Headshot jake

Building Bonsai

Patrick Sullivan, a Bronx-born and -raised son of immigrant parents, is the CEO and co-founder of Bonsai.

By Peter McDermott

“Innovate fast and fail faster,” says entrepreneur Patrick Sullivan. “You won't know something doesn't work unless you try.”

We can’t speak to the failures, but Sullivan has built companies that have generated billions in revenue. He was founder and CEO of RightsFlow, which was bought by Google for YouTube in 2011. The next company he started and led, Source3, was acquired by Facebook in 2017.

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Now he’s back doing what he loves most: building a company.

Bonsai, though, is one that’s particularly close to the CEO’s heart. It’s an online platform that connects individuals seeking career advice with professionals giving advice over 1:1 video chats. He said it “reimagines mentoring for the digital age.”

He is seeking “to make an impact and level the playing field when it comes to accessing social capital needed to kickstart a strong professional life.”

Sullivan was born and raised in the Bronx, and he didn’t have business connections to lean on.

But he believes he did inherit the entrepreneurial gene from his maternal grandfather Frank Donagher, who owned a shop and pub in Ballyshannon, Co. Donegal. And when Angela Sullivan is asked by friends where her son Patrick “gets those brains,” she’s too polite to reply with the truth — he gets them from her. His work ethic and discipline, the entrepreneur said, are gifts from his father, Patrick J. Sullivan, a retired building superintendent, who is a native of Castletownbere in West Cork. The Sullivans now live in Rockland County, N.Y.

His parents gave him the start that put him on the path to his business and academic careers. Out in the world, Sullivan met future wife Chastity Martinez, whom he calls “my rock.” The couple and their 9-year-old twin sons, Colin and Jaden, divide their time between Raleigh, N.C., and New York.

College students in both states are part of the story of building Bonsai, which was officially launched on April 28. Meantime, Sullivan and his colleagues have formed a partnership with City University of New York, which with its 25 locations and 275,000 enrolled students constitutes the largest urban campus in the U.S.

The Sullivan family, from left, Colin, Patrick, Chastity, Jaden and Charlie the dog.

The concept is much like Uber or Airbnb. “It’s an open marketplace,” the CEO said. The founders believe that $50 is what works best for the single session. And so, for example, an advice-seeker deciding whether to take six sessions on different topics, $300 in context of $200,000 fees for a mid-range college degree, is “a no-brainer,” Sullivan suggested.

“After each 1:1, advice-givers follow-up with advice-seekers by sharing industry resources, re-booking subsequent 1:1s, or making referrals to job openings or other professionals in their networks,” the Bonsai CEO said.

“We’re trying to reverse engineer what LinkedIn does,” Sullivan said. Colleges have been weak in providing career counseling. He described the system as “broken.”

Right now, Bonsai is catering to graduates interested in careers in finance, digital media, technology, music and entrepreneurship. Sullivan believes it can quickly expand to other careers, including those that begin in trade school.

Looking back, the businessman considers himself one of the very lucky ones from his neighborhood.

“But what about all of those kids out there today growing up in the Bronx? How can we help them develop, progress, and find paths to better lives?” said Sullivan, who was awarded the WhyHunger Harry Chapin Self-Reliance Award in 2013, alongside with Yoko Ono who also received a Harry Chapin Award. “We are here to build a new experience. With Bonsai, we will empower and equip those kids and every learner with a path to fly,” he said.

As for his own business philosophy when it comes to hiring talent, Sullivan likes to quote Steve Jobs: “It doesn't make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do."

The Bronx native added, “My personal belief is that you train people to leave and excite them to stay - never try to milk team members for everything they are worth.

Good pay, good equity, good work/life balance, and interesting projects to work are part of the balance, too,” he said, “but always support folks when they are ready to leave and pursue their next passion or stop along their journey.”

“Patrick is a classic entrepreneur and approaches everything with a ‘nothing to lose, everything to gain’ attitude,” said co-founder and Chief Operations Officer Jake Rosenfeld this past weekend.

“My favorite saying of his is: ‘Gotta go down to go up!’ No work is too insignificant or beneath him.

Bonsai co-founder and COO Jake Rosenfeld.

“He has the energy of an 18-year-old and the experience of a serial entrepreneur who has built and sold companies to the giants like Google and Facebook,” the Bonsai COO said. “He and I share a very important quality — we are always ‘on,’ because we obsess over our company and love solving problems through business and products.

“But we really value family time and other aspects of life that fuel our creative passions and overall happiness,” Rosenfeld added.

During the pandemic crisis, Sullivan has been spending the time away from company headquarters in New York at his new home base in North Carolina.

“First time my wife came down here she fell in love with downtown and North Raleigh,” Sullivan recalled

In 2018, a move began to appeal to the couple. “We just thought, ‘What does life look like in the next 20 years?’” he said. One vital consideration is that Colin is autistic. “So we found a really beautiful lakeside property,” he added.

“Our family feels very blessed and thankful during this period,” Sullivan said. “There’s an amazing food and restaurant scene, which we continue to support locally buying take out on a regular basis.”