What PromptWorks CEO Greg Sterndale learned from running a pumpkin stand

Every entrepreneur has to start somewhere. In Lemonade Stand, we’ll profile a local entrepreneur’s first venture or first job. Tell us about yours.

Manning a pumpkin stand by the side of the road gave a 10-year-old Greg Sterndale, now CEO of PromptWorks, his first lesson in ROI.

“Those first experiences in entrepreneurship exposed me to a whole new set of problems to solve and basic business concepts: financial inputs and outputs, supply and demand, risk and return on investment,” said Sterndale. “As a kid, I certainly didn’t use those terms, but that’s what I was pricing pumpkins or learning how to negotiate. You’d be surprised how many adults would haggle over a $2 pumpkin.”

Sterndale on flex time, 1991. (Courtesy photo)

The positive reinforcement he got from running his tiny business — which was posted up beside his driveway and eventually expanded its offering to drinks and snacks — fed Sterndale’s inner entrepreneur and led him to pursue other ventures in high school and college like a DJing business. But it all started with that roadside stand and the Pepsi Cool cans that Sterndale resold at a premium.

BTW, if we’re going to get 90s-tastic, let’s go all the way: below is the Pepsi Cool can commercial feat. Young MC.

In 2013, Sterndale joined other two cofounders and started PromptWorks, the Center City-based dev shop that recently nabbed Code for Philly’s Dawn McDougall as operations manager. There, he’s had a chance to use his pumpkin-peddling skills to good use.

“We solve business problems with software for clients, but I also get to solve for the business challenges of PromptWorks itself,” said Sterndale. “If I’m lucky, I’ll be able to continue solving problems with our team of talented, passionate problem-solvers. Growing our business continues to be the best, most fulfilling learning experience as an entrepreneur.”