937-203-0771 
Robert DiTommaso, President of the Support Services Group at Winsupply, speaks during Launch Dayton Startup Week 2025.
Some companies grow by expanding operations. Winsupply has grown by investing in entrepreneurs and empowering them to succeed.
During Launch Dayton Startup Week 2025, we sat down with Robert DiTommaso, President of the Support Services Group at Winsupply, to discuss how one of Dayton’s most successful companies has built its success by investing in entrepreneurs.
The conversation highlighted a powerful idea: when entrepreneurs have the tools, support, and autonomy to succeed, businesses and communities grow stronger. Winsupply’s entrepreneur-first business model offers valuable lessons for founders, business leaders, and organizations looking to empower people to grow.
Lesson 1: Invest in Entrepreneurs, Not Just Businesses
Entrepreneurs are at the heart of Winsupply’s mission.
Rather than operating every location from a centralized corporate office, Winsupply empowers local entrepreneurs to own and operate more than 680 independent companies across the country. Those business owners make decisions based on the unique needs of their local markets while benefiting from enterprise-level resources, strategic guidance, and operational support.
The result is a business model that combines the agility of local ownership with the resources and scale of a national organization. As local businesses grow, Winsupply grows alongside them, creating a cycle where success is continually reinvested throughout the network.
For entrepreneurs, it’s a reminder that building a successful company isn’t just about products or services. It’s about creating an environment where people have the tools and trust to succeed.
Lesson 2: Technology Should Empower People, Not Replace Them
Technology continues to transform nearly every industry, including the highly competitive markets where Winsupply operates.
Rather than viewing technology as a replacement for personal relationships, Winsupply uses it to make entrepreneurs more effective. The company invests in technology infrastructure that delivers real-time information and decision-support tools, giving local business owners access to the data they need to make informed decisions quickly.
From inventory and pricing to operational and customer insights, these tools help entrepreneurs respond faster, serve customers better, and compete more effectively in their local markets.
The lesson for founders is simple: the best technology doesn’t replace human expertise—it strengthens it.
Lesson 3: Strong Entrepreneur Communities Create Stronger Economies
One of the biggest takeaways from the conversation was that supporting entrepreneurs creates ripple effects far beyond individual businesses.
Winsupply’s commitment to helping local business owners succeed aligns closely with the missions of Launch Dayton Startup Week and Entrepreneurs’ Center. When entrepreneurs have access to mentors, technology, education, and strong support networks, they create jobs, strengthen local economies, and inspire future generations of founders.
Organizations that invest in entrepreneurs don’t just strengthen individual businesses. They create the conditions for innovation, job creation, and long-term economic growth.
Building a Stronger Entrepreneurial Ecosystem
By combining local ownership with enterprise support, the company has created a model that empowers entrepreneurs to make decisions, adapt to their markets, and build successful businesses while benefiting from the resources of a larger organization.
Winsupply’s story is a reminder that long-term growth isn’t just about expanding a business. It’s about investing in the people who build it.
Keep Learning from Dayton’s Entrepreneurial Community
Inspired by Winsupply’s entrepreneur-first approach?
Conversations like this are one of the reasons Launch Dayton Startup Week brings together hundreds of entrepreneurs each year. Join us September 15–17 to hear from founders, business leaders, and innovators sharing the ideas shaping the future of entrepreneurship in Dayton.
Can’t wait until September? Join us for our final LaunchPad event of the year on July 30 and connect with the startup community before Startup Week kicks off.
