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Bentley Magazine

Sy Gray

The PROfile

Kristin Livingston

Sy Gray ’00, MSFP ’04 routinely calls the most important moves of his life “lucky slip-ups.”

In fact, the natural-born entrepreneur has composed a career in accounting and finance on his own terms, by tuning in to his intuition. Here, he shares five cuts from his life’s soundtrack and turns them up to 11, so we can listen and learn from his “mistakes.” 

[1] Muscle Memory Maximus 

Born in England to Jamaican parents, I can seamlessly switch from speaking American English to South London slang. Ya get what I’m sayin’ yeah? When I was 10, we moved back to the island, where the educational system is very European; you pick your track by 13. I chose economics, doing a year each of macro and micro by the time I finished high school. So when I got to community college in Boston, I sailed. I didn’t ace everything because I was smart; it was just muscle memory from Jamaica. After two years, I transferred to Bentley, and maximized my dollars and course credits by taking night and summer classes.  

[2] Go Study a Book (feat. John Sims) 

Looking for advice after graduating, I went to the career center and John, the adviser, asked, “Did you ever think about grad school?” He mentioned diversity scholarships. I said, you don’t have to tell me twice. When I left Jamaica, my grandma — you know how grandmas are — says, “Go study a book.” Which means, study hard. I pushed myself to put those degrees in her hands. So, for me, the win was getting that paper on her wall. Making her proud.  

Sy Gray
So now I’m on new training ground, in a wave of hip-hop royalties, budgets and corporate tax. Figuring out withholdings abroad while we’re on tour with Chaka Khan or Wiz Khalifa.

[3] It’s Not You. It’s Me. (But Kind of You.) 

I was going to grad school, taking the CPA, the series 7/66 qualifications, all while moving around at PwC but never really going up. I burned out on January 15, 2004 — the nonprofit tax deadline — and didn’t get up the next day. Or the next. Or the next. I didn’t call in sick; I just didn’t go back. It felt like I was breaking up with someone. My friends handed me their taxes. And their moms’.  And their friends’. I ended up doing like 40, 50 returns. And what’s crazy was, you know still to this day, there’s not a lot of people of color CPAs. So it happened to be the right time, the right place, where I was serving this community that needed a classically trained guy. Word got out, and suddenly I was in business. 

[4] Def Jam Paradise 

There’s this magical thing called entertainment accounting, and I found it after I moved to Atlanta in 2007. This guy I met, a fellow sneakerhead, says to me, “I have a $2 million problem.” He had signed artists from his independent label to Def Jam, but was struggling with the finances. So now I’m on new training ground, in a wave of hip-hop royalties, budgets and corporate tax. Setting up payrolls. Figuring out withholdings abroad while we’re on tour with Chaka Khan or Wiz Khalifa — all while seeing the world. Amazed at my luck, I slept through the shows, did the early-morning accounting, and hit my bucket list in every city. 

[5] I’m With Her (feat. Beatrice Dixon) 

My first weekend in Atlanta, I met Bea — a.k.a. my business partner and chosen sister. Five years later, she comes to me, asking for help with her company, The Honey Pot: organic, chemical-free feminine products she makes by hand. I’m like, look, I know nothing about feminine care, but I invest to keep her going and the products sell out. I invite her to move her business into my space, where hip-hop artists are flowing through, picking up The Honey Pot. It gets the “As seen at Whole Foods” sticker, and, a few years later, Target calls. She quits her job to go full time, and, like I said, she’s my sister. Thrown into a new industry, I sell my business and dive in alongside her. Today, we’re in 10,000 stores and I’m a chief strategy officer. I’m working from my new home in Amsterdam, where I’m giving my kids the best life I can. Every day I think, “Wow, I made some good mistakes.” 

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