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Kyle T Webster

Kyle T Webster is an award-winning international illustrator. His work has appeared in The New Yorker, TIME, Wall Street Journal, and other distinguished clients. We talk with Kyle about navigating the creative industry, price negotiation, overcoming anxiety, and the calculated career risks he took along the way.

You Can’t Be Good At Everything
You Can’t Be Good At Everything

You Can’t Be Good At Everything

Ep
192
Jun
08
With
Kyle T Webster
Or Listen On:

How the world’s best-selling digital brushes were acquired by Adobe.

Kyle T Webster is an award-winning international illustrator. His work has appeared in The New Yorker, TIME, Wall Street Journal, The Atlantic, Nike, IDEO, and several other distinguished clients.

Acclaimed industry publications like the Society of Illustrators, Communications Arts, and American Illustration have recognized his illustration work.

Kyle also teaches at UNC School of the Arts and works for Adobe, hosting workshops and helping to make digital products like Adobe Fresco.

But you may better know him by his best-selling Photoshop brushes.

The Origin of KyleBrush

As an illustrator, having a distinct visual style is a point of pride. But that's not something Kyle was interested in. He wanted to offer clients a range of illustrative styles. And to do that, he needed a range of flexible tools.

As a result, KyleBrush was born.

KyleBrush is a collection of thousands of high-quality digital brushes originally created for Adobe Photoshop. What started as a practical necessity transformed into a full-time business.

Kyle's products became an industry staple. You could find his digital brushes everywhere, from Pixar to boutique animation studios.

In 2017, Adobe acquired KyleBrush making all of his digital brushes available to anyone subscribed to Creative Cloud. They also hired Kyle to help their product team develop new digital drawing tools.

In this episode

We talk with Kyle about navigating the creative industry, price negotiation, overcoming anxiety, and the calculated career risks he took along the way.

Beyond that, Kyle also offers a variety of practical tips that you can apply to your professional life right now. In particular, a clever way to connect with seemingly unreachable people.

Hosted By
special guest
produced by
edited by
music by
Appearances

Episode Transcript

Kyle:

I never took any risks that weren't calculated or weren't fairly well-considered. I always was like, "I'm going to do this thing, but I'm going to get myself pretty well-prepared." A lot of people I've talked to before in interviews and things they're like, "How did you have the courage to leave your job?"
I'm like, "Why? I waited three years while I was building up another business. I didn't just say, 'Bye.'"

Chris:

Kyle, just as we were talking before we started recording, it feels like we know each other, but it might be one of those, like you said, manufactured memories of false memory because we are in the same space a lot with Adobe, you as an evangelist, me as a speaker, and just, I guess, a now new partner with Adobe doing different things, but I've wanted to have this conversation with you for some time. First of all, we have the exact same haircut, which makes me already like you just from the jump, right?

Kyle:

Yeah. We go to the same barber.

Chris:

Yeah, we do, which I imagine you probably just do yourself, right?

Kyle:

Oh, yeah, yeah. I had to get good at that many years ago.

Chris:

Yes, same here. So okay, haircuts aside and everything, you come across as a really friendly, down-to-earth person, who just likes simple things and wants to keep things simple. Is that my read on you? Is that fairly accurate or there's a total different persona?

Kyle:

I think that is super accurate. You're right on the money there. Thank you for that observation. Yes, astute.

Chris:

You did a video where you said, "I get stressed out a lot." So that I wanted to ask you a little bit about, which is you seem like a super chill guy. Is this through all the meditation and Tai Chi that you're doing that you're super chill? What stresses you out?

Kyle:

I am not super chill. I'm wound up so tightly that, not to get into this in too much detail, but I've actually suffered from a host of really bad physical ailments the last few years because of this. So I'm actually working harder than ever to calm down. It's funny that you said, "You seemed a chill guide," because I was in a meeting with the chief product officer at Adobe when we were getting ready for MAX one year, and everybody was in there. I was getting down to the wire and he goes, "Gosh, how do you stay so calm and you look so relaxed through all this and that you have to get up there and present?"
I said, "Yeah, you don't see me having panic attacks backstage five minutes before I go on and do this." Nobody sees that, but I am absolutely freaking out all the time. I just wear a really good mask.

Chris:

Well, you wear it really well. I'd to just go there for a second because as a public speaker, as an introvert, as a super shy and awkward person myself, I have similar the pre-talk with myself because I'm freaking out backstage, and as much as you're a public figure, take us backstage. Tell us what it's like 10, 15 minutes before you're actually on stage.

Kyle:

Yeah. My hands are sweating. I'm pacing a lot. I've got a lot of nervous energy. Sometimes I even feel like I could pass out at any minute, yeah. Then the thing that happens is I was in theater in high school. I loved acting and I was the same way, but then the moment you're on stage, the electricity, the crowd, the feeling of being in that moment and being in action, so to speak, just takes over my body and then I'm really comfortable and really happy. I really enjoy that part of it. The lead up, the buildup is always just terrible.
So the backstage for me is me trying desperately not to completely fall apart before I make it onto stage, and that goes for lots of big moments in my life where I know that something's riding on it, but I'm sure, I don't know if you're the same way, Chris, but what I do is I build it up in my brain to be much bigger than it really is because we all know going and talking in front of a crowd is not as important as taking care of your family or these things. Everything falls out of whack with regards to perspective. So I try and try and talk myself down and be like, "Hey, this isn't the big deal. If you screw up, you screw up. There'll be other opportunities."

Chris:

Your children will still love you after this.

Kyle:

Yeah. They don't care. They don't care about anything I do.

Chris:

That is the way. Okay. So take me through some, if you may, if you don't mind, take me through some of the dark thoughts you're having. You told me the conditions. Your hands are clammy. You feel like you're going to pass out. What are you telling yourself before you calm your mind and get on stage?

Kyle:

A lot of what happens is I go through worst case scenarios that are really unrealistic. I future trip and I imagine something completely unrealistic happening where I completely forget everything I was going to talk about or I just get frozen and I literally cannot speak and cannot move through it or maybe if I'm doing some demonstration for Adobe like on the MAX stage, I think, "The iPad is going to crash and I'm not going to be able to recover and I have to stand there and just stutter and mumble and not be able to get through it."
These are the kinds of things I envision, which anybody who coaches people in public speaking tells you is the opposite of what you should be doing, but it's just, I think, what I do. I sometimes wonder if some of that comes out of what motivates me as an entrepreneur to continue to make things and build and to stay "relevant", which is a lot of that's actually motivated by fear. I think if I don't work and if I don't stay successful, my family's going to starve. I just immediately jump to the absolute worst case scenario, which is just not healthy.

Chris:

Yeah. It's not. Take me back then. As a child, because you mentioned theater, so it's not all coming together for me because as a person myself speaking, just speaking for myself, the signing up for theater would be the last thing I would want to do to be in front of people. So is there something that predates when you were much younger where you did have this thing where you're called out in public and you froze and that's lived, that's stuck with you?

Kyle:

Gosh, that's a good question. I don't remember that happening. No. It's funny that you mentioned that because, normally, these things, you have some evidence to call on of something having gone wrong in the past and so that will inform how you're thinking about it happening in the future, but no. I had really good experiences with "public speaking", I guess, which is mainly for me with theater and oral interpretation. I did a traveling oral interpretation competition and other things. I liked that stuff. I guess as you get older, things just intensifies.
So what was in high school butterflies in my stomach grew into in my 30s and 40s, crippling stomach pain and bad health problems. So I think that's what happens is everything just grows in intensity and gets bigger, but I'm actually much better now. I mean, I've really learned a lot of tricks for helping, and I'm happy to share those tricks with anybody who wants to know about them because I know there are people out there who suffer from anxiety and from public speaking issues and whatever. So yeah.

Chris:

I'd love to hear about them. So it sounds to me you were a strange late bloomer when it came to the fear of public speaking because you were okay as a kid and then as an adult, you're actually, "I'm more aware of the world. There's a lot of things that could go wrong maybe."

Kyle:

Yeah. I think the other problem is, too, when you're starting out. So the first couple of lectures I gave at universities where I'd go and talk about illustration, I wasn't that nervous because I wasn't really that well-known or anything. Then you know how it goes. More and more people start to invite you to do things and you start to think, "Oh, well, I really better not let them down because they're expecting something great." So then the expectation you put on yourself is different from when you were younger.
So now, if somebody does invite me to go do a thing, I have to talk myself out of believing that they're expecting me to really wow them and blow them away in some way or tell them something they never heard before. What I tell myself instead is if I tell them just one thing, one little nugget that they can take away, they hadn't heard before, I've done my job. That's all people can really remember, anyway. So that helps me.

Chris:

What else do you do?

Kyle:

What else do I do? So I do breathing. I really, really concentrate on breathing, and I do different breathing exercises, and I now have started incorporating, and this comes out of a thing I was doing as a service, I guess you would call it. I was doing meditative drawing workshops through the AIGA and through a couple of other organizations and helping people to use drawing as a way to calm down. I was really astonished that I wasn't doing it for myself. It was so silly that I was offering this to others and that not taking advantage of it myself. So the last time I got nervous about something, I had to do the Apple event in September last year. The morning I woke up in the hotel, I was just freaking out about going there and filming it.
I was in the process of building this app that I'm working on called Lines of Zen, which is a meditative drawing app. So I actually sat and did my own exercises for about 15 minutes and totally calmed myself down, and I just felt stupid after that because I was like, "Why am I promoting and preaching all this stuff and then not actually practicing it?" although I think a lot of us are guilty of that. I don't know about you, but exercise for me is always great, but it's not something I can always fit in right before a talk.

Chris:

So what do you do to stay healthy and fit?

Kyle:

So right now, what I do, and this is going to sound very not so impressive, but I take daily walks, and I find that just an hour long walk every day is enough to really settle things. I was jogging for a while. I'm dealing with some knee injuries right now so I'm just going to work around that, but when I get back to jogging, I think jogging even just for 20 minutes is phenomenal or any kind of aerobic exercise like that. I play tennis. I'm a huge tennis fan. Love it.

Chris:

My wife would love you. She wants me to play tennis with her, but I'm so bad at it. I just try to power the ball and it just goes out the court. I don't have that slick at the end.

Kyle:

That's so funny. We have the inverse thing here because I want my wife to play tennis and she's always resisted, but guess what? She's taking her first lesson this Friday. So I'm so excited that maybe, maybe in the future it's going to happen.

Chris:

I know a lot of people who love tennis say this is a sport you can play for all of your life because we see young people and we see really old people on the court, and it's not too demanding on your body, but it's really great for hand-to-eye coordination and keeping you moving. So if your wife doesn't get great, the next time we cross paths, I'll bring my wife, and you guys will get together and your wife and I will hang out and just watch and you guys can play.

Kyle:

That sounds like a perfect arrangement. Yes. I'll just say, too, about tennis, it's a social sport, which I love. So I spend half as much time on the court talking to the person I'm playing with that I do hitting the ball. So it's a nice way to have friends and have relationships.

Chris:

That's wonderful. Okay. So I like to circle back because you said something which really resonated with me that when you do a talk, whether it's five minutes, 10 minutes or 40 minutes or however long it is, the human mind can only process so much, but there's, at least for me, this tendency to, one, to over deliver. I used to tell myself, "If somebody paid $500 to attend a multi-day conference, it was my sole responsibility to deliver at least $500 of value no matter what." Of course, that starts to stress you out and you start putting so many things into your presentation that it just becomes overwhelming for people. Do you do this yourself like you go, "I got to give so much value"?

Kyle:

Yeah, of course. No, I mean, everything you're saying is just echoing through my head like it's my own voice because I do exactly the same thing. I think, "Well, this whole conference is riding on me kicking butt, and what a joke." I really overdid it one time and I learned my lesson. I tried to do too much. I did a presentation a few years ago at Icon, the illustration conference, where I covered way too much ground, and I even ended it with a guitar song, and I also had a special guest that a friend of mine come up and do a little comedy bit. It was just all too much to organize to keep straight. It became discombobulated, and I came off the stage and thought, "That was just such a mess of stuff."
So since then, I've really focused on narrowing it down to maybe two or three things that I think, "These are the things I want them to walk away with," and I make sure I reiterate those things a couple of times and I keep coming back to them, circling back to them so that they're really, really clear. That just also takes the pressure off me because then I feel like, "As long as I deliver on those two messages or whatever, I've done my job."
The other thing, too, is I remember being in the audience at a lot of these things. I start to zone out when it's too much, but when somebody stays focused and they're really concise and they get off the stage when it's time, I'm remembering it more fondly. So I try and be that guy.

Chris:

Yeah. It's a paradox of sorts. We want to give value, so we try to put more in it, but by putting more in it, we confuse the audience and it's so much for them to process, and their circuits get fried. It's an instinct that we have to really fight, at least for me. I'm still struggling through this because my wife will be there. She's like, "No matter how much time they give you, you'll always be jamming so much in there and rushing at the end. Can you just start editing things out?"
So in the last year, I think I've started doing a better job where I'll jam it with so much stuff. In about two days before, I'll just start deleting stuff saying, "That's not necessary. That's a tangent. We don't really need that," and then I strip it down a little bit. It's still not great, but I'm working towards it.

Kyle:

Yeah. I like that what you said about right before starting to pull stuff out. I think that's sometimes what's needed is little time between when you've actually finished preparing it and then you let it sit for a minute. You come back. It marinates. You come back to it and go, "Oh, this is redundant, this is redundant, this is redundant." Yeah, it's getting to the essence of it. I think John Cleese talked about that once with writing skits and sketches and just trimming the fat. Yeah, editing's always a huge part of the process that I sometimes overlook and need to spend more time with.

Chris:

Yeah. I find that if I over prepare, it helps to quell my insecurities about, "This is not enough," and then moments before, by editing it out and saying, "Okay. Really, this is what matters and I think people are going to be good with this." I'd like to share something that my friend Joel Pilger told me one time prior to me going on stage or the night before. He said the best advice he got from somebody who was a mentor of his, he said, "We're always busy trying to give people our top shelf stuff and so we're reaching and it's a stretch for us, and it creates a lot of anxiety and stress." He says, "Just give them your middle or even your bottom shelf stuff because even that, people will just love and gobble up."
So that put my mind at ease. I'm like, "You're right. It's always like I want to do the best job possible, be the best version of myself, this is the newest, greatest, latest thing and causes so much stress for me," but I hear those words echo in my mind every time I start to stress out.

Kyle:

That's really smart. That's wisdom right there. I don't know who it was, but you're calling to mind something. I had a conversation with somebody that was similar where what they told me was a lot of the things that I take for granted as obvious are news to a lot of people. So I think that relates to what you're saying, where instead of me trying to find that amazing new thing that even I hadn't known or discovered yet, tell them what you already know that to you just is something that's become habit or whatever, and it could be a completely new piece of information or a new inspiring idea for them. I think that's really important, too. That stuff matters. It's just that we forget it because we've been doing it for a while.

Chris:

Yeah. I think it's a form of cognitive bias. What is it called? Something, the cursive knowledge, where you've learned it, you've figured it out, and then you forgot that at one point in your life you didn't know this stuff, and then you don't want to teach it because it's like, "Duh, doesn't everybody know this?" It turns out no, not really.

Kyle:

Yeah. Yeah. That's really important. I'm so glad we're having this conversation because I know I'm going to have to do more public speaking next year when things are opening up and opening up, and I got to keep all this in mind. I'm rusty.

Chris:

So prior to the pandemic, while we stay on this theme here of public speaking, in a given year, how many times were you giving talks?

Kyle:

Well, actually, before joining Adobe, I was doing it more because I was more representing my brand, Kyle Brush, these brushes I built, and also just my work as an illustrator. I guess it wasn't that much, maybe eight to 10 times a year, either at schools or conferences. So certainly not as much as someone like yourself, I would imagine or people who really get out there and make a name with doing that work, but that's about it. Yeah.

Chris:

Okay. So how have you adjusted during the last two plus years under lockdown?

Kyle:

I've done a few little speaking things and they were remote, of course. So I found that I didn't enjoy it very much. It's just not the same. You don't get anything back from the audience. Everyone's on mute or whatever, and can't see, really. You can't feel that energy of a room full of humans, and then also, you're missing the after talk where after the talk you can talk to a few people who come up afterwards and have more questions for you and you can help them out more. You can be specific. You never know if you're covering everything people want when you speak, and it's great to have Q&A and then to have even a smaller Q&A afterwards where you feel like you can really laser focus on one person's question and help them out in some way.

Chris:

Yeah. Okay. I feel like we're the same person sometimes when you're speaking. You know what? I have to say this. I've not heard anybody else say it exactly the way you said that so speaks to my soul. What people don't realize is, "Oh, they just assume." You make YouTube videos, you do public speaking, so a Zoom calls is a Zoom call, right? No. You're exactly right. Here's what you said. No energy back. It is a draining process. You're just speaking into a camera. There's almost no feedback because you can't even see people's faces or they're muted most of the time. For me, the work is the talk. The reward is what you call the after talk. I want to meet people.
I'm a shy, weird guy. So after I do the talk, it breaks the ice and people are brave enough to come up and talk to me. That takes a lot of pressure off me. I really want to talk to them and get the feedback like, "What's going on? Did you like this? What didn't work for you? Where were you confused?" That's really helpful for me, and that's how I re-energize. So I'm feeling what you're saying.

Kyle:

Yeah. The interesting thing is with public speaking in-person, I would always come away from it feeling energized, feeling pumped. I would feel like I could just go race, I could run. I was just high. Now, with the Zoom calls, I would literally turn off the machine and then go flop down on the couch and just feel drained and exhausted like what you said. That's so interesting how you're doing the same thing but in a different environment and so the end result is either feeling energized or feeling exhausted. It's really weird.

Chris:

Isn't it? I don't know. I'm going to guess. Are you an introvert?

Kyle:

I cannot figure that out. Great question because I seem to bounce between being really, really wanting to be by myself and be left alone and have my own time and do my little projects and hobbies and things, but then suddenly going the other way and craving a crowded room full of people to have interesting conversations with. I don't know what that is. So what am I? I don't know.

Chris:

You and I, again, I think we might be the same person because there's extroverts and there's introverts and there's something I think in-between called an ambivert where we're on the spectrum. You tip the scale one way or the other and it's not by choice, but we can float, and it's interesting. I always thought myself as an introvert. I'm taking tests, but it's interesting because I take some online tests and the score puts me within five points away from being an extrovert and that surprised me.

Kyle:

Ah, interesting. Yeah, interesting. I've never taken those tests. I should take some just to see what they say about me, but yeah, that's how I feel. It's really split down the middle.

Chris:

Yeah. You know what? I realized we just jumped cold into the conversation. There's some people who might recognize your voice because I think you have a pretty distinct voice, but in case somebody doesn't know you, can you introduce yourself and tell us a little bit about you?

Kyle:

Sure. Well, I am an illustrator first. I think I like to draw. That's really what makes me happy. I started out as a web designer just because I needed a job after school and I was terrified of leaping out and figuring out how to make a living drawing, but I fortunately was laid off and then got a design job working at a design firm. That was my real education because I got a chance to learn the business of image-making for clients, commercial work, et cetera, pricing, all those important things. Then I started my own business as an illustrator four years later.
I ran that business for about 12 years. In that time, I created a really big number of Photoshop brushes for my own purposes because I like to work in a lot of different styles, and we can talk about this later, but one of the things that always bugged me that's "conventional wisdom" about illustration is that you should have this really distinct style and stick with it. I went completely the opposite direction and marketed myself as an agency where I could just work in any style that best suited the voice of the project, right?
In order to do that, I needed different tools. So I've created a bunch of brushes that had different feels to them. What wound up happening was through a friend's recommendation, I started selling them, and that actually became my primary business through a lot of luck and timing, but also a ton of effort and work and experimentation to make it into this leading brand for Photoshop brushes called Kyle Brush.
Eventually, I was able to bring that brand to the attention of some people at Adobe. Eventually, we could talk about this, too, but it was quite an amazing process getting from selling one little brush pack to Adobe acquiring the library of brushes and then bringing me on as an acquihire. So that all happened in late 2017.
So now, I work at Adobe and I bounce around. I'm a floating asset working on anything having to do with drawing and painting. I also work as an evangelist teaching drawing and painting and illustration concepts and techniques and all that stuff through Adobe live, which is free to everybody, hundreds of thousands of hours of stuff. I'm really happy to do that. It's really fun. So that's what I do now. So I still draw and I still occasionally do client work, but I limit that now to very few projects per year.

Chris:

I wanted to ask you first. Getting out of school, you said there was some insecurity. You're not quite ready to go off on your own. You got a job doing web design and, ultimately, was laid off, which was probably a blessing for you. Emotionally, how was your self-confidence when you were laid off? How did you feel about that?

Kyle:

It's funny. I look back on that time and I remember feeling relieved because I was so unhappy not doing the thing I liked. Every meeting in that web design company, and these were lovely people, I mean, they're great people, but I was just every day dreading going to work and having to sit and code when what I wanted to do was be drawing. So in meetings, I was just drawing Batman. When I got laid off, I knew that I could go get another web design job right away because this was 2001 when there were just a bazillion web design jobs.
So what I did instead was I created a mock portfolio of illustration work for brands like Nike and Lee and or Levi's, and I did a bunch of things that these were not really my clients, but I created fake projects for them, and I shopped that portfolio around, and I was transparent with people. If they asked, Did you do this for Nike?"
I said, "No," but it didn't matter because what I was trying to do is show them I could do good work. I wound up getting a lot of freelance illustration jobs for about three months before I got hired to the design firm. I learned from that that all that pressure I'd put on myself before to go out and get this work for real and stuff was garbage, I just had to show people my potential and show them I could do the work and they would trust me to then do that work for them. So it really paid off. It was really a great lesson. So yeah. Then I went into to drawing.
So the insecurity when I left school was just, first of all, I think I didn't know because I didn't have any business education. I went to a fine art program. I literally just drew naked people for four years. I was like, "How do I parlay that into a career?" So web design, I taught myself HTML senior year of college just on the side because I knew I could get a job doing it, and I was fascinated by it. It was fun, but then the moment you're actually doing it as a job and you're literally doing pricing for mattresses, which is one of our clients, it was a mattress company, I was like, "This stinks." So I was glad to be laid off, but I'm riddled with insecurities if you want to talk about those.

Chris:

You're like, "How long is this call?"

Kyle:

Yeah.

Greg:

Time for a quick break, but we'll be right back.
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Greg:

Welcome back to our conversation.

Chris:

I want to appeal back some of the layers and some of the meanings, especially for people who are in the job market right now because sometimes things are not meant to be and the universe is telling you, "This is not for you." Could you imagine if they didn't lay you off and you're just like, "Oh, I just hate work. I hate my life, but I still show up because these are golden handcuffs for a little while." You just go to work, and they did you the biggest favor, but then that points you in a different direction, which probably gave you enough courage to say, "You know what? I'm going to now do something that I love."
Some people question this practice of doing spec work to build a spec portfolio of things that you like and you love as a demonstration of your skills, not to say I've worked with these people. It's a wonderful way for you to open doors and have conversations with people. I don't know why some people frown on this, but if you're in a space right now where you don't have the work that you want to do, whether you're an independent person or working for a company, show them. Show them what you love to do. Put in your own time. Invest in that, and then hopefully, if it's good, people will start to notice and doors will open. So I love that mock portfolio led you to the design job, which then oddly opened the doors for you to learn all the business side of things.

Kyle:

Yes. Wow. I mean, it was the perfect time, too, to learn that because I had some skills at that point, but I didn't know how best to employ them and how to turn them into money and watching the design partners who were my employers, watching them navigate all that, and watching them negotiate with stuff, and get new work, and talk to clients. It was so great to be sitting right there and watch them do all that stuff because through osmosis, it all just sunk in, and when I started my own illustration business, I really got off on a good foot from day one with contracts and with things like that, and not getting taken advantage of as much as possible. I still had to learn a few things, but it was really cool to have that knowledge. I didn't feel like I was starting cold.
I had been, of course, doing a lot of illustration work on the side at that point. When I finally did quit my job and been slowly building up my business at night, I never took any risks that weren't calculated or weren't fairly well-considered. I always was like, "I'm going to do this thing, but I'm going to get myself pretty well-prepared." So I'm just not a huge risk-taker. A lot of people I've talked to before in interviews and things they're like, "How did you have the courage to leave your job?"
I'm like, "Why? I waited three years while I was building up another business. I didn't just say, 'Bye,' and then start from scratch."

Chris:

Yeah. So did they invite you into these conversations where you got to witness them doing the bidding and process, that whole thing?

Kyle:

Yeah. Well, what's cool is it was only seven people. It was a really nice small firm, but we did so much great work. In fact, we were the agency of record for Krispy Kreme donuts. At the time, Krispy Kreme just got a new CEO and they wanted to shift directions with their materials to be more illustration-centric. So that was perfect because I was the only person at the company at the time who was an in-house illustrator. So I got so much of that work and I got to sit in all the meetings with the CEO and listen to my bosses talk about the projects. So yeah, I was always there in the room when these things were happening and it was great.
Actually, I have to thank one of them, one of the partners, John Walker. He was the one who encouraged me to submit an illustration to the Society of Illustrators for the very first time. I hadn't even know what the Society of Illustrators was. Remember, I was a fine art major. So illustration to me was a really mysterious thing. I submitted an illustration of Jack Black and it got accepted. So I got to go to the Society of Illustrators in New York for the opening, and that's where I met my people. The moment I walked in that room I was like, "Oh, my gosh! This is what I want to do with my life." So that lit that spark of just, "I've got to figure out how to become an illustrator for real," and that's when I started sending stuff out and getting small jobs on the side and really kicked it off. So it was all thanks to that guy.

Chris:

There's so many things I want to follow up with you on. One is, what advice would you have for someone who is in a company but isn't invited or allowed to witness some of the business going on so they never learn that skill? How can we put ourselves in a position where we can be exposed to that kind of stuff?

Kyle:

Yeah. I would just say ask because I know it sounds obvious, but the thing is I've gotten so many opportunities in my life and I've moved my life forward career-wise simply by asking, "Can I be involved in this?" and just asking permission, and also by finding ways around things. So there are gatekeepers that we talk about all the time, and if you can find a side door. So if there's somebody else who was in that meeting who is at your level, just talk to them then. Start with that person. Be like, "Hey, what was it in there? What did you guys learn? Would you talk about it? I want to know more about that," but also, I really do believe that employers in these kinds of places, if someone comes to them with any interest in something, they're excited to know that you care and that you're passionate about it, and that you're curious rather than just a drone coming to work every day and doing what's required of you.
Certainly, I come alive and I get excited when a student comes to me and asks me a question. I'm just like, "Oh, thank God, somebody wants to learn." It's so exciting. So I probably tell them more than they want to know because I'm excited. So I feel like if your employer doesn't do that, it's also possible you're not in a good place. Why do they have to keep secret? Why are they hiding this from you? You're all working on the same team. Why wouldn't they want you to know how this works? It's weird.

Chris:

I think probably insecurity and just general suspicion of why people want to know certain things. I can see how-

Kyle:

Yeah. I guess you're right. If they think, "Oh, they're out for my job," or something, but I don't know.

Chris:

Yeah, or, "Oh, you want to know about what we charge so that you can ask for more money," or something like that.

Kyle:

Oh, yeah. Gosh, I don't think about that stuff. I mean, I really just ask. I can't think of any time when I was just outright rejected. Maybe there have been times, but I probably just forgotten them or blocked them out. Can I tell you a quick story about that because I think it's relevant to this?

Chris:

Yeah, of course.

Kyle:

When I was trying to work for the bigger publications like the New Yorker and Entertainment Weekly and things like that back in the day, I wouldn't be able to get in touch with the art director, but I knew their names. So what I finally did one day, I just said, "Forget it. I'm going to do this." I called the main switchboard at Entertainment Weekly, and I just said to the person who answered, "Hi. I was cut off with, what's his name, the art director. Could you please reconnect me?" She did, and then I had him on the phone. I knew I only had 10 seconds. I was like, "Hey, this is my name. This is my website, and I'm really good at drawing likenesses of celebrities, whatever. Give me a call if you got a job."
On the phone, that moment, he's like, "Hey, guess what? An artist just dropped a gig. We have four portraits for a movie review coming out. Can you do them this week?"
I said, "Yup," and that was it. Then I started working regularly with them. So I used that trick with several other publications. Just called the main switchboard, said I was disconnected, and the reason I realized it worked was I put myself in the position of the person answering the phone. I thought, "Who is the person sitting in this massive building answering phones? Why are they going to police the situation? They want to get the phone call over with so they can go back to Sudoku or whatever."
You're not getting training on a job like that to be like, "Don't answer them. Don't connect people to the art directors," especially not the art directors. Nobody cares about them, sad to say, but that's just the way it is. So I think there are ways around these things. You can tell white lies. Nobody gets hurt, but you can move the ball forward.

Chris:

That's a really good trick you got there. That takes a lot of moxie, by the way, to fabricate a little story so you can get on the phone and also to be able to pitch yourself in 30 seconds. What did you feel in that moment? The very first time you did that where that art director said, "Hey, I got a thing," what was going on in your mind?

Kyle:

I couldn't believe it. First of all, when I got through I just thought, "Okay. This is it. This is my moment," but the fact that I actually got a job out of it was just, I mean, I hung up and immediately ran downstairs and told my wife. I was like, "You will never believe what just happened," and I was just thrilled. I was so excited, but then also I think when I calmed down, I started to realize, and this is something I've realized year after year after year and more and more is not to be afraid of people. We get intimidated when we think we have to talk to somebody who's in a position of power, so to speak, or they're doing something we consider to be more important than whatever it was we're doing, but you really have to try and remember that they are just the same, they're just a person just like you, they have a different job, but they're not a monster. They're not there to say, "How dare you call me right now and interrupt very busy day?"
I think there are probably some people who are more like that, but I think that they are the problem. I think they've made themselves believe that they're so important. Honestly, I don't really want to deal with people like that. The day I feel I'm too important to talk to a high school kid who has a question about drawing, I may as well just retire, then I've become a monster.

Chris:

After this episode, high school students all over the world are going to reach out to Kyle T. Webster and that'll be the end of your free time.

Kyle:

Well, it depends on how they reach out. That's another topic of conversation, but I mean, I do get emails from people that start with, "Yo, dude," and I don't read them. I know that sounds mean, but honestly, I do think you should approach people with respect, and you know that their time is valuable so show them that you know that, but then you're fine.

Chris:

Yeah. So that first gig where they said yes, and I got something, did you guys talk about price on the spot or when you ran downstairs, did you already know what you're doing these illustrations for price-wise?

Kyle:

No, I did not. I went ahead and waited for the email with the budget. What I learned from Leo Espinoza, who is an illustrator, who I love, was one time early on in my career he told me, he's like, "Whatever the job is, start by asking for more," and that's what I always did. So whatever the budget was, I would just say, "Can you do it for this amount?" I never once had somebody say, "No. How dare you? No more job for you." They would either say yes or they would say no, but that's the job, but I never didn't ask for more money, and especially with editorial because editorial budgets are famously not great and have been declining for years, which is really sad. So no, I don't remember specifically on that project what I got paid. I know that Entertainment Weekly had a much bigger budget than what I was used to at the time.
A great example of the asking for more thing was a few years ago, maybe 10 years ago now, gosh, time flies, I did a emergent-C, emergent-C, that stuff you buy for when you're sick. It was through an agency, and they wanted me to do some drawings that they were going to turn into a web, animated little web cartoon thingies. So then you had 12 illustrations and they were like, they said to me, "We have a budget. We're thinking 4,500 per."
I was like, "Okay," and then I said, "I'll get back to you." I called around few friends or whatever, and they're like, "I don't know. Never done that kind of work before." So I decided I'm just going to go crazy and I said ... I remember calling them back or writing them back or whatever and I was like, "Can you double it? Let's do 9K each." They came back and they're like, "Okay."

Chris:

What?

Kyle:

They just said, "Okay," and I thought, "Wait a second. So what happened there? Did they lowball me crazy to begin with? Did they throw me something in the middle and expect me to come back with that number or was I still going low based on what the price should have been for the usage?" So it just messed with my mind for days. I was like, "What just happened? They didn't even blink. What should I have asked for?" I didn't have any friends at the time who had done this work or could really bounce it off with them, but to me, it was the biggest payday of my illustration career for that kind assignment work ever by a long, long mile.
I was happy with it, but I still to this day don't know what happened there. I don't know what is the right amount of money, and that's the problem with our business or especially with illustration. I don't know exactly what design, how it works, but there's so many question marks sometimes around pricing that it's really fluid. It's really difficult to understand. I'm very happy for that amount that I got, obviously. It made a huge, huge dent in our bills, but at the same time, I just wonder sometimes, "What was the amount that they expected me to say?" I don't know.

Chris:

Yeah. Some interesting things going on there. I get this a lot because I try and teach creatives how to value their work, and it's oddly strange because when I say to people, "Just try and double the budget or push the boundaries a little bit so that it gets uncomfortable, so you know the theoretical ceiling." I think people are like, "Yeah, let me try it," but the weird reaction that I get is, "No, I can't do that stupid. I'm going to just take it because someone else will do it for less." So Kyle, help me out here. For people who have this mindset, what kind of advice could you give them?

Kyle:

So I would say that if you're already in these talks, it's because they want to work with you. That's the assumption I make at least on my end. I assume that they're calling me because they like my work, not because they need the work to get done by any old person for the cheapest amount of money, but specifically me. So that already gives me some confidence going into it thinking I have some leverage here or at least I'm on equal footing. I'm not just begging for the job.
Then the second thing I think is, like I said before, when you're asking for more, I think that should be the expectation in any situation where you're trying to price a job like this, a creative job. I don't think it's fair to assume on the client's part that the money they have to get the job done is exactly what you should receive to get the job done because how do they know what you get paid?
It's so weird. When we had a sunroom built five years ago in our house, it's not like we said to the contractor, "Well, $15,000 is our budget and please build us a sunroom." We said to them, "We don't know what this costs. Tell us some options," and that's when you negotiate. They say, "For this kind of flooring, for this kind of siding, for this kind of whatever, these are your options." I think the same goes for creative work. "You want five logo designs, this is how much it's going to cost. If you can't afford it, I'll give you three." It's bartering and it's negotiating, but it should never be this thing where the illustrator, the designer feels they're stuck in a corner and they're the one who has to be grateful for the work. It's the other way around.
I think that the client needs this thing done because it will help their business. It has real value to their business. So I mean, a logo, it drives me crazy when someone does a logo for $1,500 or something. For 10 years or 20 years, this company's using this logo and they're putting it on everything they make and it starts to represent their brand and everything they stand for and you try and help the client see that that's what this little mark that I'm designing will mean for you in five years' time. So yeah. I don't know. I have a lot of thoughts about that as I know you do.

Chris:

You sound you have a really healthy relationship with money and you know how to value your work. Where did this confidence come from?

Kyle:

Huh. I think just from experience, experiences like what I shared a moment ago, where I did do this, where I literally doubled the budget that was suggested or where I would get in the habit of just asking for more, but also, I think it came from knowing that I had relationships with clients that they went farther than just, "You call me, I deliver the work, and then Merry Christmas." It was more like I would get to the point where an art director would call me and we'd talk for five minutes and I'd say, "How's your family? Oh, did you go on little trip? What'd you do?" I got to know these people and build meaningful relationships with clients and then see them at a conference and get to know them even better, meet friends of theirs in the business and so on.
I think the confidence came for me wanting to believe more and more that it wasn't just the work. It was me, the person, and that I feel confident that I'm a nice person to be around, and I feel like I'm personable and engaging. This is something I value and others. So I always felt like at the end of the day, if I ask for more or if I need to explain why I need more, the other person I'm talking to will care enough about me and my business to try and accommodate, and knowing that if they do that, I'm going to really give them my best. I think that's also a thing that I try and communicate clearly and show when I do work with clients is that I will give them 100% every time because I feel I'm being treated fairly and so I want to give them the best possible result at the end of the day.
So a lot of it comes down to relationships, expectations, and then just the history of things going well in that department. So I think everything like else, the confidence comes from time and from doing a thing and from experience, and probably also just that thing I said earlier about remembering that we're all just people and they're not out to get you, at least I don't think they are. I'm trying not to be negative. I'm trying to hope that people are good people.

Chris:

Most people are, I think, and we should give people the benefit of the doubt. As it relates to illustration and fine art, are there ever moments where you start to have thoughts of imposter syndrome?

Kyle:

Oh, sure, all the time, especially because now you can see how many talented people there are in the world. Talent is a scary word, but how many skillful people there are. You can see evidence of the thousands and thousands of people who draw better than you do, and it just can make you feel like, "Why am I even bothering?" I had this conversation with somebody yesterday where we were both suffering from this midlife crisis thing where we're looking at people on Instagram who are in their 20s who are drawing circles around us and going, "Well, why am I even trying to do and how can I go out there and call myself a professional illustrator?"
Then you know what's great was we came back around to what it is that we do well. One of the things we realized that we do well is we can take a client's idea and turn it into the thing they need to sell something, we can turn it into the thing they need to brand something, and that skill is what has sustained us and kept us going in this business for so long, not necessarily our ability to draw a dragon absolutely beautifully and for many vantage point or whatever.
So there are different kinds of skills. So we turned the conversation around and started celebrating the skills that we do have. Now, maybe our technical drawing skills don't compare with some of these younger people who are getting massive followings on Instagram, but we said what translates to dollars and cents and what's kept our families going and kept our businesses going is a different skillset, and that's really where we focused our time and energy, and we're glad we did.
So you can't be good at everything. Everything requires time. So I do have imposter syndrome, sure, and then I try and talk myself out of it because I look back on my life and think, "Where did I spend my time?" and then I feel good about it because I spent my time not drawing eight hours a day, but doing some drawing, but also learning business stuff and nurturing hobbies, and spend time with family.

Chris:

Right, playing the guitar, playing tennis.

Kyle:

Yeah, a little bit of guitar, a little bit of I do card magic. That's my biggest hobby, and play tennis, all these things. So lots of stuff.

Chris:

Yeah. You're a well-rounded human.

Kyle:

Trying to be, yeah.

Chris:

Yeah. Absolutely. There are three things I need to talk to you about before we run out of time here. So hopefully, we can tackle these. Number one is I've not known that many people, especially in the creative space, who've been able to turn their skill, their talent into IP. You did that with the brushes, what started out as just for you turned into a thing that you actually made money on. What was that like? How did that impact your life?

Kyle:

Well, it's certainly the thing that had the biggest impact on my life professionally speaking. It was just a massive experiment and a learning experience, really, more than anything. Just realizing, I took away so much from that experience. Probably the main thing I learned was that if I'm my own customer, I can really go to town and knock it out of the park. I can make something really good. I think that was why it succeeded was I'm an artist who needs good digital brushes for what I do. So by creating the brushes I need, it's a no brainer that the rest of the illustration community is going to need them, too. So I think that was why it really took off like a rocket was I understood the customer because that was me.
The timing was also really good. We had come to a point where technology for digital drawing had reached this level where you could pretty comfortably draw on a tablet, and if you had the right tools, which what was I was providing to draw with, the experience was pretty seamless and pretty wonderful and pretty comparable to drawing with traditional materials depending on what medium you use.
The other thing was with timing, Gumroad had just started and Gumroad became the platform where I could, for almost no money, create a web shop and sell to anyone in the world and they could pay me right then and there and download the product and use it immediately. That was amazing. Then the ability to market and advertise through social media was huge. Most of that was free. So there was a lot of organic growth through that.
Then the fact that I was already plugged into the illustration community, thanks to my profession, meant that I could send it to artists all over the world and say, "What do you think about these?" and then get them to give me testimonials that I could use and pass them around to their studiomates. That's how I got them. I was sneaking them into places Disney and Pixar that they get passed around the studio, and then I could approach the studio manager and say, "Hey, make you guys look good would be a license for these," and then everybody wins. So then I could make claims like, "These are the brushes that are used in Pixar." So it all just me figuring that out along the way, learning that. It just was such an amazing experience.
Then the other thing I learned is that you have, and I know you're familiar with this idea and I'm sure listeners have heard about it, this idea of having true fans. You have however many thousands of true fans equals the success of your business because you have a lot of fans who don't actually buy anything. So me realizing that number was growing because every time I release a new brush set, I would have these pre-sales that would just be a given. They would be granted, and then those people who would buy them would go back and buy older sets. So it was just amazing experience.
Selling the business was a completely different thing. It took over a year, and I hired a business manager for it. I think that goes to something we haven't talked about, which is when you don't know how to do something, you find help. Get help from people who do and partner with them, and you can make really big things happen that are outside of the scope of what you normally work on.
So for me, that was that. Having a business manager made that all possible and writing a real proposal to a multinational corporation like Adobe, that was terrifying idea, but it was because I had help that it went so smoothly and it worked out. There's so much to talk about there, but it was just a massive life-changing moment.

Chris:

I want to talk about the acquisition by Adobe because that's something that not a lot of people are in a place to do or to be even considered for, but before I do that, I just want to remind our listeners that we're so busy making things for other people that we don't often take time to look at, "What am I doing for myself that can save other people time?" and to spend some effort and package that, and that's how you start to package your IP and you're able to scale your business.
You mentioned before that it started to become the predominant way in which you were generating income. That gave you a lot of flexibility when it came to client work, gives you confidence to say no to people because it wasn't a good fit for you, the timing wasn't good or you just wanted to spend time with your kids or something. That's an awesome thing to have, and I encourage every single person, whether you want to be acquired by a large multinational company or not, to have some other form of income so that it gives you some of that balance and it allows you to buy back some of your time. Now, let's get to Adobe.

Kyle:

Sure.

Chris:

Okay. So somehow, somewhere a conversation has started. It takes a year to process through, and you obviously ultimately decided to sell your brushes, and now it's included in Photoshop, which I thank Adobe for buying it, and for you for creating it so that we all have the ability to use them. I use them on a daily basis whenever I'm drawing. Obviously, not so good in which-

Kyle:

I'm so happy to hear that.

Chris:

... you do it, my little chicken scratches, but it's nice to have more natural media brushes versus the soft edge brush, that's the default brush, which isn't all that interesting. How has that impacted your life and what ultimately made you decide it's time to sell?

Kyle:

There were several factors involved. One was that I had already started bumping up against the limitations of the brush settings panel in Photoshop for at least about a year. I was concerned that I would not be able to continue really innovating too much if I didn't have something else to do or if the technology didn't change, I guess. That was one thing.
Another thing was that as much as I did enjoy the passive income and it was really starting to work for me as a business, the customer service end of it became, honestly, unmanageable. The number of emails I was responding to every day and having to work through and trying to help people with the brushes and everything, that really became my full-time job more than anything. So I wasn't spending as much time growing the business, working on new products. So those two things were coming into play.
Also, I think I was starting to get a little tired. I felt I was repeating myself, and for any creative person, that starts to really feel bad. So when this opportunity came, and it was such an incredible, amazing opportunity because, at first, the idea of selling it was just exciting to me because of money, frankly. I was like, "Oh, wow! Great. Payday," although I didn't have a plan for it afterwards, which that was not good thinking, but then when it turned into an acquihire, I quickly, quickly realized that what that meant for me was that inside the company I could innovate with these resources that never before existed, literally having access to scientists and researchers in the company who build this stuff and being able to sit down with an engineer and say, "I want the watercolors to stay wet," and so Adobe Fresco, that's what we have.
So I spent the first two years at Adobe just working on Fresco on the product team and making the brushes the best we could and working with all that stuff. That product's now in its fourth year. I can finally say with sincerity that it's where I wanted it to be back in 2018. I draw it in every day, but it's because I got to sit down and to help make it. So this is a completely different job. Now, I'm on the side where if I dream it up, it could actually happen as opposed to if I dream it up, I have to work within the limitations of what the brush settings panel in Photoshop does, and then I can't actually make it happen. So that was amazing.
Then honestly, this is going to sound so practical and nothing about practicality, but at the time I joined Adobe, our health insurance for my family was just almost unaffordable, and to get the benefits of real health insurance from a company like Adobe has made a world of difference in our lives. I mean, we live in a country where health insurance is, yeah, it's not a given. Healthcare is not a given. So for a family of four, this was just amazing.
So the other thing was Adobe lets me work on what I think is important, and I respect them, and from day one, I knew that was going to be the case and they've held up their end of the bargain on that. I really get to focus on what I love, drawing and painting and designing things for drawing and painting and educating in that space. So yeah, it all worked out.

Chris:

For me to give up future earnings on a product even though it sounded like managing the customer service of was becoming a nightmare for you and to walk away from that, it'd have to be a lot of money. I'm just speaking for myself.

Kyle:

Yeah. Yeah. We definitely got paid fairly for it. What I did was I projected sales for the next four years based on growth that we currently had, and that was the number that we gave to them. So I felt at the very least I'm getting what I project will probably be my income for the next four years from that on top of my being hired at a salary that is absolutely very competitive and very fair for what I'm doing, and plus the health benefits. Financially, it was an absolutely fantastic move.
Another thing I didn't mention, Chris, was that when I was able to make that sale, I was also struggling with the problem of not just piracy, but pure imitation, where I would release a brush set and literally a month later there would be two identical brush sets from competitors or from anybody, where they just reverse engineered what I made and then just released it, and that became pretty tough to stomach.

Chris:

Right. Well, I'm glad this happened for you because it couldn't have happened to a nicer person.

Kyle:

Thank you.

Chris:

I'm so glad that you're on the inside helping to shape the future products because you're an advocate for other artists and it's like these are the tools that we need. So now, you're working from the inside making those changes and it's wonderful. The last question I have for you is, what's it like to be an evangelist? It sounds a great title. What do you get to do as an evangelist? It's fascinating to me.

Kyle:

The main thing, and I think the title's interesting. It should be more educator, but the main thing I do is teach. I spend a lot of time doing live streams where I just pick a project idea and I walk people through how to complete that project or I pick some fundamentals. When it comes to illustration, I actually spend a lot of time in my illustration masterclass every Friday, where I talk about fundamentals like shape design, line weight, and composition, and all these things that it'd be great if everybody did learn them in art school, but a lot of times they get glossed over or maybe you need a refresher. I talk about really specific things like I did a three-part series on editorial illustration and how to think through an editorial project or a poster design or those kinds of things.
So that's what I really spend a lot of time with, but I also do that more toward technical stuff like, "Here's how to use this application, that application," and I focus on Photoshop and Fresco because they're drawing and painting apps, and that's really where I spend most of my time. So that's what doing an evangelism role right now at Adobe is. It used to be that we would travel around and do these things in-person all over the world, but Adobe live has made it possible to do these remotely and broadcast hundreds of thousands of hours of content for free every week, and that's nice, but of course, I'm looking forward to doing these in-person again. The last time I did it in-person overseas was in Tokyo. It was amazing. Prior to that, I had gone to Barcelona for the off conference and done some work there and some demos and a workshop. You cannot beat that experience. It's phenomenal.

Chris:

Kyle, it's been a real pleasure talking to you. I think you're a wonderful illustrator and artist, a great teacher, and an even better human being. Thank you so much for being a part of this podcast. I hope our paths cross really soon. Maybe we can produce a workshop for you or do some other educational stuff where we can collaborate. For people who want to know more about you and find you on social, where's the best place to send them?

Kyle:

So first, let me thank you, Chris, for inviting me. I've really enjoyed the conversation and I am a huge admirer of you and everything you do, especially when it comes to designers valuing their own work. We just need so much more of that. People can find me kyletwebster.com or I'm also, as I mentioned earlier, working on a drawing meditation app. If you want to sign up to try that out before we launch, you can go to linesofzen.com.

Chris:

I love that. Thank you so much, Kyle.

Kyle:

Thanks. I'm Kyle T. Webster, and you're listening to The Futur.

Greg:

Thanks for joining us this time. If you haven't already, subscribe to our show on your favorite podcasting app and get a new insightful episode from us every week. The Futur podcast is hosted by Christ Do and produced by me, Greg Gunn. Thank you to Anthony Barrow for editing and mixing this episode, and thank you to Adam Sandborn for our intro music.


If you enjoyed this episode, then do us a favor by rating and reviewing our show on Apple podcasts. It'll help us grow the show and make future episodes that much better. Have a question for Chris or me? Head over to thefutur.com/heychris and ask away. We read every submission and we just might answer yours in a later episode. If you'd like to support the show and invest in yourself while you're at it, visit thefutur.com. You'll find video courses, digital products, and a bunch of helpful resources about design and creative business. Thanks again for listening and we'll see you next time.

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