Introduction

Bob grew up in Brooklyn. His father was a third-generation immigrant who owned a record store and a deli on Fenton Street and his mother was a Jamaican-American Jewish who worked at the Kingsbrook Jewish Medical Center. From a very early age, they taught him to value and to respect the art of hustling. “If you want somethin’ good in yo’ life, you gotta go out there and make it happen fo’ yo self, boy!”, his dad used to tell him, “Ain’t no such thing as a free meal in this life!”

Bob was known in his neighborhood as a good kid with a rebel soul. He was friend with almost everyone, but he particularly loved hanging out with the Jewish Italian teens and the other Black kids who shared his love for hip hop. He loved questioning everything and never took anything he heard for face value.

As a bright and mature kid who had big and bold ambitions, Bob excelled at school and dreamed of attending MIT like his idols Fred Wilson, John Thompson and Karl Reid. “One day, I’ll be a super intelligent and super rich entrepreneur, Ma, and I’ll buy you a big house!”, he used to tell his mother. “You’re already intelligent and rich, honey, remember that wealth is in your heart”, his mother would reply. Though he knew his parents could never afford to send him to MIT, he kept that dream alive and worked hard to turn it into a reality.

As most of the kids in his neighborhood, Bob grew up listening to New York’s finest urban artists. And as most of the kids in his neighborhood, he knew all of their lyrics by heart. From the Notorious Big and Nas, to Jay Z and Das EFX, he could quote any hip-hop artist and contextualize their lyrics to fit his own rhetoric because this was the way arguments were won in Brooklyn. Hip hop was more than just a form of art for the kids: it was a way of speaking, a way of living and a way of winning in life.

When the second Internet wave hit in the 2000’s (the so-called Internet 2.0 era), Bob was hooked. For the first time in his life, he could instantly access any information in real time and quench his renaissance soul’s insatiable thirst for knowledge. He was particularly excited to read the blogs of his idols in the tech space: VCs and leaders such as Mark Suster, Ben Horowitz (a die-hard hip hop fan) and of course Charlie O’Donnell, his childhood hero from Brooklyn.

Charlie eventually became a close friend of Bob and even served as his mentor, teaching him all the tricks of venture capital. When Bob needed an internship, he didn’t hesitate to hire him at Brooklyn Bridge Ventures, his rising venture capital firm. They would hang out every weekend during Charlie’s Open Lunch sessions which brought members of New York’s tech community together over lunch.

Bob was still a big fan of hip hop in his early twenties but his passion for music didn’t prevent him from also focusing on school. He graduated cum laude from the University of Rochester with a multi-disciplinary Bachelors in Computer Engineering, Economics and African Studies. When the opportunity came, he applied to MIT and was accepted in the MIT Sloan School of Management in Boston.

Bob loved his time at MIT. He ran for president of the Black Engineering Association, was an active member of Black Alumni network and supported the Black History Project. He even had a chance to take part in the Institute’s mythical pranks. When his AI project turned into a real startup, he was accepted into an incubation program at the Martin Trust Center for MIT Entrepreneurship where he named his startup x23. Every week he would attend classes on global entrepreneurship and spend an extra hour with Joost Bonsen at the mythical Media Lab. Bob was very grateful to MIT’s faculty for allowing him to strengthen his contrarian entrepreneurship skills and cross-cultural mindedness through such educational programming.

The values of the MIT Sloan School of Management had a profound effect on him and he strongly identified with its mission: To develop principled, innovative leaders who improve the world. “Principled entrepreneurs are the key to making the world a better place”, he used to tell his fellow classmates. And whenever he spoke about leadership at local events, he would share his favorite quote from Peter Hirst, the Associate Dean of MIT Sloan Executive Education:

“The phrase “principled, innovative leaders” —what does it mean, really? What qualities make a principled, innovative leader? Who are the principled, innovative leaders of our generation? Steve Jobs? Oprah Winfrey? Mark Zuckerberg? Are they empire builders or trail blazers? Maybe both? Are they always in the spotlight or working quietly behind the scenes?”

Despite being one of the top science students at MIT, Bob never had a problem expressing his love for the arts and he never missed the weekly lecture series from the MIT Program in Art, Culture and Technology. His favorite arts activity was the Pleasures of Poetry series that was taking place each weekday afternoon during the January winter break. He often reflected on MIT President L. Rafael Reif’s comments about the importance of art innovation:

“Humanities and arts teaching is central to guiding MIT students in their growth as human beings who are prepared to be bold, thoughtful leaders of constructive change”.

As an urban music aficionado, Bob loved the fact that he could just walk a few miles across MIT’s campus and hang out at Harvard’s Hiphop Archive and Research Institute (HARI) where he would often catch upcoming artists perform their latest songs. He enjoyed the engaging discussions he had every Thursday night with Marcyliena Morgan, the Hip Hop Institute Director, about how African Americans could leverage their culture to succeed in life.

HARI’s mission deeply resonated with Bob. Like the Institute’s team, he wanted to facilitate and encourage the pursuit of knowledge, art, culture and responsible leadership through Hip Hop. He would often lean on the team’s vast knowledge of Black culture to explore new perspectives about Black leadership.

Bob eventually became part of HARI’s family as a recipient of the Nasir Jones Hiphop Fellowship– a recognition he was particularly proud of given his admiration for hip hop artist-turned VC Nas (who generously funded the Fellowship). One of his favorite moments was drinking coffee with Bakari Kitwana by the Charles River on cold Boston nights and reflecting on Ben Horowitz (a friend of Nas) was expertly referencing hip hop lyrics at the beginning of his blog posts.

The Nasir Jones Hiphop Fellowship appointment came with considerable benefits, including an office space, full access to Harvard University’s extensive library resources and networking opportunities. Being able to mix and mingle with minority entrepreneurs, artists and fellow entrepreneurs was a dream come true for Bob. He enjoyed every single minute of his fellowship which he truly believed was God-sent.

When it was time to graduate and to leave MIT and Harvard, Bob moved back to New York to scale x23, the AI startup he had started building with the help of his mentors. But the city he used to call home wasn’t a great fit for him anymore: Facebook had just blown up on the West and he had trouble convincing the local VCs that his breakthrough AI solution was a good market fit for the East Coast. The only thing every local investor wanted to hear was growth, hype and Silicon Valley exits. For the first time in his life, he felt a stranger in his city.

Still, Bob never lost faith in himself. Instead of shattering his dreams, the rejection he faced made him cling even more to his beliefs: he was going to make it, with or without New York, and the key to his success was to live up to his favorite quote from MIT President Raphael Reif —a quote he had permanently engraved in his heart and on his left arm: