A Grenadian immigrant went from being laid off from his tech job to heading a major city agency in NYC. Here are his tips for getting back on your feet - and who to hire once you get there.

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A Grenadian immigrant went from being laid off from his tech job to heading a major city agency in NYC. Here are his tips for getting back on your feet - and who to hire once you get there.
NYC Small Business Services Commissioner Gregg Bishop

NYC SBS

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NYC Small Business Services Commissioner Gregg Bishop.

  • New York City is home to more than 220,000 small businesses, but many of them may not be aware that they have a liaison in the city government.
  • Gregg Bishop is the Commissioner of New York City's Small Business Services, where he is responsible for engaging on behalf of the city with entrepreneurs in all 5 boroughs.
  • Bishop spoke with Business Insider and shared to two key insights that entrepreneurs of all kinds can use to grow their businesses.
  • Visit BI Prime for more stories.

Almost three decades ago, in the early days of the internet - before blogs were a thing - there was Gregg Bishop and his underground hip-hop website "Da Sewaside."

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As a teenager, the self-taught Grenadian immigrant would stay up coding till the early hours of the morning while listening to artists like Das EFX in the attic of his Brooklyn home. Bishop said he used a computer his mom had bought form him with her salary from working two jobs as a nurse.

"I had to drop out of college because instead of doing my homework, I would be up until four or five o'clock in the morning, just listening to hip hop and coding my website," Bishop said.

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Today, Bishop is the commissioner of New York City's Department of Small Business Services, where he is responsible for engaging on behalf of the city with entrepreneurs in all 5 boroughs.

As his favorite track by LA rap group The Pharcyde goes, "Now that I'm older, stress weighs on my shoulders heavy as boulders. But I told y'all until the day that I die I still will be a soldier and that's all I told ya."

Bishop credits his success to two key insights, which entrepreneurs of all kinds can use to grow their businesses, and his story shows just how well-suited he is for the job he's held for the past four years.

Hire people who are smarter than you

Bishop's music website became so popular that Vibe magazine eventually acquired it to become a sub-vertical of its web presence, and after a few years Bishop was recruited to be the technical director for TheStreet.com.

While at The Street, he worked with Dan Woods, whom he credits with his first important management insight for entrepreneurs.

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"He actually was one of the key folks in terms of helping me understand how to be a good leader, how to build teams," Bishop said. "Most importantly, how to hire people who are smarter than you."

"You cannot be intimidated," he continued. "It's okay if somebody is smarter than you, because it just makes you look better when you have people who are great."

Bishop's rise continued until the terror attacks of September 11, 2001, forced his employer to shutter his division, putting him out of a job. The subsequent dot-com bubble collapse meant he was suddenly competing with an overwhelming number of highly qualified tech workers.

Roughly a decade after he first enrolled in college, he decided to go back and finish his degree, and even continued on, to earn a graduate degree in communications and management.

Ask for help before you need help

Throughout his education, and upon returning to the New York City workforce, Bishop made a point to reach out to his network for leads and opportunities at every turn. But, in retrospect, he said he still could have done a better job of that.

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"There's many points in my life where I thought I could do it on my own, and I was definitely wrong," he said. "Probably, things would have been much easier had I asked for help earlier."

Bishop said he sees this resistance to assistance almost every day in his work.

"We see that with business owners, because they don't ask for help until their backs are against the wall," he said. "Folks have an eviction letter in hand, and now they're coming to us, and it's like, we could have helped you long before."

Still, having been in the situation himself, he said he has empathy for those who find themselves waiting too long to reach out.

"A lot of times, we don't want to ask for help, because it forces you to admit that you don't know," he said. "In some cases, people might equate that for weakness.

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"I think it is definitely something that plagues a lot of us," he said, adding that he sees it as a sort of pride and an "I can do this on my own" mentality.

What Small Business Services does

In terms of numbers, Bishop's agency reports that it has served more than 19,000 unique customers and businesses, connected more than 27,000 New Yorkers with jobs, and invested more than $1.71 million in community-based organizations to develop local businesses.

SBS' flagship initiatives include providing free legal assistance to business owners, connecting minority- and women-owned businesses (MWBEs) with city contracts, and helping connect business owners to various funding sources. Businesses not based in New York can also benefit from the agency, by making use of its extensive online resources for education and training.

Bishop said the agency has grown considerably since he became commissioner in November 2015, and he is optimistic about hitting a number of important targets this year, including certifying a record number of MWBEs and helping small businesses adjust to a digital future.

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