Jack Keller built Legacy Painting on referrals and clear communication
Jack Keller is the founder of Legacy Painting, a Yorktown, Virginia, company providing residential and commercial interior and exterior painting, along with drywall repairs and deck and fence painting. The conversation traces the move from weekend jobs to full-time business and explains how referrals, careful listening and clear project updates shape the customer experience.
Referrals can bring ongoing work, but good customer communication takes more than a conversation: clarify project details, timelines and expectations, then keep clients updated. Keller also advises people starting a painting business not to let pressure to grow quickly drive decisions.
What’s the short story of how your business started, and what makes it genuinely different from the other options your customers have?
Though I spent most of my professional career in sales, the truth is that I’ve always wanted to own my own painting business. What started as DIY projects with my dad gradually grew into helping neighbours with their painting projects and eventually taking on painting jobs every other weekend. In many ways, I was already working as a painter on the side while maintaining my full-time career in sales.
Today, as a full-time entrepreneur, I can say that what makes my business genuinely different is the experience I bring from my years in sales. As a salesman, I learnt to communicate beyoun simply explaining what my business has to offer, but to instead begin by understanding my clients, their needs and the goals they intend to achieve. This means asking a lot of questions and listening carefully.
How did you win your first customers, and where does most of your new business come from today?
My very first customer came through a referral. My neighbour’s brother was moving into a new apartment and needed a painter, so my neighbour reached out. Today, referrals remain the biggest source of new businesses.
What’s one decision that changed the direction of your business, and one mistake that taught you the most?
One decision that significantly changed the direction of my business was choosing to leave my career in sales to pursue painting full-time. For years, painting had been a side hustle. I soon realized that the best way to leverage my passion, and make it a truly successful business, would have to give it my full attention. The truth is, this transition wasn’t easy given the risks involved, but I also knew i would be able to dedicate more time to growing Legacy Painting, improving the customer experience, and building the kind of business I had envisioned.
As someone who fancied himself a skilled communicator, one of the biggest lessons I had to learn as a business owner was the importance of effective communication. It was a real eye-opener to discover that having a good conversation with a client doesn’t necessarily mean you’re on the same page or that you understand each other. This taught me to be more intentional about how I communicate with customers, especially when discussing project details, timelines, and expectations.
What has changed in your industry or in what your customers expect over the last couple of years, and how have you adapted?
Today, in addition to quality delivery, customers also expect timely communication. I’ve adapted by making communication an important part of the entire customer experience, from responding promptly to initial inquiries and providing clear project estimates to keeping customers updated as projects progress.
If you were advising someone starting out in your industry today, what would you tell them to do first, and what would you tell them to ignore?
For anyone starting a painting business, my advice is not to get caught up in the pressure to grow quickly.
Thank you to Jack Keller and the team at Legacy Painting for sharing what actually worked with Leaders Perception readers.
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