• cole haan

Making the Leap

Meet three entrepreneurs who know firsthand that launching a pioneering business takes vision, passion, and the willingness to risk everything.

Making the Leap

Behind every great company is an entrepreneur who took a chance, made a leap, and risked it all to bring their idea to life. Some such leaps come in the form of ideas so groundbreaking that they have the potential to reshape industries. Others are more personal, taken by people willing to trade a successful career for a life of uncertainty. Risky? Of course. But driven entrepreneurs are more than willing to take a chance on a mission that could well change their lives–and the world.


We spoke to three such entrepreneurs about what it took to start their companies–from the moment their big idea crystallized to what it felt like when they stepped up to the edge and took the plunge.

Rachael Chong, Founder and CEO, Catchafire

Inspiration struck former banker Rachael Chong on a construction site. Chong, along with her coworkers, was volunteering to build a home when she looked around and realized that asking bankers to do carpentry was not an efficient use of their time or talent. Chong saw people with valuable accounting, finance, and marketing skills and thought, If they could volunteer those skills instead, they could make a huge difference for the nonprofits that need them. This insight led her to launch the volunteer-matching platform she calls Catchafire.

While Chong had spent time in the nonprofit world, she knew that building a tech-based company could be a risky move given her inexperience in that area. So she began building the framework of the Catchafire platform manually, pairing nonprofits she had a relationship with to her friends from the professional world, and then asking both sides to articulate their experience. From there, she refined the system in analog before taking what she learned to a team of engineers to translate her vision into a workable technology platform. Reflecting on her mindset in those early days, Chong says, “I think you just make the leap because you’re a little bit insane, honestly. It’s about focusing on the potential as opposed to all of the potential risks.”

Watch: Bringing “Skills-matching” to Philanthropy


Seven years later, Catchafire has matched thousands of volunteers with projects that utilize their skills, saving more than $40 million for the nonprofit organizations it works with. These days, the goal for Chong and Catchafire isn’t so much to facilitate individual projects, but to completely disrupt the way people think about and engage with volunteering, making it more accessible and more fulfilling for everyone involved.

Andrew Deitchman, Co-founder and CEO, The New Stand

As the former CEO and cofounder of the advertising agency Mother New York, Andrew Deitchman had the sort of glamorous career many people fantasize about. But after 20 years of creating ads and content for global brands like Target, Virgin, and Coca-Cola, Deitchman decided to make a rather unexpected career change–a move into the newsstand business.

Deitchman and his partners are reinventing the decidedly fusty newsstand concept with the New Stand, a chain of small, sleek shops in subway stations, office buildings, and, soon, airports. They’re one part convenience store–selling essentials like snacks and phone chargers alongside curated, high-end electronics and gift items–and one part media platform, based around an app that delivers a daily dose of news, music, and product discounts. An in-house line of designer sunglasses and other New Stand-branded products is in the works as well.

Watch: Reinventing the Newsstand


Rather than creating content for brands at the center of the historic shifts happening in the business world, Deitchman set out to launch a company that would allow him to be a driver for change himself. And while he had known for some time that he wanted to get out of advertising, that didn’t make leaving the business he had lived and breathed for the last two decades any easier. “Some people take a leap and feel like they are safe because there’s some netting underneath them, but for me it really felt like a big leap. I didn’t know how big or small that net was.”

Now, with the first three locations in New York City up and running, and expansion plans under way, Deitchman has more perspective on the risk and reward that goes into striking out on your own. “You have to trust yourself.” he says. “You might fall, and that’s okay, because you decided to jump in that particular direction. It’s better to fall on your own terms than trying to follow someone else’s map.”

Elizabeth Reede, Co-founder and CEO, WoofbertVR

A look at Elizabeth Reede’s winding career path illustrates that it’s never too late to redefine your career, or, for that matter, your industry. Several years after earning an MBA and establishing herself in banking, Reede felt a tug toward her first love–art. She returned to school for an advanced degree in art history and launched a second career that included a highly coveted position as an assistant curator at New York’s prestigious Museum of Modern Art.

Surrounded by the work of renowned painters and sculptors, Reede’s thoughts turned again and again to access: After all, the vast majority of people do not have the resources to visit the world’s great museums. “The mission of any great museum,” says Reede, “is to share its works with as many people as possible. Access shouldn’t be an issue of socioeconomics.”


Watch: Changing How We See Art

The moment she was introduced to virtual reality, her path became clear: She would use the nascent technology to make the arts more available, transporting people from wherever they lived to inside cultural institutions all over the world. She launched WoofbertVR, along with cofounder Robert Hamwee.

What sets WoofbertVR apart from other tech platforms seeking to democratize art is that Reede works to render each virtual exhibit just as a museum curator intends it to be seen, from the color of the walls to the space between works to the position of the lights. “All the details of an installation and of a space are presented as accurately as possible,” she says. “We take into account all the things that curators think about.” WoofbertVR then enhances the experience by adding historical, cultural, and artistic context to each exhibit. Combining technology with a deep understanding of art history and curatorial craft, Reede creates an experience that is greater than the sum of its parts.

This article was created and commissioned by Cole Haan, and the views expressed are their own.


About the author

FastCo Works is Fast Company's branded content studio. Advertisers commission us to consult on projects, as well as to create content and video on their behalf.