Swan Sit

This week we're joined by Swan Sit, global digital marketing executive, Clubhouse’s biggest star, and board member of three public companies. We chat with Swan about immigrating to the United States as a child, her incredible career, being managed by Gary Vaynerchuk, and of course, her personal life!  

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Episode Transcript

Speaker 1 (00:00):
Hi, I'm Sam Edis and I'm Amy Nelson. Welcome to
What's Her Story? With Sam and Amy. This is a
show about the world's most remarkable women, their professional and
personal journeys. Together, we'll hear from gold medalists, best selling authors,
and leaders of the world's most iconic brands. Today, we're

(00:27):
really excited to welcome Swan sit onto the show. Swan's
bio is hard to summarize quickly, but I will try.
She is formerly the head of digital as such iconic
American brands like Nike, Revlon, and Stay Lauder. She is
on the board of three public companies, and she might
be Clubhouse's biggest star. That said, I was so sad

(00:48):
to miss this conversation with Swan. I can't believe it.
I had just gotten back on a red eye and
and wasn't able to join post pandemic problem theme. It's
something that we never would have imagined just a few
months ago. But you will love her, and I will
definitely make sure the three of us get together because
I just fell in love with her. She's so candid
and so honest. I definitely left no stone unturned in

(01:11):
this interview, probably made her blush a couple of times,
but it was worth it. It was a great conversation
and I can't wait for you to hear it. All right,
let's listen. I want to start with sort of an
obvious place, which is Clubhouse. So I was one of
the early people on Clubhouse. I got on in July

(01:33):
fourth of last year, was super into it for a
few weeks, and then I thought like, what is this.
I couldn't really get my head around it, and I left.
Left for eight months. Right, big mistake came back and
they were like, all right, and they're like millions of people,
so how did how did you avoid that mistake? Tell
me I was grasping for connection a year that we
were all so separated from our friends or community, even coworkers.

(01:57):
And I was in Boston with my family, in my
childhood home, hanging out with my folks. Now they're amazing people,
but for an extrovert, hanging with your two parents for
a year really quiet. So when I started on Clubhouse
at the end of May, it had nothing to do
with room titles or programming or resetting rooms and mods.
It was a bunch of people hanging out, and honestly,

(02:17):
I think that was my benefit because when we joined
in the spring, there's maybe thirty people on to night.
You went on to reconnect with old friends and to
meet new ones, and because I think that was the
core of everything I did, even as it scaled in
July or in the fall, I didn't think of it
as a platform that we were trying to build a
presence on. It was still meeting great people and having
an online community. So I think that's why. Actually, in

(02:40):
a way, being early obviously was great because you start
building a following. But my mentality was to approach it
as a social connection piece, not as a broadcast platform.
So in a way, it accidentally served me in the
best possible way, and I just continued with it. It
was a community I loved that I wanted to serve
and continue to be a part of. So I stayed.
And how had that changed the factory of your career?

(03:01):
It's life changing. I was always behind the scenes at
brands like companies like Nike, Esta, Lauder, Revlon, and now
I think I can call myself a creator. It's so
really uncomfortable to say that, but I love amplifying people's
stories and giving people access to opportunity and information so
in a weird way, just by hanging out on clubhouse

(03:22):
and wanting to help people at scale. Now I've signed
with Vanner Talent. We just announced it yesterday, so I'm
officially a creator and we're going to develop programming that
will help people at scale. A year and a half ago,
I was still in the corporate ladder working with big companies,
which there was a time and place for. But now
I think those those networks, those skill sets will create

(03:42):
a landscape and a platform for me to do completely
different things. The irony is that I was Gary Vynerchuk's
first ever client that he managed, his first ever talent
that he ever managed, and that was in a different
stage of his career, and there was no vain or talent.
It was just a very very long time ago. And
we had a talk show that we did together called

(04:02):
Obsessed TV. And Gary would come in the beginning and
he was kind of like my outbroker, called him my gelman,
and he would be there for the whole show and
then at the very end he would have a glass
of wine with me and the guests. So that was
a very long time ago. We did seventy five episodes
of the show and Obviously, Gary's career has changed a
lot since then, so tell us about the evolution of

(04:22):
how that happened for you. Well, thank you for paving
the way for the rest of us, because look at
your career. Now you've got this incredible podcast, So hopefully
I'll follow in your footsteps. Gary and I met years ago,
I believe in a south by southwest of End, and
you know, he's a very busy man, so for us
to have time to sit and have lunch was a
pretty remarkable moment in the intersection of our lives. We

(04:44):
talked about our families, our childhood's are values and something
just connected. And since then he's someone I like to
call a friend. Tour right, somebody I've had the privilege
of calling a friend, but been incredible at a shepherding
some of the pivotal moments in my career. From when
we or at Elizabeth Arden. We used digital to save
the company and we got acquired by Revlon. I was like,

(05:04):
do I still want to keep doing this? He was
there for me when I left the beauty industry after
eight years across Laughter Arden and Revlona decided to go
to Nike. He was there for me and what was
his advice during that time, Do what makes you happy.
I know that's really trite, but when you compare it
against the corporate ladder, sometimes you don't have the luxury
of having both. And what I needed was the confidence

(05:26):
at that point to realize I've built a credibility and
a track record of doing two decades in corporate and
maybe if I were five years in it wouldn't have
been the right time to leave. But he could see
me straining at the edges as an entrepreneur. I don't
love that word, but that is what it is. When
you do digital transformation at legacy companies, you're trying to
convince them how to sell differently on e com or

(05:47):
broadcast messages on social or to let influencers in the
public represent your brand. That's really uncomfortable for legacy companies.
So he could see me straining at the edges, wanting
to do more, wanting to be bigger, and I think
at some point the confines of corporate weren't going to
allow me to move as fast as I wanted or
be as creative as I wanted. So his advice at
the point was to give me a bit of confidence

(06:09):
to say this is your time, whether it was to
move from beauty to sports or from being corporate into
my own life. I've built enough of a platform and
a network in a confidence that I could shoot off
into it. So I think it was the right time
to hear that message. The credibility he has, the experience
he has it with the confidence I needed to get
past that imposter syndrome and to really lean into this.

(06:31):
So it's beautiful that through all his advice over the years,
it's come full circle and I get to work with
manor talent now in five years, where do you hope
to see your career? You know, we all get asked,
what do you want to be when you grow up?
When you're a child, I still have no idea. I
don't even know what two years from now it looks like.
But I enjoy every minute of what I'm doing right now,
and I think the core of it is democratizing access,

(06:54):
information and opportunity. I came to the U S when
I was six years old. My parents didn't need and
finish middle school in Hong Kong, so we had some
pretty humble beginnings, and through some hard work and a
lot of luck, I ended up with some incredible opportunities,
but not everyone follows that same path. So my north
star and everything I do is to democratize that access.
Clubhouse in a way has allowed me to do that.

(07:16):
But who knows what it is. Maybe it's a book
or a podcast, or a show or more events based
things I actually don't know yet. But part of that
journey is being open to the discovery. Because I've been
so programmed in corporate for so many years. Now, we
have a blank slate. So if n f t s
come up or SPACs come up, I can say yes,
out of curiosity, go learn and play and see what

(07:37):
we can build. But as long as I'm democratizing other
people's access to it along with my journey, I'm happy
with that. Who knows what that looks like, So check
in with me in a year and we'll see. So
let's go back to your childhood. I know that you
came here when you were six years old. That's something
that you and Gary obviously have in common, is those roots.
Tell me about what it was like for you when

(07:58):
you first arrived in the US and how you assimilated.
It was such a double edged sword, Like I think
with most immigrants, kids coming over. In some ways, it
was incredible. It's a whole new land. Had never been
on an airplane, and I get dropped into this new country,
and the living situation was part of the craziness. So
my dad had eleven siblings, and his younger sister came

(08:21):
and married somebody who was born in China but grew
up in the US, and they had six kids, and
then brought my grandparents over. So you have my aunt
and uncle, my two grandparents, and then six kids, Eugene
and then Pollyanne, Marian, Rosanne and Suzanne. You've got six kids.
So now you've got you've got but ten people in
a house packed in half of a two family house,

(08:42):
My family of four, my cousin's family of three. So
seven of us get on a plane, fly to Boston,
and the seven of us move in with the ten
that were already there. So it was crazy for me.
It was like one long, perpetual sleepover with my cousins,
who are your first friends. But it really gave me
a soft landing into a country that is so different
culturally with language and customs and and how we live.

(09:04):
But it was such a beautiful on ramp to American
culture that then I still really enjoy the duality of
being Asian American. But that said, it was kind of
tough right without language, with my parents being entry level,
working class here, without even starting high school, it was
a tougher childhood. What did they do? So my dad
worked at a restaurant. He was a truck driver in

(09:26):
Hong Kong that he came to the US, worked at
a restaurant and worked his way up. Within a year,
he went from being entry level in that kitchen to
running the entire kitchen of that four star restaurant in Boston.
And it's an incredible story. I still look back to
how do you go from washing dishes and working the
grill to run in an entire kitchen of a gourmet
restaurant and then opening a second location for the owner.

(09:48):
And it's hard work, kindness and ingenuity, right. So my
dad would tell me stories about that kitchen. They made
everything from scratch, right, and that's part of the work.
Think of an immigrant mentality. You buy harder sauce, you
don't buy clam charter. You make it all from scratch.
But for every hundred dollars in revenue, my dad saved
seven dollars in profit for that owner with a hundred

(10:10):
and fifty seat restaurant. Think about the impact of how
much more money in the pocket of the owner there
is every single night. So my dad went from running
the grill to running the restaurant. Then my mom came
worked at a jewelry factory stringing beads onto strings and
became a jewelry designer. Then my parents decided to run
dry cleaners and laundromats, so I worked at a dry

(10:32):
cleaners every weekend. In my childhood. I was front of
house customer service, so you can see how I always
look at things from the customer's standpoint, right because I
worked front of house when I was fifteen years old.
All of that rolls in together to think about how
the components of business work. Regardless if you're at a
Fortune five D company or you're running a neighborhood dry cleaner,

(10:53):
it's still the same elements of service of unerstanding consumers
and giving them a product or service at a fair
price that everyone wins for. It's the same construct. So
that was super pivotal from my childhood. But layer that
on with a kid with a weird bowl hair cut,
with purple glasses, which would be cool nowadays if you're
living in Brooklyn. But back then I would run around

(11:14):
with a terrible bowl hair cut, big purple glasses. I
would talk about space all the time because I was
really into science. I didn't have a lot of friends.
But again I wouldn't trade that either, because that's that's
where the kindness and empathy come in. Right. I know
what it's like to be an outsider, and maybe I
always will be. But the more inclusive I can make that,
the richer our communities are. So there's seventeen of you

(11:34):
living in this house. How big was the house. It's
half of a two family house, so there was one room.
I think there was like five of us bunked up.
But when you were a kid, I was six years old,
that was a sleepover a paradise, I mean, how fun. Yeah,
it was super Even for your parents, it probably was
a lot easier than if they'd been alone with you
because you had instant entertainment exactly. So I learned English

(11:57):
very quickly. Running around with my cousins, you had built
an friends and family, and to this day, my cousins
are extended family. It's a really tight knit unit because
too on board to a new culture and a new
country together. I mean, there's nothing more bonding than that.
And even though we only stayed in that house for
six months as a group of seventeen, the seven of
us that came over, my family of four and my

(12:18):
cousin's family of three, we all lived in another house
for another few years together, because that's what you do,
You stretch to make the ends meet. We clipped coupons
to buy groceries, and we shared and and collaborated, and
you know, that makes you realize you can do anything
if you're doing it with good people. What have your
peers grown up to do? So your siblings and her cousins,

(12:40):
we're all so different. My little brother is in I t.
He has the same friends as he's had since childhood,
who are all my little brothers. But he really likes
the technical component of what he does. I have a
cousin who's a bigger one who's an artist, another cousin
who's in business, like meet, so we run the entire gamut,
and that also keeps me really grounded. I mean, the

(13:01):
Asian Tiger parent dream is for all of us to
go to Harvard and to be doctors and lawyers. Right,
not all of us did that, and so being able
to kind of break that norm. I'm still grateful for
having gotten to where I am, but to recognize that
each of my cousins and they're all creative in different ways,
We're equally bringing fun things to the table. I think
you see it at Thanksgiving when I come around and

(13:23):
what am I doing. I'm not giving PowerPoint presentations, but
my chef cousin is creating the best turkey and the
best cakes for us. So you know, we all bring
different skills to the table and dispelling that myth of
the Asian tiger parent. We're the only way to succeed
is the doctor or lawyer path. None of us are
doctors and lawyers. Although you did, you did end up
at Harvard, so you were the you were the tiger

(13:43):
parents dream. How did you end up at Harvard? Through
a lot of luck. I mean it was my grandfather's
dying wish I go to Harvard. And if you're an
immigrant family, you know Harvard. And we used to joke
that and a minus is an Asian f because it
was a's or nothing, And there was I do remember
one Cemes who I brought home a B. Plus my
parents didn't talk to me for a month, and so

(14:04):
it was a little bit of tough love. But gosh,
I mean, what a road it set me up for.
But the reason I got into Harvard because honestly, there
were so many applicants with better grades and s a
T scores than me. But I really enjoyed democratizing education.
I didn't call it that back then, but I loved
sharing and learning with people, and I was lucky enough
to do some enrichment programs at m I T. When

(14:26):
I was in high school, I went to school twelve
months out of the year, so there was never a
summer vacation, and oftentimes my parents would send me when
I was younger, so for example, if I was going
from third to fourth grade, I would go to summer
school with the fourth grade kids that were held back. Again,
didn't make me so popular, but my parents thought they
were getting me a year ahead, or at least keeping
me occupied for this summer. But as I got to

(14:47):
high school, m I T ran so many enrichment programs
that I could take versions of college classes and be
around other kids that thought it was cool to be smart.
So my junior year summer, I ran a program as
half facilitator, half student with m I t called MESH
and the premise is you learn the best by teaching.

(15:07):
So you have to take a course taught by another student,
but you have to teach an ap course to a
class of peers. And that made me realize, Wow, when
you teach, you actually learned better than anyone else. And
I was fascinated by that new way of learning. So
when I got to senior year, I applied early to
Harvard and I got my interview. You can't make this up,
but my interviewer was a high school teacher, so instead

(15:30):
of a thirty minute conversation, we sat for an hour
and a half talking about modes of education, how people learn.
And this was like in the mid nineties, no one
was talking about alternative forms of education. And this is
also before cell phone. So my dad's in the parking
lot panicking that it was supposed to be a thirty
minute interview and I'm gone for an hour and a half.
But I still remember that interview so well, and it's

(15:52):
because we bonded over alternate forms of education. She saw
something in me that would democratize how we teach people
how we give people access, Because to even have that
interview was so lucky for me. What could we do
if whatever we achieved we shared and we came from
a place of abundance and thanks to her. I mean,
I wish we had social media. I can't track down
who that interview or has she changed the course of
my life? But it was a whole lot of luck.

(16:14):
You graduated from Harvard in two thousand or when was
it two thousan? Yes, right at the crazy dot com boom.
I was ninety four, so I'm six years you know,
ahead of you. What was it like for you when
you arrived there and you had had such a different background.
Although I would say that everyone there has such a

(16:35):
different background that it kind of makes there's everyone there
stands out right, no one fits in. But how was
that for you when you first arrived and you suddenly
are thrust in this rooming group? What was that like?
It was so different? I think everyone ends up with
this syndrome where you're a big fish in a little proble,
no matter how good your high school was, and then
you get to college and it doesn't even matter which college.

(16:57):
Everyone realized, Wow, I'm a small fish in a really
big pond. And you know this at Harvard. If anything,
I mean, that's the biggest shock. We all know there's
people smarter than us, but when you're sitting in a
room and you're looking at that curve, it really hits home.
And I still went in head first because remember, you know,
I was doing programs un m I t I skipped
pre Captus and went straight to Calcus. I'm like, I

(17:19):
got this. I'm going to be a neurosurgeon. Because I
was still on that Asian tiger parent path. It's like,
I got this, I'm going to be a neurosurgeon. I'm
going to skip all the basic classes, take upper level
you know, genetics, and take only math and science classes.
And I got my butt kicked. So that was a
humbling experience to realize that it can't be just will.
There has to be a plan, right, Like everyone has

(17:40):
a plan until they get punched in the face, right.
So that was a good humbling modulation of how I
can cadence my path and my learning right because Will
can only take you so far. We physically just can't
take that many classes. There's not even that many hours
in a day, So that was a good learning and
I actually ended up switching from bio chem to econ
because I thought I wanted to do biotech. And then

(18:00):
when the dot com first really happened in two thousand,
I leaned into just simply doing technology. But the academics
is one piece. The social piece was a whole other
component of it. And you know this. I mean there's
in any college so many different social groups. And what
I realized is for the first time, I think M I.
T was the start for those enrichment programs, but Harvard
was really the eye opener that it's okay to be

(18:23):
smart and want to learn and be curious, because it
wasn't so cool in my high school to do that.
You know, those were the geeks in the corner. They
were the ones who studied and the rest of the
people party. Like I never went to homecoming. I never
went to a single football game. My parents were really overprotective.
So I get to college and all of a sudden,
the floodgates open. Right, I can go to football games,

(18:44):
I can go to parties. I can join sixty clubs,
which I think I might have done. So that was amazing.
I mean, it was like eating at a buffet, but
I honestly ended up having trouble finding my place because
when your hammer, everything looks like a nail. So I
managed the men's hockey tea, I did drama. I started
our first internet magazine. Right really cool, but I'm all

(19:05):
over the place. So to this day, I think that
complexity in me, like the fact that I worked in fashion,
but I summit mountains and I can love being creative
but also being a techie. That's still me. But when
you're in college finding your identity, you don't have a
core group, like my blocking group is diverse. We were
the first year that was randomized. So to this day,

(19:26):
I still love going back to college reunions, but it's
not like I have a core group to go back
to because I wasn't the athlete or the thespian or
the pre med I was a little bit of all
of them. So I wouldn't trade that. But yeah, for
I don't know if you went back to reunions. I
go back to every union, but I was. I was
an athlete, so I had the benefit of being in

(19:46):
a crowd. Was that the right crowd for me? I
don't know, But that's just the crowd. I was kind
of thrust into do you still go back and hang
out with those athletes or is your group more diverse? Oh?
I am so close with all of my call friends.
I mean we are all very, very tight, And I
would say most of them are athletes, although a lot
of my girlfriends are not. But my girlfriends, I'm super lucky.

(20:08):
There's like ten of us that go on a trip
every year for a weekend, so and only a couple
of them are athletes. Most of them are not, But
a lot of the guys I was friends with were athletes.
But yeah, I would say that my college friends are
are among my closest friends even today, even if we
don't talk a lot, there's that that thing in common.
But I hadn't thought of what you were saying, which

(20:28):
is that if you're involved in a lot of things
like it's like master of like who's your team, who's
your pocket? So are you still close with your college
friends with any of them? I am, But they're all
over the place. There's not one group. And I envy
you a little bit with your with your athletic background,
because there's an inherent structure that keeps you close. I
was part of a sorority which was off campus, and

(20:49):
that group I'm still close with, but they're all individual
pockets of people. Right. In some ways, I'm envious what
you have because you go back to reunion, you've got
your blocking or rooming group, and you roll as a tribe.
So my experience in business school was very similar to
your experience in college, where there was a big click
and I wasn't part of it. I had this friend
and this friend, and throughout my life I've been the
person who has like pockets of close friends in different

(21:12):
places and not a clicky person. So I relate a
lot to what you're saying because there is a comfort
in being part of a clique. And when I go
back to my business school Nians, I'm very aware of
the fact that there's a click that I'm not part of,
so it isn't as comfortable. But do you think that
changes over time? The only reason I ask is college
reunions at the five and ten year mark were like,

(21:34):
five year was, oh, I get to see old friends.
Ten year you're kind of looking and comparing against each
other and where your careers are because we're all over achievers,
let's face it. Fifteen is a little bit more of
the same where you bring kids into the picture and
you're kind of doing that. But what I loved about
the twenty year which I just had as we all
realized we have no idea what we're doing. We're no
longer in those clicks and silos. We're all going through

(21:55):
midlife prices. Is this the right career? Did I marry
the right person? And we all came back to the
table and we're like, we are so lost, And that
was It felt like freshman year all over again. Right
we shed all the hubrists and the constructs of our careers,
like I'm leaving corporate. This person realized they hate medicine,
and we're like, god, we're lost. And it became right
back where we were in freshman year before the clicks

(22:17):
had formed, and we were turned back to being like
eighteen year old lostles and it was beautiful. And now
for a quick break. Okay, so take us back. So
you graduate from college and your parents thought you were
going to be a neurosurgeon and then you end up
at Trilogy in a tech company. How did they react
to that? You know, at that time I had already
braced them for change, because I spent a year in college,

(22:41):
took all these upper level biochem classes and hated it.
So I said, I don't know what I want a
major in, because in their second year you have to choose.
I'm going to go abroad for a year and what
Remember I had not been an airplane on an airplane
since I was six years old. When we came from
Hong Kong to Boston. That was the only time I'd
ever been on an airplane. We had a humble background,
so we we did road trips to you know, the

(23:03):
Cape or New Hampshire for summer vacations. But we couldn't
afford to take our family on an airplane anywhere. So
they said, wait, you're going to leave college for a
year and go to London, And I said, until unless
you tie me down, I'm going because what first year
helped me realize is so many people came from all
over the world and so many different walks of life,

(23:26):
and I'd seen such a narrow slice, and I knew
I wouldn't be able to get the most out of
college unless I took a chance and just expanded those horizons.
See a different country, see a different culture, and make
decisions for myself. So sophomore year I left when abroad
for a year, my parents freaked out. They called me
every week. I think they called me every day until
I stopped picking up the phone because we didn't have

(23:46):
cell phones then, so they called the place I lived
and I just wouldn't pick up the phone. And I
trained them to realize there's different paths, and I'd call
them once in a while, and every time I called them,
I give a little bit more about the life I'm building,
the maturity I was advancing into an and learning to
make my own decisions. By the time I got back,
they were just so grateful that I was in one
piece that by the time I finished college and I

(24:07):
said I'm going to do tech, they gave me space. Well,
but it's super rare to go away our sophomore year
to another country. How did that happen? Well, I finished
the first year realizing I took all these biocam science
and math classes and none of them are going to
count for my major. And I had no idea what
I wanted to do. So you remember, we had proctors
and advisors, and I had a really good conversation with

(24:29):
some upper classmen, and also the person who was in
charge of our our house, and they said, have you
ever been away from your family, away from friends? And
I said no, Like do you know how to make
decisions for yourself? Yet I was like, I have no idea.
I was told this path is the one I was
supposed to serve, but I'm miserable. And they said, they
didn't say go away for a year. They said you

(24:49):
might want to spend some time thinking about that. So
that summer I took some courses at the summer school,
just in different areas. I'm like, let me try this,
let me try that. And I realized there's so much
more in the world out there, so I will say this.
Harvard doesn't sponsor work abroad or study abroad courses or
programs that well. But I knew I needed to do
something different. I knew I could get a work visa

(25:09):
in London. I knew I spoke the language, so with
a little bit of help from the career office, I
was able to set those up and I just picked
up and went. I didn't even have a job when
I showed up. I landed in the ground in London
and started looking for a job. But that's arguably the
shock I needed. It wasn't a predescribed path of climbing
an academic or a corporate ladder. I showed up and said,

(25:30):
oh my god, let me go get the help wanted
ads and see where I can find a job. And
that is so brave of you, and that it's really
very unusual, especially given your sheltered background. It's really incredible. Well,
I think I realized it was so sheltered and I
wasn't living the full life that I could because I'd
get to college and people had spent summers in France

(25:50):
and gotten to travel to Africa, and I was like,
I literally have not even been on an airplane since
I immigrated to the US. So, you know, in some ways,
while I've been corporate for a long time, I think
my spirit is quite adventurous. So that fed it. And
let's just say, you know, that was probably an overcorrection
to run away to another country for a year without
a job, but I came back and ended up just
like crushing the rest of college and really finding my voice,

(26:13):
finding my activities, my friend groups, and having confidence that
I am a complex and kind of random individual, but
I can have lots of different groups and interests and
that's okay. Well, that's one of the things when I
was researching your background and really China, understand your path.
It's not linear, right. You have a very strong corporate background,
but you also clearly have a strong entrepreneurial bent. So

(26:37):
when you look at if you had to look at
a pendulum and one side is entrepreneurship and one side
is corporate, where do you feel like you're naturally set?
There's a difference between inherent nature and the skills you build.
I don't think I'm a true entrepreneur. I spent a
lot of time with entrepreneurs, and they're born differently. It

(26:59):
is a different breed. So my risk tolerance, whether that's
inherent or whether that's growing up without a lot of
means my risk tolerance isn't there. But the way I
push boundaries are. So let's say in that spectrum, maybe
I'm fifty fifty, but the construct of how I think
is probably seventy entrepreneurship to corporate. The skills I built

(27:22):
to have the confidence and security that I psychologically needed
was probably the other direction. So somehow it mixes in
the middle. But what I don't think it is is
that it's it's not a static fifty fifty. It's almost
like a seesaw. Right. Some days I'm more entrepreneurial, some
days I'm more corporate. And corporate can be good. I
tell entrepreneurs there's a reason certain strategies and structures work,

(27:44):
and if you're running a thirty five billion dollar company,
you have to have hierarchy and hr practices and process
otherwise you have end ron right, So there's a balance
between the two. But it's a sliding scale day to day,
and some days I have an entrepreneurial hat where I'm
trying to figure out what this next phase of my
life is like. Other days I'm trying to wrestle this
clubhouse topic into a run of show with a producer

(28:07):
and a bouncer and structures so that while it might
look like it's a casual room on the front end,
on the back end it's very well programmed debt and
we have every contingency plan for So it's a sliding scale,
and I actually love that we can celebrate it because
the paths were so different for so long. I think,
you know, because of higher education, we've gotten really siloed

(28:27):
in the professions we do or the skill sets we have.
But go back to the Renaissance. I mean people the
same people were doctors and lawyers and philosophers and artists
all in one. And I think because we're questioning the
constrict of higher education in addition to the cost of it,
it's giving us freedom to say, well, maybe I don't
need that graduate degree. Maybe I can be a creator

(28:49):
and incorporate and an artist and an athlete all in one.
So that duality or multiplexity is actually what I think
makes us all richer, and it's becoming Are okay to
say that and be celebrated for it? Okay, So you
were running global digital marketing for Nike and then you
decided to leave. That must have been a huge adjustment

(29:10):
in terms of a lack of structure for you. I
didn't go completely cold turkey. I think my innate personality
is to be organized. So whether it's incorporate or as
an entrepreneur, my calendar is always filled out and it
has all the details and every person who's supposed to
be invited. So because you know, my friend's joke that
sometimes I feel a little German because I'm so precise

(29:30):
with the calendar, I just think it's because I'm forgetful,
because if it's not on my calendar, it won't be there.
So I create my own structure for that. It's just
what we slot in. The calendar now is much more open.
So in some ways it was a tough transition to
not have the support and the brand and the resources
of corporate but it opens up so much blue sky thinking.

(29:53):
So I would say that transition it wasn't about the
change in structure. That part was easy because I structure myself.
It was about what those possibilities were that you fit
into the structure. Because when I left Nike, I didn't
think I was going to be a creator. I was
lucky enough to get on my first public board. Then
I was on a second one, Then I was on
a private equity board, then I was advising a VC.

(30:14):
I'm like, wow, I can take everything I've learned and
help companies and entrepreneurs. Like, what a great way to
use that skill set. Right, there's the sweat equity, and
then there's sounding smart and letting people learn from the
benefit of my experiences and my mistakes. I evolved into that,
which was still structure, but I realized what I've learned
and the things I've gained can help people at scale. Right,

(30:35):
So that was the nice first transition, and then the
creator thing came later. So now it's a balance. I mean,
I do sit on public company boards, but I'm also
on clubhouse so there's not a lot of us who
do that. But the intersection, I think is where actually
our future is. So tell us about company boards. I
think that for people who are not familiar with how
you get on one, what you do once you're on one.

(30:56):
People don't realize that it's a paid position. Share the
process of getting on one and what it's been like
for you. It is the best kept secret. I had
no idea what public boards were, and it was familiar
with board positions. I've done it for nonprofits and for
industry organizations, but for publicly traded companies, board seats are
paid positions and its governance, you represent shareholders. The way

(31:21):
I describe it to people is think about Apple and
how many shares of stock are at there. There's thousands,
if not tens of thousands of shareholders, but they're technically
the owner owners of the company, and the boss of
the CEO. CEO can't talk to tens of thousands of
people and ask do you like my strategy? So we
elect a board of directors to represent the shareholders that

(31:42):
govern the company. And so when we hear about boards,
we often think of startup ones where we're helping and advising,
and a public board, you're the CEOs boss and you're
basically making sure the executive team lives up to the
expectations of your shareholders. Completely different role. So when I
first heard about it, my friend was consulting for a
small pharmaceuticals company that's public and going through a turnaround.

(32:06):
The one benefit for me in these board roles is
the average agent board members is sixty three. I'm well
shy of that, but rarely do you find people in
their sixties and seventies that are experts in digital. And
that's the one skill, universally that all companies need. So
in a weird way, being an expert in digital has
helped me get my foot in the door. Because that's

(32:27):
small farm, a company that just lost insurance reimbursement for
their key product because there's so many copycats. They needed
somebody who is going to help them pivot the business
to D to C and no one in Farm at
that's sixty five years old was going to be able
to do that. So that's how I got my foot
in the door. They needed digital. I knew how to
do it, and we've been taking this company on a
turnaround for the past year and it's working. Then it

(32:49):
opened up another door because once you get on your
first public board, you get on your second one, etcetera.
But they're paid positions. It's a completely different set of work, right.
I simply govern. I do not lean in and operate.
I barely even advise too much because we represent shareholders,
but we do shepherd the company and the future and
shareholder value. But once you get on one, you get
on another. So my advice for people who are looking

(33:12):
to get on boards is first start getting experience. If
I hadn't been on nonprofit in industry boards, I wouldn't
have been considered. It also helps that I worked at
publicly traded companies and doing strategy or digital, I often
had to prep the materials or even present to the
board about our strategies. So I've been on the other
side of the table, right and those things certainly helps.

(33:34):
So I tell people, anytime you want to think about
a board position, you have to start with baby steps,
show you know what being on a board looks like,
then start having small wins against it. But the piece
that I think is really important is understanding the gaps
and what boards need now. And it's candidly women and
people of color. Right in California, every public board has

(33:54):
to now have a female Goldman Sacks won't take a
company public without a female on its board. So for
our audience, this is the perfect time for us to
stand up and raise our hands. Build experience. It doesn't
matter if it's a nonprofit or startup, to start learning
what it's like to be a board member versus an operator.
The third pieces, raise your hand, because all of this

(34:15):
is done through networks. There's no job postings. There's a
handful of sites that people can go to, but all
of mine we're through referrals. So just by saying I'm
interested in this, if you know of one, please let
me know. That is half the battle. That's awesome, it's
really inspiring hearing you. I think that especially you just
gave us like a masterclass in in board and in

(34:36):
boards and how they work. And I think that for
a lot of people it just seems so opaque even
if you're in business, right, even if you have the
m b A, it's still this opaque process that people
don't fully understand. Let's go back to your personal life
for a moment. Who like, for example, when Gary approaches
you and says, okay, I want to sign you. Who
is your personal board of directors? Who do you go

(34:57):
to for advice? I consider some of my best friends
my friend tours. Those are the best relationships and they
don't even have to be in business. They just have
a really balanced view of not only life but me. Right,
those are the people that I can trust when I'm
out of line, They're gonna say, like Swan, you know,
maybe you should be getting more sleep, Like I know

(35:18):
this is an amazing time for you, but are you
really taking care of your health? Or hey, I was
that the path you really want to take? Right? So,
in some ways, we all have professional mentors that we
look up to. Gary's one of them, right, I have
a few more out there that you know. There's a
woman named Carol Cruz for example, that um I call
her a friend tour. But we even though she's about
a decade more senior than me and our career journey.

(35:39):
We both joined our first public board at the same time.
So what an ally you have, right? I have someone
a group called Executive Women in Business or sorry, executive
Women on Boards, and it's women on boards, especially ones
early in their journey. So in that group, this woman,
Lisa Shalott, runs an incredible platform for us to connect
with each other, brings programming. But within that she created

(36:01):
a little teamlet of us that are early for boards,
that are learning together. So I lean on those guys.
So there's the structural ones. My old boss Julie Wong,
who's another Asian Tiger parrot, but she's my old boss
from Elizabeth Arden. She's a mentor. So I have those.
But when I come to making life decisions or career choices,
my friend tour group that's my friends in everyday life
that are basically the mirror to me. Those are the

(36:23):
people I go to. So I wish I actually had
a better answer, because I tell people all the time
how important mentoring is. I do a lot of it.
I meant her at Scale, I run office hours on
clubhouse where people can come and ask me questions. But
the odd thing is the ones that are the overachievers
are generally really bad at asking for mentorship because we're
so busy moving, We're so busy helping people. I don't

(36:44):
necessarily have a you know, a tribe to go to
for that, but they're in pieces, and I think, you know,
for me, it's usually less about the opportunity and thinking
about pros and cons. It's about where it fits in
my journey in the North Star and the people that
are best quiped to give that advice or friends and family.
And now for a quick break. I imagine, given how

(37:06):
you grew up, you have a lot of perspective on
parenting and how you would raise kids. Do you see
kids being part of your future? Possibly when I was younger,
I subscribe to societal norms that you're supposed to get
married and have kids, And all of a sudden, I'm
forty three and at the most amazing inflection point of
my career. So I'd like to keep the possibility open

(37:30):
for children. I know how hard it was for my
parents to re establish themselves in this country and create
so much opportunity for me and my brother, and I
know I don't want to do it alone, and I
know that it has to be the right time of
life where if I do find a partner who also
want kids, we have time for us and then we
have time for a family, because you're in that for
eighteen years, if not more, And so I'm open to it.

(37:53):
But I'm also okay with the fact that if I
don't have children, did I contribute to making this earth
a little better? And that's what I hold myself to
every day. And if I can answer yes honestly in
the mirror at the end of the life well lived,
then with or without children, I've done a service to
our community and to this greater globe. But I like
the idea of it sometimes, but candidly, the idea of

(38:13):
waking up at four am for a dirty diaper scarce
the crap out of me, no pun intended. So I
froze some eggs, which I don't think women talk about
nearly enough, but I did freeze some to keep options open.
My mom was unofficially adopted, she was taken in So
for me, I mean whatever that looks like, whether it's
biological children, adopted children, a tribe and you know, community

(38:34):
of mentees that who knows, right, But it's something I'd
like to be open to. I just know that it
takes time, it takes a partner that sees life the
same way you do and wants things at the same time.
So I'm open to it. But you know those are
not things I'm overly concerned with planning the structure on
my calendar. Maybe the rest of it will see right. Well.

(38:54):
You know, it's interesting hearing you because I think you
have such a beautiful perspective on it, which is like
you're open, and I think so many people are not open. Right.
You don't know what that's going to look like. You
have no idea that could happen tomorrow, today, in ten years.
You just don't know. And I think the idea of
being open to whatever that looks like means you're going
to find whatever it is that's supposed to be part
of your life, I hope. So, I mean, even going

(39:16):
from corporate to being nomadic, I don't keep a place anymore.
So you talk about the change in structure, I think
I went from one end of the spectrum to the other.
So being nomadic and spending different time and different places
depending on where my work takes me or where the
communities take me. That amount of openness is what's really different,
But that applies as much to the career piece as
it does the personal piece, because you just never know

(39:37):
who you're going to. Mean, where is your home right now?
I'm currently in Miami because I came here to speak
at a conference a few weeks ago and just stayed.
The incredible concentration of people from so many different industries
means that it's a great hub for creating connection right now.
Maybe I'll go to l A next, I'll go back
to Boston and spend some time with my family. But

(39:58):
my stuff is literally in storage and then literally nomadic
because I think a lot of people have moved around
since COVID. I was nomadic six months before COVID even started.
It's funny because my kids are always like, you don't
have that many friends in our town, mom, And I'm like,
that's true, that's true because I don't. My friends are
all over I'm a lot more like you, although I
have three kids, so I'm certainly have to be in

(40:20):
one place a lot more than you do. However, I
do think of my closest relationships as the ones that
are kind of all over the place because they're doing
similar things to what I'm doing and they're trying to
change the world and they're trying to make things happen,
and they're hustling. Yeah, how do you find them? I mean,
they're all over right, and it's a little less you know,
it's it's it's harder to hop around when you've got

(40:42):
three kids. How did you find them? And how do
you maintain those relationships? Such a great question. I work
very hard. I collect people. Okay, so I am friends
with people I went to preschool, you know with I'm
friends with people I met last week. So for example,
next time you come to l A, I will insist
on taking you out to dinner. I'll either like days okay, amazing,

(41:03):
So what We'll have to make a plan. So that's
the kind of thing I do that when I meet
people that I connect with, whether it's online or on
clubhouse or or at a conference, I stick with them,
and then when I go back to Austin, or when
I go back to to London, or when I go
back to Miami, I will make sure to keep in touch,
to have a cocktail, to have dinner, to get in

(41:23):
touch with them. So We're going to go now to
our speed round um where I'm just gonna ask you
quick questions. You can give me quick spontaneous answers, and
then Lou Burns will come on with the male perspective.
Lou has been listening to this entire interview and he
usually comes in with some huge question at the end.
No pressure, Lou, if you're listening, okay, so speed round.

(41:45):
So I know you're nomadic, but what is your morning routine? Coffee,
text and emails and singing out a song and belting
it because music gives me joy and it wakes me up,
and I dance around and I sing a few lines
to us song that's playing in the background, and it's
the start of my day. Oh I love it. What
was the song today? Exile by Bonavre and Taylor Swift.

(42:08):
Not the most upbeat, but so beautiful and you can
just belt out to it. It's great. If you could
change one thing about your life today, what would it
be having more time for exercise in peace? In This
past year has been crazy for all of us, but

(42:28):
since clubhouse is really kicked into gear. I mean, I'm
working crazy hours, seven days a week and it doesn't
feel like work. But I wish I had a better
handle on sleeping more on exercise because I'm trying to
burn the candle both ends. I'm trying to do my
advisory gigs, I'm trying to do clubhouse. I'm trying to
figure out what the next stage of life is. Not
resting a lot, so if I could change it, I

(42:49):
wish I was making a little bit more time to
self care. But this is an iron while it's hot
kind of period. So let's burn hard. Let's do that
hustle for a few months and then see if we
can catch a bun sleep after. I love it, And
do you ever have any trouble sleeping? Never? That's my
best skill in life. No matter where I am, no
matter how much I've slept, I lay down and I

(43:10):
must sleep in thirty seconds. So that also means when
I'm flying to Asia, I get on a plane, I
fall asleep before we take off. They wake me up
for meals. I land and I'm like, what time is it?
Oh it's three pm. Cool, I'm good. My best skill
in life. Amazing. Okay, you have a lot of famous friends.
I don't know how you accumulated all these famous friends,
but you did. So is there anyone that leaves you

(43:31):
star struck? I wouldn't call him a friend because we
don't know each other. Elon Musk is high on the
list because for somebody to dream that big but then
to execute it's pretty incredible. Gwyneth Paltrow is another one.
I met her randomly at south By Southwest a few
years ago, and we see her public persona when you
talk to her. This woman, when she was launching goop

(43:53):
dot com, knows the back end infrastructure of her company. Right.
So we've all heard the stories about the badge and
little eggs and the candles that smell like vaginas and stuff.
I mean, it's it's, you know, tabloid worthy. But when
I talked to this woman, I realized, you understand the
back end infrastructure of your website, and you're looking at
analytics tools yourself. Arguably not where she should be spending

(44:13):
her time. But talk about a person who really truly
runs the business. Is not just the name or the
face of the brand, but truly runs the business day
to day. All right, Lou, welcome back, lu. So my
question is just I want to hear my adversity. You know,
because I grew up in the in the ghetto of Miami, Florida.
Actually neighborhood called Little Haiti. Death's been beautified and now

(44:37):
it's like a historical landmark. It is no longer a ghetto.
My mom's property value up, you know. But um, but
my my girlfriend's Korean. You know. So I got a
chance to actually see the total opposite spectrum of what
it's like to grow up in an Asian household. You know.

(44:57):
It's totally different from mine, but similar in this name
because my mom was an immigrant, you know. But I
love to hear the adversity of people who are like
quote unquote perfect to other people. You know, So, do
you have any stories about that? And as you're coming
in to maybe even being a board member, adversity is
something that either you're born with or you adapt to.

(45:21):
The ability to deal with adversity is not always in name.
There are some people who have a grit whole fight
through it. There are some people who have been when
placed in a situation, find the grit through fighting through
that adversity. I don't think it's nature versus nurture. I
think it can be both, and it's situational what it
is for me, and I think it's common with a

(45:42):
lot of immigrant kids. Is you just get it done right,
whether it's a child and you're trying to finish homework,
or whether in the corporate ladder and you're trying to
figure it out, or even when you're trying to figure out,
like a fight you're having with your friend, you figure
it out, you get to the outcome, right. So when
I think about a versity, for some people, it's a
lot more emotional. I'm a problem solver, so I try

(46:04):
to remove the emotion, like whatever adversity I mean, I
feel that emotion very heavily because I'm an emotional person
for a couple of days. But throughout all that, my
mental model is mapping what are the solutions, what can
I do? What are the paths, what are the outcomes,
and what are the consequences of each. So it just
happens naturally with me. I don't think that I consciously

(46:26):
do it because I'm such a logical person. My heart
feels my while my brain is working on that solution. So,
whether it was trying to figure out, Okay, if I
want to get to a good school, how do I
get there? Well, let me go find out what it
is that they're looking for and see if I can
serve myself up in that way. The whole time, I'm
feeling imposter styndrome, I'm never going to make it. I

(46:46):
go to this tiny school that's never had anyone get
into Harvard. So I'm feeling the weight of that of
that stress and that um and that expectation of my family.
But the other side of my brain is like, Okay,
what are they looking for and how do I serve
myself up to that? They want a well rounded person?
Well cool. I was in school twelve months out of
the year, so I didn't play any sports. I couldn't

(47:07):
even ride a bike. But I hear they wanted well
rounded people. So I'm like, let me do theater. What
can I do as a sport? I mean, I literally
didn't even have jim after sixth grade, so I couldn't
play any sports. But I'm like, well, track and field,
you just have to run. I don't have to win,
but everyone can run, so let me run. Oh, no
one's doing hurdles. Let me participate in at least I'll
be first at my school and hurdles because there's only

(47:28):
one person running hurdles. Right. So, while I'm feeling the
weight of all this, you just figure it out. So
if they want someone well rounded, let me be well rounded.
Now this stage in life, I'm more intentional. I'm not
trying to meet someone's checklist anymore. But at the time,
if you want something that someone has access to, you
deliver what you need and after you get in there,
then you figure out what you need to do to

(47:49):
change things. And that was the same as getting access
to a great college education. That's the same as being
on my boards. Right, you do what you need to
get through the door. They need diversity, they need board experience,
and they need digital I served all that up. But
once you're in then you can make the changing. Me
more thoughtful about where you want to go. So adversity,
I think can be emotional, it can be logical. I

(48:10):
think it's both. But part of being that immigrant kid,
I just had to figure it out. And so what
I've realized is sometimes for me mapping those steps, then
once I get there being able to, you know, enact
the change that I want. That's been actually a better
one to punch for me than to carve my own path,
because I don't think I had the confidence or or

(48:30):
the network to be able to do it from the
ground up quickly. Did your mom put a bowl on
your hair when she actually cuts your hair? No, gosh,
I'm gonna have to send you guys a picture of this.
I know we don't have visuals on podcasts, but it
wasn't even really a bowl. It was like a helmet
shaped haircut, so it'd go like across the forehead and
then down around the ears and around the back. So
you know how when you have Legos the hair comes

(48:51):
off as a single piece. It looked like a Lego hair.
So I will send you the photo that shows my
lego hair. I'm also wearing a sweater with farmhouses on it,
which I have no idea where my parents got it,
and now, of course I wish I still had it,
but it is the most awkward third grade photo. I'm
going to send it to you and give you full

(49:11):
license to use it as a visual companiment to this podcast.
But it was like a helmet. I'm gonna bring it
back someday. Amy. One of the most remarkable things is
that Swan apparently gets asked to be interviewed all the time,
which is of course not a surprise given her new profile.

(49:33):
But this is the first podcast she said yes to
That is amazing. She listened to some of her episodes,
she saw you know, our bios, and she just decided,
I'm going to do this And she was actually really
nervous afterwards because she had never done one before. That's
so cool. I love it. I think that we forget

(49:54):
that when you're in corporate America like you and I,
entrepreneurs were asked to do podcasts all the time, right
to be an reviews, And when you're in corporate America,
you forget that you have to ask corporate communications department
if it's okay, and and so so often someone who's
you know, a VP and corporate America just says no
to everything having to do with press. So it makes

(50:16):
sense that this is an entirely new world to her.
That is awesome, how exciting. So Amy, I'm just dying
to know what did you think of our conversation. So
one thing that's really interesting to me about your conversation
with Swan Sam is her story about Clubhouse. You know,
Swan's career so interesting, right, A lot of it seems
quite planned in some ways, right, that she's kind of

(50:39):
you know, built digital at these amazing companies but the
Clubhouse thing is super interesting, and I have to admit
I am slightly jealous because I am the person who,
you know, early this summer when people started joining Clubhouse
and you joined and invited me, and I was like, Sam,
I am drowning in my startup, and how can I
possibly find time for this? And you kept only need

(51:00):
to find time and I didn't. And like, if you
look at what it's done for Swan, I mean it's
transformed her career. Sometimes the most unexpected things can do that,
It's true. And I also think she was well positioned
in her life to do that, right, because she was
at a point in her life where she was on
a few public board she had moved back to Boston
to spend time with her parents. She she was in

(51:22):
a position to take advantage of Clubhouse, and she's always
been kind of comfortable being a bit nomadic, as she
describes it. So this kind of new life where she's
you know, going away from corporate America and now Gary
v is managing her and she's going to be traveling
you know the world presumably and doing all of this
like you know, being an m C and kind of

(51:44):
going where it takes her, it almost goes back to
an earlier life that she really feels comfortable with. Yeah,
it's super interesting. What else were your were your takeaways? Well?
I just really appreciated her candor about kids and family
and and I think that so often we don't hear
that part of the story. So I bet that you

(52:06):
know a lot of people who think they know swans
story or or see her career might not hear that
personal side of it. I mean, that's by the way.
That's one of the luxuries of this show is that
we really get a chance to talk to people, not
just about their careers, which obviously a lot of podcasts do,
but we really have enough time to get to the
heart of their untold stories. Thanks for listening to What's

(52:31):
Her Story with Sam and Amy. We would so appreciate
if you would leave a view wherever you get your podcasts,
and of course, connect with us on social media at
What's Her Story podcast. What's Her Story with Sam and
Amy is powered by my company, The Riveter at the
Riveter dot Co. In Sam's company, park Place Payments at
park place payments dot com. Thanks to our producer Stacy Para,

(52:53):
our social media manager Phoebe crane Fest and our male perspective.
Blue Burns