Now 34, James Hirschfeld started Paperless Post with his elder sister, Alexa, because he had a problem planning his 21st-birthday party—a Bostonian, winter-defying, beach-party-themed bash. James realized it was too late to send invitations by mail, while e-mail felt too dry and informal. “I called my sister, and I was like, There needs to be a way of creating invitations that are as efficient as an e-mail,” but which would still have “the customization and beauty of printed ones.”

Since launching in 2009, Paperless Post has circulated millions of invitations and now employs 130 people. It’s the epitome of a disrupting tech start-up, but Hirschfeld, the C.E.O., describes it more as an art project. “I’ve never been that into computers,” he says from his office in Manhattan’s financial district. “Tech is more of a tool for me to share my love for beauty and design.” It lead him to partner with designers such as Oscar de la Renta, Kelly Wearstler, and John Derian.

They go way back: siblings and Paperless Post co-founders Alexa Hirschfeld and James Hirschfeld.

It helped that, in 2007, Harvard, where he studied comparative literature and English, was still very much in its Zuckerberg era. “Everybody was really excited about start-ups,” he says. “Zuckerberg had left this feeling on campus that anybody who had an idea could create a business.”

“Tech is more of a tool for me to share my love for beauty and design.”

James and Alexa developed the idea for Paperless Post for two years, and when James was a senior in college they started meeting with potential investors, many of whom quickly dismissed the concept as far-fetched. “No one will ever pay for this,” they were told. “Nobody cares about design on the Internet.” But the siblings weren’t deterred. “To really throw yourself into a start-up, you have to believe that you’re going to be successful,” James says. “Many warning signs will come up, and so many people say no—my advice is to ignore them.”

After they launched on a small scale at Harvard, their popularity grew quickly: students began using Paperless Post for invitations to student clubs, and then Harvard’s president’s office started using the service as well. By the summer of 2009, Paperless Post invitations had even circulated to Obama in the White House.

James and Alexa handle separate sides of the business.

After James graduated, he and Alexa started building the company out of their parents’ New York City town house. James, who has no artistic training and is color-blind, was designing the original invitations while Alexa found and managed employees and the business side. “By 2012, we dreamt we would have 4 designers; we had 20.”

“Many warning signs will come up, and so many people say no—my advice is to ignore them.”

Today, users can pick from an endless series of pre-designed cards for every occasion or upload their own designs. Prices are low, only a few dollars per batch of invitations, and, most importantly, the process is effortless.

Paperless Post’s Black Lives Matter cards come at no charge.

Lockdown or not, people still want to meet up; the difference now is that, much like the invitations, events themselves are happening remotely. “The coronavirus initially drove down business,” James says, but things have since picked up. Virtual events now make up 50 percent of the company’s revenue. Paperless Post also launched a series of Black Lives Matter cards, available to users throughout the holidays for free. These include “a line of cards for Breonna Taylor that users sent to government officials in Kentucky on her birthday,” says James.

Future projects are shifting in the direction of mobile features and more casual text-message invites. “We’re always trying to keep up with the way people communicate today.”

Elena Clavarino is an Associate Editor for AIR MAIL