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FORTUNE.COM// FEB.1 .19“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’sThe
Wolf of Wall Street—there were hundreds of
costumes—and Matos became a local film in-
dustry 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 book-
ing 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.)
Also in February, Matos is stepping out from
his fellow partners as the solo host ofHustle,
an eight-episode reality show on Vice that
aims to 10x startups—the premiere showcases
a jam maker in Brooklyn—from the same de-
velopment team behind MTV’sPimp My Ride.
He is perfect in the role. In lectures—at a
black tech conference held by Spotify, for ex-
ample—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 Fountain-
head’s Howard Roark and says he has a radarfor 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 producingHustle. “His
presence is infectious. He has a
beautiful ability to be every-
where. 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 busi-
ness 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 commu-
nity. He makes his passion and
talent a whole world.”
At theEbony awards, as soon
as Harlem Capital is recognized
with an on-screen shout-out
in a sizzle reel of other entre-
preneurs, Matos has departed.
AfterPose’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.“He makes
himself
known. his
presence is
infec tious.
he has a
beautiful
abilitytobe
everywhere.”THE HARLEM
CAPITAL WAY
THREE WAYS THE FIRM
FINDS INVESTMENTS.DON’T SLEEP ON
LINKEDIN:
“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.”PUT OUT CONTENT:
“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.GO OUTSIDE SILICON
VALLEY:“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 inter-
esting investment
opportunities in the
years to come.”