Networking, Marketing, Sales, Business Coach, Painting Contractor

EP44 Jim Kaloutas: What It’s Like Running a $21M Painting Business


Jim Kaloutas, owner of Kaloutas Painting in New England. Jim immigrated to the USA from Greece with his family at a very young age. His father got a job with Jim’s entrepreneurial uncle as a painter, which exposed Jim to the painting industry early in his life.

Jim went to college after high school only to drop out after one month of class. He felt that he wasn’t ready for college and didn’t have the discipline necessary, so he returned to what he knew: painting. He started the business with his father over thirty years ago, and while they did have sporadic arguments, it was a great partnership. Jim learned a lot from his father, but the most crucial thing passed down was his father’s work ethic. Jim says that people sometimes compliment him on his own work ethic, but he argues that his does not compare to that of his father’s.

From startup in 1987, in took ten years to go from $0 to $1,000,000 in revenue, and then ten more years to increase revenue to $10,000,000. This year, Jim expects the business to generate over $20,000,000 in revenue. Jim shares what each of these stages of growth looked like in his company, as well as what he has learned along the way. One of the most important factors that Jim credits his success to is his employees and creating a great company culture that reflects his own values.



  • The importance of a strong work ethic as an entrepreneur.
  • Jim’s process for investing in himself and his employees.
  • The hiring process Jim uses to hire people with values that align with his.
  • How to keep your business efficient.
  • The method Jim uses to help his employees realize their goals.




“The wake-up call was when we would do a job and we would actually make less than our employees. We didn’t know any better. We didn’t price it right.”

“I always believe in investing in myself. It’s where I should spend most of my money… in the past seven to ten years I’ve realized ‘it’s not just me running this company; I should invest in my employees, too.’”

“Being able to understand my values and start to define them in the early years was very helpful for me to realize [how to grow the business]. Then, it became easier and easier because I attracted people who were similar to me.”

“’Could I ever become a level five leader?’ Have it not be about ‘me’; have it be about the people and the organization. That’s what drives me now. I’ve been fortunate to be surrounded by the people that I have on my team and watching them grow gives me more fulfillment than the money.”

“Sometimes when I’m talking to the people that I work in the company, I can almost see their potential a little bit better than they can. I think sometimes they’re drawn to me. I say ‘listen, you have it. You need to start believing in yourself as much as I do.”



[01:42] How did Jim get involved in painting?

[02:32] When Jim first started, how did he generate leads?

[04:11] How did Jim and his father continue to grow their business?

[07:16] What are Jim’s process and habits for investing in himself?

[10:01] How quickly did Jim’s business grow from startup and what did the different stages of growth look like?

[14:24] How has culture played a role in Jim’s success?

[16:59] What does Jim’s company do to make sure they hire people with similar values?

[18:21] What is the company’s structure and how does it remain efficient?

[21:46] What are some difficulties in operating a company of this size?

[23:45] What books have inspired Jim?

[26:34] When Jim gets his employees to write down their goals, what growth does he see?

[29:36] What final comments would Jim like to make?



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About the Author

As a newly single father of two from MI, he struggled to start over as a paint contractor in FL, going door to door. His situation was so bad, even the IRS had mercy on him.

 Feeling completely hopeless, he remembered the story of King Solomon praying for wisdom. Could it be so easy? 

He felt he had absolutely nothing to lose. So, as a bankrupt, divorced, high school dropout, single father of 2 young kids, now living 1250 miles away from all friends and family, started to pray for wisdom.
 And while he continues to wait for the wisdom to arrive, what did come was an insatiable desire to learn and read books… 
Thanks to God for giving him the burning passion to read books, and attend seminars, (oh and winning the wife lottery) he not only cracks the success code and overcomes the struggle, but also streamlines his painting business in less than 3 years, published a how to book, then sold the company. Now he leads a business coaching company for painting contractors so he can help other businesses, like yours, to do the same. Hear more... Or