Founder Talk: The Art of Making the Perfect Marketplace Match

Marketplace startups are always playing cupid.

Whether they are looking to connect freelancers to businesses or homeowners and contractors, marketplaces are all about curating the perfect connection between buyers and sellers.

So in honor of Valentine’s Day, we connected with marketplace startup founders to learn more about how they are building and what advice they have for others looking to build something similar.

Measuring Customer Love

What makes building marketplaces a uniquely difficult process is the fact that you have to build up two complete and distinct user bases. It is a "chicken and egg" problem, where you need buyers to attract sellers and sellers to attract buyers. Beyond simply attracting two groups, you have to simultaneously cultivate value for both sides, ensuring each finds the platform beneficial enough to join and stay.

So how do founders think about building up customer love on both sides of their marketplaces?

For Cesar Flores, founder of Atlanta-based Hearthmates, customer love isn’t just about engagement, it’s about creating efficiencies for users.

“Our North Star metrics for customer value are Ease of Use and Time to Successful Outcome,” Flores told Hypepotamus. In the case of Hearthmates, which connects potential roommates via a matchmaking-style app, that means “measuring how quickly users get to their first match and the ratio of matches to meaningful housing conversations.”

For a little Valentine’s Day flair, founder Jonathan Dickerson describes his startup as “Tinder for Lenders.”

Gumption, a marketplace startup building in Chattanooga, helps commercial real estate (CRE) owners source “the best financing terms for their properties in record time,” Dickerson told Hypepotamus.

For Dickerson, a sign of customer love for the product is repeat transactions from both borrowers and lenders.

“Gumption is delivering several financing options to borrowers in just a few business days. This saves them time and money. Gumption doesn’t get paid unless we deliver. Why wouldn’t they use us for all of their deals?” Dickerson added.

Similarly over at ServeScape, the Atlanta-based landscaping marketplace, said customer love comes from building long-term trust.

"Customer love at ServeScape is all about trust and repeat engagement. We measure it through return purchases, referrals, review ratings, and overall customer lifetime value. Our best customers don’t just buy once—they come back for more plants, design services, and installations, building long-term relationships with us. [Yesterday], we had a customer reach their 50th order. We also track Net Promoter Score (NPS), customer reviews, and interactions with our loyalty programs. If someone refers ServeScape to a friend or pro contractor, we know we’re doing something right," said founder and CEO Mario Cambardella.

Marketplace Realities

We asked our founders what advice they’d share with other entrepreneurs interested in bringing a two-sided marketplace to life.

When asked what advice he’d give to others looking to build a marketplace startup, Dickerson doesn’t hesitate: “Pivot. Don’t do a marketplace. It’s way harder than it sounds.”

For Flores, it is all about finding ways to meet the customer’s needs.

“[We] have a built-in support chat so our users can directly reach out to us with any comments, questions, and concerns. Free-form feedback is critical at our stage, so we're constantly reminding users that help is always just a chat bubble away. Today's complaint is tomorrow's killer-app feature,” he told Hypepotamus.

Cambardella said that many of ServeScape's challenges to date have come from the unique products they have on the site.

"Unlike other marketplaces where brand differentiation is clearer, plants often seem interchangeable to customers, making it hard to compete beyond just price. Logistics for live goods has also been a learning curve—getting plants delivered in top condition isn’t as simple as shipping a book or a gadget. No cardboard boxes for us. Just today we delivered a dozen 20 foot tall trees," he told Hypepotamus. "What surprised me most is how fragmented the landscape industry is. There’s no single dominant player, and much of the business still happens offline. That means we’ve had to build the marketplace while also educating customers on the convenience and value of buying plants online."

Building a marketplace isn’t for the faint of heart. Success requires more than just connecting buyers and sellers. It’s about earning trust, delivering value, and navigating the unique challenges of a two-sided platform. Be ready to embrace the challenge...because as every good matchmaker knows, the best connections take work.