2-14: "The Alchemist" - Andrew Essex

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"The Alchemist"

Today’s conversation is with Andrew Essex. He’s the co-founder of Plan_A - a self described marketing services company. He’s best known for his time as the CEO of Droga 5, and before that as the Chief Executive Officer of Tribeca Enterprises, the parent company of the Tribeca Film Festival.

He’s sharp witted, a quick thinker and has a relentless curiosity for what’s next.

This episode is called “The Alchemist”.


Three Takeaways

  • Relentless curiosity

  • A willingness to support others’ needs

  • Clear leadership values


"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT

Episode 2-14: "The Alchemist" - Andrew Essex

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

When we launched Season 2 back in October, I said that we’d identified 13 themes that show up consistently among the most fearless of creative leaders.

Over the last 13 weeks, we’ve covered all of them. From Action to Vulnerability.

I have some thoughts on what these themes mean that we’ll talk about in another show. 

Today’s conversation is with Andrew Essex. He’s the co-founder of Plan_A - a self described marketing services company. He’s best known for his time as the CEO of Droga 5, and before that as the Chief Executive Officer of Tribeca Enterprises, the parent company of the Tribeca Film Festival.

He’s sharp witted, a quick thinker and has a relentless curiosity for what’s next.

This episode is called “The Alchemist”.

“I wanted to do something that brought both hemispheres of the brain together, and I think that monetizing creativity, that turning creativity, which I think is a business imperative, into money, to be crude, is my calling.”

If you’ve listened to this podcast for very long you’ll know my feelings about creativity. That it is, quite simply, the most valuable business resource in the world. 

We’ve been working on something that turns that belief into something much more substantial and practical. More to come on that over the next few weeks.

Creativity has many definitions. Mine, and the one I find most interesting, relevant and valuable is this. Creativity is original thinking that solves business problems.

It takes a certain kind of leader to build a company that is capable of unlocking the business power of creativity every day. A company in which creativity is as reliably available as electricity. 

These kinds of companies don’t flip a switch. They create the conditions in which creativity can flow from its human conductors and become powerful game changing ideas. 

They do this Because, making sure that creativity is being applied to solve meaningful problems attracts original thinkers.

These companies build systems and practices that allow original thinkers to be more focused on the problem - and that ability to contribute to something meaningful encourages them to stick around.

These companies measure progress in ways that include but are not limited to money, because they know that the personal investment that creativity depends on is motivated by more than just money. .

Put all these factors together and the result is creativity at work. Which ironically, is where it is happiest.

Here’s Andrew Essex. 

Charles:

Andrew, welcome to Fearless. Thank you so much for being here.

Andrew Essex:

Thank you for having me.

Charles:

What's your relationship with fear?

Andrew Essex:

My relationship with fear? It's intimate. I experience it on a daily basis.

Charles:

Through what? How does it manifest?

Andrew Essex:

Oh. Fear of the unknown, fear of my own inadequacy, fear of my children, fear of my wife. I am quite familiar with it.

Charles:

And are you conscious of having to move through it or pass it in any meaningful way? I mean, is it something that occupies a lot of your thought, or is it just around?

Andrew Essex:

Actually, I'm being completely facetious. I think what I'm more familiar with is anxiety. I don't experience fear. I really am not familiar with fear. I actually run towards the sensations that I associate with fear, which is usually speed, recklessness, the unknown, but anxiety is fear's handmaiden and she torments me on a regular basis.

Charles:

That’s well-put. What's your first memory of creativity showing up in your life? When did something first occur to you that, oh, that's creative?

Andrew Essex:

I think it was in the music store a few blocks from my house, where they had a collection of Fender Stratocasters, and there were people playing instruments on a regular basis. I wasted a good chunk of my 20s as a musician and creativity was first made manifest to me through the ability to make a piece of wood and metal make beautiful sounds.

Charles:

How did your parents feel about that?

Andrew Essex:

They were ambivalent. Actually, it kept me off the pole, off the streets, so when I started to get serious and practice X number of hours a day, they were quite happy about it.

Charles:

So that was a really important part of your life?

Andrew Essex:

Oh, absolutely. From age 12 to age 22, that was the be-all, end-all, and that was the only thing that was going for me.

Charles:

So did that guide your education choices?

Andrew Essex:

Absolutely. I stayed local, because the band practiced in my parents' basement. I went to a local college, and I chose not to go to a better school or to have a dorm experience, because the band was too important.

Charles:

How interesting. Where was this?

Andrew Essex:

This was in a magical place called Queens.

Charles:

I've heard of that.

Andrew Essex:

Yes, yes.

Charles:

Hard to get into, I understand.

Andrew Essex:

Right. It's produced fantastic presidents though.

Charles:

Yeah. Yes, indeed. Yes, we could spend several days  [crosstalk].

Andrew Essex:

That's another podcast.

Charles:

Right, exactly. I think one that's been covered in other places. What took you from music into the world of, well, in your case, journalism?

Andrew Essex:

The dawning realization that I was just not quite good enough and that I wasn't going to make a living. There's nothing more humiliating that carrying your own amplifier down a flight of stairs at 2:30 in the morning with five dollars in your pocket and drunk. So I decided to apply to graduate school, I always wrote on the site, and that took me on another path. I started to work with the word more than the guitar.

Charles:

What did you write?

Andrew Essex:

I wrote fiction at first. So I wrote stories, short stories, tried to write a novel. Actually, went to graduate school for writing, believe it or not, and for English, as we call it, and that led me to journalism.

Charles:

How interesting. So expressing yourself has always been at the core of who you are.

Andrew Essex:

Oh, 100%, 100%, and I had very expressive hair for a long time as well.

Charles:

What form of journalism? What drew you to journalism?

Andrew Essex:

I started to read voraciously around the time that I was 18, and there was literature and there were magazines, and I guess my first way into the written word was music magazines, which employed a lot of great writers, a lot of great journalists, and then from there, one went to ... Well, I guess Rolling Stone, of course, was fantastic for journalism, then you could graduate to the New Yorker, theoretically more prominent publications, and then I got politically engaged and I loved reading about that. I loved reading criticism, music criticism, movie criticism, film criticism as we say, and just decided to pursue that and got lucky with a few early jobs, and probably would have stayed in that line of work for the rest of my life if there wasn't also the realization that that industry was facing some challenges, as we alluded to earlier.

Charles:

You spent how long in the journalism world?

Andrew Essex:

I would say, all told, let's call it two decades, just under, about 18 years.

Charles:

What did you learn about yourself during that?

Andrew Essex:

That I had tremendous respect for craft, that I had a lot of disrespect for institutional ... What's the right word? Recalcitrance. It was more important to me to move forward than to stay in one place, even though it was incredibly prestigious, and that celebrity profiles were not as glamorous as you might think.

Charles:

Were you a risk taker growing up?

Andrew Essex:

That's a really good question. I never thought of myself that way, no. I had a very provincial, all-American childhood, riding a bike through a park on a regular basis.

Charles:

So combining self expression with, "How do I actually turn this into making a living?" was kind of the equation you were.

Andrew Essex:

Yeah. I think it was the tension between art and commerce, or being a poet or a practitioner, and just the grotty business of having to pay the rent.

Charles:

And did you get experience as your journalism career evolved in terms of managing others and directing others?

Andrew Essex:

Yes. So, having done it for so long, or seemingly so long, you move up the food chain, and you start having to take on the responsibility of human resources and direct reports, and I climbed up the editorial ladder from a peon to an editor in chief, and at various points I had large staffs reporting to me, so you learn what's most important to you in that regard, if you're a finder, a minder or a grinder.

Charles:

What did you find was most important to you?

Andrew Essex:

That's a very good question, because I never thought of it in those terms, but I think what is actually interesting, and the most important skill that you learn from journalism is knowing what a story is and what a story isn't, how to find the inherent, interesting element of anything, and how to surface that in a way that makes others agree with you.

Charles:

Yeah. I mean, there's a real art to that, right, and a real ... Well, let me ask you that question, is it art, is it skill, is it training? Where you do you think that ability comes from?

Andrew Essex:

That's also a very good question. So, as I'm speaking, I'm thinking that you make a pivot from writer to editor in the magazine world. Writers have the glory, editors have the power. You see your name, you see your byline, and it's incredibly gratifying, I wrote that story, everyone sees that I wrote that story, and then, at some point, you are rewriting other people's stories and assigning stories, and have the power to decide what's on the cover, what's going to be 10,000 words, what's going to be 100 words, and you start having to build a universe, and those skills, the sum of the parts, the right length, the right image, the right pun, they become part of your craft.

Charles:

And how does the power change you? Because you're right, that's a tremendous amount of power in the context of that world.

Andrew Essex:

It changes you the way any power changes you. It makes you conscious of your decisions, how they affect other people. There's an inevitable seductiveness to it. There's the also inevitable increase in compensation. It's gratifying, very gratifying.

Charles:

And were you conscious then that the industry was struggling?

Andrew Essex:

Oh, painfully so. I'm one of the last generations of people that lived in a pre-email world, so there was a time when you had to physically bring copy to someone else in those old interoffice memos, and I remember sending first emails, getting the first chunky Blackberry, and then starting to see this thing called the internet and digital media start to disintermediate traditional publishing, and we know how that story turned out.

Charles:

Yeah, exactly. What made you jump to the advertising world?

Andrew Essex:

To the dark side. Well, it's a slightly long-winded story, so I'll try to be succinct, but, as you move up the food chain on the editorial side, you go on sales calls with what used to be called a publisher, which would now be called the chief revenue officer, so you might meet the head of LVMH or the founder of some interesting unicorn. You start realizing that these people are just as interesting as some of the stories that you've featured, sometimes smarter in certain respects, because they've figured out how to make themselves very successful or found a way to invent something brand new. You meet people on the business side and you realize that it's a much more complex ecosystem. When I came up as a journalist, we were kept separate from the business itself. We didn't have any responsibility vis-a-vis modernization, so it became more and more of an education the much larger world, and I started to think, "I need to think about where I'm going to be in the future, that there's an evolution happening here, and this is interesting to me."

Then, at the same time, I had a friend, named David Droga, who was in transition himself and looking to start something more entrepreneurial, and we were social friends, and he made a proposition and it was the luckiest thing ever to happen to me, and we started on that great adventure in 2005.

Charles:

What do you think he saw in you?

Andrew Essex:

I think it's one of those grass is always greener scenarios where, if you work in field like advertising, you tend to self-flagellate, you think it's much more glamorous to be in the journalism game, and perhaps even purer, but the irony is that I felt the exact opposite, that I was in a stultified world that was a classic ivory tower, that wasn't evolving in any way, that was participating in its own demise, and I think it was the cross pollination that made the thing so interesting.

Charles:

Do you think he was looking for certain characteristics in a partner?

Andrew Essex:

I think so. I wouldn't want to speculate. Maybe just also he wanted a provincial New Yorker.

Charles:

I think that's unlikely, just based on watching from afar, but ... And what were you drawn to in him?

Andrew Essex:

Height. David is an unbelievably charming, self effacing guy, and he wanted to punch the industry in its face and that was very appealing to me, the idea that advertising didn't have to suck, that it didn't have to be lazy, that it didn't have to be lowest common denominator, so to bring in editorial sensibility to what we used to call advertising, which we now call content, was incredibly exciting. Even when you work at a place like the New Yorker, with all due respect to my former colleagues, there is a formula, you produce the same structure, same format every week. The content changes, but it can be repetitive, especially in a weekly, and with David's enterprise, it was completely unclear what the output would be.

Charles:

And did you see risk in making this leap? I mean, this is a quantum leap, right?

Andrew Essex:

Oh, tremendous risk, but I thought, what's the cliché? No risk, no reward? It was a chance to reinvent, and probably used this line before, but it's like Madonna, you have to reinvent yourself or you're stuck.

Charles:

What did you think you would bring to that?

Andrew Essex:

A different sensibility. So what you don't want is a bunch of people with the same perspective, so you want a little friction, you want a different sensibility, you want different perspective, and I think that proved to be correct. I think I just brought a different set of references, a different type of Rolodex, and that was to the benefit of the enterprise.

Charles:

So, as you were beginning to put this thing together, together, what kind of environment did you want to create? What had you learned at that point that you thought, "We have to build it around these kinds of principles"?

Andrew Essex:

It was never so cut and dry where there was a lot of thought put into it, but I think you know, intuitively, that culture is super important. We were not young by any standard, so people in their 30s and 40s, and had never truly been in charge. Both had been high paid serfs on other people's plantations, and so you have an opportunity to be in charge. So you make decisions about how you comport yourself, how you're going to treat other people, who's responsible for cleaning the toilet if something goes bad, or filling the fridge if it runs out of food. So you try to create a kind of utopia that you would want to work in, had you had that option earlier on. I had been fired once and a half times in my previous career and worked for people that I despised, and I didn't want to be that person again. So it sounds contrived, but we at least tried to create a slightly more enlightened workplace.

Charles:

What was the half?

Andrew Essex:

You could argue that I quit, but I think I was actually fired, so let's call it twice.

Charles:

It's right, you can't fire me, I quit.

Andrew Essex:

That's right, that old game.

Charles:

Yeah. So, as you walked into this new world, what did you think it was going to be like, and how did the experience differ from that?

Andrew Essex:

Well, on the first day, we were working at someone else's production company, sitting around a round table, and two things happened that set the stage for the rest of my time there, which was the elevator stuck between two floors and we were trapped in an elevator for about 35 minutes, and then we went and saw Bill McDonough, who is the author of Cradle to Cradle, about a project to turn his idea into a business, into a platform, to think about reframing the art direction, and I thought, "This is fantastic. This is exactly what I want to be doing, because I can deploy some of my talents already," and it was a nonstop series of interesting opportunities, and never the same. You could literally make things up as you went along, and every day was an adventure.

Charles:

And what kind of people did you find you were looking for who met the need of [crosstalk]?

Andrew Essex:

On the client side or on the staff side?

Charles:

Well, actually, no, interesting question, both actually.

Andrew Essex:

Well, on the client side, you can't really choose, so you're looking for people that present challenges that you can rise to. Early on, we had a call from Esquire magazine who was working with a very prominent behavioral economist, who wanted to incentivize inner city kids to achieve, but to make achievement as tangible as a Jay-Z record, and he had given students cash and they wanted something less gross, so we proposed to give kids airtime on their mobile devices instead. You can't contrive, you can't imagine that you could make a client like that happen, it just appeared. So I guess the answer is you try to enable yourself to be in a position where serendipity can happen, where opportunity can present itself. And then on the staff side, it became apparent that we needed professionals. You need to invest in things like strategy, account management. You need a team around you that is rooted and competent to enable some of the flights of fancy to land.

Charles:

So, as you're building this company that is, by its definition, disruptive, and you're recognizing, "We need professionals," right, that's a complicated marriage.

Andrew Essex:

That’s right.

Charles:

How do you manage that?

Andrew Essex:

Very, very carefully.

Charles:

How do you get the kind of skill that you're looking for, but with the right kind of attitude?

Andrew Essex:

Yeah. I think you learn the hard way, really. So there were some ups and downs, but coming from the background of being in a band, I always thought that it was a collaborative effort, so you have your guitarist or your lead singer with the flamboyant hair and you need to have a great rhythm section. It's the sum of the parts. So you look for people that have what you don't have, that's really critical, that call bullshit on you when necessary, and I think that's a skill too. Some people surround themselves with people that remind them of themselves. I think that's a mistake. You want to have people that have something that you do not have.

Charles:

I'm struck by the fact, in my work I see this quite a lot, the companies that have incredibly talented founders with really differentiated points of view and a courageous, disruptive mentality, are fantastic at all of that stuff, and get a lot of attention, and generate a lot of success. The thing they often don't do very well is design the future, and they don't build, from the ground up, infrastructure that allows the companies to scale. Did you find that was true at Droga, or have you seen that as a general observation in other places? Is that a fair observation?

Andrew Essex:

What you're referring to is sometimes called the founder's dilemma.

I think founders, by definition, unless they're complete and utter egomaniacs, can't necessarily predict tremendous success. Some do, and some achieve it, but many fail epically. So you start recognizing that things are looking positive, this is moving in the right direction, and that's the moment of truth. Which is to say, are we going to just believe the hype, or start constantly questioning every step?

I will say that one truth about Droga5 was that there was any, there was not any self-aggrandizement. There was much more self-flagellation, like, how we do sustain this, how do we maintain this, how do we double down on this? And never ever being satisfied with anything.

Charles:

In other words, the fear of failure prevents you from planning for success.

Andrew Essex:

That's exactly right. Right. Or just the fear of being exposed. How do you make sure that this isn't a fluke, and how do you ensure that momentum doesn't slow down?

Charles:

What do you think the risk of exposure is in that situation, is that we are floored? That we are inadequate? That we are ... what's your perception of where that sort of fear of failure comes from?

Andrew Essex:

You know that line, "The further the monkey gets up the pole, the more you see its ass"? I just don't think that anyone who's reflective doesn't recognize, that when the spotlight turns your way, it's going to show some flaws. And you have to be prepared for that. You have to think a few steps ahead. What's going to happen if this succeeds? You live long enough, you see failure, and you learn more from failure than from success, as far as I'm concerned.

Charles:

Have you come across leaders for whom that's not true? I think that you're right, and I see that a lot, but have you come across leaders for whom that's not true?

Andrew Essex:

Absolutely. Yeah.

Charles:

How does that manifest?

Andrew Essex:

Well, some people are so, at least, they appear to be so completely untouched by metaphysics, that they just ... they will success. Going back to our fearless leader, for instance. Just that nothing can ever go wrong, and that they're incapable of making a mistake. That works for some people. They lead through their own egomania, but I find that pretty repellent.

Charles:

Can you think of an example?

Andrew Essex:

Not that I would name publicly.

Charles:

Right.

Andrew Essex:

But there are several, let's just say, prominent tech icons who've had tremendous success, and continue to have tin ears, and seem to lack the ability to look at their own belly buttons.

Charles:

As Droga's starts to become successful, what were the challenges that you were confronted with?

Andrew Essex:

Scale. So there is, as you get bigger, you get bigger, and it's hard to sustain a culture. There are also challenges that become much more driven by commercial realities. The bigger your clients get, the more they are encompassed in some long form irreversible decline, so they become a little less, a little more risk averse. That is dangerous, and frankly, they're not always buying what you're selling. So, just maintaining culture.

What's that other cliché? How big you have to get, before you get bad? So, trying to avoid that problem. Then you run out of space, so you have a certain magic in a physical space, and when you change offices, I think you risk a lot. Because you can't necessarily put that genie back in a bottle.

Charles:

And often, I think, because people take on too much space. Part of the magic of early stage development, the early companies, is that you're squashed together.

Andrew Essex:

That's exactly right.

Charles:

Right? The energy of that is actually palpable, and then, you put people into better design spaces, and all that energy just gets dissipated.

Andrew Essex:

That's right.

Charles:

That's actually physically too far apart.

Andrew Essex:

And that's something that's very hard to plan for.

Charles:

Yeah.

Andrew Essex:

Because no one necessarily wants to keep their grotty startup culture, but there is something to be said for that. I think, when you are a founder, or one of the people who's there in the very beginning, you have a certain longing, nostalgia, for the good old days. When they might, in fact, have not been that good, but there is a tendency, then, to become complacent.

Charles:

Yeah. "Well, we're in all this together, right?" is a much more present mindset. Whereas, when we've got beautiful office space, we're clearly not.

Andrew Essex:

Exactly.

Charles:

"My office isn't in the right place, or not big enough," or all of those kinds of things. How did you address scale, the problems of scale?

Andrew Essex:

Trying to hire more thoughtfully. You tend to just fill seats, at a certain point, because things are going so well, you just need bodies, and I think that's a huge mistake. Starting to define what you won't do, as much as what you will do. Tasking people with very specific roles that aren't related to culture. Talking about it publicly and privately. Providing more almonds.

Charles:

That notion of defining what you won't do, I mean, the advertising industry has got to ... the biggest fundamental of the advertising industry is the most business model, right? The notion of, "We're just going to hire people, mark up their value and then, sell them on, on an hourly basis", typically.

Andrew Essex:

Yeah.

Charles:

I find there are a lot of creative companies, but agencies, I think, are particularly bad at this. Who don't really define, "We'll sell anything we can." How did you deal with that mentality at Droga? Because for, at least from the outside, Droga, the perception of Droga is that it's not built that way.

Andrew Essex:

Yeah. I think you try to be fairly firm about your principles, to put those principles on paper, and to make sure that everyone who's in a decision-making role shares those values. Though we did go through the effort of putting that down, after a few bad experiences. These are the type of people we'd like to work with. These are the characteristics that we recognize. No douche bags!

Charles:

You became CEO after how many years?

Andrew Essex:

Pretty early on, I think, after about ... six months?

Charles:

How did that change your perception of yourself? I mean, that was a grand title, in a way.

Andrew Essex:

Yes, that's right. Well, when there are seven, maybe 15 people at a company, you can be the receptionist and the CEO. So I thought of it as chief email opener. It just meant that you have to walk the walk a bit more. It also forced me to do an MBA by fire.

Charles:

Yeah.

Andrew Essex:

Just to learn a lot more very quickly, and to rise to the responsibilities of the title.

Charles:

It's interesting how quickly one runs out of technical skill in those positions. We had a smaller company than Droga, but nevertheless, it had four offices, and a relatively large number of people. I was conscious, too, very early on that I didn't have all the technical skills. And those, you have to fill those in, so I think that is part of the journey of becoming a leader, is realizing the things you don't know.

Andrew Essex:

That's exactly right. There are technical skills, and then there are intangibles, and-

Charles:

Yeah.

Andrew Essex:

How do you master those intangibles? What is the role yourself? There's a lot of dispute about what the role of a chief executive is right now, and I think that was a work in progress too.

Charles:

How did you define it for yourself?

Andrew Essex:

Well, it-

Charles:

After you got past opening the email.

Andrew Essex:

It is different when you have an eponym at a company.

Charles:

Yeah.

Andrew Essex:

So I think the dynamics of Droga were pretty unique, so I think of a friend who's another CEO at a company led by a powerful eponym. You have to be someone who thinks more about the custodian of the brand itself, of the workplace, a liaison between the art and the commerce. I thought of it as an editor-in-chief, in some respect. That the project was the business, not specific elements of the business.

Charles:

Was there a frame of reference of, "What does David want in this situation?" Was that a constant presence, or where do you move past that, to, "This is what the company wants"? I'm always curious, in a founder-driven company, when does that transition happen?

Andrew Essex:

I think it was very much about what the company wants, and that the founder is very much part of the company, but if it's just a founder's point of view, then it's tyranny. And that's not healthy. Then everyone becomes dispensable. So how do you build a culture, so that the name of the agency is a brand that transcends the individual who gave name to the brand.

Charles:

Yeah.

Andrew Essex:

Then you have longevity as a result.

Charles:

Yeah. What did you find out about yourself as you grew into that role? That must have been a really interesting journey for you.

Andrew Essex:

Oh, so many things. Where do I begin? That I like beginnings, more than middles and ends? That there's nothing more seductive than new business and new opportunities, and from building incubators, to M&A, to expansion? That it was incredibly fun, to be on the front foot, to be the pointy tip of the spear? And that I could probably do without some of the tedium of management.

Charles:

Yes. Chief operating officers come in handy about that.

Andrew Essex:

Yes, exactly. Chief operating officers, presidents and fantastic CFOs.

Charles:

Yes. Managing directors, all of those roles we learn to love.

Andrew Essex:

Yes.

Charles:

For somebody who grew up expressing themselves, artistically and creatively, in very personal ways, suddenly you're now in a job in which caring about everybody else's expression becomes the primary reference point. Did you find yourself missing the first part of your life? Did you find, did you wish that you were able to express yourself more?

Andrew Essex:

Sometimes, yeah, absolutely. Because there's nothing more personal than filling a blank piece of paper, but-

Charles:

Yeah, or an empty room with sound.

Andrew Essex:

Or an empty room with sound, but I continued to think of the business as a canvas, so you could express yourself by the wallpaper in the new bathrooms. Or the architect that we choose. Or even copyediting a presentation, and explaining to people that there was a difference between "principle" with an L-E, and a principle with an A-L.

Just that the business was the expression, and every touch point could be a way to express oneself.

Charles:

As you look at the business from here, back, and out from the outside in now, do you see yourself still ... do you see parts of yourself still in that business?

Andrew Essex:

I hope so. I hope so. I try not to look back. I really don't believe in that. I just drop the mic. But I think that there are definitely parts of me in there that are very clear.

Charles:

It's an interesting reference, actually. When we sold our interest in the business that we had built, my wife and I, and I wish that drop the mic had been a thing back then. Because we did everything right, and had a drop the mic moment standing on the street outside of the office, where we just stood there for 15 minutes and cried at the separation, right?

I mean, it had been our choice, and we were ready and excited to go, but nevertheless, you are giving something up.

Andrew Essex:

Yeah.

Charles:

You've seen it, right?

Andrew Essex:

Sure.

Charles:

And we cried, and I wish now we'd had a mic just to be able to drop on the street, and turn around, and walk away. That would have been great, yeah.

Andrew Essex:

It's a good sound, especially when the mic is on.

Charles:

Yeah. Maybe we'll go back and recreate that moment, just for that. That's good. So you moved on from Droga. Why did you do that, and what happened next?

Andrew Essex:

Well, we sold the business in 2013, and then, 2015, I had been there 10 years. There was a very big birthday approaching, and I woke up one morning and said, "I'm done. I'm done." It reminded me of my experience in publishing. "This is the conclusion of the chapter, and I would like to take a summer off, and write a book." I have a policy that I take one summer off every 50 years, and I adhere to it very strictly!

So I spent my fiftieth summer in a house by the beach, which was well-timed and very fortunate for me. Learned how to make compost. Wrote one proposal, which couldn't sell, wrote another proposal, which I did sell. Wrote the book for six months, and then thought, "Okay. I should probably get a job." I had no plans whatsoever, but I knew that I wanted to do something slightly different, and I was hopeful that I could use my position as a creative executive in a meaningful way.

Charles:

So when you go into that moment of saying, "I've done this, and it's time for something else," what was that experience like? I mean, from an emotional standpoint, how did you look at what was ahead? What might be ahead? Again, were you afraid of that moment? Were you concerned about this, or did this seem risky to you?

Andrew Essex:

In retrospect, it seemed foolish, on some level, because I was extremely comfortable. But I was pretty convinced I wouldn't have to sell pencils on Fifth Avenue, and that I maybe, I would never work again in any meaningful way. But that I would be okay. And I was willing to throw a little caution to the wind. I literally had no plans, so I just wanted to have that experience of not having plans, and to see what fate would present, and if I would be proven wrong.

It wasn't fear, it was hope. It was hope that something would present itself, and something did.

Charles:

It's an interesting transition to go through. We went through it a couple of times, and I ask you, because I'm always interested in those moments where people can make the safe choice. Like you, we were very comfortable, in lots of different ways, and it just seemed like there was another part of the journey, that there was more to discover about what we were capable of. That, I think, gave us the impetus to say, "Let's walk away from something that is very safe, very known, very secure, to a large extent, somewhat predictable, and see what else is out there."

But I'm always interested in understanding how somebody takes a moment, or a point of safety, and says, "I want to put that aside." Because most people are working towards that.

Andrew Essex:

Yeah. I don't think it was a "Eureka!" Moment.

Charles:

Right.

Andrew Essex:

You start having a feeling-

Charles:

Right.

Andrew Essex:

Which involves insomnia, and sometimes resembles what would be the pretentious word "ennui"? You realize, "Maybe I'm repeating myself, maybe I'm a little bit bored"?

Charles:

"I've solved this problem before."

Andrew Essex:

Yeah, exactly.

Charles:

"And before."

Andrew Essex:

Right, I'm not using every one of my skills. Or I'm not being challenged enough. Also, I believe in the handing of the baton. So there are people, Incredible second- and third-generation management here, that would do my job better than I would, and they should.

Charles:

Yeah.

Andrew Essex:

Get out of the way. I remember that feeling when I was in my twenties: "Get out of the way, old man!" And, so I tried to get out of the way a little bit.

Charles:

As you were in your summer off, and the following six months in writing the book, and reflecting back ... what did you decide you wanted? If there was going to be a next chapter, what did you decide you wanted to have be part of that?

Andrew Essex:

It goes back to this idea of learning that publishing was a business. I have always had a somewhat hostile position on these cliched bifurcations of humanity, the suits, and artists? I don't like creatives who can't show up on time, or business people that have never read a book of fiction.

I wanted to do something that brought both hemispheres of the brain together, and I think that monetizing creativity, that turning creativity, which I think is a business imperative, into money, to be crude, is my calling.

And I wanted to do that. I wanted to help, use creativity to accelerate business.

Charles:

Yeah. I call it profitable creativity.

Andrew Essex:

Yeah.

Charles:

There's nothing more powerful, right?

Andrew Essex:

Yeah. I completely agree.

Charles:

I mean, nothing's more powerful. Yeah, it's remarkable. So that led you to, or allowed you to receive, the possibility of, what? How? Tell us what happened next.

Andrew Essex:

I got a few calls that seemed familiar, and I was very grateful to get them, and then I found myself sitting in a room with Robert DeNiro and Jane Rosenthal, talking about the Tribeca Film Festival.

Charles:

As one does.

Andrew Essex:

As one does, right. I remember going into that meeting and not feeling nervous as much as feeling, "This is going to be surreal," and that was barely the word that described it. But they were in a position where they had this fantastic platform that was facing some headwinds.

The headwinds are pretty clear, but one of them had to do with the fact that there was this thing called Netflix, and these streaming services, and people were watching movies at home. On their televisions, on their mobile devices, not going to film festivals, to see independent work that they had never heard of. And “What are we going to do?”, and “You might have a point of view on this,” and it seemed like this is the perfect challenge. This is exactly what I want to be doing, and I spent two very full years there turning that baby around.

Charles:

And did so successfully.

Andrew Essex:

I'd like to think so. Yeah, I think so.

Charles:

What was it like working with somebody like a De Niro? Not him specifically, and not to tell stories out of school, but I'm curious, working with a massive presence and personality and world famous, what's it like trying to unlock the talent of somebody like that?

Andrew Essex:

Well, it's a similar situation with a founder. So, a founder, especially a very famous founder, creates something out of whole cloth and that's to me that's the hardest thing to do, so tremendous respect there, but Tribeca was in its I think its 16th year when I got there, sweet 16 and there were difficulties in sustaining some of that momentum. So what it's like working with someone like that, is to have to put yourself in a position to say, “You asked me to do something specifically, and I'm going to do it.” So it means, not being overshadowed by reputation or by stature and recognizing that you actually have to have a seat at the table, and sometimes say things that might be unpleasant for others to hear.

Charles:

Because otherwise, what's the point?

Andrew Essex:

Because otherwise, what's the point?

Charles:

Yeah. So interesting.

Andrew Essex:

Droga was acquired by William Morris, or partially acquired and I had done a bunch of those horrible celebrity profiles in my previous life and I don't have a sycophantic bone in my body, so it's exciting to work with movie stars, but if it's a business, they have to be focused on the business.

Charles:

So candor.

Andrew Essex:

Candor.

Charles:

Empathetically delivered.

Andrew Essex:

Yeah, exactly right. There are new ways to express oneself. Getting Bob to use Snapchat, may have been my single greatest accomplishment.

Charles:

How did you get him to do that?

Andrew Essex:

Well, because he wouldn't do Twitter.

Charles:

Smart man. Very smart man.

Andrew Essex:

But those that don't, are not fluent in social media, sometimes ignored at their peril, especially if you are trying to raise awareness of a cultural event in a world that's extremely cluttered.

Charles:

So was that about finding a medium that physically was comfortable and familiar for him?

Andrew Essex:

No. It was about the dual challenges of relevance and revenue. So relevance obviously drives revenue. How do you make a cultural event feel relevant in a world that's changing dramatically?

So I had seen that movie before, in publishing. I worked at the New Yorker for seven years. An incredibly important publication that had at some point, become less relevant and that required a constructive agent of disruptive change to reposition it, to make it more relevant. I forget what the original question was, but there was a need to introduce new ingredients that were more of-the-moment.

Charles:

What do you think made him willing to change? Was it that Tribeca itself mattered so much to him, that he wanted to make it succeed?

Andrew Essex:

Yeah. I think that's the single quality of founders, to recognize when they need to evolve, step aside or reinvent themselves.

Charles:

Right, and sublimate themselves to the greater whole.

Andrew Essex:

Exactly. Well said.

Charles:

Yeah, it happens too rarely, doesn't it?

Andrew Essex:

It happens very rarely and it's very difficult, because it's not an admission of failure, it's just an admission that things change.

Charles:

Yeah, exactly. So from Tribeca, where then?

Andrew Essex:

After Tribeca I spent some time consulting, and I've launched now a new company with my partner MT Carney, called Plan A.

Charles:

And Plan A is?

Andrew Essex:

Plan A is a creative holding company. So we're trying to get our Martins Sorrels on, but in a subtly different perspective. We have a pretty bald thesis, which is that automation is going to take, has already in other worlds, 80 to 90 percent of the marketing services business, and displace many jobs but it will not take the role of human ingenuity. And as a result, human ingenuity matters more than ever so we're going to over-index on human ingenuity, broadly defined as strategy, creativity and relationships. Only the things that people can do, especially highly skilled, very talented people.

Charles:

And so you've got multiple companies obviously if you're a holding company?

Andrew Essex:

Yeah.

Charles:

So you're brokering relationships between them, on behalf of clients?

Andrew Essex:

That's exactly right. So we've acquired five firms, soon to be seven, all of whom specialize in some form of the human ingenuity that I mentioned to you, and then we provide to clients, a way to have access to all those boutiques with one contract, with centralized account management strategy.

Charles:

How do you get people who are so entrepreneurial that they have built their own businesses and bring all the pride and all the fastidiousness of that, having lived that life myself I speak from personal experience, right? I mean we are birthing these businesses, these companies, what have you learned about how do you get people who are that iconoclastic and independent to decide we're not just willing to talk about working together, we are actually willing to work together?

Andrew Essex:

It's such a good question and there are precedents, by way of an answer. So whether it's a French cheese collective or the United States of America, you have can Texas and Maine which would seemingly have nothing to do with each other, but are part of a federation.

People like the idea of being part of something bigger. Generally speaking, if the entity shares the same values and stands for something, I think in advertising companies, the holding companies, with all due respect, run primarily by financial engineers who again with all due respect, might not have huge amounts of interest in the product itself.

So you bring a bunch of crafts people together by having tremendous respect for their craft, and allowing them to work on their craft while you bring business to them. So that's the premise of Plan A, it's a federation, it's a collective really, but we have shared ownership and we stand for something, which is that we believe that creativity is the business imperative and good work moves the needle.

Charles:

What are the challenges?

Andrew Essex:

The challenges are the exact underside of that utopian vision that I just laid out, which is that human beings are involved. So, human beings and their work product is human and keeping it together requires walking the walk and holding that principle up all the time, so it's not just hot air.

Charles:

So this is a very different relationship for you with an organization than you've had before, right? I mean, this is one point more into it because it's yours, but also more removed because of the nature of the structure of it.

Andrew Essex:

That's exactly right. That's very astute. So I'm hovering above in a different way, and trying to exist more on a 20,000 foot basis than in the trenches, and that's to be the big difference. It enables me to work with more people, to see the landscape a bit better and see the patterns, and to build something different that just a single firm. It doesn't feel as Mom and Pop, it feels more … it feels bigger.

Charles:

I bet. What have you learned about yourself in this guise? Do you like this?

Andrew Essex:

I do like it very much. I've learned that I'm older now and [inaudible] so I see people making assumptions and mistakes, better now. So I've learned that I have I think, a better sense of ... I'm more worldly. That's what I've learned about myself, that actually this experience has been a creative in many respects, so I often practice ageism through various stages of my life, and now in my early 50s I feel incredibly youthful and wiser and thus, much more valuable and formidable.

Charles:

That's interesting. What kind of attributes are you looking for in the companies that you're pulling together? What do the leaders of those companies have to bring?

Andrew Essex:

They have to have something that's truly differentiated. One of the things that I dislike the most about this business is that much of it has been commoditized, and I don't even mean the programmatic side, I mean that there are some agencies that are indistinguishable from other agencies. And it can't just be the quality of someone's tattoo, or the crispness of their accent. They have to have some distinctive sensibility or angle that is unique, and it transcends categories whether it's experiential or strategic or influencer based, they need to be different. And when you bring a bunch of different practitioners together, you get something that's quite special.

So hopefully, we're producing a unique stew that becomes a very seductive offering to the right clients.

Charles:

When you think about the conditions in which creativity is unlocked in a way that drives business value, what have you learned is necessary about the environment that produces that? What has to be in place?

Andrew Essex:

I think, a point of view, for God sakes. A point of view on some kind of principle, and talent, which is the hardest thing to quantify, right? You know it when you see it. Like the Supreme Court definition of pornography is? You recognize someone who's got something.

That's the other thing that comes with a bit of experience, the ability to recognize who seems special and to understand how to, God forgive me, productize that or even merchandise that.

So I'd say talent is everything. Talent and principle. Character. Talent and character.

Charles:

How do you lead?

Andrew Essex:

I have a friend who said, you're still captain even if you have one finger on the wheel so I actually believe in an incredibly light management style. I can't stand being micromanaged, I think micromanagement is the single worst quality in a leader. So I believe in working with great people and just trusting in their own ability to maintain their own reputations. And then I make suggestions, I try to open doors and I'm present when I need to be present, and available when I need to be available, but I never get in the way.

Charles:

What are you afraid of today?

Andrew Essex:

That I'm wrong. There's a certain wager here, that some of the gravitational forces driving our industry are too powerful for anyone to contend with, but I'm going to continue to … that this is the right play in this incredibly turbulent time.

Charles:

As you look back at your career, can you point to an example or a time when you made a big bet and were wrong?

Andrew Essex:

Pregnant pause, not so good in a podcast. The big bet and I was wrong? Well I-

Charles:

Actually I think pregnant pauses in podcasts are very good.

Andrew Essex:

Oh good, okay. So maybe early on, you know, I thought I was going to be a rockstar, I really did. I had such excellent hair and I was pretty good and I thought that that was going to be the case, so I bet on that and chose a lifestyle that didn't allow me to live in a dorm, but just afforded me many, many other experiences.

But I don't think I would undo anything that I've done since then. Maybe sometime I'd like to take back some ill-considered choices, but all in all, a quick answer to your question would be no.

Charles:

I think I have to ask your ill-considered choices.

Andrew Essex:

Oh dear. Well you said, wrong or poorly timed. So the story people often ask me about is Honeyshed, so when Droga5 was starting up we had a social commerce play that I thought was a brilliant idea, and the elevator pitch was, QVC needs MTV, straight up infomercials, episodic with attractive people, some kind of narrative and clickable video. It was just woefully ahead of its time, for a variety of reasons.

And I think what you're asking me is, did you ever get so seduced by something that it pulled you into a path, and you weren't able to recognize it was not happening, it was not working? And that would be the closest case, where I just keep believing that something is going to happen until you recognize that it is categorically not. So I generally have the ability to recognize when something is not working, and either fix it or walk away and this was a case where it seemed so perfect, and was not.

Charles:

Did that make you shy away in the future, from situations like that? Did you find yourself bailing on investment opportunities sooner?

Andrew Essex:

No. Not at all. No, it makes you recognize the elements of something that will not be successful. So risk isn't the problem, it's more about the quality of the idea and whether you have the right components to increase your chances for success.

Charles:

[inaudible] I wrap every episode with three takeaways.

Andrew Essex:

Okay.

Charles:

That I've heard, I think contribute to your success.

Let me throw these at you. So the first thing that strikes me is that you have a relentless curiosity for what's next. That the present is interesting, but I think the future seems more interesting to you often, and so you're drawn to pushing yourself through that lens.

Two is, when you're in those situations of building something, you seem able to sublimate your own ego in order to support the egos of other people around, whether those are founders with big egos, big names or whether they are just talented people who need the space in the room.

And then third I think, is that you have a very strong sense of self and a set of leadership values that you show up with, it seems to me that based on what you've described, you're pretty clear about the kind of behaviors that are important for you to follow, and the kinds of behaviors you're looking for in other people, and that gives you a compass and a reference point in the middle of the maelstrom.

Does those resonate?

Andrew Essex:

They do. That's very, very flattering and I just want thank you for reminding me about the word curiosity, because that is one of my favorite qualities in all people and the lack of curiosity is soul crushing.

Charles:

Can't beat that as an ending. Andrew, thanks so much for being here today.

Andrew Essex:

Thanks for having me.