arts and the DIY mindset for nearly 10 years. [Photo by Amanda Boleman]

After a jam-packed afternoon of crafts and cake, Jodie Deschler had a hard time rounding up the crowd of seven-year-old girls to get a photo in the homemade puppy shirts they had just made. “I want to see your best poses!” shouted Deschler, 30, who has been working to empower young girls through arts and the DIY mindset for nearly 10 years. [Photo by Amanda Boleman]

“With the new name, I wanted to be literal and to the point—We sew. We craft. We’re a studio. No pedicures and manicures here. Even though I love those,” she said with a laugh, explaining how people would always assume the Glitter Girlz offered the same services as Libby Lu. This time around, Deschler wanted to make it clear what her company was all about and never let the setback of her partner leaving get in the way of her vision for Sew Crafty. “It was scary at first, but I’m kind of glad it happened because now I have all this,” she said, admiring her bright and beautiful studio.

Despite being a hit at their first fashion show, Loiacono and Sutter struggled to progress their company due to their lack of brand identity and a clear business plan. They were quick to hire an investor who was all about the bottom line, pushing them to go where the money was, rather than where they knew they should be in their hearts and heads. “If a shirt with lights on it would sell, that’s what he wanted to do,” said Sutter. “But that wasn’t what we were all about.” He was ready to take it from 0 to 100 while they still needed to figure themselves out as a brand. “We wanted to put on this front that was just like fake it ‘till you make it and it didn’t do us any good,” said Loiacono. “We tried to be something we weren’t and it didn’t work out.” After another failed attempt with a separate investor, the guys knew it was time to re-evaluate. “We sat down and realized that all we really needed was ourselves,” said Sutter. “With all the immediate buzz you can get from your Twitter, Instagram and Facebook, we realized we just needed to put out a good product and utilize the resources already available to us.”

The Art of Social Media

Both Deschler and Burley have also found that social media has been a strong catalyst in growing their companies. For these creative entrepreneurs, social media has become an art form in and of itself. “People see how cute and adorable the things are that the children and adults sew and create [on Facebook and Instagram], and they’re like, ‘I wanna do that, I’ve never tried making that,” said Deschler. They can put out highly visible content across multiple platforms and start a conversation for free using everything from Pinterest to Tumblr and Twitter to Facebook. “People of our generation have a huge advantage. We don’t need a million dollars to start a company because we have all this tech stuff,” said Burley. “Understanding social media—that’s the only reason all of this is possible.”

From the office of Tolo Designs, Loiacono attributed his entrepreneurial spirit to his family, describing the days he’d be out building for his father and brother’s construction company Loiacono Construction. Sutter, whose father is also in construction, jumped in to comment how technology has made growing their own business much easier than it had been for their fathers. “Our parents could have never thought of reaching people in New York with their website and goods that they were selling,” he said. “Everyone just comes together on the Internet and that’s how stuff gets started now.” Loiacono also noted that in his parents’ generation, a college degree meant a lot more and people were could actually get jobs with a bachelor’s degree. “Now, college degrees are a dime a dozen,” he said. “Our generation is going to be forced into being entrepreneurs—but that’s definitely all right with me.”

Zachary Sutter looks into various content curating websites during a DPTR Friday night work session. [Photo by Amanda Boleman]

Zachary Sutter looks into various content curating websites during a DPTR Friday night work session. [Photo by Amanda Boleman]

A Bright Future

Looking to the future, the DPTR guys are excited to expand their social media presence and hit the ground running with their website later this spring. “Our vision has been derailed three times. It’s been three years of trial and error, but now we finally believe we have what will work,” said Sutter. “You just have to keep going. If one thing doesn’t work, it could lead to something else that does.”

No one understands this better than Deschler, who marks the Sew Crafty storefront as her biggest accomplishment yet. One day she hopes to expand her studio into a destination location for people from around the country to come and get the best quality crafting advice and experience. She also hopes to sell craft kits for people to take home and host their own parties or craft nights. “Know that building a business takes time,” she said. “Be prepared to find some odd jobs on the side to make ends meet and always be as resourceful as you can.”

As for Colors & Bottles, Burley has already received over 20 requests from people interested in franchising. “Instead of me controlling it all, I’ll sell each city as a franchise and make royalties,” she said. She believes her success has stemmed from hard work and dedication, but also from the tough lessons she learned working in the corporate world. “Do the 9-5 job thing. I am who I am because of that experience,” she said. “Work in the industry to get the vibe and see how it works. Everything had to start somewhere.”