From Paintbrush to President: Jon Winters’ Journey from Summer Painter to Flooring Industry Leader
On the latest episode of The Entrepreneur’s Journey, host Michael Pallozzi sits down with Jon Winters, President of MSC Flooring (formerly Michigan Specialty Coatings), to explore a career that evolved from painting houses during college summers to leading a $16 million-a-year company with more than 70 employees.
Humble Beginnings with a Paintbrush
Jon’s entrepreneurial spark first lit during his high school years, armed with a paintbrush, artistic talent, and a desire to earn summer cash. Working on small residential projects, often sourced from family and school connections, Jon learned early lessons in pricing, customer relationships, and the value of doing great work. Living at home and attending a small liberal arts college in Iowa, Jon admits he had little grasp of financial reality—”no overhead” and being supported by his parents. But these experiences planted seeds for what would become a lifelong business journey.
A Detour Around the Globe
Rather than leaping straight into the corporate world post-graduation, Jon chose a different path. He spent 18 transformative months traveling through Southeast Asia and Australia, soaking in diverse cultures, sleeping in remote Cambodian villages, and embracing challenges that few business schools could teach. This chapter wasn’t just adventure—it was personal growth, resilience, and a masterclass in adaptability.
Serendipity and the Start of Something New
A chance encounter with friends at his sister’s wedding led to Jon joining a fledgling business focused on decorative concrete coatings. Although the products initially wowed customers, recurring performance issues revealed that the original company was unstable—eventually facing a class action lawsuit. Rather than walking away, Jon and his partners pivoted, leaned into what worked (epoxy and polyurethane coatings), and formed what would become MSC Flooring.
Rising from the Ashes
The early years were anything but smooth. Fixing failed projects, losing money, and rebuilding trust with clients was exhausting and financially draining. But Jon and his team remained committed to their word, ensuring every customer was made whole. This integrity-driven approach, paired with a switch to more reliable suppliers, laid the foundation for MSC’s long-term success.
From Chaos to Clarity
Fast-forward 20 years, MSC Flooring now spans two offices across Michigan and employs over 70 people. Jon attributes much of this success to embracing business coaching, organizational development (including the Entrepreneurial Operating System), and never losing sight of the early financial pain that shaped his philosophy: build a business that can weather any storm.
“Don’t live above your means. Live below your means, and you’ll live a much less stressful life,” Jon advises.
Legacy Lessons for Fellow Entrepreneurs
Jon’s story is a testament to resilience, reinvention, and relational leadership. From climbing ladders with a paint bucket to leading a high-performing, culture-driven organization, his journey reminds us that success often emerges from setbacks—and that coaching, humility, and financial discipline are vital tools for building something that lasts.
To hear more inspiring stories from business owners like Jon, subscribe to The Entrepreneur’s Journey wherever you get your podcasts, or visit hfmadvisors.com.
This blog post is based on Episode 22 of The Entrepreneur’s Journey podcast hosted by Michael Pallozzi, President of HFM Investment Advisors, LLC.
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