Doug Winston on Building a Successful Contracting Business, Learning from Failure, and Mastering Cash Flow

What does it take to build a successful contracting business from the ground up? For Doug Winston, it started with a clear goal at just 17 years old, a willingness to take risks, and the determination to learn from every challenge.

In this episode of the NY Professional Spotlight Podcast, host Roman Kirzhner welcomes Doug Winston, an electrical and utility contractor based in Westchester County, New York. Doug shares his journey from discovering his passion for electrical work to building multiple businesses and managing large utility projects throughout the Northeast.

Finding His Path at an Early Age

Doug's career began with a conversation with his high school guidance counselor. After realizing he enjoyed working with his hands and solving electrical problems, he explored the possibility of becoming an electrician.

A visit to his cousin, who owned an electrical contracting business, helped him see the opportunities available in the trade.

By the time he left that meeting, Doug had set two goals: earn his electrical contracting license by age 25 and build a house by age 30.

He went on to accomplish both.

Turning Expensive Mistakes into Valuable Lessons

Success didn't come without setbacks.

Doug recalls taking on a multimillion-dollar substation project that resulted in a loss of approximately $500,000.

Rather than abandoning that type of work, he treated the loss as an investment in experience. When another similar opportunity came along, his team used what they had learned to complete the project profitably.

His experience shows how setbacks can become opportunities to improve business decisions and operations.

Why Cash Flow Matters More Than Growth

One of Doug's biggest lessons involves managing cash flow.

While many entrepreneurs focus on growing their companies and winning larger contracts, Doug explains that taking on additional work without enough cash or staff can create serious problems.

He emphasizes the importance of understanding payroll requirements, available resources, and financing before committing to new projects.

His advice includes establishing strong banking relationships and securing lines of credit before they become necessary.