Last week was incredible! Not only did The Entrepreneur Cafe, LLC celebrate it’s 13th year in business helping startups scale but did so while taking in all of the festivities of National Small Business Week. At a time when sole proprietors are failing at rates three times as fast as their larger counterparts, for an entrepreneur to have survived a decade in business is no small feat. Only an owner that has managed to maneuver this ever-changing landscape for so long knows the highs and lows of running a business. I was interested in gaining a different perspective of what running a successful business long-term looks like and had the opportunity to attend a Crain’s 10 year Small Business Week event.

The following interview has been edited from a panel discussion hosted by Crain’s and moderated by Jan Parr/Assistant Managing Editor of Crain’s Chicago Business as they invited the following four entrepreneurs to share the successes and struggles of their first ten years in business. Panelist included: Jeff Drake, CEO of Protein Bar & Kitchen; TJ Mapes, Co-founder & CTO RIPT Apparel; Katie Pape, Owner Windy City Paws and Iqbal Shariff, CEO Best Home Healthcare

What were you thinking about starting a business during the recession?

According to Katie, some businesses are born out of necessity. A lay-off spurred her to pursue her own small business idea which combined her passion for animals and love of dogs. “It’s the boldest people that take chances during a recession.”
Where an economic downturn often takes its toll on various industries, Iqbal found that the economy did not affect his company’s business efforts as much. Some industries like senior living and health care related fields can be somewhat insulated. If you are going into business try and find something that might weather the economic storms over time.
TJ and his fellow co-founders took a calculated risk on their small business idea during the downturn. The company was started with just a few thousand dollars, their team was young and they felt they had time to turn things around or do something else if things didn’t work out. A small investment, low risk, and the customers’ connection to their designs have been positive.

What has changed in the last as it relates to your business over the last 10 years?

Iqbal says his company has had to pay more attention to and has been affected more by regulatory or legislative reform which has been a key driver in his industry.
Protein Bar started as a shake company and expanded once the founder realized that they needed to expand their offerings if they were going to survive long-term. As a result, So the company expanded to healthy meals that track major health food trends in the fast-casual dining space. Remembering who we were at the beginning has been key for us.
Katie says that more people are adopting sheltered dogs which has changed the landscape of their business. Windy City Paws has taken steps to become a fear certified company in order to establish trust with the animals. Also, low unemployment has made it harder to recruit and retain the right people. So the company has been exploring different kinds of compensation, programs, and events to keep the team cohesive long-term. “The emergence of the gig economy has forced them to consider how these new types of workers fit into the companies personnel plans.”

What is the one thing you wish you would have known that nobody told you at the very beginning?

Katie says that being an entrepreneur can be a lonely profession. Over the years she has focused on networking and being open and more transparent with others. “I learning not to take things so personally.”
TJ adage is to fail fast and fail often. The company has and implements new designs everyday. “Listen to your gut and don’t fall for the flash.”
Most people think that unlimited investment is the holy grail for a startup. Jeff says that unlimited money does not help but having enough money does not hurt.

What role does social media play in your company?

Katie says that social media is not as vital but it does help her company create a trust point among its members and its constituents.
TJ says that all of their designs are curated and that social media is key in helping the company obtain immediate feedback on new designs. He and the other co-founder handle all of the company’s social media efforts.
Jeff says that Protein Bar uses social media to engage customers and show their appreciation for customer feedback. In the age of social media (especially in the foodservice industry) “The phone eats first”.
Iqbal says that social media has no impact on his company as it does not get used.

What’s next for your business?

Jeff says that Protein Bar took some time off and is now looking to expand by opening smaller box stores in the suburbs. Going forward the company is looking at franchising and how the use of mobile technology will further drive their business.
Katie says that the company will need to expand offerings going forward and is looking to offer more services for cat owners.
TJ says that going forward RIPT will look to hit the reset button and is now focused on managed growth.
Whether you are looking to measure success on your own terms, navigating the regulatory issues of your industry or trying to figure out how to bring new concepts to market, there is always an opportunity to learn a little something from other entrepreneurs that have already walked the path.


Cavanaugh L. Gray is the founder of The Entrepreneur Café, LLC. As a small business development specialist, he brings two decades of experience implementing entrepreneurial-based business strategies that help startups scale. He has served as a business advisor to Innovation Award Winners and is the author of The Entrepreneurial Spirit Lives (An Amazon Top Read) and Bridging the Entrepreneurial Divide. With more than a decade as an academic, he currently serves as Adjunct Professor of Entrepreneurship at Loyola University Chicago. For more information on how to start, grow and succeed in small business Connect With Us at, 877-511-4820 or on social media @TheECafeLLC. Copyright 2019.


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