November 29, 2021 • 31 mins
This week, Big Money Energy gets a momentary glow up as founder of Rent The Runway, Jenny Fleiss, joins the show. She and Ryan discuss how to use tech to disrupt the fashion industry, Jenny’s decision to leave Rent the Runway and pursue a new opportunity as a VC and what the future of customer service might look like.
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Speaker 1 (00:01):
Welcome back to another episode of Big Money Energy, the
greatest podcast in the history of the world, where we
talked to inspiring entrepreneurs to find out how they went
from nothing to something, What are their thoughts on money,
what are their thoughts on entrepreneurship, and how do they
build the company that they built? And today we have
note other than Jenny Flice who co founded a company
(00:21):
that you probably have heard of called Rent the Runway.
I know me in New York City when Rent the
Runway started, all of a sudden, every woman around New
York had like these new dresses everywhere. There are on
Instagram wearing their stuff. I'm like, damn these women into
buying all this clothe They know they're not buying it,
They're renting it because the company got invented by these
two amazing women that connected fashion to technology and changed
(00:45):
the world of fashion forever, changed the paradigm of how
people think about owning or not owning clothes for the
rest of time. She is a tastemaker, a trend setter,
and an all out total mogul who's now a better
capital listen our own right investing tech companies around the world.
I am super excited. Let's go, Jenny Flice, Welcome to
(01:06):
a new episode. I'm a huge fan and I followed
your entire career for a really really long time. And
I'm a big fan too of female founders rent their
one way and we can get to that, but it's
(01:27):
obviously huge. Every single woman in this entire office that's
ever worked for me has used it. Of my company
is women, and they've all they've all experienced it, they've
all gone through it. But then you left. You went
to Jet Black with Mark, who we know, and so
I'm glad he was able to make this introduction UM,
and now I am waiting for you to tell us
(01:48):
all live what's your next company is. There's some stuff
in stealth mode. Okay, this isn't public. Yeah, okay, So
first off, I do a lot in the investing side,
right I'm at a growth equity fund called Volition Capital,
so I touch a lot of different businesses and founders.
So I'm lucky to see like the full ecosystem of
all the exciting things going on right now. There is
(02:11):
a team that I'm super excited about that I've been
helping to form a product um and it's in the
customer service space, um, and so it's not fully ready
for prime time, but that is also somewhere where're going
to spend some time. I think customer services this like
forgotten industry that people are so focused in the digital
world of like reducing the amount of customer service interaction
(02:32):
because it saves you money and cost. But it's this
amazing opportunity to sell, to understand your customer, to have
that touch point, which is so rare in a digital world.
So it's kind of flipping that on his head and said, like,
what if we actually deliver like a best in class
customer service experience, use that as a differentiator, funnel the
data back to make your product and your company even better,
(02:53):
and use it as like a third party service so
it could be plugged in play for the next digital
startup to just kind of outsource their customer or service
and have it be best in class customer services. My
whole business. I was gonna say, you definitely understand this
right between the businesses that we have here. It's it's
a lot of our business and then we have an
education tech platform and we've been hiring customer service people
left and right, and that's a big way that that
(03:14):
business grows and salespeople join us is because it just
doesn't exist anywhere, and they email us and we email back,
or they call us and they have a question about
a deal or anything that we're doing, and we respond,
and then they talked to another agent and that person
joins and so on and so forth. It's probably next
to content um those two c's, right, content and customer
service almost go hand in hand and your ability to sell. Well,
(03:37):
if you think of like the initial businesses like Zappos
on the Internet, they had this deep understanding of how
important customer service was and not just like let's fix
your problem, but the idea of having a human touch
point right, So Zappos mantra was like call the number,
it's plastered up on the screen, they'll talk to you.
There was no limit, they're not measuring the time you
can talk to you all day, and that was the
cornerstone of their business. So this realization of people like
(03:59):
the further you go into the digital world of making
things fast and easy and transactional, the more important it
actually is to have that in person kind of touch
pointed to feel like there's an entity behind the business
and the product you're buying to answer your questions and
what have you. And I think we've really lost that.
So I think it's a hidden opportunity. We saw it
with jet Black, So jet Black personal shopping over text
message I worked on with Mark Lore at Walmart U
(04:22):
and versus an Amazon where you're thinking, like, this is
a transactional, glorified search bar, Like, what is the ability
to differentiate it's in these like touch points, these human
more human feeling touch points. What was something you were
super naive about in your early days building rent runway?
I mean, just one thing. Um, So, first off, I
(04:44):
think that like being naive is one of the greatest
gifts of being a first time entrepreneur ignorance. Yeah, like,
had you ever known how hard it was, you would
have never tried. Um. And so a couple of examples
come to mind. You know, one is Jen and I
built a fashion technology business with no fashion background and
really no technology background either. But would you have built
(05:05):
it had you had either of those backgrounds. I think
we wouldn't have had the same fresh lens on the
fashion industry that we were able to really disrupt that industry.
And I think on the technology and logistics we would
have been probably too intimidated by how complex what we
were doing was that it would have just been too
daunting to go after it. But with technology, we thought
we could like outsource tech, you know, we like put
our request for proposal out. We found like what we
(05:27):
thought was the best engineering team, and we're kind of like, okay,
like see you in two months with our tied with
the bow package of a website that will like launch
and nothing like that. Nothing works like that right in
the world. It's like anything that's mission critical you need
to have your hands on, you need to own. So finally,
like flying to Canada where this team was and realizing
there was really not a team and the product was
so far from where it should be. Was this like
(05:48):
very naive moment of hey, we got to figure this
part of the business out and be much more hands
on and logistics to write like the amount of dry
cleaning you have to do. I mean, so I ran
logistics for about four years of my time. It rent
the runway. I joked it was like the last straw
drawn because just it was hard to hire for, it
was complex, it was a lot of work. We initially
used our local dry cleaner company called Slate in the
(06:10):
West Village, and it was like I was asking him
about dry cleaning to learn and to understand the pricing,
and then I was like, hey, you have some empty space,
like could we store our dresses here? So for a
while we had like a free warehouse essentially, but we
gave them all of our dry cleaning business, and pretty
soon it was enough money that we were spending and
we were busting at the seams from this dry cleaner
that we needed to create our own facility. Yeah, it's
(06:31):
like Coca Cola on the bottling yeah yeah. So yeah,
so we have our own facility. It's actually the largest
dry cleaner in the US, possibly the world, that's debatable,
but we have New Jersey and now we have a
Dallas facility as well. A lot of people that I
(06:51):
speak to, and a lot of people who listened to this,
are either like one or two spots. They have an
idea that's germinating that they want to do something with
and so they find inspiration from your story and your
multiple stories, or they're starting something and they have pain points,
right and they're trying to figure out like, Okay, is
this real? Is it not real? Or I'm trying to grow,
trying to get to that next spot. What was a
(07:12):
and I'm sure there's thousand of them, But what's a
pain point that sticks out to you today that someone
might encounter now in the ties kind of post COVID,
Like you just talked about customer services, something that maybe
we wouldn't have thought about so intently in two thousand eighteen,
but now is a big, big deal, especially digitally. So
I actually think ironically in customer services one example, the
(07:35):
rise of digital and the efficient transactions that it enables
has created all these I call them like taxes of
of e commerce. So for example, the idea that we
have everything in our fingertips now is actually really time consuming.
Like you used to be walked into a store there
was five types of shampoo or whatever it was, and
all of a sudden you can literally get access to
thousands international options and it creates this like analysis proalysis,
(07:59):
this rabbit hole where then we have to do the
research of which is the best and we can easily
spend like an hour of our time, which is our
most valuable commodity trying to decipher from this like all
these options, which is the best. Um so That's one
area that I think about. Another is like these hidden um,
these hidden costs of your time and things like returns.
So obviously, if you're not trying something on, you're not
(08:20):
going to the store in the first place, the odds
that you're going to get it right are a lot smaller.
And that could because it doesn't fit, or it could
be just because like you didn't actually like the product,
the quality wasn't good, it was the wrong you know,
the wrong color what you know, it's harder to tell
online and the process of returns right now takes a
lot of time and energy printing a label, going to
the hub spot to deliver and return the item. Um.
(08:43):
So there's like quite a few examples of these hidden
costs of time, even entering your credit card information and
your details right that that we all kind of encounter
on a daily basis. What was a career highlight for you, Well,
definitely co founding rent the Runway has been like this dream.
The day that we launched, um, we were covered in
the front page of the Tech section of the New
York Times, and it was when most people still had
(09:05):
physical New York Times delivered doorstep that moment, Yeah, where
I went to my own doorstep and saw it and
we were right there on the cover. And then you know,
going into the office that day, because we all went
into the office also at that moment in time and
like being able to jump up and down with the teammates,
my co founder and celebrate that special moment because a
lot of hard work goes into that that moment um.
(09:26):
So that that for sure was one. I mean, getting
our term sheet from a venture capitalist for Rent the
Runway was another. Getting a film before after that came
before the New York Times. Yeah, and you had a
publicist who helped you get that article. No, Actually it
was really fun entrepreneurial story where we had about thirty
customers when we launched Rent the Runway in like a
(09:47):
private beta launch and one of those emails natural organic Growth.
We were hustlers, like we got those email addresses through
our friends, our family, We hosted, like we would throw
parties for our friends if they gave us like the
most email addresses. We would go to the movie theater
lines of relevant movies like Sex in the City movie
and get with the clipboard like collect email address it.
(10:09):
Like we did whatever we could to get that email list. Um.
So when we launched to this initial group, there was
someone and then people started chattering and shared it as well.
But there was a New York Times email address on
the list. And we noticed this because you're kind of
if you're a good entrepreneur early on, you're paying attention
to like every customer and every piece of information. Um.
And so we reached out and we're like, listen, we're
(10:30):
psyched that you're a customer, Like, let us know if
you ever want to chat and lo and behold like
she did. And it was a young Newish reporter at
the time who came to our office and wind up
covering the story. Um, so yeah, it was she was
a customer. She was a customer, one of her first customers.
That's awesome. Yeah, it was incredible. And you know, we
then of course realized that if we she was a
(10:51):
tech reporter. So we saw that also and we're like, well,
there really aren't many women in tech, Like this was
a very to have a fashion article in the tech section.
I think also from like a strategic buy, were like,
this could be really interesting, and so we were like,
do you want some photos, like come to our warehouse
and we wore like these fun dresses and stood up
on ladders in the dry cleaner warehouse. I think we
had enough of the strategy ourselves, combined of course, with
(11:12):
some luck and you know, proactivity to just make this happen.
Were you spending marketing dollars yet at the time? Not really.
I mean I think that for for rent the Runway,
up until a few years ago, we were like plus
organic word of mouth. The big insight for us was,
you know, when you're at an event, the natural conversation
started for a woman is you look great? What are
(11:33):
you wearing? Right? That's how most women start, like break
the ice. If we could own that moment and have
someone say thanks, like I rented the runway, that would
be everything. You would answer a questions like what's round
the runway? How does it work? What if I spill wine?
What if it doesn't come or doesn't fit? And because
it was such a new behavior at the time, we
needed that trust and that you hear it from a friend, right,
(11:54):
you hear it from someone at a party. And so
we really invested in our brand. If anything, um so
not the traditional digital marketing, but yeah, making sure they
are packaging our website looks beautiful and aspirational, that we
had beautiful designer addresses, yes, and that the customer experience
was really good. So our customer service team, I mean
initially was us answering the calls and stuff, but we
tried to just nail that customer experience and you also
(12:16):
really nailed and you might tell me I'm totally wrong
with this and said, no, Ryan, that was a massive issue.
But like I don't ever remember when you started, um
there being an issue with the fact that people were
renting dresses and not owning them. Like there wasn't a
social issue, right, there was. There was no ego attached
to it, because like if you think about it now,
if you go twenty years ago and you're gonna pitch
(12:37):
that idea, it's like, no, I want to own my clothes, right,
that shows that I make enough money to be able
to do that and bypassed that wall. That wasn't. Yeah,
that was not a given and was something we were
nervous about and that the designer partners we worked with
were also nervous. And I'm sure because at the time,
you know, we launched two thousand and nine, many designer
brands were just starting to sell online let a interest
(13:00):
someone else to rent their products, pre owned products, and
so that was a lot to triangulate, and we definitely
didn't know if customers would think this was like ikey,
like how would they perceive it? Um. I think the
tail ones have really been at our favor and we
were kind of a little bit ahead of the game
and able to be a part of adjusting consumer behavior.
Sustainability has been a big piece of this mix too.
(13:21):
Write like, we've always been a sustainable concept, the idea
that if you rent and you buy less, it makes sense,
you know, it saves waters so many pieces from a
sustainability perspective, but customers really care now and when we
ask the main reasons people rent, that's now one of
the top three reasons. Yeah, Like because there's there's stat
(13:42):
that at least half the stuff in your closet you
really don't wear more than once or twice. And then
I feel bad for my clothes that I don't wear.
They're not getting a turn. I do feel all that.
I feel like we all kind of feel bad, right
Like I have I have like seventy suits. You don't
need that many suits. You would think I don't, um,
but I do. I do have a lot of suits,
(14:03):
and I built a new house around our closet. Um.
That was like the one thing we designed first, right,
it was to have like the greatest closet. You're such
a close I'm not really, I just wear a lot
of suits, um, and so I and I do feel bad,
like if I walk by a suit I haven't worn
in a little while, Like sometimes I'll whisper and say, like,
I'm sorry, going to give it a spin. Yeah kind of.
(14:23):
I think that's so so true and right, And I
think that in my head, Yeah, I hear you, yeah,
because I don't know, maybe because I saw a toy
story like a long time ago, and I'm like, I
wonder if my suits talk to each other, and like Ryan,
it's aware us anymore. Like the coloring is so cute
and so funny, and like, you know what in your industry,
clearly like presentation is first impression, impression if you're not
carefully And so that was actually a big piece of
(14:46):
Round the Runway in the sense that like we know
that as women, the way you look determines how you act,
how you feel, like the brand that you put out there.
When we launched social media was hotter, you know, I
mean now it's hotter than ever, but it was very
much on the rise. So the idea that you are
also putting a photo out there into the world that's
going to be this forever indelible like print of who
(15:06):
you are. You're sharing your brand. But then the way
it makes you feel, right, You're like I can take
on the world. And the brand that we built for
in the runway was around female empowerment and self confidence,
the idea that, like, your dress is not just an outfit,
it's how you feel and how you're going to take
on the day. So New York Times article comes out,
Were you prepared for the rush that came right after that? Lost? No,
(15:28):
But we knew enough to think about. We were always
going back to the customer experience, right, and so we
knew as customers ourselves, right, we were women in our
twenties launching the business. If we came to that site
and there wasn't a great selection of dresses of product,
that it would be a terrible experience. So we knew
that couldn't happen. And so what did we do. We
paid a lot of attention to waiting to launch until
(15:49):
we had a great beautiful website, great designer dresses in
enough sizes, some amount of quantity. And then we put
up a gate on our website, meaning that we only
let a certain number of people in, which really let
us control the traffic and demand. It also created took
away from the like rental could be down market. It
made it more like an exclusive thing. Yeah, and we
were coming up the tail winds of Guilt Group, who
(16:11):
who did the same thing. They had like this gated site.
They made shopping at a discount cool and exclusive and luxury.
So we drafted off of that and it let us
really control the experience customers had. So we stopped letting
people in. You know, we let in some every day,
but we tried to do it in a way that
we could manage. Um, and we were still figuring out
kinks and bugs as we grew. Um. There was the
(16:32):
second day we had the idea that you could get
a second size for free. So we didn't know we
knew people would have concerns oversizing, and so we're like, okay,
if you rent a size six, you get a size
eight for free. Like as we let customers do that,
and all of a sudden we saw no one was
renting a second size. We're like, it's free, Like why
wouldn't people do this? And we dug into it and
our chech was broken around like enabling you to show
(16:53):
move someone did this, and so what do we do?
We called everyone who had rented, because a couple hundred
people and it's not that it's not possible, and we're like, hey,
so excited, you're one of our first customers. Just want
to confirm the details of your order. And so it's
moments like that where you're kind of like drinking from
a fire hose. You're just trouble to figure it out.
You cover your ass, like yes, you figure it out.
(17:14):
And there was so many moments like that where, you know,
photographing our first stresses. It was like a week before
launch and the developers are like, okay, now we need
to load the photos and I'm like okay, great, Like
the designers give us photos and it's like no, no,
like we have to run a photo shoot. We're like
we have to run a photo shoot, like and then retouching,
like we had never done this. We didn't know what
(17:34):
this was. We didn't have a placebook, and so you
pull all this stuff together in like forty eight hours. Right,
another example of you knew how hard and all the
things you had to do, like you probably wouldn't have
done it, and you started with a co founder, yes,
and relationships are always hard, yes, right? How was that
kind of doing it together at the beginning, And it's
the two of you where their struggles as you grew
(17:54):
and as it was like Okay, I'm gonna handle logistics,
but I don't really want to. Could you do this?
And then the company grows and grows and grow. Yeah.
So I think it's first off, a lot more fun
like doing something with a team or co founder. It's
just more enjoyable how you spend your day to day. So, um,
it helps in terms of the complement of skill sets.
And for sure Jen is big picture strategic visionary thinker
(18:18):
much in the way Mark Laura is as well. Um,
and I'm like, how do you get from point A
to point B? So we recognize and respected in one
another those skill sets, and so I think the same
is true of when you you know, you pick your
partner and your spouse, when you pick your co founder,
it's like, as long as you respect them, and like,
I think so highly of them, it's hard to go wrong, right,
So the pieces of the business that she ran, it
(18:39):
was always like she is the best person to run
those parts of the business. And I think likewise the
pieces that I ran, That's how she thought of it
as well. So we reach doing so much and working
so much and so clearly like bought in that it
wasn't really a question of like who gets to do
this or who gets to do that? There was way
too much to do. It was just like if you
you know, if could take it on your plate. So
(19:01):
we didn't sink is what it felt like you would, um,
but the foundation of respect, a ton of communications and
just like then realizing, yeah, we're having more fun doing
it together. So there was never a tough point. There's
always tough points. I mean there's tough points with like
any relationship. And I think at the end of the day,
like forcing yourself to have sometimes weekly conversations whether there's
(19:22):
anything good, bad or otherwise going on, to like keep
the dialogue going and then you just be like super
candid honesty. But like we lived through so many moments
and experiences. I'm jen still running the business. She CEEO
of the business I'm still on the board of the business.
We still talk both as friends and as business partners,
like at least weekly, if not, like I probably text
(19:43):
with her daily. Right, So I think this underlying like
respect these moments that you've been through, um, Like she
is the best, but she's always been CEO. I've always
wanted her to be CEO because that is how our
business will be the best business. Like, That's how highly
I think of her. And there's many things I know
She's thought that I was the best person to handle
in the company as well. How is she living without you? Well,
(20:05):
we do still interact a lot. Um. I didn't leave
until I really felt like I had built an amazing
team around her. Sum, I don't think. I mean, first
of all, from a financial perspective, when I went and
joined Mark at Walmart, Um, I you know, I would
have never felt good about leaving, but that I knew
the company was in a good place and that she
(20:25):
had the right team around her. So I just helped
her hire like three really strong people in the leadership team,
and things were ticking and cranking, and I knew it
would be fine. Right. Can you tell me about that
moment though, deciding oh my gosh, to go do something different,
(20:50):
and that first conversation or was it something that was
kind of like, once I get us to this point,
I'm going to build something else. Well, So one thing
I think that helped was throughout the life the business
when we had we would have often conversations on our
life goals or ambitions, our aspirations, including from the beginning
when Jen was like, I really want to be CEO
and I was like, great, I think you'd be amazing
(21:10):
and SEEO right, And so she very much knew and
we would talk about the fact that I had this
serial entrepreneur tendency, meaning that like I always loved like
ideating starting new things, and so that at some scale
of the business it might not be my forever thing,
where Jen was like, I'm in this forever, like this
is my lifelong child like passion, you know. And so
we had that understanding behind the scenes for a long time.
(21:33):
Now what we were able to do is I laded
business development for a period of time at the business,
which meant that Jen was running the day to day
and I was like, what's coming next? Kind of what
Mark was doing for Walmart right, especially with the incubator
that we set up store number eight. It's like you
have the day to day and then if you have
a pot of people who are thinking about the next steps.
And so through that business we launched our retail stores UM,
and we launched our subscription service through that business development.
(21:55):
So I was kind of running like a mini startup
focused on the future with and Rent the Runway for
few years, UM. And I think because we would always
just talk about, honestly, like what our natural skill sets
and passions were. It wasn't a huge thought shock. It
was a conversation around like what was the right timing
so that like I could do what I wanted, but
also so it was the best thing for the business.
You are so positive, Um, what is what I was like,
(22:19):
can you talk to me about like a low day
Rent the Runway. It's still everything's great and it's awesome,
but there was just a tough COVID is hard, right,
COVID run the Runway and for your business, Like those
are hard moments, UM. I think you know. So this
was not that long ago. I was dealing with it
as a board member and as a friend and something
(22:39):
last big skin and really hard for the team. You know,
I think the flip side positive of that is if
that team can live through COVID, it's like you can
live through anything. If that business can survive COVID, then
you can. Like we were literally running a business that
was based on getting dressed for special events in a
moment when people didn't even need to get dressed, let
alone have events. So it's like, if you could live
through at it's like all those things that you thought
(23:02):
were problems like falls by the wayside, and so I
see it now on like a weekly basis, issues that
I think would have stressed Jena, would have stressed the
team out, roll off your back, and it's like that's
what I say about having kids too. It's kind of
like you learn not to sweat the small stuff and
like to like funnel up where you want to spend
your time and your energy. Um, but that for sure
was a hard period of time. I mean I think
(23:24):
that like for UM, for jet Black and the business
we started for Walmart, like hard that they decided not
to keep the consumer facing part of that business. So
the text platform that we built to enable text based
commerce is something that they leverage and so from a
impact on the world in Walmart. I feel great about that.
I feel like shopping over text and conversational commerce is
(23:46):
like the future. Um, but there were really pieces that
I feel like we're delivering to a consumer that I
miss on a daily basis as a consumer, and that
I hear from our customers all the time that they
miss So that like it feels a hard moment or
like an itch that I just need to scratch. And
I try to think of it that way that it's
not like it's not as much of them sad about
it is just like something I yet to tackle in
my career. What is a just thinking about this? What's
(24:08):
a good piece of advice that someone gave you not
to do where you follow the advice and thank god
they gave it to you. Okay, So two things that
come to mind. One is don't give up. So you know,
the first meeting that Jen and I took with the
designer was Diane fon Furstenberg hated our concept. I left
that meeting like, well that was fun for a few days.
(24:28):
Like the business. We we barely just started talking about
it and Jen was like, no, she just told us
all the things that were wrong, and now we know
how we need to reframe our sales pitch and go
back to the table, right and so like this no, no,
it means not right now or just you know again
the reframing, like I said, you know, I get to
be a mom or like hey, we get to receive
this amazing feedback from this really famous fashion designers and
(24:49):
now we can build anything stronger, right, Like I think
that lens has been really important. Um. You know another
thing and I now give this advice is not to
hire someone unless you feel super psyched about it. And
it's often so right, so tempting when you feel a
hole in your organization or you need to let someone go.
What I mean logistics at Runt the Runway, we needed
(25:11):
to let two key people go and we had no
one else to run the business. And we were like,
that's how I wound up running logistics. So for better
or worse, I think it was the best and I
know it was the best answer for our business. It
can be painful sometimes, but like you need to find
the right people. You need to like fire when you
know they're not right, and you need to wait to
hire until you're so excited about the person, and then
everyone has to be excited about them, right, everyone should
(25:33):
be yes, especially early on. I mean at some point,
however big the company is not everyone can know them.
Or you have different cults. You know, we have somewhat
of a different culture in our warehouse and logistics versus
our customer service versus the home office versus our retail stores.
Like so it starts to change a little bit. Where
do you see opportunity the future? Right as somebody who
(25:57):
because you you change the world of fashion right totally.
You brought fashion technology together in a way for women
people now that have never been there before renting clothing.
So two areas that I find really exciting. One is
what i'll call like infrastructure enablement. This idea that there's
certain parts of your business that are going to be
like the differentiating thing, the most important thing of your
(26:19):
business that like that is the core of what you
need to get right. Sure, there's a lot of other
things that like you can plug and play, you can outsource,
you can buy from someone else. That ecosystem is getting
better and better of the pieces you can plug in.
So think of Shopify for example, Like you can get
a website up and running in an hour. It's pretty good.
Now to shop by apps that like you can plug
in to do more and more things and customize it
(26:41):
more and more. The pace at which everyone is moving
because of these tools like requires you to have more
and more of them. So you know this company I
mentioned earlier, Cube Financial, it's like a financial budgeting planning tool.
Um that like it's much more plug and play than
like Microsoft Excel in terms of just letting you get
up and running more quickly. Right, you should have um
you have Carter who's helping you do like legal share management.
(27:04):
So these like infrastructure enablement, plug in play solutions is
one area I find particularly exciting, and that one also
I think is fun because it lets you as a creator,
like this whole world of influencers, Instagram, etcetera. Being a
creator if you wanted to start a business. You know,
Emma Chamberlain started a iced coffee business, right like she
can just go on Shopify. I think more and more
the supply chain of like how do you make icce coffee?
(27:25):
Like she needs to be good at what she's good at,
like her brand, how she talks about it, how she's
going to market it, but all the pieces around it,
like she can now build a whole business off that
platform and doesn't really have to do much except for
what she's uniquely good at. Right, So so that's part
of why I love that that infrastructure enablement. Then another
one that I find interesting is just old school, like
viral marketing and brand marketing. Paid marketing, paid acquisition has
(27:48):
gotten so expensive, especially recently with like the changes and
the stands around privacy, like and it's like there needs
to be a different way, And so we saw that
with run Through one Way, Right, I gave you the
example of just like the viral word of mouth marketing
is being so much more powerful, authentic, it cuts through
the clutter. We were also marketing for our designers, so
the idea of wearing a dress from a designer, having
that experience talking about it actually helps the customer eventually
(28:11):
buy from that brand. So I think finding these authentic
different ways to market college campuses, how bumble started right,
Like that tap tap into this conversation. Starters are the
most powerful, and like, that's what I look for in
a lot of businesses. Did you ever think about affiliate
partnerships with those designers that if that customer then comes
back and buys at another store, somewhere right that that
(28:34):
name is attached and you own that client. Yes, so
we we have. Um. I even at one point was like,
sometimes it's hard to capture it because someone might buy
the store and as you're seating, I was like, can
they bload a receipt and maybe they get a site credit? Yeah, indirectly,
you know, we've done click through partnerships. We do have
an affiliate program UM where you can kind of I
(28:55):
don't think we're capturing all of it, but these brands
are seeing enough of a feedback loop in terms of
the performance of their products, what customers are saying, as
well as a lift in their sales, as well as
real revenue that we're driving. So it exists. It's it's
hard to track. I wish it was easier to track,
but it was somewhat of a line item. Yeah. Yeah,
and and something we've iterated and talked about a bunch, right,
(29:16):
I'm sure. Yeah. I have one last question for you.
Can you describe for me your best day two years
from now? Um? So, the best day two years from
now is this business that Stealth business is raising not
only like maybe their Series A, but you know, first
of all, hopefully they don't have to raise a series
(29:36):
be raising money isn't always great, but it's just like
rocking and tacking along and it has a ton of
customers and is making millions in revenue and it's like
a party, just crushing it. Yeah, we're doing a big
party for them. I'm taking actually the founders out tonight
to celebrate because we just closed the initial like seed
funding and they worked for me before, so like part
(29:56):
of it is just I'm so proud because like I've
seen them in own them for years and they gave
so much to me to be able to try to
pay it forward and to see the success for them
now and like you know how exciting it is when
you get that first term sheet and funding and to
be like leaving a job at a big corporation to
take the sleep of they can risk and it's real
and it's happening for them, and so it's like, in
this weird way almost like more rewarding seeing it for
(30:17):
someone else. Um. So yeah, I just right now, I
think I'm pretty focused on getting them to their next
stage of success. One thing I say to entrepreneurs is
and like create an email address that's just like memories
that Rent the Runway dot com memories, is it right,
and just copy it on stuff like like moments right
that you have no time, Right takes you no time.
You can send photos, you can just copy it. When
(30:38):
you're sending something to someone else, you're sending a board
update with the key milestone, a partnership meeting, and like
emailing with Dan Dan when person and then like, at
some point you'll go back and look at that. In
the moment, it is so hard to realize and appreciate
the amazing stuff that's happening, and so like, now if
that lends looking back a Rent the Runway, it's like
one thing I tell all founders what's to do. Big
Money Energy is hosted by me Ryan Sirhant. It's produced
(31:02):
by Mike Coscarelli and Joe Loreesca and executive produced by
Lindsay Hoffman. Find more podcasts like Big Money Energy on
the I Heart Radio app or wherever you get your podcasts.
Welcome back to another episode of Big Money Energy, the
greatest podcast in the history of the world, where we
talked to inspiring entrepreneurs to find out how they went
from nothing to something, What are their thoughts on money,
what are their thoughts on entrepreneurship, and how do they
build the company that they built? And today we have
note other than Jenny Flice who co founded a company
(00:21):
that you probably have heard of called Rent the Runway.
I know me in New York City when Rent the
Runway started, all of a sudden, every woman around New
York had like these new dresses everywhere. There are on
Instagram wearing their stuff. I'm like, damn these women into
buying all this clothe They know they're not buying it,
They're renting it because the company got invented by these
two amazing women that connected fashion to technology and changed
(00:45):
the world of fashion forever, changed the paradigm of how
people think about owning or not owning clothes for the
rest of time. She is a tastemaker, a trend setter,
and an all out total mogul who's now a better
capital listen our own right investing tech companies around the world.
I am super excited. Let's go, Jenny Flice, Welcome to
(01:06):
a new episode. I'm a huge fan and I followed
your entire career for a really really long time. And
I'm a big fan too of female founders rent their
one way and we can get to that, but it's
(01:27):
obviously huge. Every single woman in this entire office that's
ever worked for me has used it. Of my company
is women, and they've all they've all experienced it, they've
all gone through it. But then you left. You went
to Jet Black with Mark, who we know, and so
I'm glad he was able to make this introduction UM,
and now I am waiting for you to tell us
(01:48):
all live what's your next company is. There's some stuff
in stealth mode. Okay, this isn't public. Yeah, okay, So
first off, I do a lot in the investing side,
right I'm at a growth equity fund called Volition Capital,
so I touch a lot of different businesses and founders.
So I'm lucky to see like the full ecosystem of
all the exciting things going on right now. There is
(02:11):
a team that I'm super excited about that I've been
helping to form a product um and it's in the
customer service space, um, and so it's not fully ready
for prime time, but that is also somewhere where're going
to spend some time. I think customer services this like
forgotten industry that people are so focused in the digital
world of like reducing the amount of customer service interaction
(02:32):
because it saves you money and cost. But it's this
amazing opportunity to sell, to understand your customer, to have
that touch point, which is so rare in a digital world.
So it's kind of flipping that on his head and said, like,
what if we actually deliver like a best in class
customer service experience, use that as a differentiator, funnel the
data back to make your product and your company even better,
(02:53):
and use it as like a third party service so
it could be plugged in play for the next digital
startup to just kind of outsource their customer or service
and have it be best in class customer services. My
whole business. I was gonna say, you definitely understand this
right between the businesses that we have here. It's it's
a lot of our business and then we have an
education tech platform and we've been hiring customer service people
left and right, and that's a big way that that
(03:14):
business grows and salespeople join us is because it just
doesn't exist anywhere, and they email us and we email back,
or they call us and they have a question about
a deal or anything that we're doing, and we respond,
and then they talked to another agent and that person
joins and so on and so forth. It's probably next
to content um those two c's, right, content and customer
service almost go hand in hand and your ability to sell. Well,
(03:37):
if you think of like the initial businesses like Zappos
on the Internet, they had this deep understanding of how
important customer service was and not just like let's fix
your problem, but the idea of having a human touch
point right, So Zappos mantra was like call the number,
it's plastered up on the screen, they'll talk to you.
There was no limit, they're not measuring the time you
can talk to you all day, and that was the
cornerstone of their business. So this realization of people like
(03:59):
the further you go into the digital world of making
things fast and easy and transactional, the more important it
actually is to have that in person kind of touch
pointed to feel like there's an entity behind the business
and the product you're buying to answer your questions and
what have you. And I think we've really lost that.
So I think it's a hidden opportunity. We saw it
with jet Black, So jet Black personal shopping over text
message I worked on with Mark Lore at Walmart U
(04:22):
and versus an Amazon where you're thinking, like, this is
a transactional, glorified search bar, Like, what is the ability
to differentiate it's in these like touch points, these human
more human feeling touch points. What was something you were
super naive about in your early days building rent runway?
I mean, just one thing. Um, So, first off, I
(04:44):
think that like being naive is one of the greatest
gifts of being a first time entrepreneur ignorance. Yeah, like,
had you ever known how hard it was, you would
have never tried. Um. And so a couple of examples
come to mind. You know, one is Jen and I
built a fashion technology business with no fashion background and
really no technology background either. But would you have built
(05:05):
it had you had either of those backgrounds. I think
we wouldn't have had the same fresh lens on the
fashion industry that we were able to really disrupt that industry.
And I think on the technology and logistics we would
have been probably too intimidated by how complex what we
were doing was that it would have just been too
daunting to go after it. But with technology, we thought
we could like outsource tech, you know, we like put
our request for proposal out. We found like what we
(05:27):
thought was the best engineering team, and we're kind of like, okay,
like see you in two months with our tied with
the bow package of a website that will like launch
and nothing like that. Nothing works like that right in
the world. It's like anything that's mission critical you need
to have your hands on, you need to own. So finally,
like flying to Canada where this team was and realizing
there was really not a team and the product was
so far from where it should be. Was this like
(05:48):
very naive moment of hey, we got to figure this
part of the business out and be much more hands
on and logistics to write like the amount of dry
cleaning you have to do. I mean, so I ran
logistics for about four years of my time. It rent
the runway. I joked it was like the last straw
drawn because just it was hard to hire for, it
was complex, it was a lot of work. We initially
used our local dry cleaner company called Slate in the
(06:10):
West Village, and it was like I was asking him
about dry cleaning to learn and to understand the pricing,
and then I was like, hey, you have some empty space,
like could we store our dresses here? So for a
while we had like a free warehouse essentially, but we
gave them all of our dry cleaning business, and pretty
soon it was enough money that we were spending and
we were busting at the seams from this dry cleaner
that we needed to create our own facility. Yeah, it's
(06:31):
like Coca Cola on the bottling yeah yeah. So yeah,
so we have our own facility. It's actually the largest
dry cleaner in the US, possibly the world, that's debatable,
but we have New Jersey and now we have a
Dallas facility as well. A lot of people that I
(06:51):
speak to, and a lot of people who listened to this,
are either like one or two spots. They have an
idea that's germinating that they want to do something with
and so they find inspiration from your story and your
multiple stories, or they're starting something and they have pain points,
right and they're trying to figure out like, Okay, is
this real? Is it not real? Or I'm trying to grow,
trying to get to that next spot. What was a
(07:12):
and I'm sure there's thousand of them, But what's a
pain point that sticks out to you today that someone
might encounter now in the ties kind of post COVID,
Like you just talked about customer services, something that maybe
we wouldn't have thought about so intently in two thousand eighteen,
but now is a big, big deal, especially digitally. So
I actually think ironically in customer services one example, the
(07:35):
rise of digital and the efficient transactions that it enables
has created all these I call them like taxes of
of e commerce. So for example, the idea that we
have everything in our fingertips now is actually really time consuming.
Like you used to be walked into a store there
was five types of shampoo or whatever it was, and
all of a sudden you can literally get access to
thousands international options and it creates this like analysis proalysis,
(07:59):
this rabbit hole where then we have to do the
research of which is the best and we can easily
spend like an hour of our time, which is our
most valuable commodity trying to decipher from this like all
these options, which is the best. Um so That's one
area that I think about. Another is like these hidden um,
these hidden costs of your time and things like returns.
So obviously, if you're not trying something on, you're not
(08:20):
going to the store in the first place, the odds
that you're going to get it right are a lot smaller.
And that could because it doesn't fit, or it could
be just because like you didn't actually like the product,
the quality wasn't good, it was the wrong you know,
the wrong color what you know, it's harder to tell
online and the process of returns right now takes a
lot of time and energy printing a label, going to
the hub spot to deliver and return the item. Um.
(08:43):
So there's like quite a few examples of these hidden
costs of time, even entering your credit card information and
your details right that that we all kind of encounter
on a daily basis. What was a career highlight for you, Well,
definitely co founding rent the Runway has been like this dream.
The day that we launched, um, we were covered in
the front page of the Tech section of the New
York Times, and it was when most people still had
(09:05):
physical New York Times delivered doorstep that moment, Yeah, where
I went to my own doorstep and saw it and
we were right there on the cover. And then you know,
going into the office that day, because we all went
into the office also at that moment in time and
like being able to jump up and down with the teammates,
my co founder and celebrate that special moment because a
lot of hard work goes into that that moment um.
(09:26):
So that that for sure was one. I mean, getting
our term sheet from a venture capitalist for Rent the
Runway was another. Getting a film before after that came
before the New York Times. Yeah, and you had a
publicist who helped you get that article. No, Actually it
was really fun entrepreneurial story where we had about thirty
customers when we launched Rent the Runway in like a
(09:47):
private beta launch and one of those emails natural organic Growth.
We were hustlers, like we got those email addresses through
our friends, our family, We hosted, like we would throw
parties for our friends if they gave us like the
most email addresses. We would go to the movie theater
lines of relevant movies like Sex in the City movie
and get with the clipboard like collect email address it.
(10:09):
Like we did whatever we could to get that email list. Um.
So when we launched to this initial group, there was
someone and then people started chattering and shared it as well.
But there was a New York Times email address on
the list. And we noticed this because you're kind of
if you're a good entrepreneur early on, you're paying attention
to like every customer and every piece of information. Um.
And so we reached out and we're like, listen, we're
(10:30):
psyched that you're a customer, Like, let us know if
you ever want to chat and lo and behold like
she did. And it was a young Newish reporter at
the time who came to our office and wind up
covering the story. Um, so yeah, it was she was
a customer. She was a customer, one of her first customers.
That's awesome. Yeah, it was incredible. And you know, we
then of course realized that if we she was a
(10:51):
tech reporter. So we saw that also and we're like, well,
there really aren't many women in tech, Like this was
a very to have a fashion article in the tech section.
I think also from like a strategic buy, were like,
this could be really interesting, and so we were like,
do you want some photos, like come to our warehouse
and we wore like these fun dresses and stood up
on ladders in the dry cleaner warehouse. I think we
had enough of the strategy ourselves, combined of course, with
(11:12):
some luck and you know, proactivity to just make this happen.
Were you spending marketing dollars yet at the time? Not really.
I mean I think that for for rent the Runway,
up until a few years ago, we were like plus
organic word of mouth. The big insight for us was,
you know, when you're at an event, the natural conversation
started for a woman is you look great? What are
(11:33):
you wearing? Right? That's how most women start, like break
the ice. If we could own that moment and have
someone say thanks, like I rented the runway, that would
be everything. You would answer a questions like what's round
the runway? How does it work? What if I spill wine?
What if it doesn't come or doesn't fit? And because
it was such a new behavior at the time, we
needed that trust and that you hear it from a friend, right,
(11:54):
you hear it from someone at a party. And so
we really invested in our brand. If anything, um so
not the traditional digital marketing, but yeah, making sure they
are packaging our website looks beautiful and aspirational, that we
had beautiful designer addresses, yes, and that the customer experience
was really good. So our customer service team, I mean
initially was us answering the calls and stuff, but we
tried to just nail that customer experience and you also
(12:16):
really nailed and you might tell me I'm totally wrong
with this and said, no, Ryan, that was a massive issue.
But like I don't ever remember when you started, um
there being an issue with the fact that people were
renting dresses and not owning them. Like there wasn't a
social issue, right, there was. There was no ego attached
to it, because like if you think about it now,
if you go twenty years ago and you're gonna pitch
(12:37):
that idea, it's like, no, I want to own my clothes, right,
that shows that I make enough money to be able
to do that and bypassed that wall. That wasn't. Yeah,
that was not a given and was something we were
nervous about and that the designer partners we worked with
were also nervous. And I'm sure because at the time,
you know, we launched two thousand and nine, many designer
brands were just starting to sell online let a interest
(13:00):
someone else to rent their products, pre owned products, and
so that was a lot to triangulate, and we definitely
didn't know if customers would think this was like ikey,
like how would they perceive it? Um. I think the
tail ones have really been at our favor and we
were kind of a little bit ahead of the game
and able to be a part of adjusting consumer behavior.
Sustainability has been a big piece of this mix too.
(13:21):
Write like, we've always been a sustainable concept, the idea
that if you rent and you buy less, it makes sense,
you know, it saves waters so many pieces from a
sustainability perspective, but customers really care now and when we
ask the main reasons people rent, that's now one of
the top three reasons. Yeah, Like because there's there's stat
(13:42):
that at least half the stuff in your closet you
really don't wear more than once or twice. And then
I feel bad for my clothes that I don't wear.
They're not getting a turn. I do feel all that.
I feel like we all kind of feel bad, right
Like I have I have like seventy suits. You don't
need that many suits. You would think I don't, um,
but I do. I do have a lot of suits,
(14:03):
and I built a new house around our closet. Um.
That was like the one thing we designed first, right,
it was to have like the greatest closet. You're such
a close I'm not really, I just wear a lot
of suits, um, and so I and I do feel bad,
like if I walk by a suit I haven't worn
in a little while, Like sometimes I'll whisper and say, like,
I'm sorry, going to give it a spin. Yeah kind of.
(14:23):
I think that's so so true and right, And I
think that in my head, Yeah, I hear you, yeah,
because I don't know, maybe because I saw a toy
story like a long time ago, and I'm like, I
wonder if my suits talk to each other, and like Ryan,
it's aware us anymore. Like the coloring is so cute
and so funny, and like, you know what in your industry,
clearly like presentation is first impression, impression if you're not
carefully And so that was actually a big piece of
(14:46):
Round the Runway in the sense that like we know
that as women, the way you look determines how you act,
how you feel, like the brand that you put out there.
When we launched social media was hotter, you know, I
mean now it's hotter than ever, but it was very
much on the rise. So the idea that you are
also putting a photo out there into the world that's
going to be this forever indelible like print of who
(15:06):
you are. You're sharing your brand. But then the way
it makes you feel, right, You're like I can take
on the world. And the brand that we built for
in the runway was around female empowerment and self confidence,
the idea that, like, your dress is not just an outfit,
it's how you feel and how you're going to take
on the day. So New York Times article comes out,
Were you prepared for the rush that came right after that? Lost? No,
(15:28):
But we knew enough to think about. We were always
going back to the customer experience, right, and so we
knew as customers ourselves, right, we were women in our
twenties launching the business. If we came to that site
and there wasn't a great selection of dresses of product,
that it would be a terrible experience. So we knew
that couldn't happen. And so what did we do. We
paid a lot of attention to waiting to launch until
(15:49):
we had a great beautiful website, great designer dresses in
enough sizes, some amount of quantity. And then we put
up a gate on our website, meaning that we only
let a certain number of people in, which really let
us control the traffic and demand. It also created took
away from the like rental could be down market. It
made it more like an exclusive thing. Yeah, and we
were coming up the tail winds of Guilt Group, who
(16:11):
who did the same thing. They had like this gated site.
They made shopping at a discount cool and exclusive and luxury.
So we drafted off of that and it let us
really control the experience customers had. So we stopped letting
people in. You know, we let in some every day,
but we tried to do it in a way that
we could manage. Um, and we were still figuring out
kinks and bugs as we grew. Um. There was the
(16:32):
second day we had the idea that you could get
a second size for free. So we didn't know we
knew people would have concerns oversizing, and so we're like, okay,
if you rent a size six, you get a size
eight for free. Like as we let customers do that,
and all of a sudden we saw no one was
renting a second size. We're like, it's free, Like why
wouldn't people do this? And we dug into it and
our chech was broken around like enabling you to show
(16:53):
move someone did this, and so what do we do?
We called everyone who had rented, because a couple hundred
people and it's not that it's not possible, and we're like, hey,
so excited, you're one of our first customers. Just want
to confirm the details of your order. And so it's
moments like that where you're kind of like drinking from
a fire hose. You're just trouble to figure it out.
You cover your ass, like yes, you figure it out.
(17:14):
And there was so many moments like that where, you know,
photographing our first stresses. It was like a week before
launch and the developers are like, okay, now we need
to load the photos and I'm like okay, great, Like
the designers give us photos and it's like no, no,
like we have to run a photo shoot. We're like
we have to run a photo shoot, like and then retouching,
like we had never done this. We didn't know what
(17:34):
this was. We didn't have a placebook, and so you
pull all this stuff together in like forty eight hours. Right,
another example of you knew how hard and all the
things you had to do, like you probably wouldn't have
done it, and you started with a co founder, yes,
and relationships are always hard, yes, right? How was that
kind of doing it together at the beginning, And it's
the two of you where their struggles as you grew
(17:54):
and as it was like Okay, I'm gonna handle logistics,
but I don't really want to. Could you do this?
And then the company grows and grows and grow. Yeah.
So I think it's first off, a lot more fun
like doing something with a team or co founder. It's
just more enjoyable how you spend your day to day. So, um,
it helps in terms of the complement of skill sets.
And for sure Jen is big picture strategic visionary thinker
(18:18):
much in the way Mark Laura is as well. Um,
and I'm like, how do you get from point A
to point B? So we recognize and respected in one
another those skill sets, and so I think the same
is true of when you you know, you pick your
partner and your spouse, when you pick your co founder,
it's like, as long as you respect them, and like,
I think so highly of them, it's hard to go wrong, right,
So the pieces of the business that she ran, it
(18:39):
was always like she is the best person to run
those parts of the business. And I think likewise the
pieces that I ran, That's how she thought of it
as well. So we reach doing so much and working
so much and so clearly like bought in that it
wasn't really a question of like who gets to do
this or who gets to do that? There was way
too much to do. It was just like if you
you know, if could take it on your plate. So
(19:01):
we didn't sink is what it felt like you would, um,
but the foundation of respect, a ton of communications and
just like then realizing, yeah, we're having more fun doing
it together. So there was never a tough point. There's
always tough points. I mean there's tough points with like
any relationship. And I think at the end of the day,
like forcing yourself to have sometimes weekly conversations whether there's
(19:22):
anything good, bad or otherwise going on, to like keep
the dialogue going and then you just be like super
candid honesty. But like we lived through so many moments
and experiences. I'm jen still running the business. She CEEO
of the business I'm still on the board of the business.
We still talk both as friends and as business partners,
like at least weekly, if not, like I probably text
(19:43):
with her daily. Right, So I think this underlying like
respect these moments that you've been through, um, Like she
is the best, but she's always been CEO. I've always
wanted her to be CEO because that is how our
business will be the best business. Like, That's how highly
I think of her. And there's many things I know
She's thought that I was the best person to handle
in the company as well. How is she living without you? Well,
(20:05):
we do still interact a lot. Um. I didn't leave
until I really felt like I had built an amazing
team around her. Sum, I don't think. I mean, first
of all, from a financial perspective, when I went and
joined Mark at Walmart, Um, I you know, I would
have never felt good about leaving, but that I knew
the company was in a good place and that she
(20:25):
had the right team around her. So I just helped
her hire like three really strong people in the leadership team,
and things were ticking and cranking, and I knew it
would be fine. Right. Can you tell me about that
moment though, deciding oh my gosh, to go do something different,
(20:50):
and that first conversation or was it something that was
kind of like, once I get us to this point,
I'm going to build something else. Well, So one thing
I think that helped was throughout the life the business
when we had we would have often conversations on our
life goals or ambitions, our aspirations, including from the beginning
when Jen was like, I really want to be CEO
and I was like, great, I think you'd be amazing
(21:10):
and SEEO right, And so she very much knew and
we would talk about the fact that I had this
serial entrepreneur tendency, meaning that like I always loved like
ideating starting new things, and so that at some scale
of the business it might not be my forever thing,
where Jen was like, I'm in this forever, like this
is my lifelong child like passion, you know. And so
we had that understanding behind the scenes for a long time.
(21:33):
Now what we were able to do is I laded
business development for a period of time at the business,
which meant that Jen was running the day to day
and I was like, what's coming next? Kind of what
Mark was doing for Walmart right, especially with the incubator
that we set up store number eight. It's like you
have the day to day and then if you have
a pot of people who are thinking about the next steps.
And so through that business we launched our retail stores UM,
and we launched our subscription service through that business development.
(21:55):
So I was kind of running like a mini startup
focused on the future with and Rent the Runway for
few years, UM. And I think because we would always
just talk about, honestly, like what our natural skill sets
and passions were. It wasn't a huge thought shock. It
was a conversation around like what was the right timing
so that like I could do what I wanted, but
also so it was the best thing for the business.
You are so positive, Um, what is what I was like,
(22:19):
can you talk to me about like a low day
Rent the Runway. It's still everything's great and it's awesome,
but there was just a tough COVID is hard, right,
COVID run the Runway and for your business, Like those
are hard moments, UM. I think you know. So this
was not that long ago. I was dealing with it
as a board member and as a friend and something
(22:39):
last big skin and really hard for the team. You know,
I think the flip side positive of that is if
that team can live through COVID, it's like you can
live through anything. If that business can survive COVID, then
you can. Like we were literally running a business that
was based on getting dressed for special events in a
moment when people didn't even need to get dressed, let
alone have events. So it's like, if you could live
through at it's like all those things that you thought
(23:02):
were problems like falls by the wayside, and so I
see it now on like a weekly basis, issues that
I think would have stressed Jena, would have stressed the
team out, roll off your back, and it's like that's
what I say about having kids too. It's kind of
like you learn not to sweat the small stuff and
like to like funnel up where you want to spend
your time and your energy. Um, but that for sure
was a hard period of time. I mean I think
(23:24):
that like for UM, for jet Black and the business
we started for Walmart, like hard that they decided not
to keep the consumer facing part of that business. So
the text platform that we built to enable text based
commerce is something that they leverage and so from a
impact on the world in Walmart. I feel great about that.
I feel like shopping over text and conversational commerce is
(23:46):
like the future. Um, but there were really pieces that
I feel like we're delivering to a consumer that I
miss on a daily basis as a consumer, and that
I hear from our customers all the time that they
miss So that like it feels a hard moment or
like an itch that I just need to scratch. And
I try to think of it that way that it's
not like it's not as much of them sad about
it is just like something I yet to tackle in
my career. What is a just thinking about this? What's
(24:08):
a good piece of advice that someone gave you not
to do where you follow the advice and thank god
they gave it to you. Okay, So two things that
come to mind. One is don't give up. So you know,
the first meeting that Jen and I took with the
designer was Diane fon Furstenberg hated our concept. I left
that meeting like, well that was fun for a few days.
(24:28):
Like the business. We we barely just started talking about
it and Jen was like, no, she just told us
all the things that were wrong, and now we know
how we need to reframe our sales pitch and go
back to the table, right and so like this no, no,
it means not right now or just you know again
the reframing, like I said, you know, I get to
be a mom or like hey, we get to receive
this amazing feedback from this really famous fashion designers and
(24:49):
now we can build anything stronger, right, Like I think
that lens has been really important. Um. You know another
thing and I now give this advice is not to
hire someone unless you feel super psyched about it. And
it's often so right, so tempting when you feel a
hole in your organization or you need to let someone go.
What I mean logistics at Runt the Runway, we needed
(25:11):
to let two key people go and we had no
one else to run the business. And we were like,
that's how I wound up running logistics. So for better
or worse, I think it was the best and I
know it was the best answer for our business. It
can be painful sometimes, but like you need to find
the right people. You need to like fire when you
know they're not right, and you need to wait to
hire until you're so excited about the person, and then
everyone has to be excited about them, right, everyone should
(25:33):
be yes, especially early on. I mean at some point,
however big the company is not everyone can know them.
Or you have different cults. You know, we have somewhat
of a different culture in our warehouse and logistics versus
our customer service versus the home office versus our retail stores.
Like so it starts to change a little bit. Where
do you see opportunity the future? Right as somebody who
(25:57):
because you you change the world of fashion right totally.
You brought fashion technology together in a way for women
people now that have never been there before renting clothing.
So two areas that I find really exciting. One is
what i'll call like infrastructure enablement. This idea that there's
certain parts of your business that are going to be
like the differentiating thing, the most important thing of your
(26:19):
business that like that is the core of what you
need to get right. Sure, there's a lot of other
things that like you can plug and play, you can outsource,
you can buy from someone else. That ecosystem is getting
better and better of the pieces you can plug in.
So think of Shopify for example, Like you can get
a website up and running in an hour. It's pretty good.
Now to shop by apps that like you can plug
in to do more and more things and customize it
(26:41):
more and more. The pace at which everyone is moving
because of these tools like requires you to have more
and more of them. So you know this company I
mentioned earlier, Cube Financial, it's like a financial budgeting planning tool.
Um that like it's much more plug and play than
like Microsoft Excel in terms of just letting you get
up and running more quickly. Right, you should have um
you have Carter who's helping you do like legal share management.
(27:04):
So these like infrastructure enablement, plug in play solutions is
one area I find particularly exciting, and that one also
I think is fun because it lets you as a creator,
like this whole world of influencers, Instagram, etcetera. Being a
creator if you wanted to start a business. You know,
Emma Chamberlain started a iced coffee business, right like she
can just go on Shopify. I think more and more
the supply chain of like how do you make icce coffee?
(27:25):
Like she needs to be good at what she's good at,
like her brand, how she talks about it, how she's
going to market it, but all the pieces around it,
like she can now build a whole business off that
platform and doesn't really have to do much except for
what she's uniquely good at. Right, So so that's part
of why I love that that infrastructure enablement. Then another
one that I find interesting is just old school, like
viral marketing and brand marketing. Paid marketing, paid acquisition has
(27:48):
gotten so expensive, especially recently with like the changes and
the stands around privacy, like and it's like there needs
to be a different way, And so we saw that
with run Through one Way, Right, I gave you the
example of just like the viral word of mouth marketing
is being so much more powerful, authentic, it cuts through
the clutter. We were also marketing for our designers, so
the idea of wearing a dress from a designer, having
that experience talking about it actually helps the customer eventually
(28:11):
buy from that brand. So I think finding these authentic
different ways to market college campuses, how bumble started right,
Like that tap tap into this conversation. Starters are the
most powerful, and like, that's what I look for in
a lot of businesses. Did you ever think about affiliate
partnerships with those designers that if that customer then comes
back and buys at another store, somewhere right that that
(28:34):
name is attached and you own that client. Yes, so
we we have. Um. I even at one point was like,
sometimes it's hard to capture it because someone might buy
the store and as you're seating, I was like, can
they bload a receipt and maybe they get a site credit? Yeah, indirectly,
you know, we've done click through partnerships. We do have
an affiliate program UM where you can kind of I
(28:55):
don't think we're capturing all of it, but these brands
are seeing enough of a feedback loop in terms of
the performance of their products, what customers are saying, as
well as a lift in their sales, as well as
real revenue that we're driving. So it exists. It's it's
hard to track. I wish it was easier to track,
but it was somewhat of a line item. Yeah. Yeah,
and and something we've iterated and talked about a bunch, right,
(29:16):
I'm sure. Yeah. I have one last question for you.
Can you describe for me your best day two years
from now? Um? So, the best day two years from
now is this business that Stealth business is raising not
only like maybe their Series A, but you know, first
of all, hopefully they don't have to raise a series
(29:36):
be raising money isn't always great, but it's just like
rocking and tacking along and it has a ton of
customers and is making millions in revenue and it's like
a party, just crushing it. Yeah, we're doing a big
party for them. I'm taking actually the founders out tonight
to celebrate because we just closed the initial like seed
funding and they worked for me before, so like part
(29:56):
of it is just I'm so proud because like I've
seen them in own them for years and they gave
so much to me to be able to try to
pay it forward and to see the success for them
now and like you know how exciting it is when
you get that first term sheet and funding and to
be like leaving a job at a big corporation to
take the sleep of they can risk and it's real
and it's happening for them, and so it's like, in
this weird way almost like more rewarding seeing it for
(30:17):
someone else. Um. So yeah, I just right now, I
think I'm pretty focused on getting them to their next
stage of success. One thing I say to entrepreneurs is
and like create an email address that's just like memories
that Rent the Runway dot com memories, is it right,
and just copy it on stuff like like moments right
that you have no time, Right takes you no time.
You can send photos, you can just copy it. When
(30:38):
you're sending something to someone else, you're sending a board
update with the key milestone, a partnership meeting, and like
emailing with Dan Dan when person and then like, at
some point you'll go back and look at that. In
the moment, it is so hard to realize and appreciate
the amazing stuff that's happening, and so like, now if
that lends looking back a Rent the Runway, it's like
one thing I tell all founders what's to do. Big
Money Energy is hosted by me Ryan Sirhant. It's produced
(31:02):
by Mike Coscarelli and Joe Loreesca and executive produced by
Lindsay Hoffman. Find more podcasts like Big Money Energy on
the I Heart Radio app or wherever you get your podcasts.
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