“The Journey Was the Exciting Part”

Robert Reffkin ’00, BUS’03 started his first business when he was just 15 — a DJ company funded with his bar mitzvah and babysitting savings. This was in 1994, long before the era of music streaming and easily shuffled playlists. Reffkin invested in high-tech equipment that mixed CDs and guaranteed he’d play any 50 songs clients requested — then frantically stocked up on Now That’s What I Call Music! mixes and compilations.

By the time he graduated from high school, Reffkin’s Rude Boy Productions had earned him more than $100,000. The experience was largely guided by his teenage involvement with the Network for Teaching Entrepreneurship. “NFTE taught me that if you set a dream, you can realize it,” Reffkin says. “And if someone were to tell me no — which my mom did initially — it’s more a reflection of their fear than my ability.”

Jörg Meyer

Twenty-three years later, that lesson has paid off several times over. Reffkin has navigated the world of finance, worked for the White House and launched a nonprofit that went national. Returning to for-profit entrepreneurship in 2012, he co-founded and became CEO of Compass, a real estate company that’s revolutionizing the industry by developing software that both speeds up and simplifies the home-purchasing process.

With the mindset of a local, friendly shop, Compass quickly became competition for mom-and-pop offices and real estate heavy-hitters alike; in 2015 it was named Mid-Sized Business of the Year by the Manhattan Chamber of Commerce. Reffkin has been named to both Crain’s and Fortune’s “40 Under 40” lists, included in Business Insider’s most “exciting startups in New York City” and was recently honored with the Business School’s Distinguished Early Achievement Award. In less than five years, Compass has grown from a single New York City office into a billion-dollar enterprise with 30-plus offices nationwide.

But for Reffkin, the definition of success is not a financial bottom line but a rewarding work environment and a mission to transform lives. In his mind, people are motivated by meaning: “I believe Compass will help more people realize their dreams than any other company on Earth,” he says.

Reffkin doesn’t think that’s idealistic; you only have to talk with him for a few minutes to recognize his sincerity. His big dreaming, along with his drive and belief in the power of community, are the hallmarks of his personality. And they have been with him since childhood.

Reffkin grew up in Berkeley, Calif., as an only child. His mother, Ruth, emigrated from Israel with her family when she was 7, but became estranged from her parents in adulthood. Reffkin’s father was absent from his life, too, having passed away when Reffkin was 11. “I didn’t have a dad, grandparents or anyone other than my mom. But I had everything,” Reffkin says. “Although I had little, all was positivity. My mom, collectively or reactively, only accepted that around her.”

Ruth worked hard to seek out a better future for herself and her son. When Robert was an infant, she started a daycare program in their home, attending to 25 children on the first floor and in the backyard. At night, she put Robert to sleep by telling him to imagine all the wonderful things he could be and the impact he could have on the world.

Reffkin was a bright and ambitious student, and by his early adolescence, Ruth had closed the daycare center and would soon start over as a real estate agent. “Seeing her choose her own life, again and again, bouncing back after failure, made me believe that the journey was the exciting part,” he says of the drive she instilled in him. But there was only so much time in the day she could devote to “do everything.” They needed guidance, and more opportunities not yet financially available to them.

Before he started high school, Reffkin and his mother found A Better Chance, a nonprofit that connects talented students of color from underserved communities with top boarding, private day and public schools. Mother and son filled out a common application that ABC then distributed to a selection of schools, sidestepping the repetition that often dissuades potential candidates who cannot afford a pile-up of costly fees. Reffkin matched with San Francisco University H.S., and eagerly enrolled.

He filled the two-hour commute dreaming of what his future held — a practice he admits calms him in adulthood, too. The student body lacked diversity to such a point that Reffkin was the only black student in every class, which instilled in him a profound understanding of how certain environments can be horribly isolating. “Being alone is a very hard thing when you want to feel connected to something more,” he says.

ABC required regular meetings with fellow students in the program, and there Reffkin found friends who felt similarly and were energized to seek opportunity and adventure. In the summers, programs like Summer Search and Outward Bound took him further and further from home, expanding his view of the world and idea of community involvement. “I realized there were more organizations that wanted to help me than there was time in the day; they had staff and board members who wanted to see me be successful,” Reffkin says of the surrogate siblings and family members who guided him during this time. “I quickly started to believe that opportunity is everywhere. I felt exhilarated. I felt excited.”

At 14, Reffkin began to hone his business acumen through NFTE, which teaches skills vital in entrepreneurial and leadership positions to those in high-need communities. With NFTE’s guidance, he laid out his plan to build Rude Boy Productions — a name chosen in a nod to Bob Marley’s first band. “There’s something about Bob Marley that resonated with me,” he says. “He was mixed — half white and half black, from Jamaica. That’s why he grew dreadlocks and loved the idea of Rastafarianism and started playing the music he played. In a way, he was searching for his place in the world. I’ve been on a search my entire life.”

Although NFTE and the other organizations he joined — seven total — introduced Reffkin to a diverse group of similarly ambitious teenagers, he never felt he found his community. “That’s why I came to New York, the city of diversity,” he says of crossing the country to study economics-philosophy and history. “If there was any place that would accept me, it’s this city.”

At the College, Reffkin met students from around the world. Working alongside them, he learned that “the probability of success is enhanced when you collaborate with people who have different perspectives and different ideas. I became addicted to diversity. That’s what led me to pursue many kinds of careers.”

“No matter how good you are — no matter how good — your mind is telling you to quit ... You’re working against that part of your mind to say: ‘I know you can do it, just keep going.’”

After graduation, Reffkin was an analyst at McKinsey & Co. for two years, then returned to Columbia for an M.B.A. He worked for two years in finance at Lazard, one as a White House Fellow in the U.S. Department of the Treasury and then moved back to New York City to work at Goldman Sachs.

But in the finance world he once again “felt alone — like there wasn’t a community that I felt a part of,” he says. “What motivates me is community and impact. I wanted to be a part of building a better community.”

In 2007, Reffkin began to lay the groundwork for the nonprofit New York Needs You (NYNY; now America Needs You). For inspiration, he thought back to the childhood programs where he felt most empowered and engaged. Across the board, they’d left him with lessons about the rippling influence of mentorship: “I literally didn’t know what the word ‘Columbia’ was when I was a junior in high school,” he says with a laugh. “If no one had told me, we wouldn’t be talking right now!” He decided to create an organization, focused around the idea of mentorship, that would offer career development, college support and summer internships — one that would focus on ambitious low-income students who were the first in their families to go to college and so needed the same kind of advice he had.

Robert Reffkin ’00, BUS’03 ran a marathon in every state to raise money for his nonprofit, New York Needs You.

Courtesy Compass

“But then I had to finance it,” he says.

In a grand visual gesture, Reffkin set out on a mission: He’d run a marathon in every state and set an overall fundraising goal of $1 million. Some funds would go back to the organizations that helped him in his youth, and the rest toward NYNY. He registered under the name Running to Support Young Dreams.

Reffkin started at California’s Death Valley Marathon in December that same year. In January, he ran in both Mississippi and Florida. For a time he ran a marathon every month, with his mother there to cheer him on. He kept working at Goldman. By 2009, he had enough funds to start NYNY. He began dating the woman who would become his wife, and later the mother of their two daughters. As the years passed, more time passed between remaining marathons.

“No matter how good you are — no matter how good — your mind is telling you to quit,” he says of the incessant routine. “It’s a constant environment of give up, quit, give up, quit. All the trainings — give up, quit. Every morning — give up, quit. Every marathon — give up, quit. You’re working against that part of your mind to say: ‘I know you can do it, just keep going.’”

Six years after he began, Reffkin did his final fundraising run, the New York City Marathon. With 12 friends and colleagues now involved with NYNY joining him, the team raised more than $150,000, topping his $1 million goal.

During this time, Reffkin became acutely aware of the emotional muscle that pushed him past moments of self-doubt, and how it gave him confidence at other points of possible self-defeat. He remembered both the loneliness of isolation and the energy of found community. He thought back to how being a real estate agent had offered his mother flexibility and high income. And he started to become increasingly inspired by colleagues who were starting their own companies and putting community and meaning first in their work.

In 2012, it all came together when Reffkin took the plunge and founded Compass.

As a high-tech real estate company, Compass develops software for both buyers and sellers. Its programs provide details about which houses are moving on the market and what industry trends might affect price, interest rate fluctuations and other factors. Forbes hailed Compass’ most recent “high-tech and high-touch” software, Collections, as the “Pinterest of real estate”; the user-friendly program allows potential homeowners to create photo galleries of intriguing properties, share and talk about them with friends and families, and connect with agents to supply details.

Reffkin now celebrates collaboration and diversity of ideas by having designers, programmers and agents work together under one roof. He builds inclusive workspaces through social events and networks like Women of Compass that have philanthropic programs. Reffkin wants agents to help clients not only find their dream homes, but also ideally, community: “A place where they can feel valued and safe, and have a sense of belonging,” he says. “What inspires me the most about Compass and our mission is that we’re helping people find their place in the world.”

Last year, Reffkin’s mother joined Compass as an agent. At a recent Shabbat dinner, she shared her pride that the company she’ll retire from will be one that her son built, that treats its employees well and that offers them a quality of life they deserve.

“I feel very fortunate,” Reffkin says, “after getting so much from my mom in terms of inspiration and support, that I’m able to provide the same things.”

And in turn Reffkin hopes his success will inspire others to start their own companies, create communities and have lasting, positive impact, too. “The more people pursuing their dreams, the better the world will be.”