2-7: "The Inner Voice" - David Lee

David-Lee_Headshot.JPG

"The Inner Voice"

David Lee is the CCO of Squarespace.  

He is thoughtful, self-aware and restless. As you’ll hear, he’s allergic to the status quo. 

Which makes David and Squarespace a good fit.

In many ways, Squarespace have been at the heart of the democratisation of the internet. Unleashing creativity for millions of people who suddenly found they could be the designer of their own web presence. 

As a species, human beings crave control.  With control, we can take care of the bottom two layers of Maslow’s hierarchy of needs. Without it, everything else that we aspire to and yearn for is hopelessly out of reach with the emphasis on the hopeless.

This week’s theme is Listening.

And this episode is called. “The Inner Voice”.


Three Takeaways

  • An allergy to the status quo

  • Openness to inspiration from many places

  • The ability to inspire others and to help them focus that inspiration


"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT

Episode 2-7: "The Inner Voice" - David Lee

Hi. I’m Charles Day. And this is ‘Fearless’.

David Lee is the CCO of Squarespace.  

He is thoughtful, self-aware and restless. As you’ll hear, he’s allergic to the status quo. 

Which makes David and Squarespace a good fit.

In many ways, Squarespace have been at the heart of the democratisation of the internet. Unleashing creativity for millions of people who suddenly found they could be the designer of their own web presence. 

As a species, human beings crave control.  With control, we can take care of the bottom two layers of Maslow’s hierarchy of needs. Without it, everything else that we aspire to and yearn for is hopelessly out of reach with the emphasis on the hopeless.

This week’s theme is Listening.

And this episode is called. “The Inner Voice”.

“And I got to Hong Kong International Airport, and I got stopped at immigration, and they basically looked at me and they said, "You have no room in your passport for an exit stamp at all." The second one in three years I think I'd filled up, just from all the travel that I was doing.

Finally they let me through on to the flight, and on this 15 hour flight back, it had dawned on me as like, "Is this the sign that this chapter's closed, and that I wouldn't even be able to travel unless I get a new passport anyways? And could this be this epiphany that I was waiting for?" Like, a literal metaphor of this chapter's closing.”

Leading a creative business is relentlessly demanding. You’re either putting out fires or starting them. 

The most successful leaders build teams and organisations that put out fires by design so that they can spend more time on disrupting the status quo - by design.

Disrupting the status quo matters most and works best when the intention behind the disruption is to make the world better. 

Which brings us back to Maslow. 

Most of us are so busy racing around, trying to respond to the day to day of jobs, families and life that we can’t find or more accurately won’t make the time to listen to the most important voice of all. Our own. 

So much of my work these days focuses on helping my clients to listen to what really matters to them. To ask them questions, kindly and empathetically, that they’re too busy or perhaps too hesitant to ask themselves. 

Only when we are clear about the answers to the kinds of questions can we bring our full energy to solving the problems that matter most to us. Which is when we are at our best and our most impactful.

Which means we are our most important audience. 

We are our most important clients and customers and employees.

We need to listen to ourselves first. 

So that we can then maximise what we can do for others.

Here’s David Lee.


Charles:

David, welcome to Fearless. Thank you for being here.

David Lee:

Thank you for having me. It's good to be here.

Charles:

What's your relationship with fear?

David Lee:

My relationship with fear. I have ... there's a lot of talk about fearing failure and more like fail harder and you're going to learn something from it. So I definitely believe in that mantra. I kind of look at it more ... like, fear for me has become a little bit of a catalyst to learning new things.

I've learnt, I think, at a younger age to try, and embrace the uncomfortable, I would say. In a sense that ... you know when you get that feeling of butterflies in your stomach? For me, it's kind of turned into almost like a human radar to kind of know that something's about to happen. You might fall flat on your face.

Something great might happen from this, but either way I think it's an indicator that you're challenging  yourself. You're going to do something new and whether you think it's worthwhile or beneficial at that moment in time, it will make you a better person.

Charles:

So do you welcome that feeling?

David Lee:

I do. I actually feel, if I don't have that feeling in my stomach, it probably means I've become way too complacent and it's ... again, it's a little-bit of a radar of are you challenging yourself or have you become so jaded and comfortable that you're just kind of going through the motions in life, which might make me happier.

Just going through the motions, but I do sometimes catch myself getting a little complacent and not feeling those butterflies anymore. So I do use it quite a bit as a barometer on am I learning anything new or challenging-[crosstalk]

Charles:

So the absence of that actually is kind of an early warning sign for you that you're-

David Lee:

Yeah, I think so.  And sometimes you're not expecting it and it comes and the normal ... it's normal human nature to want to try, and get rid of that feeling and go the other way, but I've just learned that, look, life is short. It's not that serious. Whatever happens, people will forget about it the next day. You don't have to take it so seriously. But it will be a valuable thing for you, I think.

Charles:

And you felt this early on in your life?

David Lee:

Yeah. I felt this quite early. I think in  college, I would say. I remember ... I kind of studied as a graphic designer and coming from Montreal, I always knew I wanted to find my way out and I think I used whatever half decent talent I had, had in putting a portfolio together and pitching it over the fence stateside. I applied to all of these schools and ended up in the smallest state of the United States, in  the smallest city of Providence, Rhode Island and ended up going to this school called RISD, which for people that don't know is the Rhode Island School of Design.

For some reason, I ended up beginning as a sophomore or junior, rather than freshman. I can't really recall why. I don't think it's because I was talented. I think they just didn't understand the Quebec educational system and high school goes to grade 11, not 12 and you have pre-college, which is called CEGEP,  but either way I was very happy to not have to take more school loans for that one year and a half, but I did have to do freshman foundation summer classes if I was going to do a step function and jump to being a sophomore/junior. So I said, "Absolutely."

I was always a pretty visual kid. I always used to draw a lot and one of the ... it was one of the things I was the most confident about actually. If there was anything I was more confident  about, it was that I could draw with the best of them. I had just gotten into this school. So my confidence was high and I went to this freshman foundation class, which was a drawing class and I think within the first week or so we had to do these still life nude drawings of a model. I had done this before, so I did it in my usual way and was quite content with the artifact that I put out to the world.

I remember very, very vividly ... and I've actually told this story before  to a couple of people. I remember the teacher coming up to me and it was my time to get critiqued and he said, "Well, that's just a fabulous image that you just come up with." And in my head I was like, "I know. I'm glad you also appreciate it. I'm quite content with it." And he began to say is that this is absolutely stunning. It is a perfect rendition of this model. It's so realistic it's almost like photographic in nature. I said, "Well, thank you. I also agree."

I remember these words that came out of his mouth right after and it kind of felt like the floor just kind of fell beneath me. I was in this sunken place. He basically looked at me and he said, "I don't even know why you're here. You should take up photography. You'll get to that result so much quicker. So much quicker than what you just went through."  He goes, "You could just snap a photo and you would get the same result."

The whole class was there. I just had this feeling in my stomach. I remember going home and fearing going into class the next day with my tail between my legs. I went to the class and he came up to me and he said, "Look, I didn't mean it. I do this quite a bit, but ... he said that he felt that I was so controlled  in what I was doing and that ... he basically said my job here is not to teach you how to draw. It's to teach you how to find another way of bringing that to life. Because drawing is not ... you're not trying to represent what everyone else sees in front of you. You're trying to find the spirit and the soul of what you're drawing and you're trying to find it in a way that's through your own lens.

I want you to lose control because I can tell that you're very, very talented, but you have a certain way of drawing that I do not want you to do ever again in my class. And I said, "Well, that's easier said than done. I've been doing this way for the whole time." And he said, "Look, just draw with your left hand for the rest of your class."

Charles:

I was going to say, the first piece of provocation was extraordinary. The second one on top of that ... I mean, that's really, really insightful and inspiring.

David Lee:

So he just forced me ... he's like, "Just draw with your off hand."

Charles:

What a gift actually.

David Lee:

Yeah. And it forced me to be really, the naivete of using your off hand ... it was almost childlike. It almost brought this childlike wonder and I have a daughter now whose five years old and she's, well she's left-handed. She's a southpaw. But she draws all the time. I kind of look back at her and I go, there's a purity to what she's drawing and she likes to draw portraits. And so I kind of like  closed the loop a little-bit in terms of just trying to look at solving the problem through a different lens.

Look, today I barely even pick up a pencil. It's like everything ... I don't even know how to hand write anymore, but would I have become the best draftsman or artist? Probably not, but I think that lesson that I learned there has actually built some building blocks and set a foundation to kind of how I deal with these emotions of uncomfortable  or embarrassment. It's also just trying to ... purely from a creative standpoint, make sure you're not doing things the same way that you're doing. You've got to look beyond two inches in front of your face.

Charles:

That aside too, actually about ... just joking aside about the ability to actually hand write anymore, I'm not sure I can write anymore.

David Lee:

I actually did it the other day and it was shockingly bad. It looked like chicken scratch. I don't think I was ever going to be writing Hallmark cards or anything like that,  but it was shockingly horrendous. It was a little-bit of an epiphany on just how technology has just changed everything-[crosstalk]

Charles:

Yeah, really changing us, right?

David Lee:

Yeah, it's really truly changing-[crosstalk]

Charles:

Physically changing us.

David Lee:

And in kind of a sad way.

Charles:

Yeah.

David Lee:

Actually.

Charles:

It's a good call out actually. There are some parts of the past that you want to hold onto, you actually have to exercise them.

David Lee:

Or else it's gone.

Charles:

Or else it's gone.

David Lee:

It's completely gone.

Charles:

Yeah, we think it's just going to be a part of us, but forgotten the pain of ... remember what it was like to go through handwriting classes  as a child. So you go through college focused as a ... from a design standpoint?

David Lee:

Yep.

Charles:

You went through college as a designer.

David Lee:

Yeah. I majored in graphic design. I think I graduated in 2000. Maybe because I graduated a little-bit quick, I kind of felt like I took a sabbatical from my career even before it started. What do they call that in England? Is it a gap year?

Charles:

Yeah, gap year.

David Lee:

I ended up-[crosstalk]

Charles:

I think it's become obligatory now.

David Lee:

I ended up moving to Hong Kong just to kind of see the other side of the world, for  almost a year. Then kind of left and went back to Montreal, which is where I started my professional career. Back home on home soil.

Charles:

Was there a reason you went back home?

David Lee:

I think I'd just been gone ... like, I had graduated school and I hadn't seen my parents and my family in a while. I was gone for a year. I figured I should do a pit stop back home. In doing so I had this opportunity to work with this company,  which I ended up working for, for almost six years, which the company was called Diesel. It was an amazing company in the sense that it was like you were getting paid to be at school.

They did so many different things. It was a design agency. It was an advertising agency. It was a technology company. It had architecture as a practice. It was almost kind of like a pentagram in Montreal. Yeah, I cut my teeth there. And  what most people don't know today is that there's a very, very well known great agency called Sid Lee, which is also based in Montreal. And what most people don't understand is that Sid Lee is just an anagram of the word Diesel.

And Diesel eventually changed its name to Sid Lee, probably because there was another brand who had a little-bit of ... another fashion brand that had some equity be built into that name. But yeah, so I essentially, I was there even before  Sid Lee was called Sid Lee. So I've kind of cut my teeth there. I still root for them. I think they do amazing work.

But we were just talking about how I ended up back stateside and I ended up going to San Francisco purely  through pure serendipity. I went to a talk in Montreal and there was this gentleman by the name of Rei Inamoto. He was giving a talk in Montreal and I remember listening to this and being quite inspired.

So after the talk I just went up to him, I said ... never met this guy in my life and I said, "Hey, I loved your talk. Here's a card. I would love to talk to you about what you're up to. If you have any time. I would love to just have a chat whenever you can." He was like, "Absolutely."

I'm just going to fast forward to this, fast forward half a year later and I'm actually at AKQA San Francisco right after, I think I was one of the first people to be hired when he left RGA to go to San Francisco. Yeah, I ended up moving to San Francisco and for me, as a Canadian who was primarily working on like provincial and national clients in Canada, it was such an amazing opportunity to work on these massive global brands like Nike and Xbox  and Microsoft. I think I learnt a lot over there in terms of really pushing the web forward and ... when the web was a really, really creative kind of medium, but then at the same time working on very big dot com platforms as well. So I learnt a lot.

Charles:

Was there a cultural difference between-[crosstalk]

David Lee:

Massive. [crosstalk] I mean, the Montreal experience ... just because ... for people who don't know, Montreal is a very unique city. It's raw. It's unpolished. It's a little rough around the edges and I mean that in the most positive way. It's Bohemian and punk rock at the same time. People work to live there. People like to enjoy life. It's a little-bit of a bubble. But it's a very artistic and creative city and has some of the best design and arts and music that's coming out of there.

San Francisco  was very different for me. It was ... I forget what year. Maybe 2005 or 2006. Probably 2005. It was after the bubble popped on the first dot com kind of bust. I remember living in Soma, south of Market and it was a ghost town. You saw all of these signs of what could have been. You had  conversations with taxi drivers who were like, "Oh, I was an engineer. Now I'm driving a taxi."

San Francisco in a certain way had the same very polished, but very rough and rough around the edges. But I think, going AKQA was, as a digital agency, only ... at least at that time, was a new experience for me and I really appreciated deep diving into one thing and trying to really  hone the craft and grow from an art director to a creative director and working on these bigger clients. It was a great opportunity.

Charles:

I'm struck already actually. Just in your story. In how fluent your life was and has been. The willingness to go from Canada to go to college in Rhode Island. I mean, head overseas and then come back and then San Francisco. Moving and transplanting yourself didn't seem like it was a big deal for you.

David Lee:

No,  it was never a big deal. I still do it today actually. Surprisingly.

Charles:

Where do you think that comes from?

David Lee:

I don't know. I think it has to do with us not being able to choose how you come into this world and there's all these rules and things put into place that you can't really control. At a certain point ... I don't know, I was kind of a shy kid. But I was quite temperamental and rebellious. I went against the grain very, very early. Even as early as when I was in grammar school.

I just had this weird competitive fire too. And combined with being a very bad kid and an even worse teenage, I got into a lot of trouble and part of me just felt like I needed to leave Montreal and  I wanted to work with best, learn from the best, and I didn't think I was going to get that in Montreal.

Then I think after a certain ... there's always a threshold where you're in a city, in a new place, a new environment where you feel like you've figured it out. It becomes normal. Work becomes a little-bit normal and you just kind of want to go on to another chapter. Again, going back to that feeling of am I kind of just  on ... in second gear just kind of going, humming along or do I actually need to shift gears now and try something else? I mean, it happened after San Francisco as well.

Where I ended up moving to London to go work at Wieden+Kennedy and being the first digital hire ever actually at Wieden London and being an interactive creative director who was going to try, and help  build some sort of capability and bring it-[crosstalk]

Charles:

So this was what? 2005-6?

David Lee:

This was 2007. I think I was around two years in San Francisco. Probably around 2007 now. London was just such a strange place when I landed. It was ... you're talking about ... London and San Francisco couldn't be the most polar opposite cities in every  regard. It was a new challenge at work with a completely new kind of company with a very, very different culture then AKQA in every regard. But it was the city too, which was just ... it was just such a contrast to San Francisco that it took me a little-bit to get up to speed.

But once I got to figuring it out, I actually ended up spending some of the most memorable and best years of my life in London. I met my wife in London too at Wieden+Kennedy.

Charles:

What were the biggest differences between the two cultures? I'm interested to ... between AKQA and Wieden. Because you're right. They both have such specific cultures.

David Lee:

Yeah, they have very specific cultures. Both are great in their own bespoke way. I think AKQA was very methodical. It was  very detail oriented. It had a much better process, I would say. It was just something that I actually appreciated as a creative person.

Charles:

You like the discipline and the rigor of-[crosstalk]

David Lee:

I like creativity and constraints. I feel like if you don't have these constraints put into place, creative people will just go around in circles, which is a good segue to why I didn't ... so when I ended up at Wieden, it was kind of like a zoo. It was kind of like the wild, wild west. There wasn't a process and the creative process there was ugly, but it was also beautiful at the same time. It was amazing to see how serendipitous thought comes into play and how I just learnt and appreciated a lot more, the art of storytelling during my time over there. Just being able to see some of the great work that came out of there.

I think Wieden had ... AKQA had this as well, but  Wieden had this way of everything that they produced had the Wieden+Kennedy stamp on it somehow. There was some sort of creative excellence to ... like, nothing left those doors unless it was vetted and the agency appreciated it. It's still to this day probably the only agency that I even see today that still has that and they had an appreciation for the craft too.

Where they'll go to that last, last 1% to try, and fine tune  it and make it better. So very, very different cultures, work cultures and then if you take the context of the city, you're talking about very, very opposites. Both in a very different, but positive kind of way.

Charles:

Can you combine those cultures do you think? I mean, do they represent polar opposites of the same continuum or do you think there are elements that you can ... can you take the best of each of those and put them together?

David Lee:

I think you can. I don't know if you can divide it up 50/50.  I think you're going to have to lean one way or the other. I don't think you can have a perfect middle in this gradient, but I definitely appreciate both and I use that still today in my ... later on in my career in my current role.

But yeah, it was interesting. I learnt the ... I just went really, really deep in the craft with AKQA and one kind of discipline and then at Wieden

That kind of opened it up a little bit, and really appreciated just the art of storytelling. Which then, now to close the loop back to New York, I then ended up getting this opportunity to come to New York, and I think another one of the great individuals that you've actually talked to, Colleen DeCourcy, actually got me to come to TBWA to-

Charles:

So she got you to leave Wieden?

David Lee:

Yeah.

Charles:

Ironic, that. Ironic.

David Lee:

Today, right? Yeah, we actually talked about that not that long ago, but yeah, she was the one who convinced me that there was this massive opportunity. I never worked at a big network. Everything else before then was a private boutique kind of company. AKQA was independent, Wieden still independent. Siddeley was independent back at the time, so this was the first time where I was a worldwide executive creative director with this triple barreled title that probably meant nothing of a 12,000 employee network, 250 offices, 10 regional hubs. And I spent most of my time traveling around those 10 regional hubs trying to pitch new business, trying to defend business not leaving.  I helped create a digital network on the side, and I also strangely enough, created a product that I pivoted into a presentation platform that ended up winning the best educational product of the year and [inaudible] by 2012, and also ran a product development company at the same, all within the TBWA network.

I think what I really learned from there is ... I think I learned the art of the pitch. I definitely honed that ... That was definitely the takeaway from that experience. I also think I ... because I was so close to some of the senior leaders there, that I kind of felt like I got my MBA there the hard way, and I kind of, just in traveling and seeing all the different operations that ... I felt like I really figured out how a 12,000  employee network operated. And to see that in action was a very unbelievable kind of experience. Yeah, that's how it [crosstalk].

Charles:

What did you take away from that? What works about that, do you think?

David Lee:

I think ... TBWA was interesting because it was almost like there's multiple brands within the network. Shyatt has a brand over here. Like Wiedens is  kind of over there, and then you have ... It was all these sub-brands that came together, all creatively-led agencies that came together, and that backslash became the unifier. And I think there was ... I still think to this day ... People call it Shyatt in LA and New York. They don't call it TBWA. And the ... It was interesting to see the micro-cultures that happened where  you went in the world. TBWA France and the 20 other agencies under that umbrella had a very unique culture that ... Shyatt has a very, very unique culture. The difference between Shyatt New York and Shyatt LA were also very, very unique.

Charles:

To the point that they felt like different agencies?

David Lee:

No, I think there was always a connective thread, which made it feel like it was the same  family. But I think it was also the part of its uniqueness as a network that you could these different characteristics, and these different ... kind of like micro-families, that still maintain the heritage and DNA from the past. And I actually think that's a fantastic thing. I don't know if you want to have a very homogeneous culture where everyone's dressed the same, singing the same tune. So I actually kind of appreciated that, and it's-

Charles:

It's a hard balance to find, isn't it?

David Lee:

Yeah.

Charles:

We need to allow local influence to be what it needs to be, while maintaining a ... to your point, a through line of, "This is what the company stands for."

David Lee:

Yeah, absolutely. Yeah. I actually learnt a lot. I think I also learnt a lot about branding processes at place like TBWA, where at first I thought, "This is just like mumbo jumbo."  They really champion disruption, and then they really champion media arts. And the more that you think about it, it absolutely makes sense, and it's ... I remember, they just had a way with clients on how to fish out the best ideas by going through these workshops and these processes that was very new to me. There was never any agency that I went through that put such rigor in branding these processes, and these kind of ideas.  And I thought that was quite interesting as well. I don't know if they still ... I'm sure they still stand by this today, even ... I've been gone for a while, so ... yeah.

Charles:

So TBWA led you to ...

David Lee:

To Squarespace, actually, which is where I currently am-

Charles:

Why-

David Lee:

At least six years, actually. In January.

Charles:

Wow. What made you make the jump?

David Lee:

This is an interesting  story. It might be a little bit long, but maybe there's some insight in here somewhere. During my TBWA days, I developed this infatuation with entrepreneurship, and maybe it was because I created this product by accident, almost, that ... which was ... I basically just had a brief to redesign the worldwide TBWA website. And I basically said, because I'd been around the network, is that there was a consistency problem with the network. And to our point of just, you want to find a thread, but you want people to have their own individual characteristics. But I think it got to a point where the idea stemmed from like, why just make one individual corporate global website, when we can actually create kind of a CMS, a content management system, where anyone else would be able to use it within the network as well.

We created a very, very simple website,  and I remember [inaudible], I remember presenting it to him. He loved the idea of trying to create this into a product internally that TBWA would be able to use. And it was a very simple, reductive kind of website, but it was a good place to showcase work. And then I remember just sending a [inaudible] ball to the network saying, "Look, our new global website is built on this thing that we created. If anyone else wants to use it, you're free to use it." And I think it was in a year, 100 agencies actually ended up using it as their main website.

Charles:

Wow.

David Lee:

And strangely enough, there was ... What we started to see is that people were trying to use it for presentations as well, because it was very slide-based. And we then decided to pivot it, and turn it into a presentation platform that would bring in live data from Twitter and social media. And we just pivoted it, and turned it into a presentation platform, and opened it up to the public, just to see what would happen. We thought it would be a good press kind of moment. I think it ended up having ... I can't be ... over 100,000 users. And as you do in an agency, you submit it to awards and all this stuff, and then that [inaudible] in 2012, and I've said enough about that.

But I think it was through that, that I got the entrepreneurial itch.  And I started to see the impact you can make by trying to create something sustainable that isn't a one off, creating a platform that can actually solve a lot of different problems. And I ended up meeting Anthony Casalena, who's the founder and CEO, and I consider him a good friend too now. I don't think it was because of that.  I forget how we met, but I remember just having a chat with him, and Squarespace at that time was much smaller than it is today, and was primarily ...

They had just launched a new version, which was really focused on creatives and artists and being able to put out portfolios, and it was definitely the most bleeding edge content meeting system out there. We had a lot of commonalities in the sense that we had both created these things. Mine was very, very amateur. His was very polished and bleeding  edge. But he was looking for a creative director at the time to try and help build the brand. And they hadn't done a lot of marketing outside of basic performance marketing kind of things. And they had never done any brand marketing or anything substantially from a creative standpoint. He needed someone who understood how products are built, and how they work, but he also needed someone who understood  how to build a brand.

We ended up just casually talking over time, and to make a long story short, it took me over a year in speaking with him, to actually decide that this is something that I would take a risk on. When I say risk, I mean that in a most positive way. This was right after the housing crash, and I had a very good job at TBWA. I actually liked it quite a bit; I didn't really have any complaints.  But yeah, I just had a mortgage that I just started. At that moment, Squarespace was much smaller and wasn't going to be able to pay me the same compensation. Not that that was the main reason for wanting to do it or not, it just didn't feel like it was the right moment in time. I had this big role, I was traveling constantly, and most days I would wake up going, "I should probably just stay here, and just let him know." And there was this one day of the week that I would wake up and kind of go, "I don't know. I feel like if I don't do this, I'm really going to kick myself for not trying this out. I can always go back. Give this a year, and try and re-appropriate everything you've learnt in your career so far, and apply it to one thing that you genuinely care about. And give it a year. You can always go back."

For some unknown reason, I just couldn't bring myself to do it.

Charles:

What was stopping you, do you think?

David Lee:

I think ... probably 'cause I was just gone so often on the road that I almost didn't have time to think about it, but there was something incubating in my head and growing that just wouldn't go away. And look, ultimately I think I got to an age and a time in my career where ...  I know this kind of sounds cliché, but I felt I wanted to find a little bit more purpose in what I was actually doing. And as much as I appreciated the time at all these different agencies, I would catch myself sometimes going, "What brand am I working on or pitching on? Why am I slaving away for months or weeks on things that ...? I get it, it's a business, but ultimately, just things I'm not passionate about at all." And I think that was the thing that was ... It was irking me a little bit; it was this constant scratch that you couldn't itch off. It was just there.

Charles:

Do you think ... To what extent do you think that fact you had built something that to a point had had real impact, where people had been viscerally drawn to it, connected to, and had changed the way that they were able to connect ... Was that a lingering sensation for you?

David Lee:

I think so. I think it became the catalyst for me to even open the doors to the possibility that I would do something like that, because I didn't even think about it. And it was an accident. It was just an idea. There's millions of ideas; it was just a dumb idea at the time of spending more time and resources to make it.

Charles:

It's a powerful moment, isn't it, when ... Obviously, creatively gets expressed in so many different ways, including in the business world; it gets expressed in a lot of different ways. But I'm often struck by the fact that when you first  start to experience what it means to have an idea and bring it to life and change the way that people can behave, and people can express themselves ... When you actually use creativity to help other people do something in their lives, it brings a different level of connection I think for your own life.

David Lee:

100%.

Charles:

Right?

David Lee:

It's infinitely more gratifying-

Charles:

Yeah.

David Lee:

... I would say, just because it's something ... It's helping others, right? It's not ... You're not navel gazing on something that you've made that is going to go out into the world and then it's gone, and then you're on to the next thing. You're trying to do things in a new way; you're trying to bring the creativity and the love of design and trying to build the best products, but you ... It's really different. In the agency world, for the most part, when you put something out into the world,  it's the end. And you pat yourself on the back, and then you go on to the next thing. In the product world, when you work yourself nights and days to put something out, that's a starting block.

And it's just a really different mentality to have. It's why I felt, even though I had the opportunity to do that within Omnicom and TBWA, I kind of knew that it's like oil and water in terms  of how the business operates. One is about charging dollars on heads for a service that you've provided. Another one is about doing things as quick and nimble as possible with the fewest amount of people to put something out, and then to iterate on it, and hopefully you have something that prints money while you sleep. It's a very, very different way of working, and I think that's what drew me over a little bit. But it took a long time for me to figure that out. I was waiting for some sort of epiphany to slap me in the face. And it did happen, actually.

Charles:

It did?

David Lee:

It did. And this is how I actually ended up at Squarespace. And to go back to years ago, it happened in Hong Kong. I remember I was on one of those trips where I had to fly 15 hours to Hong Kong to go to ... I think it was a disruption kind of day, a session with a client, and  I remember going there, and just wasn't a great session.

Charles:

15 hours on a plane for a mediocre session. That's [crosstalk].

David Lee:

Yeah, and it ... I remember leaving 40 hours later to come back to New York. Some sort of ridiculous trip. And I think I was tired; I think I'd gone through the motions, I think I was out last night. And I got to Hong Kong International Airport, and I got stopped at immigration, and they basically looked at me and they said, "You have no room in your passport for an exit stamp at all." The second one in three years I think I'd filled up, just from all the travel that I was doing.

Finally they let me through on to the flight, and on this 15 hour flight back, it had dawned on me as like, "Is this the sign that this chapter's closed, and that I wouldn't even be able to travel unless I get a new passport anyways? And could this be this epiphany that I was waiting for?" Like, a literal metaphor of  this chapter's closing. And on that flight back, I had made the decision that no matter how uncomfortable I actually felt about this, I needed to do this. And I landed at JFK, I remember, and I called my wife, who I'm surprised was even my wife, 'cause I was gone for so long. She was in advertising, so she understood what life we were getting into.

I  remember calling her and saying, "I have my bags. Let's just go to dinner. I have something I need to tell you." I met her at the restaurant; she was sitting there. And I put my bags down. I remember looking at her. I said, "Okay, let's get a bottle of wine. I got something I got to tell you. It's going to be okay." And she stopped me right in the middle, and said, "I've got something I want to tell you too." And at one moment I was like, "What could be more important than this epiphany that I've just had?" But I let her ... gentleman, like, "Okay, you go first." And she took this box out of her bag, with a little bow tie on it, and she just moved it across the table. And what struck in my head is, "Did I miss an anniversary? Or did I miss some sort of milestone?" And I was really feeling gutted, and then she just said, "Open it." And she had this weird look on her face.

I opened it, and there  were two baby Converse shoes and a scan of an ultrasound in the actual box. And I had no idea.

Charles:

Wow.

David Lee:

I had absolutely no idea, and with a little tear coming down her cheek. And it had dawned on me, I had made this decision on this flight; an even bigger thing happened that trumps all of that right after. And while she was always supportive, it was hard for our relationship to be gone all the time, like, "How do we ever raise a kid  in that way?" And Squarespace was a five minute walk from where we lived in Tribeca. So I couldn't even make that up, even if I wanted to. And I actually had a conversation with my wife about it, and I was like, "Should I tell them that story? Is that okay?" That's how it happened.

Charles:

What an extraordinary conversion.

David Lee:

And then I resigned the next day.

Charles:

You had to, right?

David Lee:

I had to [crosstalk]. I resigned the next day.

Charles:

I mean on a personal level, you had to.

David Lee:

Yeah. It was ...

Charles:

How extraordinary.

David Lee:

It was an extraordinary moment, and I went right into the abyss of uncertainty, of how are we going to pay our mortgage, and how are we going to keep the same lifestyle, and we'd have to tighten our belts a little bit, but it's going to be ... We convinced ourselves that I have to do this, and it'll be great. [crosstalk].

Charles:

What was ... As you went through that  process, what was your worst case scenario? Where did you get to in your head about how bad this could be?

David Lee:

I think ... I'm always quite rational in terms of ... I always try and undersell and over-deliver, or think of the worst case scenario. I said, "Look, worst case scenario, you do this a year. If you hate it, if the business isn't doing good, or you just miss the agency life," which I assumed I would to be completely fair. "  I just need to get this out of my system, to just try and do this entrepreneurship for real, and really go deep into this." I said worst case. It doesn't work out. Gentleman's handshake, and hopefully my stock doesn't drop so much in that year that I can't go back to the agency world. And I always had that in my back pocket as a plan. The first year was tough. It wasn't ...

Charles:

It's a very healthy perspective, though. I was talking to somebody else on a earlier episode, of the fact that most of us can go ... When we're imagining the worst case scenario of a circumstance or situation, can in five steps or fewer, go from what we're doing today, to living under a bridge by ourselves. It seems like a very obvious path for most of us, and so the fact that you were able to I think to put in a kind of floor to that level of anxiety and say, "The worst that could happen  is I go back to doing what I could do."

David Lee:

Yeah, it was way for me to rationalize in my head that this risk isn't so bad, but going back to-

Charles:

And that's the truth, right? In situations where you're confronted with the opportunity to so something significant, the fact, the reality is, the floor is essentially what you've already established.

David Lee:

100%. And when I talk about embracing the uncomfortable, that was one of the most uncomfortable feelings I've ever had. And almost

To a point where I was like, just this one, maybe I won't pursue this one.

Charles:

Where's the Pepto Bismol for this one?

David Lee:

Yeah. Where's the Pepto? I didn't feel that but it's strange how things work itself out or they don't and six years later I'm still here and still fighting the good fight and now I'm sitting here talking with you.

Charles:

That's a remarkable story. So tell me through the journey that you've gone through both through your agency experience and now at Squarespace,  what have you learned about creating conditions in which creativity flourishes? How do you build an environment in which people can do the best work?

David Lee:

I think creativity is a hard thing to explain at the end of the day and I think as much as you can build a creative environment to foster ideas, I think it requires much, much more than that and I think creativity  at least in my mind is based on what you've experienced in your life whether it's a conversation you had yesterday or a song you heard 10 years ago that you kind of remember to a feeling you had when you were at a museum somewhere in Chelsea over here and you're taking these disparate thoughts or experiences that you've had and one day you make some correlations and connections with these and all of a sudden that's an idea,  right?

What I try, and tell everyone, maybe because I have led this nomadic life for so long and you have to ... we can make the best environment but you've got to live life, you've got to be a cultural sponge. You've got to have more inputs beyond what you're doing, what your role is, what your company is, what the walls confine you to because if that's the only place for inspiration, the stuff's going to look the same and you will  get complacent so you've got to put yourself into situations where you're seeing different things, going different places, talking to a random stranger, asking a question. You've got to put yourself into places where you're just getting more inputs and you've just got to be a sponge. You don't know what that's going to lead to in the future but one day, I guarantee you, you'll make some correlation to these things.

Charles:

Do you hire against that? Are you looking for that in people that you're bringing in?

David Lee:

I wouldn't say I necessarily have  that written down in a job description. Maybe I should, maybe I should. Unfortunately I don't meet every creative or designer now that comes through the door at Squarespace but I remember when I did, when it was just me and a skeleton crew of misfits, trying to figure it out, I would ask the questions beyond your portfolio, beyond  where your work experience or where you went to school.

Which to be fair, as much as I went to a great design school, I almost never really look at where someone went to school, at all. Some of the best people I've hired never went to college, right?

I ask them about not only what their passions are outside of design or advertising or creativity but I  think one of the main things I always look for is some sort of pilot light somewhere and I'll always take the person who I thinks hungry versus the person with the raw talent with all the awards and accolades who feels like they deserve it and might have a little ego.

I've tried both of these out, obviously many different times and a lot of the people that are still here are the ones that are  still hungry to this day and so it's a little bit of a tangent to your question but yeah, I think ... it's interesting what works and what doesn't depending on the context.

Charles:

Where does that hunger come from do you think? What drives those people to, even after years of success, still want to get up the next morning and do it again and prove it again?

David Lee:

I can only speak for myself where ...  it's a long journey and the reason why I came to Squarespace is I believe in the product. I believed in Anthony, if I were going to partner up for six years I would have to believe in him and his vision for what this thing could be.

That's what drives me, if you're going to spend 10 years of your life on something,  you better care about it. It's one of the things I'm actually scared of the most is time. How do you spend your time wisely? How do you squeeze out more time during your day or even the scariest thing, am I going to spend the next 20 years of my life living someone else's dream because I was forced into a situation and  you wake up one day and go, you don't have time for your own?

Or you're simply just chasing a monetary goal, which a lot of New Yorkers do, they've got some number in their head and that's the goal. Which has never been how I operated because you could spend your whole life chasing to this number and then realize you're the richest person in the grave and you'll never be able to enjoy any of it so I think it's ... if you're going to do something, you've got to have some fire, you've got to  know that it's a long journey, you've got to really believe in it, you've got to care about it and ... which is what I've realized is what has kept me here for six years is that is could easily could have gone south and I could have lost interest and go on to a different chapter but the jobs not done and the mission of our company is almost the story that I'm telling you, right here.

We want people to go after their passions and we want to provide tools  to allow them to do that and to be successful. If I had something like Squarespace when I was going out of school I may not even be here, maybe I'd be doing something else so I think it’s ... time is the thing I'm probably the most scared about in a sense that's going really, really fast, I kind of wish I had this feeling of an endless summer again.

I look at my daughter, she's five. I literally thought she was born a year and a half ago, you look at six years at the same company now it feels like two, three, it's like, where does the time go by. I think the people who are hungry will apply their energy to the right things and you'll know if it's the right thing if you're still hungry six years later, I'd say.

Charles:

That was really well put. What does failure look like to you? What is failure to you?

David Lee:

Failure to me, I definitely have done some of that. I'm okay with it, obviously I don't want to fail. Every time I have failed or have been embarrassed about something I put out into the world or it was something that wasn't critically acclaimed, you don't love that feeling but you learn something from it, right? It's going back to that, it's going to be fine, no one cares,  you know. Your legacy will be okay.

It kind of sucks at that moment in time but you've got to take a bigger, long view kind of picture, I guess.

Charles:

So is failure for you whether something works or not or is there another component to it?

David Lee:

I think that's one, that's a kind of more static way of looking at it. I think I worry about failure a lot in terms  of beyond work. As it relates to business you want the company to do well, you don't want that to fail. You don't want to fail as being a husband or a father, I'm someone who has a hard time switching off, when it's work. There's a cost to that, right?

I'm constantly cognizant of the things that I can be doing much better and I'm trying to figure out how to be better at those things but it's time and it's I think, the way my brain works is that in my older years I'm not a very good multi tasker anymore so I can pick a couple, few things to really concentrate on and I throw myself at that so I definitely ... I think  about failure but I'm not scared of it because I have failed before and I think those experiences have made me much stronger and I will fail again. I can guarantee you that, I might be failing at this interview. It's definitely on my mind but it's not a deterrent by any means in the way I go about my life, I think.

Charles:

How do you lead?

David Lee:

That's a good question, how do I lead? I was wondering if you could figure that out for me? This is a therapy session.

At a certain moment in time I think self awareness has a lot to do with creating the foundation for leadership. If you're not self aware I think you're just going to be a poor leader. You can't be good at everything and you've got to look at what your strengths are and what  your weaknesses are.

I am not the best creative person. There are plenty of people who can write a better TV script than I can, right? I am not the best designer, I'm not going to think of these holistic end to end design systems better than a lot of designers that I have now, which is why I don't do it but I think what I've realized over time is that I'm good at taking complex problems, breaking them apart and trying to find some way of threading them together into something that  hopefully makes sense and is original and is impeccably crafted, and I think that's what I realize is that what my strengths are, and I need to build a team around me that also believes in these things and I need to hire people who are much better at me in the things that we need to be better at and you're trying to hire people who are better than you, it was always hard for me when I was younger, I was a perfectionist.

I didn't want to give away my ideas for someone else to make, I didn't care about deadlines or budget or anything like that. You just want to make the thing that you wanted to make and you fast forward, 18, 19 years now and now I'm not the one coming up with the ideas. I am the one who has to put in a deadline and I am ultimately responsible  on the efficacy and if I will go over budget on something so it's a completely different side of the story that we're all on.

It's interesting, I was thinking about this too. I think being a leader in an agency and on the brand side are very, very different from what I've experienced.  If you're a creative director in an agency you're ultimately responsible for the creative work output that goes out the door and of your teams.

I think where agencies can do better is that they don't train creative people how to be good managers of people. It was very shocking when I went to Squarespace where I realized that, that's half the job, maybe even more.  It's where I see a lot of agency creative directors who go brand side for the first time, where I see them fall flat and decide either it's not for them or just don't have the experience in dealing with the managerial things that come with being a creative director on the brand side.

I think it's a tough balance, I think creative people are not typically meant to ... we're kind of weird. It's a little introverted, not always the best people person but it's half the job, you've got to do one on ones with every direct report, you've got to do comp reviews, you've got to do feedback loops, you've got to take your team out for team bonding events and off sites and it's a lot of work but it's mandatory when you work at a brand and the company where this younger generations not just looking for you to help them do better work and  I want people to come to Squarespace to do the best work of their lives but they're looking at you as a mentor and they're trying to learn and they want to know very, very precisely what it's going to take for them to get to the next level and it's your job to listen and it's your job to also understand that you have to be a chameleon as a leader, you've got to be able to adapt.

Not only to the changing things that are happening in the business and changing  briefs and strategies but you have to understand that everyone on your team's very, very different and you can't do some umbrella leadership, you can't read a leadership book and expect this to be the same strategy for everyone. You have to treat people as being quite unique, they all have different DNAs.

I'll give you an example, you can give tough love to someone and it inspires them to spark that pilot light and really gets them going. You do that  same strategy with someone else and it's disastrous, disastrous. You treat that person with tender loving care and you try, and really be sensitive around them and you do that with someone else and they think that's almost condescending and it makes them uncomfortable.

I think what I've learnt is that I don't think there's some boilerplate leadership thing that applies to everyone and you've got to try, and learn  and really get to know everyone on your team and that's increasingly harder when your teams getting much bigger but you have to try, and you've got to be able to just be a chameleon and try, and listen and try, and give as much bespoke advice to that person as possible.

Charles:

Last question, what are you afraid of?

David Lee:

I'm definitely afraid of time but I've already talked about that. I think  I'm also afraid that this sci fi movie portrait of what dystopia is going to look like is actually coming a little bit sooner than we actually think and I think because we're talking about creativity, I actually think creativity is actually one of the main if not the only thing humans will have as a value add in the future, this serendipitous thought  because any repetitive task is already getting commoditized and being run by algorithms and robots right now. I don't want to go into a dark place but you're asking me what I fear and I work at a tech company out of all things.

I think we should embrace the fact that humans are able to have this serendipitous thought and be creative and I think we need to change how we educate people, very early on to be critical thinkers about things  and we live in a world where you can speak to your phone and get an answer to any questions within a millisecond so do we even need to memorize anything anymore?

I worry about that because I look at my daughter and she's just so much older and more advanced than I was but I want her to keep the childlike wonder and maybe I just don't want her to grow up but  there's a ... I want her to keep that naivety a little bit and yeah, so that kind of scares me, I think.

I think as it relates to our business today, I think it's working in advertising or marketing is very different then what it used to be 10 years ago where everything is about micro optimizations, AB testing and everyone's looking at the same data.

I think it's really hard for  me to be surprised anymore or feel something anymore. There's too much content, everything's in a feed, everything starts to look the same so I think it's really important for brands like ourselves and any brand today to make sure that there's some good data driven insights there and that there's a steady drumbeat of work that you can optimize and tinker with on the fly but I think that's also ... if that's the only thing that you're doing that's the highway for your brand  to say and look exactly like everyone else in your category so you need to take some big bets, I'm glad that we've tried to make some big bets at Squarespace in the past.

When I look back those are the things that have created these bigger step functions, it'll ultimately define what your brand is by these big bets and I think it's really easy in today's world to just say what you do on your sleeve  and say your product is the message, I just think we're drowning in a sea of sameness right now that scares me a little bit. And time, I need more of it, I want to appreciate more of it, I want to be present for more of it and I want to make sure I enjoy it so it's ... I would say those are the three things.

Charles:

I wrap every episode with three takeaways  that I've heard that I think are foundation to your success, let me throw these at you and tell me what you think.

One is, I think you have a really healthy restlessness, I would almost think of it as an allergy to the status quo. You're constantly looking for, what's next, how do we make this better, where do we go from here, what does the future look like, how do we confront it on our terms?

Two is, I think  that you do that through a lens of being open to possibilities coming from a variety of places including what we might esoterically describe as the universe speaking to you, not just that, clearly other influences as well but including that which I think is ... makes you, I think rare from that standpoint.

And then three, the third part that I think strikes me overall is that you have  a real commitment to, concern for, interest in the human part of the journey and the fact that you're concerned about where people get their fire from, how do you help them keep it ignited, how do you help them brighten it, bring it to bear on something that's important, do that with a sense of urgency, feels to me like it's a very sort of personal journey that you're on as well from a leadership standpoint. How do those sound?

David Lee:

I mean they sound great coming from you. No, I think I would agree. I never really thought about it in that way, it's been quite a therapeutic session in that regard and I genuinely appreciate it.

Charles:

I appreciate you being here, thanks so much for coming on the show.

David Lee:

Thanks for having me.

Charles:

Thank you David.