Rashaun Williams’ HBCU pride guides his path as an entrepreneur and serial investor.
The South Side of Chicago native, who will be appearing on Season 17 of “Shark Tank” as a guest judge, comes from humble beginnings. During the Clover x Shark Tank Summit held at The Venetian in Las Vegas, he recalled to AFROTECH™ a time when he’d run extension cords from next door through a window just to power hot plates, relying on kerosene heaters, and looking to the Sears Tower from a distance — now renamed the Willis Tower — at those who were living the American Dream.
Williams Enrolls in Morehouse College
Over time, Williams vowed to change not only his own circumstances but those of his family and community. He wanted to attend a school that created Black leaders, guiding him to Morehouse College, he told AFROTECH™. Determined to secure his place, he drove his application to the campus rather than mailing it. He enrolled in 1997.
“Morehouse is kind of the Harvard of the Black community. The first thing that Morehouse taught me was about my own history,” Williams said.
“Chicago Public Schools, I didn’t learn anything about my history that was positive. Then you are in a school with 3,000 other Black men who all had the same mission. When I was in high school, I was the only Black dude in the top ten … At Morehouse, everybody was captain of the basketball team. So to be in that environment, it was unbelievable for me,” Williams continued.
He told AFROTECH™ that his Morehouse coursework included professional development, professional communication, and leadership. According to the college’s website, Morehouse mandates that students participate in Crown Forum, a course that hosts speakers from across the globe to discuss leadership and inform students of their responsibilities to their community.
“The experience on the campus was one that laid foundation for me to have the confidence and the competence to go out and to compete in a country that wasn’t checking for me,” Williams mentioned.
In 2001, Williams earned a bachelor’s degree in economics from Morehouse College, graduating summa cum laude, according to ABC Entertainment. He told AFROTECH™ that he views Morehouse as his first investor, and in everything he does, he strives to return their investment in him.
Rashaun Williams’ Investments
Williams’ first job out of college was as an analyst at Goldman Sachs, according to his LinkedIn. As his career progressed, he later held director roles at Wells Fargo and Deutsche Bank. From there, he began a venture capital journey that spans over a decade.
Williams holds over 170 investments in his portfolio — including Robinhood, Coinbase, Casper, Ring, PillPack, Lyft, and Dropbox — and over 50 exits, his LinkedIn notes. However, Williams missed out on the chance to invest $50,000 in Airbnb. He seemingly regrets that decision, estimating that the investment could have been worth $50 million today.
“It’s the biggest one. It’s painful … Do you understand that $50 grand would have been $50 million? So, do you want me to cry now or later,” Williams joked.
“Look, I had some other ones. I put $50 grand in Coinbase and it turned to $20 million. I put $25 grand into Robinhood and it turned into $11 million. I invested in Ring and Dropbox and Lyft. So I did make money on a lot of companies. But Airbnb and Uber, because they’re the biggest, missing out on those and it’s like, it’s even more game changing,” he continued.
Narrowing further on why he passed on Airbnb, he cited their pitch deck as one of the primary factors.
“They were raising money and a lot of people passed on that. Just couldn’t get their heads around it. The team, the product, the deck … It was terrible … With the bubbles on it from like 1988. So I passed on it. I’ve been regretting it. I still have nightmares about it every night,” he explained.
Williams certainly doesn’t have regrets over his $750 million sports private equity fund, Harbinger Sports Partners Fund, which aims to secure minority stakes in North American sports franchises, particularly the NFL, NBA, and MLB.
As AFROTECH™ previously reported, in 2025, Williams became a limited parter in the Atlanta Falcons. Williams also tag-teamed with Steve Cannon — former CEO of AMB Sports and Entertainment — and billionaire Mark Cuban — former “Shark Tank” judge and Dallas Mavericks minority owner — on the venture. Cuban’s participation resulted from Williams’ signature “just here me out” phrase, which he mentioned served him well for over 35 years.
“I remember being in high school thinking like ‘I’m a straight A student..captain of the basketball team, National Honor Society, all of this. But here I am, I don’t have a dime for school and I have to compete with thousands of people to get into only one school that I’m applying to,’” Williams told AFROTECH™.
“So for me, I was always like, ‘I need to sneak in the room.’ When people discover I’m not supposed to be there, I just give them this one phrase, ‘Just hear me out. Let me explain to you why I’m here before you kick me out,’” Williams continued.
When the opportunity to build Harbinger Sports Partners Fund arrived, Williams used this phrase to get Cuban onboard.
“I just called him up. I was like, ‘Hey Mark, I know you sold the Mavericks, and I know you’re super busy. Everyone comes to you for everything, but just hear me out. Here’s what I want to do, and I want to do it with you,’” he told AFROTECH™.
