and Amazon’s Jeff Bezos, it’s no wonder her
approach is sucking people in.
“She’s so open to talking about those
aspects of her life,” says Christine Medina, a
27-year-old who lives in Staten Island, N.Y.
“That’s why I look up to her.”
Medina is a jill-of-all-trades in the
brand marketing space—she does a little
consulting, a little design, a little content
creation. (One side of her business card
simply reads, “LET’S MAKE MONEY.”)
She sits next to Jennifer Lyn, a 27-year-old
accountant from Queens.
Last year, Lyn started a podcast,The
Weekly Hustle, inspired by Amoruso’s
#Girlboss radio show. Instead of
interviewing mega-famous guests like
designer Rebecca Minkoff and television
host Maria Menounos, though, Lyn talks to
people “in the midst of figuring it out.” Like a
digital marketing consultant she went on a
Bumble date with. Or a friend who
moonlights as a burlesque dancer. Or her
own mom, who moved to the U.S. from the
Philippines at 24 and took as many
housekeeping jobs as she could find.
“Success looks different for everyone,”
Lyn says. “That’s something Sophia
constantly reiterates.”
Shortly after launching the podcast,
Medina—a friend of a friend Lyn had never
met before—reached out to her on Instagram.
They quickly became close friends, calling
each other up for advice on professional
dilemmas and brainstorming ideas for
creative projects. And when Lyn heard about
the Girlboss Rally on Amoruso’s podcast, they
decided to go together.
The truth is, being a #Girlboss isn’t
easy. The entrepreneurial grind can be
long and lonely. Dealing with rejection,
and uncertainty surrounding projects and
payments, takes thick skin. Friends and
family don’t often “get it.”
At the rally, Lyn and Medina mingle with
kindred spirits—staying until it’s dark
outside and they each have a pile of business
cards in their tote bags.
“When you work on your own, it’s hard not to feel alone,”
Medina says. “Being in a setting where it’s all women with the
same mindset as you, and the same struggles, there’s something
powerful about that.”T
hese days, Amoruso likes to tell people she’s “90%
healed.”
She’s got some residual wounds, and they reopen a
little every time she talks about Nasty Gal onstage. Or
when a reporter comes calling.
But overall, she’s in a much better place than she was a few
years ago. And as the CEO of a media company that’s, per its
own tagline, “redefining success for women in progress,” she
knows being candid about her past is what got her here.
“I feel like yesterday’s iPhone, because there are so many
amazing entrepreneurs who are telling stories of the kind of
growth that we had,” she says. “But I’ve never been dependent on
what’s to come. I have to keep hustling and not retire on whatever
could have happened on Nasty Gal, and that feels really good.”
“I know that sounds like spin, but it’s not,” she adds. “I’m
happy.”
At Girlboss Media, Amoruso says she’s more willing to pass
the baton to people with experience in the areas she’s lacking.
She works in an open office with everybody else now—no more
corner office.
Her evolution underscores the simple idea guiding
#Girlboss 2.0. This is a community content with being a work in
progress—and scraping by together. If Amoruso can come out on
top, everybody else’s failures, and potential failures, don’t seem so
harrowing.
This summer, Amoruso will host the fifth Girlboss Rally, in
Los Angeles. If everything goes to plan, her new social media
network will launch around the same time. The company is
exploring different tiered pricing, but expects entry-level
membership to cost less than $20 per month.
There are still kinks to work out. And there’s no telling
whether this, or any of Amoruso’s post–Nasty Gal endeavors, is
built to last. But having an audience of enterprising, self-
sufficient fans certainly works in her favor.
Nasty Gal’s early years were a knockout success because she
tapped into something already happening—fashionable
twentysomethings buying cute clothes online—and made it a
little easier. As a career guru, Amoruso has more experience,
resources, and woman power than she ever did as an
e-commerce wunderkind.
“I like to think this is my second brand, but the first I
created on purpose,” she says. “I have a chip on my shoulder
to get it right.”THE #GIRLBOSS REVOLUTIONMARCH 2019 MONEY.COM (^41)