We recently had the chance to connect with Cindy Pillow and have shared our conversation below.
Hi Cindy, thank you so much for joining us today. We’re thrilled to learn more about your journey, values and what you are currently working on. Let’s start with an ice breaker: What do you think is misunderstood about your business?
I think the most misunderstood thing about our business is how unconventional it is. We’re not a traditional brick-and-mortar store — we’re a pop-up market that supports multiple small businesses, both those who sell with us and the broader community. Out-of-town vendors stay in local hotels, eat at restaurants, and shop at nearby stores, so our markets really help boost the local economy. Because of the unconventional setup, some people don’t always see us as a ‘real’ business in the traditional sense, but running this takes just as much planning, dedication, and hard work, and we love seeing the positive impact we create for the entire community.
Can you briefly introduce yourself and share what makes you or your brand unique?
We’re Mike and Cindy, owners and operators of Montgomery County Market Days. We also run our own small business that sells at the market, and we wanted to create a safe, community-minded space where other vendors — like us — can sell their products, connect with customers, and feel supported. Our goal is to make the market a welcoming environment that helps small businesses thrive while bringing people together.
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What breaks the bonds between people—and what restores them?
I think bonds are most often broken by mistrust. Once trust is lost, it’s hard to ever fully restore that connection. I also believe that people come into our lives for different reasons — some for just a season, and some for a lifetime. Choosing to rebuild or reaffirm a bond is a deeply personal decision, and it’s something each person has to decide for themselves.
Was there ever a time you almost gave up?
Growing a market from scratch always comes with its challenges, especially when it comes to building awareness and foot traffic. Events like the Pickle Festival on October 25th are a great example of how we bring the community together and give local small businesses a platform to shine. Having such an incredible group of vendors who believe in the vision and continue to support what we’re doing makes all the hard work worthwhile and keeps the market moving forward.
So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What are the biggest lies your industry tells itself?
One of the biggest misconceptions in our industry is that some promoters believe they have the right to exclusivity over the small businesses we’re here to support, sometimes even requiring no-compete agreements. But we’re in America — the land of free enterprise — and while we own our markets, we don’t own the small businesses that come to sell with us. True support means helping them grow, not restricting their opportunities. Keeping them from other markets stifles their business and limits their potential. I’m not here to compete with another promoter — the only person I’m in competition with is myself, pushing to be better and create the best opportunities for our vendors. Supporting small businesses should always be about growth, opportunity, and community, not control.
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What is the story you hope people tell about you when you’re gone?
I hope people remember Mike and me for honesty, heart, and helping small businesses thrive — and that our monthly market and pop-up Pickle Festival were their favorite!
Contact Info:
- Website: https://MontgomeryCountymarketdays.com
- Instagram: https://www.instagram.com/montgomery_county_market_days?igsh=MXg0dzBzb3dsdWpnaA==
- Facebook: https://www.facebook.com/share/1Jt7hDxKzy/?mibextid=wwXIfr
Image Credits
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