This is Reinamoto's Podcast, The Creative Mindset.
Hi everyone. Welcome to The Creative Mindset, a podcast about what the future holds at the
intersection of creativity and technology. I am Reinamoto, the founding partner of I&CO,
a global innovation firm based in New York and Tokyo.
How can a creative profession have a meaningful impact on business?
This has been a consistent question that I keep asking myself,
and that I explore in this podcast as well. In the previous episode, I had the conversation
with David Lee, the Chief Creative Officer of Squarespace, who went from being a designer
to a right-hand person to the CEO of one of the most successful tech companies in New York City.
And I really wanted to understand his journey and how he made that transition and transformation
being a hands-on designer to a business executive and business leader.
In part two, he talks about creativity at the adult′s table.
Having been a creative myself and him being a creative throughout our careers,
we know that creatives and designers often, for better or worse, get seen or we are seen
as the crazy ones or the wild ones. But that may not be good enough for us to be relevant
and to survive. And he shares his thoughts and insights on how he made that transition
and how he sees the role of creativity and role of creatives moving forward in the context of
business and technology. So, let′s get started. Going back to the original topic of creatives
and creativity having a seat at the adult′s table. So, a couple of questions from that.
What do you mean by the adult′s table is one. And second is, was it when you were at TVWA
within the Omnicon family that you talked about when you went to a big agency network and you
started to see the importance of the business aspect of the given business and learned how to
speak the language. And then you eventually made your transition into the tech space, product
space with SquareSpace. But two things. One is, how do you define, what do you mean when you say
creativity at the adult′s table? And for you, what was that transition? When was that transition
specifically? Well, I can certainly start with what I mean by why creatives need to
seat at the adult′s table. I think for some odd reason in our industry, in our business,
we′re taught to treat creative people like kids. And what I mean by that is
we′re always sat at the kid′s table. We′re the kids. There′s music blaring. We′re throwing
food around. It′s like we′re at the children′s table. And every once in a while, one of those
kids will go up to the adult′s table. And you′ll sit in a chair and go, Hey, what′s all this
business stuff that you′re talking about? I wouldn′t mind helping out and what have you.
And for some odd reason, we′re always told, Don′t worry about it, son. Just go back to the
kid′s table. Continue your potato painting, drawing that you′re doing. And I would argue
in 2023, that is the most archaic org design model that I could see, especially if you′re
on it. I mean, look, when you′re at an agency, yes, creative is part of it, obviously. It′s
one of the trifecta of like client services, strategy, creative, production. But when you
get to the brand side, what you realize is that creative is usually not as respected
as an agency, I would say. And I′m speaking in very broad, sweeping generalizations, right?
I would say that′s like number one. Number two, it′s usually a creative department
and creative people are usually buried multiple levels deep, right? You′re not very close to
where the ultimate business decisions are actually happening. And especially in a world where I believe
where you have so much machine learning, automation, artificial intelligence, large
language models and what have you that are going to completely wipe out certain white collar jobs
and what have you. I would argue that in today, creativity might actually be the only job left,
right? And I′m not talking creative as in people who are labeled as creative. I would actually
argue in every discipline, in every role, right? Is that if you wake up one day and realize that
you′re just doing the same repetitive task every single day, I would watch out, right? And it
doesn′t matter what job you have, right? Because there is a tech company, there is a brand that′s
going to try and automate that way, automate that job away in the very near future, right? And I
would argue that this might actually be the next golden age of humanity where
creativity is really the only thing humans have as any value add back into the world.
So, it would behoove any Fortune 500 company or even a startup not to have people sitting at that
executive table, at that adult′s table who are about thinking critically about solving problems
in unique and innovative kind of like ways, right? And like that′s kind of like what I mean.
The reason why I think I found that at Squarespace is because I believe the DNA of the company is
very much rooted in the things that I care about, right? So, when the founder and CEO started this
company, he wanted to create an all-in-one platform for anyone to create an online presence,
right? But I would argue it′s like the value proposition really stems from the fact that he
was looking at the World Wide Web at that point and it was the Wild West. It was the most
unconsidered, undesigned place in the world and he wanted to beautify the World Wide Web and he
wanted to create a platform that could actually take all the best things in design and to allow
people to put out something that really they felt proud of and that felt representative of
their personal brand. So, the company was founded with creativity, design, and brand as a huge part
of the genesis story of the company. And what I tell people is that you learn a lot about the
company when you can hear it from the horse′s mouth, from the founder, from the person who
started the company, why they created the company, right? You can learn a lot purely just from
getting that information out there and you can learn a lot about who they put in that first
concentric circle outside of him or her, right? That′s a quick tell on what that company actually
cares about. And in the case of Squarespace, you know, he wanted someone who obviously understood
the product world and like the tech world, but someone who knew how to build a brand. So, I
guess I kind of fit that kind of like overlap, right? And I kind of hit that in the middle of
that Venn diagram. And but he was, I mean, this is someone who cared so deeply about these things
right from the start that it made my life much easier, right? And it made, you know, at that
point, I think we were like, I don′t know, maybe 75 people or what have you. It made it easy for
me to, you know, kind of like partner up with him and to be that design and creative and brand voice
alongside with him. But I would argue it′s still the reason why we′re really proud of some of the
work that we put out into the world, why we′re proud of the product that we put out into the
world is because during my 10 years, it′s still the same thing, right? Design and creativity has
that seat at the executive table and I don′t see that changing anytime soon. Yeah. So, a couple of
follow-up questions from the points that you just made. The first one would be, what is specific
things that the founder or the CEO of Squarespace said to you when you were considering Squarespace
as your next chapter? What is specific things that were the tell that he cared deeply about the
things that you care and not just the functionality of the product but the brand of the product,
right? Or the brand itself. Do you recall any specific conversations that made you think,
okay, this person gets the things that I get? Yeah, I do actually. I do. I actually remember it
pretty vividly and the reason why I can remember this is that it took me a long time
to actually convince myself that Squarespace was the next move for me because, I mean,
the way I telegraphed this story, it made it seem like this was like a natural next step but in
reality, this was right after like the 2008 housing crash and what have you. It was a little bit of a
tumultuous time. The economy was a little bit shaky and here I was. I had a really great job
at this worldwide network and had met someone who I could only have conversations with every
once in a while because I was just consistently like never in New York and traveling all the
time. So I think it took me maybe a year and a half or two years of speaking with Anthony,
the founder and CEO, for me to get convinced that this was the next chapter for me.
I can recall a couple of things. So number one, I remember the first meeting. I went to go see
him at their current office and I always tell this story because another thing which I find is a quick
tell on if a company really believes in design and creativity is that you get to learn a lot about
that you get to learn a lot about someone when you visit their house or their office
very, very quickly. It's why I actually say it's one of the best brand expressions of any company
or brand or individual is that you don't have to say anything. You can just view and take it in
and you will learn a lot about an individual or a company purely just by being inside their home.
And I remember this when I went to the office. And again, the company wasn't the size as it was
today. But the amount of care and the amount of nuances that were put in this office still in
startup mode was pretty impressive. Way more impressive than some of the past agencies that
I had worked with that I'd worked for. You could see that he questioned every single nuance of
every single design element of that office and it made an impression on me.
Like furniture and the interior design of the space? Is that what it is?
Yes. Alongside the choice of the block that you put your office in and this was like right in the
middle of Soho, to the experience when the elevator doors open up, how you feel, to how
all the meetings rooms were partitioned, to the fact that all the desks were very, very well
designed. And there were no trash cans anywhere because he just did not want to see trash just
strewn on everyone's desks underneath it. There was something really considered and really thought
out about how it was designed, how the programming was, what was the flow going from meeting room to
meeting room, what the interiors of the meeting rooms actually looked like, to the furniture,
to all of the above. And that's just simply not something that a startup at that stage...
Most startups just don't care about those things, but Anthony did and Squarespace did.
So I would say that that was a very first impression, a very good impression that I knew
that this is ultimately a tech company that really cared about design and brand.
I would say another thing, after meeting him multiple times and we had quite a
fractured... we would speak, I'd be off for a month, I'd come back, we'd speak again.
It was a little bit of a fractured, stop and go, stop and go kind of conversation
that we had. But I think when I was getting a little bit closer to convincing myself that
this was the right next chapter for me, there was this conversation that I remembered, which was,
it was a little bit of this competitive fire in him, which is something that I genuinely have
as well. I remember him saying, look, we're either going to have a story on a yacht one day of how
great this is going to be, or we're going to have a story at the local bar down the street of what
could have been. But either way, I'm not here to waste anyone's time. He wanted to swing for the
fence. And he would go down swinging and striking out, but he wasn't here to do incremental
kind of like gains. He wanted to create these big step functions, like these big seismic step
functions. And what I took away from that is that this is someone who's
his ambition is very big, right? He had a great product, I believed his product was one of the
most progressive and avant garde versions of any web publishing platform out there. It was focused
solely on the creative community at that time, which is another tell on what he and the company
cared about. Because he did say that the reason why we started with the creative community is
because creative people are the most fickle, right? They're gonna argue about every single
design element, every single nuance of something. If you can make the creative community happy,
everything else will fall into place, right? Every other kind of like vertical, every other cohort
of an audience will appreciate that we started there because creative people are the most fickle,
right? So I already got that from the product standpoint, which is what drew me in. I could
already understand from knowing him, that he cared about, he actually walked the walk, even
in like the office, and even how he kind of like behave. But the third thing, which was probably
the catalyst that I just mentioned was, there was this ambition, and bravery, and that I really
appreciated. Because truthfully, what I told myself is that, look, I'm going to give this a
year. And if I feel like this isn't working out, hopefully, I can, you know, walk back to the
agency world with the tail between my legs, and hopefully that they will welcome me back. But
I had no idea that this would last 10 and a half years, right?
10 years, yeah.
I had no idea, right? And I had no idea of, you know, us being a public company now and,
you know, being like 1700 employees. And it's just, that's just, I would be lying if I told
you that that's where I saw the, you know, the reality of where this would be 10 years later. But
I liked the competitive fire in him. And the belief that we have the best product,
but we have to build the best brand at the same time, right? Like we had, he felt we had the best
brand, the best product that no one heard about, right? And we want to start with the creative
community. But then we would go really, really horizontally. And look, 10 years later, that's
what we've done. We've taken some really, really big gambles and some big bets. We started with
the creative community, and we've been slowly trying to convince people of the power of design,
the power of branding, right? To different verticals and different audiences now. And like,
that's kind of where we are in the journey of where we are right now at Squarespace, right?
You know, the web has changed dramatically in 10 years. And obviously, it's up to us, you know, to,
it went from there to, you know, web 2.0, everything went mobile. And then it went to like
the transactional part of the web, where, you know, people want to be able to transact and sell
things and like what have you and kind of onward. So it's our job to obviously keep track of where
the web is going. But the constant has always been making sure that our value proposition of
democratizing great design, right? Stressing the importance of your brand, whether it's a personal
or business brand, is really going to be the difference maker in the world. Because in the
past, we would meet IRL like this. And that first impression you make really matters, right? I would
argue today, that first impression does not happen face to face anymore. It happens online. So we use
the saying that it's almost it's almost like what your what your Google search results of your name
or your company is really that first impression. So what do you want people to see when they get
there? Right? It's the official, it's the official you, right? So in some ways, I feel like we're
selling online real estate. That's actually what we're selling. Right. And right, right. Now, this
is a run on sentence. So, yeah, no, got it. Got it. The speaking of the creatives and creativity
being at the adults table. And you talked about big bets and swinging for the fence that you and
Anthony have done in the past decade plus. But can you recall a moment or two when because you were
in the room, right, the decision that Anthony or the business made swayed one way versus the
versus another way. And the business benefited from creativity. Give us give us a sense or give
us an example or two of those moments. I mean, I can give you a lot because even today,
there's a lot of decisions made. Obviously, keep making sure that business is on track.
But there's still some, you know, some some significant bets that we that we make constantly.
Look, I think it's no surprise if you followed, you know, my career trajectory at Squarespace or
or the narrative arc of Squarespace over the last 10 years, is that Super Bowl has been a big part
of what we've, you know, we've made big bets on, right? Because these are like expensive.
These are very expensive endeavors. And here's the one example that I'll say,
that I'll say, which was definitely a big gamble, a big financial investment,
and one of the scariest moments of my career, all all at the same time. So you have to understand,
I was literally only at Squarespace for maybe seven months, when I remember, I think having
like a good drink with Anthony, and him kind of going up to me and saying, like, what are ways
that we can just create that big step function? Right? Like, how do we, maybe it's it's both of
our impatience, right? Or maybe it's both of our competitive fire, where we had this conversation,
and I had no, this is almost as a 100% joke, I went up to him and said, Well,
you could do a Super Bowl ad, that'd be pretty funny, that'd be a pretty big bet.
Completely thinking that this would be out of the ballpark of things that we could actually do.
And I think it took him about 10 seconds. And he said, Let's do it.
Like, within 10 seconds, and he might remember the story a little bit differently. But
that's how I remember it. And I literally went from laughing, going, haha, that's funny,
to the next morning, just like double checking with him. It's like, you don't actually want to
do this, right? He's like, No, no, let's, let's scope this out and see, like, like, what better
way to introduce the brand to the world and on the world's biggest stage, like, that we went
through the exercise of like, how much does it cost? And how are we going to produce this? This
is at the moment where we didn't have an in house agency, it was basically me, and a few designers,
right? So there was no reason why we should be doing a Super Bowl ad, number one. Number two,
there's no reason we should be doing it in house at that time, at all, without any help of an
external agency. And truthfully, that was kind of one of the scariest moments of, of my career.
And it was in the first year, it was in the first year of Squarespace. So first,
it was 10 years ago.
Yeah, it was, it was, it was, it aired about nine years ago, I think, but it started
like the making, like the conceiving of what the idea is, what the, what the message is,
how are you going to pull this off and bringing in like a skeleton crew of like freelancers,
like, like some creatives and some producers to actually make this to find the right director
and production company without anyone knowing who Squarespace was, right? On a little bit of
a shoestring budget, because, you know, obviously, we were much smaller at that time. And just the
media dollars alone of buying that 30 second spot on the Super Bowl was very, very expensive,
right? So...
Well, it's in the millions. I mean, it's public image. It's in the millions, isn't it?
It's in the millions. I don't recall, it's definitely much more expensive today,
you know, with inflation, like over time, but you know, for a startup, that's pretty,
that's pretty expensive, right? So the pressure, the pressure, I remember the pressure cooker,
like feeling like the anxiety and the pressure of this. And it was one of the most interesting
visceral moments that I can remember during my tenure at Squarespace. And I remember
when we were making it, I was second guessing myself, you know, is this even going to move
the needle at all? Am I going to fall flat on my face? Because ultimately, I have no one but myself
like to blame for something like that, especially if you're going to do this all in house.
And I remember being so afraid that I didn't want to watch it with anyone at Squarespace or what
have you, I had to watch it alone. And I went with my, with my wife at the time, and we went
to Miami just to be completely away from it. I didn't even watch the Super Bowl. I remember I was
at dinner. And I get a text from him going, it just it just went live. And I was like, I'm not
going to pay attention to this. And look, the TLDR here is that, is it the proudest creative moment
of my life? Probably not. But did I learn something from it? More than you can ever imagine
and more than I could ever articulate from just the process and the fear. And, and, but it ended
up doing a sizable, we actually ended up tracking it. And then all we saw were landings on squarespace.com.
And then trials, trials, trials, trials, trials. It was pretty unbelievable to actually see
something like a Super Bowl ad actually go into motion, and seeing how quickly something like
that could actually move the needle. And I think it almost took down Squarespace. At that time,
there was so much like, like, like, there was so it was getting so much traffic at the exact same
time, right? Probably because no one had ever heard of Squarespace. We had a very brave ad,
which was pretty, pretty odd.
What was the first one?
This was literally there was no celebrity, we couldn't afford one. This was all about
painting the picture of how the World Wide Web was the Wild Wild West. Right? So we had this idea
of that a better web awaits. And that's what Squarespace was. So we tried to pitch this
really dystopian future idea where we took, like what the experience was online. And we brought
that into the real world, like with all the pop up banners and things like this, and all the clickbait
kind of like rabbit holes that you can fall towards. And we tried to paint this really dystopian view
of what the internet was. And then right at the end, we were our job was to help beautify the web.
The idea was actually pretty great. I think trying to in hindsight trying to do a dystopian future
Blade Runner thing on a on a shoestring budget probably wasn't
for our first Super Bowl ad, I probably could have conceived something a little bit simpler
than that. But yeah, I'm proud of it. I still got an ulcer in my stomach from all the stress
of putting that out. And it tangibly did something to the business, I would say it's, it's, it's,
it does. Like we you could actually tell, right, just from like the business metrics and seeing
like the traffic and seeing the trials kind of going up and seeing, you know, all the PR and
the aura and the organic buzz that it actually generates in this one water cooler moment,
like undeniably, like at that moment, like you can tell what, you know, what the results are,
because it's really hard to track something like that. Right, right. You know, like, it's really,
it's really hard to track like, you know, was it is every subscription we have attributable to
a piece of brand advertising we do, you know, no, right. Right. But right. It definitely did
something to the business, which is why it's been, you know, a staple thing that we've done
almost consistently year over year, ever since that point. And we've gotten a little bit better
at it. But yeah, right, right, right. Tech companies are notorious for hating advertising.
Right. Starting with somebody like, like, like Jeff Bezos saying that advertising is a,
you know, is a price you pay for the for bad product that you have. Right. So it sounds like
if I'm dissecting what you have said, and just the fact that Squarespace has advertised,
especially things like Super Bowl and other places fairly consistently, you know, is this something
that works that well that you would recommend to every company tech owner? I am not here to
recommend... Maybe we need a separate episode to just talk about that possibly. Would I recommend
this strategy to other tech brands or other just kind of brands in general? Probably not.
Probably not. I think for all the reasons that I just explained about what the unique DNA of
Squarespace, that the Squarespace has, and what we care about, and our competitive nature and drive,
right. And it's kind of in the water that everyone drinks at the company. It's kind of
like baked into the DNA of the halls of the company, at this point, that it's become a
thing where we've proven to, you know, that it not only does something tangibly for the business, but
it's also just something that we want to challenge ourselves creatively every single year as well,
because we do care about that. And we do care about our brand a lot. I also think that we
have a very different lens on how we do a lot of our marketing and our advertising,
and our creative storytelling. I think the reason why most people say advertising
is bad is because most advertising is bad. We don't treat the consumer with respect,
right? We hit them on the head with the same thing. Most companies just say what they do,
and they wear it on their sleeve. We tend to do something a little bit different, where if we're
going to put advertising out into the world, we want to make sure it's entertaining. We want to
make sure there's a wink. We want to make people kind of like laugh. We want to actually respect
people's audience and put something out that we're actually proud of and hopefully that people
like enjoy, right? That's a big part of it. And we will stop ourselves at a certain point and kind of
go, I don't know, like if we're going to pummel someone with a campaign, we better make sure that
not only are we proud of it, but that we're respecting the audience with the type of work
that we do. And I don't know if there's a lot of brands out there who have that same mentality.
It has to work, obviously, or we wouldn't do it, right? We're the first to kind of pivot.
If we see something not work, we'll pivot strategy, we'll pivot the creative and like,
you know, swap it out. But it's not the only thing. There are times where we still want to
put things out that we're just proud of because we feel it's a good representation of the brand.
And you know, you might call that cavalier, you might call that risky, but we care about it.
We care about our brand massively at the company. Yeah. And I mean, just the fact that you've been
doing something like a Super Bowl ad fairly consistently in the past almost 10 years or so
means that it's having a positive impact on your brand and your business.
It has. We even took a year off in between and decided to not do the Super Bowl to see
what it does or did not. You know, because, you know, we're obviously curious, right? And we're
business owners at the end of the day, right? So I remember we took a backseat one year.
But here's the test. We did a campaign, right? That was equally as big as a Super Bowl. It had
a celebrity director kind of attached to it, right? And we actually did one, except it wasn't
on the Super Bowl. And we put it out to see what was the difference in results. And I can tell you,
it was a campaign I was really proud of. But there's...
Which one was that? Which campaign was that?
This is the one we did with Idris Elba.
Yeah.
And it was directed by Spike Jones, who's obviously a director that I've always wanted
to work with, who did an amazing job. And it ended up being like a very award-winning campaign that
we've done. And the thing that was missing, no matter how big of celebrities you have,
you are missing out on a pop culture moment by not being on the Super Bowl.
If you think about this, the Super Bowl is the only time where people even care about advertising,
right? And there's been studies that most people who are watching don't even care about the game.
They're there to be entertained by the ads, right? And the amount of organic PR
that you get pre, during and post the thousands and thousands of mentions is very valuable.
And it's all earned, right? It will cost you a lot of money otherwise to get that amount
of mentions of your brand. I'm not here to justify it costs X amount of millions.
But what you're talking about is, there's something that you just cannot put your finger on
that is this pop culture moment where everyone just talks about it.
And you cannot get away from it, right? And so, I call it like a game within the game. There's
the actual game where people are throwing a pigskin football across the field. And then
there's the advertising game, right? And again, going to our competitive nature.
Right, right, right.
We like that challenge, right? We like being the indie alternative brand that shows up on the
world's biggest stage with all the pop stars, right? Because we're still consistently one of
the smaller companies, right? That do a Super Bowl ad each and every year. But we like that
David and Goliath feeling. It requires us to do things that are a little bit different,
or a little bit odd, or a little bit weird, where we go really quiet when everyone's
posting fireworks and things like that. It requires us to think about what makes us different,
and to try and find ways of standing out. And I like that feeling like your back's against the
wall. I like the feeling that you're in like the minor leagues, and now you're in the major leagues.
And hopefully, that's something that we'll never lose, even if we get 10 times the size of where
we are today, because we haven't lost it even when we were like 50 people when this started out.
Right, right. What keeps you up at night as a professional?
I've always known where the North Star is pointed to. And I'm always someone who likes to put flags
in the ground. And I like to have these like micro goals to like walk towards. And then as
soon as you get there, you pat yourself on the back, you plant the next flag in the ground.
I think it's only been in the last couple years where it's been, at least professionally,
career-wise, this has nothing to do with Squarespace, right? This has to do more with like
me personally, looking at my professional career. I think this is the first time where it's been a
little bit hazy what that next flag in the ground actually is for me personally, as a professional,
which is probably why I feel like I'm in good hands right now. And I'm actually in a great
situation, because I've always known where that next flag in the ground is. But I'm someone who's
just constantly trying to reinvent yourself, who's constantly trying to push
to do different things. And yeah, sometimes I worry about
am I on? Have I been in the same gear? You know, for a little while, is it time to switch gears,
try something completely different? And you know, for what it's worth, I've convinced myself
otherwise. And I'm still here, because for some reason, I thought doing an initial public offering
and actually becoming a public company at Squarespace was the end. It was like the end zone,
because we've been trudging this thing through the mud for so long. And when we finally got there,
it was such a great feeling. And by the way, as a side note, to represent design and creativity
at that stage, to be at the New York Stock Exchange, to ring the bell, to actually be
there at that adults table, was one of the best feelings in my entire life. I would say,
outside of like the birth of my daughter. Which I wish, I really wish everyone could actually
experience once in their life. However, it was a quick fast follow to the day after you wake up a
little hungover. And you realize that this wasn't the end zone or the end goal. This was actually
just the starting blocks. This is actually just the starting point. I actually spent 10 years to
get to the starting line. And that was a weird, that was a very weird feeling. That was a very
weird feeling to actually have. And, you know, we just passed our two year anniversary of being a
public company. And like, there's just so much work to do. I would say other things that like,
keep me up at night. It's part professionally and part personally is, I don't know about you,
but time is going by so quick. In my mid 40s, like I blink and years have gone by.
And I'm trying to find ways to slow down. And it hasn't worked quite well, where I'm someone where
if I do something, I have to put the blinders on and like, go directly at this challenge and this
goal. And there's a residue of that, you know, from a personal standpoint, like families and
things like that, where I'm trying to become more present, you know, when I'm with my family.
And I think I've gotten a little bit better at that. But I'm still someone who's, my mind is
constantly turning. And it's really hard to stop that hamster wheel. And the, I guess maybe this
is just getting, you know, mid age and realizing that half of your life has passed. And so much
of it, especially in the last for me, like 23 years has been spent just being on this hamster wheel,
and going really, really hard for so long. Is that the best use of time? You know, I used to
care about legacy. We actually had this conversation. Not too long ago. Yeah, I used to care
about leaving some sort of imprint in this world before I leave and go off to Never Neverland.
Right? And I think the older I've gotten, I'm starting to question that a little bit. I don't
know why. I don't know. I don't know what's happened. Maybe it's like having a 10 year old
daughter now where I'm starting to see that maybe that's all the legacy I actually need. Right? And
maybe it's fool's gold. Maybe this whole thing that we've been on and this hamster wheel that
we've been on is fool's gold. And that like happiness is a very weird thing to explain.
Right? And I'm not saying the goal of life should be happiness, because I actually think that's also
fool's gold. But maybe it's just me, midlife crisis at this moment in time,
where I'm starting to question a lot of the things that I thought were
absolutely things that I needed to do, where now I'm starting to think a little bit differently
about that. I'm always going to be someone who's going to be busy. And I have tons of hobbies and
things that I want to do. But yeah, maybe I'm at this weird crossroads in life of like,
what is the meaning of it all? How much time have we spent burning the midnight oil on both ends
in like the jobs that we've done in a search of something in the quest of something
that we won't even be able to appreciate when we're gone? Right? So yeah, those are things
I'm trying to find a way to pause and slow down time. And I think boredom is ultimately the thing
that leads to slowing time down. Because I think we live in a world where we're just inundated
with way too many inputs that the brain isn't able to actually really absorb all of this stuff
that I think even my memory has turned pretty shit at this point. Because I don't think this
membrane in your head is supposed to have this many inputs, these many notifications,
this many slacks, this many emails, this much content, right? This many distractions
that time is going by very, very quickly, where I'm trying to find a way to like,
be more present at this point and to smell the roses a little bit more. But I worry about the
future generations a little bit. Well, maybe then the next time we record a conversation,
we can inquire about the meaning of life. I don't know. I don't know if anyone wants to hear that.
During the interview, we dig deep into different topics surrounding creativity.
On the contrary, with this section, we ask the same questions to the guests to react on the spot,
and we don't let them see the questions in advance. If you weren't doing this job,
the career that you've had, what else could you see yourself doing?
Build my own company, build my own brand. If you could live anywhere in the world,
where would you live? Asia, Seoul, because I don't speak Korean and I want to force myself
to be put into a professional situation where I have to learn Korean. A close second would be
Tokyo because my wife grew up in Tokyo. Where's the next place that you want to travel to?
I travel way too much in my life, both professionally and personally,
that the next place I want to travel to and stay for a while is my home.
What's your favorite food or favorite dish?
Kimchi jjigae. It's a kimchi soup. My mom used to make it. I hated it when I was a kid,
and now it's the thing I crave the most.
Comfort food. What's your favorite song or your favorite type of music?
Well, the only music I can listen to now is Taylor Swift because anytime we're in the car,
my daughter hijacks the stereo pretty consistently. So, all I've been hearing
is Taylor Swift. And she's now asked me to go to a concert for her birthday,
which is going to cost me a pretty penny if I actually do that. So, yeah.
Well, she's on a tour. So, you know, it might be the timing.
It's going to be tough.
What's the most important turning point in your life?
I think the birth of my daughter, for sure. Not even comparable.
What's your superpower?
You know, I just had this conversation because I actually don't think I really have
a superpower. I think there are better designers than me. I think there are better
art directors than me. I think there are better copywriters. I think there are better people who
can write a TV script, what have you. I think if you ask someone else, because I find this quite
narcissistic of me even mentioning it like on my own, but I think my superpower is connecting
the dots and willing things into existence. I think it's like putting things out into the
universe and making it happen. If you ask other people what my superpower is, that's probably
what they would say.
Last question and something that we talked about in this episode quite a bit.
To you, what is creativity?
Coming up with a unique idea to a very regular problem.
This was part two of my conversation with David Lee, the chief creative officer of Squarespace.
Looking back at my history with David, it was refreshing to have a proper conversation about
his career and the role that he plays as a business executive and business leader in
a company that I've followed for a long time. Also, I've used the products that Squarespace
has released into the world. It was really, really interesting and inspiring to hear
from a good friend of mine in a conversation that I wouldn't normally have at a dinner table
or over drinks. One unexpected anecdote that David shared that I wasn't expecting was
his experience right after he released the first Super Bowl spot that he led.
He said that it was too nerve-wracking to watch in front of TV with other people,
so he watched it by himself. Having known David for such a long time, that was an unexpected
episode that he shared and that made me chuckle and smile.
There were a couple of key takeaways, as usual, from this part of my conversation with David.
Takeaway number one was you learn about someone by visiting where they work and live.
He revealed that it took him a long time to decide to join Squarespace. I think he said a
year or a year and a half before he finally decided, particularly because at that time,
the economy in the U.S. was right after or right around the Lehman Shock, and it was very,
very uncertain. But he made that decision, or one of the factors that influenced his decision was
when he went to visit Anthony, the CEO of Squarespace at his office, and he noticed
that there were no trash bins in the office because Anthony didn't want that kind of clutter
in that space. David says, like I said, you learn about someone by visiting where they work or even
live. And Anthony's philosophy, whether conscious or subconscious philosophy of creating beauty
in the context of the web, was diffused into the environment in which he worked as well,
and the elimination of trash bins was an indicator to David, okay, this person cares about
beauty, and this is somebody that I can work with, and he cares about the same things that I do.
I actually have met Anthony a long time ago, I think over drinks or over dinner, but I wasn't
able to pick up on that side of him because he was in a public space, and I didn't really see
that kind of detail. I wasn't able to pick up on those elements of an individual, and I give
Anthony for having that kind of care about beauty, but also I give a lot of credit to David for
picking that detail up and using it as a way to make a decision. Another thing that stood out
in this conversation was how he was talking about the first Super Bowl spot that he created,
and he said that as a joke, almost as a joke to Anthony, and Anthony turned around to him and
said, let's do it, and David was completely surprised by that. What that story told me,
and he used this term in my conversation, was swinging for the fence. It's not just about,
you know, doing multiple things to see what sticks, but picking something and really trying
to hit a home run, swinging for the fence, and that's a trait that few people have because it's
easier and potentially it's safer to hedge bets, you know, multiple pieces going on at the same
time or multiple chips in different stacks of your bets and see what wins. But in Squarespace's case
and in David's case, they tried to swing for the fence, and that's why they've had such an
incredible success as a company. Anthony started on his own when he was in his 20s, and several
years later, 10 years later, David joined Anthony, and then now they, I think in 2022 or 2021,
they went public at the New York Stock Exchange. And, you know, it's taken a while, but because
of these moments where they decided to swing for the fence, and sometimes they may have struck out,
sometimes they may not have hit a home run, but, you know, if you look at their company and their
success, they have definitely hit several home runs. That's why where they are in terms of success,
and I wish nothing but the best moving forward for them. And finally, this is less of my takeaway, but
it's a message from David, as well as myself included, but, you know, David was the one who
emphasized the importance of having creatives and creativity at the adults' table. Traditionally,
in environments that we worked in, creatives were technically at kids' table, and the money
decisions were being made by, you know, other executives and suits, so to speak. He made the
point of going to those adults' table and seeing what they were doing, and eventually earning the
seat to be at that table, and he continues to be influential in the context of the company that he
works for currently. I hope that more people, more executives, realize the importance of creativity
in the context of business, and having that voice be present in order to propel the company
forward, and having creativity at the adults' table can really make that difference. To summarize,
key takeaway number one, you learn about someone by visiting where they work. Number two, swing for
the fence, and number three, have creativity at the adults' table. That was David Lee, the chief
creative officer of Squarespace. In the next episode, I explore the topic, is creativity nature or
nurture, further through my conversation with one of the world's leading educators and the former dean
of Apple University, Joe Polanyi. So, stay tuned. I am Reina Moto, and this is The Creative Mindset.
See you next time.