Networking, Marketing, Sales, Business Coach, Painting Contractor

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

SUMMARY:

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.

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WHAT YOU’LL LEARN:

  • 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.

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LISTEN HERE:

QUOTES:

“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.”

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HIGHLIGHTS:

[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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LINKS & RESOURCES MENTIONED IN THIS EPISODE:

Join DYB

Good to Great: Why Some Companies Make the Leap…And Others Don’t

Generations, Inc.: From Boomers to Linksters–Managing the Friction Between Generations at Work

Outliers: The Story of Success

https://www.kaloutas.com/

jaykaloutas@kaloutas.com

ADDITIONAL FREE RESOURCES:

Schedule Your Free Strategy Call With Steve

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About the Author

As many of you know, my journey has been one of grit, grace, and transformation. At 19, I was a high school dropout, single father, and struggling paint contractor in Michigan. I later moved to Florida, where I faced both personal and professional hardships. With nothing left to lose, I turned to prayer—and was blessed with a relentless hunger to learn. I devoured books, attended seminars, and discovered better ways to streamline and grow my business—even through the Great Recession (and yes, I did hit the wife lottery along the way!). In 2014, I published How To Double Your Business and later sold the painting business, launching a new chapter: coaching others to grow their businesses. For the past 10 years, I’ve dedicated myself to helping business owners scale through the DYB System, while also drawing from frameworks like EOS, Scaling Up, and The Four Disciplines of Execution. Yet something was still missing—something more adaptive, integrated, and complete. Then I found Pinnacle. After months of research and interviews with other Guides, I joined Pinnacle. Their tools and strategies have exceeded every expectation. Now, as a Pinnacle Business Guide, I help leadership teams implement a custom-tailored operating system that draws from the best in the industry—but flexes with your unique business. It’s a dynamic, proven approach to achieve clarity, momentum, and lasting growth. I’m no longer taking on any more 1:1 coaching clients… Instead, I now specialize in working with visionary business owners who are ready to get their leadership teams aligned—around a clear vision, a focused strategy, and an actionable execution plan. With the tools and process I now have as a Pinnacle Business Guide, I help turn alignment into momentum, and momentum into results. If your business is growing—but your leadership team isn’t fully rowing in the same direction—let’s talk.