The television actor Cedric Yarbrough looks understandably perplexed. Between tables for Amazon and BET at the annual Ebony Power 100 awards, in the same Beverly Hilton ballroom that hosts the Golden Globes, his tablemates are the four young black partners of venture firm Harlem Capital and their dates. Next to him is the group’s de facto front man, John Henry Matos, the 26-year-old son of Dominican immigrants who goes by only his steel-driving, two-part given name. Matos disappears and returns with a tale of slipping backstage to personally congratulate Chris Tucker on his job as the show’s emcee.
“You can do anything at these things if you hold a glass of white wine,” he says as he refills.
Yarbrough’s eyes widen. “Whatever you’re selling,” he tells Matos, “I’m your next investor.”
But Matos is off making a run to glad-hand the A-list tables: actor David Oyelowo, politico Andrew Gillum, and executives from Nationwide and United Airlines.
“Daaamn,” says Henri Pierre-Jacques, one of the Harlem partners, as he watches.
“The brother is fearless.”
It has worked for him so far.
Matos bills his life as going “from doorman to landlord” (he owns 17 apartments in two buildings in Allentown, Pa.). A community college dropout and erstwhile jazz guitarist, he worked as a doorman in Williamsburg, Brooklyn, where a tenant gave him access to dry cleaning equipment. Matos’s first dry cleaning client was, astonishingly enough, the costume department for Martin Scorsese’s The Wolf of Wall Street—there were hundreds of costumes—and Matos became a local film industry fixture. (He was subsequently fired from the doorman job for hawking his dry cleaning services to tenants.) The dry cleaning business became Mobile City, an off-hours on-demand dry cleaning app he sold to a wholesaler for an undisclosed sum (although an independent assessment puts it at $1 million).
He used that money to create incubator Cofound Harlem and accelerate four startups for nine months, including workspace booking service Croissant and music collaboration website Bandhub. From there he helped run Area, a real estate technology fund for angel investor David Rose, until he joined Harlem Capital, which spent 2018 soaking up headline hype for promising to fund 1,000 minority founders over the next 20 years. (In June 2018 it debuted a $25 million fund campaign and secured $5 million by November, aiming to hit $10 million in February and $25 million by June 2019.)
The Harlem Capital Way
Three ways the firm finds investments.
|Don’t Sleep on LinkedIn:
||Put Out Content:
||Go outside Silicon Valley:
|“It’s a massively underutilized social network we’re paying close attention to,” says Matos. “One of our partners [Henri Pierre-Jacques] reached out cold to a founder of color whom we admired and ultimately ended up investing in.
||“Unlike a lot of other VCs, we’re taking a highly transparent approach to building our firm, and that visibility has been directly correlated to a strong increase in deal flow,” he notes.
||“A number of our deals have come from places like Columbus, Baltimore, San Diego, L.A., and more,” he adds. “We believe secondary markets are more likely to yield interesting investment opportunities in the years to come.”
Also in February, Matos is stepping out from his fellow partners as the solo host of Hustle, an eight-episode reality show on Viceland that aims to 10x startups—the premiere showcases a jam maker in Brooklyn—from the same development team behind MTV’s Pimp My Ride.
He is perfect in the role. In lectures—at a black tech conference held by Spotify, for example—he speaks in the Instagrammy lingo of energy, passion, success, trust, truth, and vibes. At any given moment, he is likely #blessed, #grateful, #humbled, or #inspired. And he has a giddy, earnest way of name-dropping: “a K in KKR!” for Henry Kravis or “the M in L+M!” for Ron Moelis. “JH is a straight-up entrepreneur,” blares his website (buildwithpassion.com). He socials his own Gillette ads with his father. He casually compares himself to the Fountainhead’s Howard Roark and says he has a radar for fellow Roarks. He keynotes in Aruba. He has a monogram-style personal logo. Imagine a young Junot Díaz as Gatsby.
“He makes himself known,” says chef Marcus Samuelsson, who along with singer Alicia Keys is producing Hustle. “His presence is infectious. He has a beautiful ability to be everywhere. I’ve rarely met a person that intelligent and also just so happy. Once you meet him, you remember him.”
Christina Lewis—daughter of the legendary late black business dynamo Reginald Lewis—who leads All Star Code, a nonprofit that teaches coding to black and Latino boys, met Matos through Samuelsson. She agrees: “For most of my life, I’ve met people trying to do the same thing as John Henry. He’s distinguishing himself. It’s not just about John Henry but about John Henry’s community. He makes his passion and talent a whole world.”
At the Ebony awards, as soon as Harlem Capital is recognized with an on-screen shout-out in a sizzle reel of other entrepreneurs, Matos has departed. After Pose’s Dyllón Burnside stops him to say they should DM, Matos walks his date—an Olivia Munn doppelgänger—to her Maserati and hops in an Uber for LAX, in and out of Los Angeles from New York in less than 24 hours.
On the ride to the airport, he says an A-list actor has shown interest in buying his life rights. “I dunno,” he muses. “My life? In 20 years, I could be President!”
As he dashes to his gate, he remembers—“Oh, shit!”—a celebratory marijuana joint in his pocket that never got used in all the eventful night’s hubbub. “It’ll be fine,” he shrugs and marches it through security without so much as a drop of Chardonnay in hand this time—fearless in his own right, and about to 10x the flight of whoever sits next to him.
A version of this article appears in the February 1, 2019 issue of Fortune with the headline “Live For the Hustle.”