What should founders be aware
of before taking venture capital?
When Rent the Runway first raised
funding, we were so excited to get
a term sheet from Bain Capital that
we signed it right away. We might
not have given due time to meeting all the players out on the West
Coast. Taking a couple more weeks
in those critical moments and
exposing yourself to all networks
of venture capital can be valuable.
What are some of the challenges
that women entrepreneurs face
that men don’t, and how did you
Women often start businesses
that address a female need. Rent
the Runway is a good example.
We were our own customers. The
problem is that most venture
capitalists are men, so getting
them to relate to the problem that
you’re solving can be challenging.
We came up with a good solution:
Show, don’t tell. We took videos
of our trial runs showing the emotional connection women have to
fashion, which can otherwise be
lost on men. You want to point
them in the right direction of your
How has being a mother changed
your view of entrepreneurship?
The nice thing is that you don’t
take things for granted as much,
and that definitely applies to
startup life. When I advise young
startups, I tell them not to forget
that these are the best of times.
These are the memories. Write
them down, because this is the
stu; you’re really going to miss at
some point. Last night, I was up for
most of the night with my young-est kid, but it was a moment in
time, and I know that eventually
she will grow up. Drink lots of
co;ee and try to enjoy the ride.
You’re now CEO of Code Eight, a
company launched by Walmart’s
tech incubator. How do you know
when it’s time to leave your company and start something new?
I compare it to when your kids are
ready to go o; to college: You
realize they don’t need you in the
same way, and it’s bittersweet, but
it’s a natural next step. It has to be
this combination of personal drive—
you’re excited to go back into the
trenches of starting another
company—and that the company
is ready to let go of you.
The co-founder of Rent the Runway saw
the fashion-rental service grow to six million
customers and a reported $100 million in revenue.
Then she realized it was time to walk away
By ZOË HENRY Photograph by SHANIQWA JARVIS
need to understand
that VCs usually don’t
go for conservative
ideas, says Jenny Fleiss.
“The main thing I wind
up advising them is to