A few years ago, Austin Woolridge tried to convince venture capitalists to invest in his esports start-up, Players’ Lounge. It wasn’t an easy sell. Esports had yet to become the global phenomenon it is today, and VCs were skeptical: “How do you make money off of this?” They asked. “How is this different from gambling?”
If the esports stigma wasn’t enough, Austin also faced an uphill statistical battle: only 0.1 percent of all VC money goes to Black founders.
“You think about those odds every time you go into investor meetings,” he said. “It can be demoralizing.”
But Austin, a former hip hop producer who’s created tracks for the likes of French Montana and Fabolous, didn’t let the stats slow him down. In 2017, he and his co-founder, Zach Dixon, got their big break: an invitation to Y Combinator, the most prestigious startup accelerator in the world. Empowered by the once-in-a-lifetime experience, they landed a game-changing $3 million investment in 2019. Among the funders for the Series A investment were Take-Two Interactive CEO Strauss Zelnick, former President and CEO of Yahoo Marissa Mayer, and none other than hip hop megastar Drake.
Austin’s advice for beating the odds as a founder and person of color? Believe in yourself and your business.
“There’s no point in fixating on the negative because it’s only going to muddle your mission,” Austin shared in the latest installment of Pursuit’s Fireside Chat with leaders and experts in technology.
Austin’s experience resonated loud and clear with Pursuit Fellows. They come from communities that are underrepresented in the tech industry: 70 percent are Black or Hispanic, 40 percent are immigrants, 55 percent do not have bachelor’s degrees, 50 percent are women, and 100 percent come from low-income backgrounds. Because many Pursuit Fellows lack traditional markers of success — college degrees, professional experience, and networks — breaking into tech presents systemic challenges.
Pursuit Fellows like Adam Jackson are changing the face of the industry. Adam doesn’t have a college degree. His last job was an assistant at a ticket office. But after completing Pursuit’s rigorous, 12-month training program, his tech career is right around the corner.
“Pursuit is a space for me, a minority in tech, to not only learn the skills I need to succeed, but also to have a community to support me along the way,” said Adam, who moderated the Q&A portion of the Fireside Chat.
Austin is helping to change the industry as well. Pursuit recently formed a partnership with Players’ Lounge to hire our Fellows to join the company’s engineering team. It is one the many companies we work with to secure job opportunities just for our Fellows.
“I love what Pursuit is doing for Black and Brown people in tech,” he said. “There hasn’t been a very clear avenue for people like us. Pursuit is changing that.”
Austin added that the current movement for racial and social justice has only accelerated the drive toward inclusion.
“If there was ever a time for PoC founders to raise money, now is it,” Austin said.
While Austin is now a successful tech entrepreneur, a career in the industry was far from guaranteed. For a time, it looked like music would define his future.
Propelled by his passion for technology and hip hop, Austin began making beats on Fruity Loops, the popular digital audio workstation. Turns out he had a knack for it. Together with a high school friend, Austin formed the hip hop production duo The Arsenals. Scoring their first major hip hop radio hit with the production of rapper Serius Jones’s “Smoke,” they went onto sign with Electric Feel, the prominent indie management label, and produced tracks for the likes of Kid Ink, Fabolous, and French Montana.
“I was a 16-year-old high school kid sending rappers beats,” Austin recalled. “We were doing this on the side. But people started messing with our tracks, so we said, ‘Let's take this seriously.’”
Then came what looked like a major breakthrough: the chance to produce a French Montana track featuring Drake. Unfortunately, the song deal fell through and it never got made (“There’s a lot of pump fakes in the music industry,” Austin explained). But he and Drake would end up crossing paths a few years later, in a much different context: the tech industry.
Austin may have left his career in music behind, but he took his hustle with him into tech.
In 2014, Austin had quit his job as Head of Operations at Fueled, a technology consultancy, to become a full-time producer. But a career in music wasn’t in the cards: in just six months, he had run out of money. It was around the time of the 2014 FIFA World Cup. Austin, a diehard soccer fan, was feeling nostalgia for the late-night FIFA video game tournaments he would play in college. But there were no groups to game with, no Meetups to attend. So, Austin started one.
Turns out, he had also started a business. The Alligator Lounge, the Williamsburg bar where he and Zach hosted the weekly event, was pushing capacity. Austin’s Meetup had blown up. But how would they scale beyond Brooklyn?
“A physical space was too capital intensive,” Austin said. “We realized we needed a website.”
So, Austin and Zach got down to work building the digital product that would become Players’ Lounge — “a fully digital, scalable website and app,” Austin said, “Where people can wager on video games with other people around the world.”
Building a product was hard. But finding investors to fund it was even harder. There was the skepticism of esports. The statistics about VC money and Black founders. But Austin and Zach kept hustling.
Family and friends gave a few small grants. Zelnick, whom Zach befriended while attending weekly 6 am workout sessions at the Harvard Club (“A true hustle story,” Austin recalled), cut a $60,000 check. But it wasn’t until they applied for and got into Y Combinator that Players’ Lounge truly gained traction.
If companies perform well in Y Combinator, “they can raise a ton of money,” Austin said. So he and Zach made sure to knock it out of the park. After going through the three-month accelerator program, they earned a spot in Y Combinator’s prestigious Demo Day. It was “an opportunity of a lifetime” — a chance to pitch Players’ Lounge to the entire Silicon Valley investor network. Flying out to the Bay Area a week before their interview, Austin and Zach booked an AirBnb and spent the week before Demo Day “memorizing every possible question that could come up.”
“We must have memorized 300 to 400 questions,” Austin recalled.
It was hard work. But that hard work paid off. They raised a whopping $4 million from VCs. Austin may have missed the chance to produce that track for Drake. But he had something better: a sizable investment from the hip hop mogul.
It goes to show that, with hard work, perseverance, and most importantly, believing in yourself, you can overcome anything that stands in your way. Even the statistics.
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In our Pursuit Fireside Chat series, we bring in leaders and experts from the tech industry to share their stories with our community. Past Chats have featured:
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- Sander Daniels, co-founder of Thumbtack
- Amit Paley, CEO of The Trevor Project
- Andy Dunn, founder of Bonobos
