Young Entrepreneurs Spotlight: Seamless and Seniors Connect

I don’t know about you, but when I was in high school, I wasn’t thinking about how to start a company. (About how to start a relationship, or get on the tennis team, maybe… but those are other stories of learning to “fail fast, often and cheap.”)

For at least four of this year’s accelerator participants, however, starting a company in high school isn’t a question; it’s a reality—and one that they’re running with.

This week, I spoke with four of our earliest entrepreneurs—Clara Duffy and Leela Ghaemmaghami of Seniors Connect, and Seamless’s own Tyler Cosgrove and Rheisen Dennis—to understand how they got started, as well as the unique motivators and challenges of starting a business in high school.

While the missions of Seniors Connect and Seamless are quite different, their founders’ stories shared some elements worth noting. Both partnerships came out of school environments that at least in some way encouraged students with entrepreneurial interests to do something about them. Multiple founders told stories about even earlier moneymaking schemes they'd had as children. And interestingly enough, all had computer science backgrounds.

For Clara and Leela, rising seniors at St. Anne’s-Belfield, it was an entrepreneurship intensive course that led them to realize they had the means and the drive to start Seniors Connect—and this with virtually no expenses. (The largest expense they pointed to was, in fact, printing business cards.)

Starting simply with who they were, what they knew about technology and a “pain point” that their own grandparents didn’t know how to use their gadgets, they came up with an idea that won the Crowdfunded Pitch Night competition at the 2016 Tom Tom Founders Festival. Now the two are working to connect high schoolers with spare time and tech know-how to the literally thousands of seniors in the area who would like to learn what they’re offering.

Rheisen and Tyler, who graduated from Albemarle High just this year, first met as programmers in their school’s engineering cohort and have since worked together on various feats of programming brilliance. It wasn’t until after they got involved with their school’s entrepreneurship community, though, that they realized they had a potential business and Seamless was born.

The idea for the Seam app, which will help online shoppers find clothing that fits, came about after Rheisen had a somewhat negative shopping experience and wondered whether they could create a more social shopping platform. The idea evolved several times (as things often do in the entrepreneurial world) before it got to where it is now, and there’s still the challenge of writing code that does what it’s supposed to do.

Emphasizing that they haven’t “made it” just yet, the two remain stalwart in their efforts to develop the app, while also learning to develop the business side of the business, and juggle future plans.

The high schoolers and now-recent grads face a unique challenge in that just as their companies are getting started, so are their lives. Rheisen is headed off to college next year, while Tyler will start a new job; and as Leela and Clara enter their senior year of high school, they’ll begin the search not only for colleges but also for employees to whom they can pass off the torch of Seniors Connect in Charlottesville.

There are, however, also some unique perks to starting a business in high school—ones that led one of our young founders to say, “Now’s actually pretty good as times go to start a business.” They have families that support them with housing and food, and business risk tends to translate less into their personal lives.

Despite the overwhelming multiplicity of options in front of them, the four agreed that they ultimately chose to be at the i.Lab because of the mentorship and community it affords them as their ideas keep brewing. “We wanted to learn something,” said Leela of their decision to be here.

And learning something they are, indeed--everything from accounting and "real life" finances, to how to do effective customer interviews, to the need for self-doubt next to self-drive in the creative process. And all of this next to others who are doing and learning the same.