September 5th, 2019

How Casey Clark Helped Build Cultivate Advisors into One of America’s Fastest-Growing Companies

Casey Clark talks about his entrepreneurial journey at Catapult.

Most successful entrepreneurs remember the defining moments that helped shape their mindset.

Casey Clark remembers several of the crucial moments that helped define his entrepreneurial mindset. The first was when he was down to the last $10 in his bank account, bills due, failing to land a contract with the 30 potential clients he had reached out to with his College Pro Painters franchise. Clark, then an 18-year-old at University of Illinois in Chicago (UIC), found himself getting emotional in front of a woman he had just met when explaining she wasn’t ready to decide on the potential painting contract.

“I just started tearing up in front of her; I was losing confidence in my ability to achieve my dreams as an entrepreneur,” Clark said. “I’ll never forget her reaction, she told me I had impressed her and that she knew I was going to be successful at this. She ended up signing the contract and then walked me to her neighbor and convinced him to sign as well. I went from having no faith and no hope to hours later driving home with $4,000 in my bank account. It was a simple moment, but it was one of my first wins and she helped me learn to persevere through self-doubt. I still think about that moment as my team and I are now tasked to instill confidence in other entrepreneurs everyday.“

College Pro franchise owner.

Fast forward, Clark, now 33, runs Cultivate Advisors, which was just ranked No. 280 on the Inc list of 5,000 fastest-growing privately held companies in the United States. Cultivate Advisors, co-founded by Clark and Dan Gramann in November of 2013, partners with entrepreneurs to grow their businesses by working one on one with Cultivate’s business advisors. Cultivate achieved the ranking with Inc because the business grew from a few hundred thousand to over $3.6 million in revenue in just 3 years.

With a goal of surpassing $10 million in revenue over the next two years, Clark and his team of now 40-plus employees have grown from their headquarters in Chicago to having advisors throughout North America. The company recently expanded and opened offices in Denver and Vancouver with plans to open more in the near future. Cultivate has partnered with more than 800 businesses that pay an average of $1,500 a month for advising services through a subscription model.


Cultivate Advisor's team social.

“We help our clients grow through our five proprietary Stages of Entrepreneurship that we believe all small business owners experience in the journey from $0 to $10 million and beyond. All of our advisors are prior business owners that know what it takes to scale. They know how to help the owners navigate the emotional rollercoaster of running a business. Every entrepreneur started their business with a goal and vision. The team and I are so fortunate in that we get to wake up every day and help these owners work towards and achieve their dreams, we just love what we do. It’s a lot of hard work, but we hire skilled people and outwork most as we continue to push ourselves to new limits each year” said Clark.

Entrepreneurial Stages

Cultivate has identified 5 key stages on the Journey from $0 to $10 million.

Clark, who lives in Chicago’s Logan Square neighborhood, said that his upbringing and his family also helped shape his entrepreneurial journey. He learned how to have a strong work ethic from his grandfather, Cliff, and his father, Ken. His grandfather owned a successful vacuum retail and repair business in Peoria, IL which showed Clark at an early age that being your own boss could be a reality.

Clark’s father, who was nicknamed “Superman” by countless folks in Decatur, Illinois, where Clark grew up, worked several jobs, including a newspaper route where a 7-year-old Clark would jump out of the car and deliver the papers around the neighborhood while rollerblading.

His father loaned Clark $2,000 to help get the College Pro franchise off the ground. After achieving success in the franchise his first year, Clark, who at the time was on a full ride scholarship for theatre at UIC came home and told his family he was ditching the scholarship and was changing his major to entrepreneurship. His father couldn’t stop smiling.

“He wanted me to go after my dreams, even if that meant I had to start paying for school myself,” Clark said.

Years later, Clark helped his dad achieve his own post-retirement entrepreneurial success by helping him start his first business, Clean Cut, that was just starting to take off when Ken Clark had a fatal heart attack on Christmas Eve 2017. Two months later is when Clark decided to take out a loan to scale Cultivate Advisors.

“My dad was my hero,” Clark said. “After he unexpectedly passed, I didn’t want to take time for granted and I committed to taking the business to a whole other level. I knew this business could scale if I took the right risks and I knew my dad would be telling me to go for it. It’s been fun to see the growth of our clients and team. The accolade from Inc only fuels my fire to achieve further business success.”

Casey & Ken Clark at Chicago Blackhawks game.
Vickie & Ken Clark representing Clean Cut.

Clark credits Cultivate Advisors for more than just business success. In March 2016, one of Clark’s early clients found out he was single and introduced him to his sister-in-law Emily. Three and a half years later, Clark and Emily are married and expecting their first child in early November.

Casey & Emily Clark's wedding day.

For more information on Cultivate Advisors, visit


Founders Story

Learn how Cultivate came to be right from the Co-Founders, Casey Clark and Dan Gramman.

Cultivate Advisors

Learn how we use a combination of advising and implementation hours to support small business owners.

The 5 Stages of The Entrepreneurial Journey

CEO Casey Clark shares vital challenges every business owner faces as they grow from 0-$10 million

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You’re a hustler, you know it. You’ve created a business that’s more than a hobby and you may be wondering, where do I go from here?

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As an experimenter you’re running to keep moving, but you’re not making the progress you want in your business due to bottlenecks, lack of systems and constantly ‘putting out fires.’

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As a visionary you’ve grown your business organically, opening up more time for yourself. But you’re struggling to grow bigger and you’re not sure how to push over the $1M mark.

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As a systemizer you’re fixated on refining and documenting everything as you’ve  learned scale requires bringing on great people, and integrating them quickly and seamlessly.

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As an influencer, you’ve built a growing business through the previous 4 stages. You’ve got the right people, systems, and product/service. But what’s next? You need someone to partner with to get to the next level.