The Risk/Reward of Saying Yes: What We Learned as Pop-Up Vendors

Every time we sign up for an event, we're making a bet.

We're betting that the venue is the right fit, that the audience is our audience, and that the energy we put in, the packing, the driving, the setup, the days on our feet, will come back to us in some meaningful way. Sometimes that bet pays off big. Sometimes it teaches you something instead.

This past weekend was a teaching weekend.

The Inherent Risks of Pop-Up Vending

Here's something we don't talk about enough: there is always risk in saying yes to an event. Always. And as we grow, one of our most important jobs is learning to evaluate that risk before we commit. Not after we're already in the mud.

This particular festival was in its first year. We knew that going in. First-year events are a gamble by definition because the organizers are figuring it out in real time, and so is everyone else. Sometimes that energy is electric. Sometimes the pieces just don't come together.

For this one, a few things compounded at once. The sunflowers the event was named for bloomed two weeks early and were gone by the time we arrived. Heavy rain in the days leading up to our weekend left the grounds soft and muddy, not ideal for an outdoor market, and particularly stressful for a bookseller watching inventory sit close to the ground. And the venue charged visitors a $19 entrance fee, something we didn't know at the time of booking. For a family of four, that's $76 before they've bought a single thing. That affects foot traffic. That affects sales.

We covered our vendor fees. We had a solid sales weekend. But we also came home with a clearer picture of what to look for next time. 

What We're Taking Forward

The lesson isn't that first-year festivals are bad or that outdoor events are too risky. The lesson is that we need to ask better questions before we say yes.

Going forward, we're evaluating events on:

• Admission cost to visitors. Is the barrier to entry reasonable for our audience?
• Event history and track record. Has this run before? What do other vendors say?
• Ground and weather contingencies. What happens if it rains? Is there infrastructure to handle it.

Risk is part of this business. We accept that. But smart risk means doing the homework first and not just saying yes because it's ten minutes from the house.

What Made It Worth Showing Up

Even on a tough weekend, there were real highlights.

The vendors around us were generous, warm, and good company, the kind of camaraderie that forms when everyone's navigating the same challenges together. We brought the Elders Mailbox, our invitation for visitors to write a short letter to a local elder. Letters came in. People stopped, sat down, and wrote. That part worked exactly as we hoped.

And we donated 10% of our weekend sales to the Imagination Library in honor of Dolly Parton. Books still found their people. That always matters.

What's Next

We're already looking ahead to events we know and love like the Hopewell Harvest Fair on September 19th and Books, Blooms, and Magic at Calgo Gardens in October. Established. Beloved. We know these are our crowds.

Every event teaches us something. This one taught us to slow down, ask more questions, and make sure the risk is worth the reward before we load up the cars.

See you out there. 📚

— Kimberly & Todd
Main Street Chapters