A Brush With Success - Illustrator Kyle T. Webster


Kyle built up a successful career as a freelance illustrator for major advertising agencies and the likes of The New Yorker... and then he had kids.

He realised he needed to create things on a bigger scale, that took him on a fascinating journey of trial and error with digital products of various kinds. Now, illustrators around the world create their work using his Kylebrush.com Adobe Photoshop brushes.

Hear how this 'accidental expert' looks ahead, spots opportunity and finds ways to use his illustrative talents to cash in on trends.

Keep scrolling for key takeaway points and links but first...

Key Takeaway Points

  • take baby steps towards your big goals as you step into being freelance: Kyle worked up from small local papers to the big players all whilst still employed full time
  • quitting your job is a good thing to do, it puts pressure on you to make being freelance work
  • work on your cold calling - phone up and say you’d like to send them an email, make that first introduction
  • Kyle is always looking 5 years into the future
  • don’t rest on your laurels: if business is going well, don’t forget that that could change
  • Kyle’s always paying attention to pop culture and trends; he's looking for ways to profit from them using his skills
  • you may already be an expert at something, an ‘accidental expert’, and not even realise it
  • don't be afraid to invest financially in your business in order to grow


More from Kyle

Kyle's site

Kyle on Twitter



Who the hell is Steve Folland?

You know how everyone bangs on about how powerful video and audio content can be?
Yeah, well Steve helps businesses make it and make the most of it. Find out more at stevefolland.com, track him down on Twitter @sfolland or lay a trail of cake and he'll eventually catch you up.

Transcription of freelance podcast interview with Kyle Webster

Steve Folland:    Hey. How you doing? I'm Steve Folland. Thanks for listening. Let's find out what it's like being freelance for illustrator Kyle Webster.

Kyle Webster:    I had this light bulb go off and thought, "Okay, I need to be more than an illustrator. I need to be something that's just ... I want to create stuff, reaching a much larger audience than who I was reaching when I was just drawing pictures for money, you know?"

Kyle Webster:    You may already be an expert at something and not realize it, like an accidental expert. Got to thinking always, "What's going to happen five years from now? Where are things moving?" I'm trying to always sort of look into the future a little bit, and I think just having that mentality, that's helpful for a freelancer, not to rest on your laurels. If business is really good, then it's safe to assume that that could change.

Steve Folland:    Man, you are in for a treat. You may have already seen how long this episode is, which is much longer than the normal. But I thought about cutting it down, and I thought, "Do you know what? That would be a disservice to you, because Kyle's story is so interesting in the twists and turns that it has taken, the lessons that he's learned.

Steve Folland:    And I know that whatever you do, whether you're an illustrator or not, you're going to get tons out of it. I will keep this bit brief, just, as ever, to remind you to go to beingfreelance.com. Right. Let's crack on, and let's say hello to Kyle Webster, freelance illustrator, somewhere near New York in the States. Hi, Kyle.

Kyle Webster:    Hello. How are you?

Steve Folland:    I am good. I'm intrigued because we've already, before we started, ended up having a discussion whether or not to call you a freelance illustrator, which is interesting, because you're an international award-winning illustrator. It says right there on your website. So let's find out how you've ended up in the dilemma of whether to even call yourself that anymore. How did you get started being freelance?

Kyle Webster:    I got started when I still had a full-time job, working in the evenings on building up a small client base of what are called alternative news weeklies here in the States, which are these weekly newspapers that are free, and they have a small budget to pay illustrators to illustrate a few stories here and there every issue.

Kyle Webster:    It's usually things like local politics or maybe some strange local story, something bizarre that's happened that would be better suited for an illustrator to handle than ... or they don't have any photo reference and things like that. There are lots of them all over the country, maybe about 100, and so all I had to do was get five or 10 of them to give me some work every week, and I was quickly able to build up a little client base.

Kyle Webster:    When I had enough income coming in from that, I decided to send some work around to some larger publications. And after another year or two of that, I had enough work coming in that I could quit my design job. I was a designer at a graphic design agency. I quit my job in 2006. I'd started the freelance thing in 2003.

Steve Folland:    So you start off with the newspaper journey. Where did you go from there?

Kyle Webster:    Let's see. So I went in baby steps. I then sent work to city magazines. They have a better budget, but they're still not huge. And then from there, I started to send out work to national publications. I started with more trade publications that people aren't maybe so familiar with, but eventually worked my way up to things like Entertainment Weekly and the New Yorker, and so on. And then I was getting enough work. I felt pretty confident that I could get out from there. And I quit my job.

Kyle Webster:    Quitting your job's always a good thing to do if you want to freelance, because it puts a lot pressure on you to take it a step farther and really make it work. So it was a good thing.

Steve Folland:    How did you go about approaching those places?

Kyle Webster:    Let's see. This was more than 10 years ago, so at the time, emailing somebody cold wasn't such a bad thing. It wasn't really an irritant. I think now, it's getting harder to contact art directors via email directly, because they get so much of it that it's a bit of a nuisance. But at the time, it wasn't such a big deal to track down their email addresses. Sorry, I don't want to sound like a stalker. And I'd find out what the contact information was either by simply calling the newspaper and asking for it, or by looking at a masthead, or things like that. And then just send an email and say very briefly, "This is who I am," and "I'd love to work with you. Here are some samples of work, and here's my website." And just leaving it open.

Kyle Webster:    Fortunately, a lot of them liked what they saw and I got hired. I think cold calling is something as well that's a little bit of an art form that freelancers should work on. I did a lot of that with the larger publications. Rather than emailing them, I would actually call them directly in their offices and introduce myself, and then say I wanted to send them an email. It's kind of stepping stone towards sending them an actual email, I would call first. I guess it was a courtesy thing, and most of the time, that worked  I'm not sure if that still works. Maybe it's kind of a treat for art directors to get a voice rather than something electronic. I don't know.

Steve Folland:    You might well be right. Like you say, they're getting so many emails. At least if they know, "Ah, I've already spoken to Kyle." When it does appear in their inbox, it's already gonna stand out.

Kyle Webster:    Yeah.

Steve Folland:    So that took you up to national level magazines and what have you. So what kind of year is that then?

Kyle Webster:    So that was about four years in to starting, so maybe 2007 or so. Then I was doing things for national magazines and newspapers, and by that point I was also starting to slowly expand into doing advertising and a tiny bit of book work, thought not much. And book work is never something I've done much of. I just haven't spent time marketing to those art directors and those publishing houses.

Kyle Webster:    But the advertising work, I found to be a great thing because the budgets were usually significantly larger, and the way I did that was by first working for the company that I left on good terms, and I continued to work with them on some projects. And then slowly visiting other agencies that were within driving distance, and showing them my work and getting some small projects here and there. And then eventually entering work into some competitions like Communication Arts, and How, and things like that. And getting on the radar of agencies all over the country, and slowly doing some more work that way.

Kyle Webster:    So I don't remember actually ever directly contacting any art directors or creative directors at agencies outside of my region, but I think they found me mostly through those annuals or through my website, or through blogs and things like that. I've always had a very active online presence, as much as I could manage anyway. And that really helps.

Steve Folland:    Did it feel like there was a point where perhaps it started to snowball?

Kyle Webster:    Yeah. The New Yorker was sort of a tipping point. The New Yorker and The New York Times, because those are publications that other art directors pay attention to in New York. Once I was published in The New Yorker, I had a flood of jobs come in, and that continued to happen every time I was published again in that specific publication. If I was in The New Yorker, I could kind of assume I would get some work over the next few weeks. Potentially from people I'd never worked with, but also people who just remembered that, "Oh yeah, there's Kyle again. I should hire him again." You know? And The New York Times is just good that way as well.

Kyle Webster:    And also, I just think, I hate to say it, there's something about those names. I'm not sure if this is still true, but I think it is, I assume it's still true, that if you can say, "Oh yeah, I illustrate regularly for The New Yorker," it adds a little something to the equation that makes you somebody that other people want to work with. I guess it somehow validates you. I don't know. I don't think there's any getting around that. It does certainly help.

Steve Folland:    For sure. There's gotta be that prestige attached to it, I think. I mean before we kind of continue on your story, I guess, as to where you are today and the dilemma you're in, you mentioned, just to pick up on a couple of bits, you mentioned your online presence and how you've always sort of been strong with that. Is that mainly through a portfolio site? Or through social media? Or a combination? Or what?

Kyle Webster:    I've always struggled to keep my portfolio up-to-date. And I know lots of other friends of mine have the same problem. They say, "Oh, I'm going to do it now. This is the time I'm really gonna have this new site that's very easy to update, and I'm definitely going to keep it updated." And then of course it doesn't happen.

Kyle Webster:    There was a period of time where my blog was the best place to do that, and I get semi-regular traffic to it, and people kind of expected to see work there. But lately I've found that Instagram and Twitter are the places for me to just post new work and get, at least from what I can see, the biggest response to it.

Kyle Webster:    The times I hear people reference my actual website are usually when I've never worked with them before, and somehow they've arrived at my site and seen something they've liked and they reference a specific piece, usually, from the portfolio. But the way I sort of stay out there with current work is through Twitter and Instagram. And really Twitter more than Instagram, because Instagram, I sort of post everything. I post sketches and doodles and experiments, and I guess the portfolio is kind of this place where I'm really selective, and just try to put together the best representation of some of my best work.

Kyle Webster:    When you get to a point where you've been illustrating regularly on and off, what, 12 years? I can't do math. 12 or 13 years, you have over 1,000 jobs you've done for clients, it gets hard to even whittle down to even 50 pieces that you like. You wanna include more. But I'm also somebody who has this, some would call it a problem, but I call it a strength, which is that I work in so many different styles, that when I put together a portfolio of work, I've given up trying to categorize this style, that style. I just throw everything in there that I think is just something I did well. Yeah.

Steve Folland:    And you mentioned competitions as well.

Kyle Webster:    It's something that I do out of habit. And I can't speak for everyone out there. I know that most people who are my age or older, we do this every year just as sort of a ritual, because we were kind of programmed to do it, and told that's how you get your work out there and get it the kind of recognition it deserves, if it does deserve that recognition.

Steve Folland:    Oh, right. Like a thing from art college, or whatever it might have been. That sort of-

Kyle Webster:    Yeah. I think there used to be this badge of honor if it said on your website, "Kyle's work has been recognized by the Society of Illustrators and Communication Arts," and so on, I still think that has some meaning. I'm not sure if that meaning is as great as it once was, or as important as it once was. I honestly don't know. So I think just out of habit, I do it every year. It's a good feeling to get in, it's a nice feeling to go to these parties and meet people, and hang out with people you already know. You just feel good that your work is on the wall and gets in the book.

Kyle Webster:    These days, it's hard for me to say if, for example, to younger illustrators out there if they're curious about it, it's very hard to say whether or not actually getting printed in the Communication Arts manual, or in the Society of Illustrators book, or American Illustration Annual, I don't know if it matters that much to art directors, or if they even look at those publications as much as they now just simply surf the web like the rest of us. But I think they have value and worth, and I like them. I just really like looking through them at the end of the year and seeing a nice collection of work. What is considered to be the best of the year in the eyes of, whatever, seven people that look at it when they're judging.

Steve Folland:    But you felt like it would boost your confidence, I guess?

Kyle Webster:    Definitely boost your confidence, and you know, early on when I was in Communication Arts, it did help me to get in front of some art directors and advertising agencies who I had never heard of you, you know?

Steve Folland:    Okay, so back into your story, and you're now working for ad agencies and stuff. So what happened next?

Kyle Webster:    Yeah, so I had a baby with my wife. We had our first child, a daughter, and we had decided she would stay home and raise the kids. And I quickly realized that even if I was doing two or three hundred jobs a year, and the money was okay, I also felt like, "I don't wanna be hustling so much and working this hard all the time to rustle up business and to always be drawing," and so on. So I decided to change my business model. And instead of always waiting for people to call me and to ask me to do work, I would instead create work first and then try and find a market for it. And so that was my new strategy.

Kyle Webster:    So I started just kind of blindly creating things and trying to sell them. And the first thing I did was start a little blog of daily figure drawings that were these quick gestural, but highly stylized drawings of figures. I enjoyed working that way. They were quick, it was an exercise, and it was something I could sort of brand as my own thing. And it became pretty popular and I got a following and stuff.

Kyle Webster:    So I turned it into a little shop with a calendar and things like that. T-shirts. You know, it's not like I sold a ton, but I started to sell things with these images on them, and that gave me the confidence to realize that, "Okay, this new business model could work." So I poured a lot more energy into making it work. One thing I did was I took that style, and I marketed it to all my existing clients. And what was good about it was I was able to do that kind of work much more quickly than the other kind of work I was doing, and yet I would still get the same fee. So that was good. I could gang up a lot more jobs. It was more enjoyable, I really just love drawing that way. And it had a look to it that was unique and very own-able.

Kyle Webster:    So from there, I then decided I'd try something completely different and make iPhone games, because this was 2009, and iPhone games were really kind of not yet as big as they are now. I mean the market wasn't saturated yet. So I just did a little scan of what was out there, and everything was very colorful and sort of arcade-looking. So I decided to make a black-and-white game that was very quiet, just to make it stand out.

Kyle Webster:    I hired a very wonderful app developer out of Ireland. Thanks to Twitter, I found him. And I worked for just two weeks and made the game. And I think my total upfront investment was about 1,600 dollars. And because the game looked so different and played differently, and because I also had a marketing spin on it, which was that it was a game to improve your memory, and I'd even had this validated by a professor at a university here in town. I'd asked, "Could this be used just to improve memory, or at least work out memory?" And he said yes. So I said, "Okay, good. I've got scientific proof that this is something."

Kyle Webster:    And then I wrote a press release and had it distributed to all the places that write reviews about iPhone games, at the time. I created some paid ads for it. You know, I really went all out for it. Spend another four or five hundred dollars to try and make it work, and I got lucky. And Apple featured it on homepage of the iTunes store. I think just because it was so different. And I created a website for it and made it very professional-looking and everything.

Kyle Webster:    So within the first month, I earned about 23,000 dollars in sales. That was one of those moments where I had this light bulb go off, and thought, "Okay. I need to be more than an illustrator. I need to be something. I want to create stuff." Drawing's still a part of it, but really what I need to look at is reaching a much larger audience than who I was reaching when I was just drawing pictures for money, you know?

Steve Folland:    That's amazing. So partly, that's actually driven by the fact that you had a kid. The fact that you wanted to be able to bring in more money, but also spend more time with them, right?

Kyle Webster:    That's the theory. Of course it always winds up that I spend more time on work than I want, no matter what I do. No matter what it is I'm working on, I'll say, "Okay, this is project," like the Photoshop project I'm working on that we can get to later, I think, "Okay, this is gonna be that automated thing." But nothing's ever automated. It always requires. It's like a plant, you're just constantly watering it. But yeah, that was at least the reasoning behind why I started changing my business model.

Steve Folland:    I just wonder whether you would have even had that motivation were it not for having the kid, do you know? Like you might have just kept going with what you were doing.

Kyle Webster:    Yeah, no. Sure. Having children ... I think most of the decisions I make with my business are based on fear, which is, I don't know, I guess that's just a natural animal thing. Or it's a survival thing. I'm thinking always, "What's gonna happen five years from now? Where are things moving?" And I'm trying to always sort of look into the future a little bit. Of course I have no idea, but I think just having that mentality, that's helpful for a freelancer to not rest on your laurels. If business is really good, then it's safe to assume that that could change.

Kyle Webster:    Also, illustration is kind of the fashion business in a way where these trends come and go with styles and so on, and thinks good be really painterly and heavy in that area for five or six years, then suddenly they go really graphic again, and really flat color. Simple shapes and shape-based art. And then suddenly they come back to really intricate drawing, and that's really hot for awhile. Anyway, so I try to avoid getting locked into any one way of working.

Kyle Webster:    So yeah, I was afraid, not in a sort of cowering in a corner kind of way, but I was thinking about making sure that I wanted my children to have a comfortable life, and what would be a way to make that happen without killing myself drawing all the time and worrying about deadlines, and worrying about, "Is somebody gonna call me next year?" You know? I don't wanna think about that stuff if I can avoid it, so.

Steve Folland:    So you created the app, this is 2009. So it's you and Angry Birds, basically. I mean, you've got a lot of success, really, with an iPhone app. So I'm guessing the temptation is to keep going with that?

Kyle Webster:    Yeah, so of course I thought, "Oh, wow. Easy money. I'm gonna keep doing this." And this is good, I always have these good lessons that smack me back into reality. I thought, "Well I'll just make a much better game than that." And I did, I made a much better game. But you have to always factor luck into the equation. And even though the second game I made, which is called Hot Plates, was much more playable, much better graphics, and you could play it for a much longer time and not tire of it. None of that mattered because Apple didn't highlight it. With the thousands of games that come out every month, you have a team of people at Apple who just look and they say, "Okay, let's highlight this." If they highlight it, you're gonna get a lot of sales. If they don't, you're either gonna have to spend a ton of money on marketing it yourself, or you may as well just say, "Well, onto the next."

Kyle Webster:    So that's what happened. I made a game that I was really happy with. I made my money back on it, and then a tiny bit of profit. But at the end of the day, it was basically a five-month period of time that I worked on it where I didn't get that time back. I got some of the money back. And of course during that time, I was talking on other jobs and things like that to make sure everything was good. But I quickly realized that iPhone games could be profitable, but were not gonna be the way I was gonna make my living.

Kyle Webster:    So I went back to the drawing board, ha ha. And decided to come up with some other ideas. And the first idea I had was, "Well, why I don't I just tell all of my clients, especially the agencies, that I can now make them an iPhone game?" And that's what I did. So that was a good choice. They already knew who I was, they already trusted me to do good work for them, and so within the span of a year, Dennis, the gentleman with whom I made the first two games, he and I partnered up and worked on a whole bunch of projects for clients. And it was much better money than illustration, that's for sure.

Kyle Webster:    So for a year there I was an illustrator and also a game and app designer, with Dennis doing all the development work. And that went really well. Remember this was, again, 2010 or around that time. I know this doesn't seem like that long ago, and it wasn't. But things have changed so fast. In 2010, every company out there was coming out with an app to just jump on the bandwagon, and so we took advantage of that. I think that's another thing I should mention, is that I'm trying to always carefully pay attention to pop culture and to trends and things like that, and see is there some way as an illustrator or artist, I can take advantage of this trend, and make some money while it's happening. And that was what made sense for me with the apps at the time. And a lot of them did take me up on it, and that's how we got some work. And it was just good timing, you know?

Steve Folland:    But really smart. So you're going to the people you have a relationship with, and then suggesting that they sell it on to their clients?

Kyle Webster:    Yeah, exactly. So it was, for some of them, something they were already doing, but they were glad to have me a resource because rather than go try and hire someone they never worked with, they could just say to me, "Well we already know who you are. We've already worked with you. Look, we have this thing in development. Can you give us a quote?" And Dennis and I, being that it's just two of us, and we worked very efficiently and very well together, would give them really good quotes, and it was easy to get work. So, yeah. It just worked out for a little while there.

Kyle Webster:    But again, these things change quickly. So that business started to fade away, and I also wasn't doing much to promote it. I wanted to get back to making art somehow, so I had to think of something else.

Steve Folland:    So after the apps, what were you thinking next?

Kyle Webster:    Yeah, so that was when I decided to try and start selling digital products. And at first I thought, and I'm glad I didn't do this, but at first I noticed people were starting to sell WordPress themes, and the Society6 thing was taking off, which is this website where you can sell an imagine printed on pretty much anything. Pillows and blankets, and whatever. And I do have a Society6 page. I just am terrible about marketing it.

Kyle Webster:    Anyhow, so I thought, "Okay, maybe I'll make some WordPress themes. Or maybe I'll try and make a font," you know? And the answer was always just there in the background, I just hadn't paid attention to it. I'm actually gonna give a talk about this at ICON, the illustration conference this summer. I'm gonna touch on the fact that you may already be an expert at something and not realize it, like an accidental expert, which is what I want to talk about.

Kyle Webster:    I'd been making Photoshop brushes for myself for various projects when I would need to emulate some kind of natural media. I had been making these brushes since 2003, when we had this project to do for Krispy Kreme Donuts. We had to an annual report for and illustrate for them, and the CEO wanted it to look like kind of acrylics on wood panel. And we had a very short deadline, and I made some brushes in Photoshop that would do what I needed them to do, and slapped on a wood texture. And when we were all done with the project, he asked if he could buy the originals. So that was a good sign that we had successfully we had done this, that the illusion was successful.

Kyle Webster:    And anyhow, I just got kind of addicted to that, and for my own purposes was always just fiddling around with making brushes. People who were illustrator friends of mine would sometimes ask to borrow them. I'm not sure you can borrow them, but they would ask me, "Could you send me some of your brushes? I want to try them." And I would always say, "Sure. No problem." Finally, I just realized, "Why am I not selling these?" Instead of going and trying to learn how to make a WordPress theme, or make a font or something, talk about a great digital resource, Photoshop brushes.

Kyle Webster:    I thought, you know, "There's gonna be a good 100 to 200 people out there who, like me, really love emulating natural media in Photoshop." So I'll sell some of these and I'll move on. That's not what happened. It's now how I spend the bulk of my time, working on this business.

Steve Folland:    That's amazing. So there you are, you've been doing it for years. Finally you twig. And when was that?

Kyle Webster:    In 2013, I released my first set. It was just 25 brushes. I don't want to say anything bad about my own product, but I'm really not that thrilled with that first set. I mean, it was really just an experiment. I was just throwing it out there to see if it would work. It all happened in the span of, literally, about six hours.

Kyle Webster:    I went on Twitter, and I said, "Hey, does anybody out there know of a good website to sell digital stuff that you make?" And this guy, Cory Godbey, who's a really talented illustrator, I saw him mention Gum Road. So I checked them out, and it looked extremely easy to set up a shop. So I set up a shop, and that took about 10 minutes, you know. Then I had a list of like 200 brushes that I'd made, just sitting around, and I narrowed it down to 25 of what I thought were some, you know, it was a good little selection of tools. I went to QuickTime and just turned on Screen Capture, and made a silent film of me just fiddling with those brushes in real time, one after another, just caveman stuff. Nothing fancy.

Kyle Webster:    I put the video up as the main image, or featured media, for the shop. And I sold the brushes as a zipped file for five bucks, thinking, "Maybe some people will jump on this." And I made a little announcement on Twitter and Facebook and Tumblr, and that was it. I sat back, messed around with some illustration jobs, I'm sure for the rest of the day, I can't remember exactly. But I got home that night, logged into Gum Road, and I think it was, I don't know, 20 or 30 people had bought 'em. I was ecstatic. I thought, "Oh my God, this is fantastic." You know, that was nothing. Because at the end of the week, I had made over 1,500 dollars. I just couldn't believe it.

Kyle Webster:    I realized, this is the lesson. The lesson I took away from it was, if you have a job doing something, and you have a thing that makes your job a lot easier, and for me, that's really good quality brushes. I can work quickly and emulate any media I want. Then why on earth would you assume that you're alone, that other people who are doing the job that you do wouldn't also want that resource? It seems obvious, but to me, it wasn't obvious at all until I actually went through the motions of doing it. Once I had done it, it seems to me like, "Why haven't I been doing this all along?"

Kyle Webster:    So I had a choice to make then. I decided I could either let them sit there and do fine, selling 30, 40 bucks a day or whatever. And that was amazing to have a little passive income, but a great feeling. Or I could turn it into an empire, and I opted for the latter. I decided to really go for broke and become the leading authority on what a Photoshop brush is, what a good Photoshop brush is. I not only think there wasn't such a thing, I know there wasn't anything like that. I'm not that person, but I sort of invented this job title because I wanted to. I could have failed miserably.

Steve Folland:    So how did your brush empire, as you call it, evolve from there? And did you do it all yourself? When it comes to building the e-commerce and the website and all of that, is it you or did you bring other people on board to help you as well?

Kyle Webster:    No, I mean the development of the brushes, and the marketing of the brushes, and the testing and all that, that's a hundred percent me. So no, it's me. And that's, you know, it's time consuming. I do all the customer service emails. I probably spend now a good two hours every day just answering emails from customers. I wish it were not so. I wish I could take that time and use it in some other way, but it's just the only way I know how to do it.

Steve Folland:    And all of the web design and that, so everything-

Kyle Webster:    No, no. So for the first, almost two-and-a-half years, I just used the gumroad.com site as my, that's where I sold them. I also have them for sale on Creative Market, because that's a great marketplace for me to reach a whole new audience. But I wasn't branded in a way that I was happy with, and so I hired a friend of mine who lives in LA, and he's just one of these great people to work with. I love him. And he has two business partners. And the three of them took a design that I made in Photoshop and turned it into what is currently the website, just using WordPress.
Kyle Webster:    It's not too complicated on the backend, you know, but I could never have done it on my own. I don't have the skills. And they also did some really smart, smart stuff to make it very quick for me to update. So now it feels branded. If you go to kylebrush.com, it feels like a company. It doesn't feel like a guy who threw some html up there, you know?

Steve Folland:    Now I love that there's a real, it seems like there's always been a real, entrepreneurial side to you. You're looking for the opportunity, you're willing to take a chance and invest money to try to make it work.

Kyle Webster:    Yeah. Not always. It took me a long time to be comfortable with the idea of spending money to make money. But now I'm a very big fan of that approach, because every time I've taken money out and decided, "Okay, I'm gonna spend some money to do this the right way, rather than torture myself trying to figure it out the wrong way 10 times in a row and waste a lot of time." It's always paid off so much, you know?

Steve Folland:    And that's not he end of this story, by it sounds of it, because you've mentioned speaking. I can see from kylebrush.com that there's training has emerged as well.

Kyle Webster:    Yeah, the training is coming at the end of summer. I'm building some really good tutorials for people, and how I use the brushes, and how they were designed to be used so that they can get the most out of them.

Kyle Webster:    There are some things I can't talk about, unfortunately, because of nondisclosure agreements, but I'm doing some consulting with some great people about building better digital tools. I've had just some really wonderful opportunities come up as a result of this business, having nothing to do with my illustration work, which sometimes, like I said earlier before we started recording, it's a bit of a blow to my ego sometimes as an artist to not be known for drawing anymore so much, even though I still continue to do illustration work for lots of people. It's just not something I think I'm as well known for as the brushes. In fact, I know I'm not. That's just something I have be okay with, and that's fine. You know?

Steve Folland:    Yeah, but at the heart of that brush is your art and your illustration, right? And when you're still getting freelance work, 'cause you just said that you're still doing freelance illustration, are you pitching the work? Like putting yourself out there now? Or is it people coming to you?

Kyle Webster:    Well I'm sorry to say that in the last calendar year the brushes have taken up so much of my time that I haven't done a lick of self-promotion. But I'm glad to say that even without doing any, I think the years I spent building up a client base have paid off enough to where I got enough work from people all year long, who have worked with me in the past, that my illustration business was style fine. It didn't grow, and that's something that I also struggle coming to terms with. I had growth in my illustration business every year since I started, and last year was the first year there was no growth. It was completely flat.

Kyle Webster:    And at first I was sort of sad about it, but then I was like, that's crazy to be sad about that when I didn't do self promotion, and also I spent so much time on building this brush business. So I'm glad that people didn't totally forget me. I also have to be careful and realize that if I continue doing this for too long without doing more promotion and reminding people that yes, my first love is illustration, then certainly I'll stop getting work, and I'll have to really hustle to get it back. So it's a balancing act.

Kyle Webster:    But I will say that the greatest thing about the brushes, and, of course the business, the income is very exciting, there's a million things I love about it. Especially seeing artists that I am so much in love with, or who are heroes of mine, actually buy them and then use them for a project, that just blows my mind. But really the greatest thing that came out of it was I got to realize this lifelong dream of doing a picture book for kids. A children's book. Which is something I've always dreamed of doing, ever since I was a kid.

Kyle Webster:    And I think the only reason I was even able to do it because I was able to take time off, three months, to make the art for the book that I wrote. It's coming out at the end of July. Because I was relying on the income from the brushes during those three months, and not taking on any other illustration work. So that was really great.

Steve Folland:    Congratulations. You said this is "Please, Say Please." Was that a side project? Because this is your first one, I presume you haven't pre-sold it or anything like that. So you took three months off to work on a passion project sort of thing, or ...

Kyle Webster:    No, I have this really wonderful agent for picture books named Laurie Ab I found her through social media, which is amazing, and sent her some samples of work and asked if I could send her a dummy for a book I'd been thinking about. And that was "Please Say Please," and this was about two years ago. I sent her the dummy, which is just a really rough sketch of the book, along with the manuscript. And she liked it and agreed to be my agent, and she was able to sell it to Scholastic, which is just an amazing thing.

Kyle Webster:    So once that happened, I thought, "Okay, if the only way for me to make the deadline to get all this art done and make it something I really am proud of and not something I rushed through, I have to not take on even an ounce of work from anyone else." And I never would have been able to do that without the brushes. There's just no way. Because being a first time author-illustrator, the advance I got on the book was not very much, and it certainly wasn't enough to pay for what wound up being about five months' worth of solid work, you know. And to still feed my family and everything.

Kyle Webster:    But fortunately, just giving the brush business a little bit of water, so to speak, while I was doing the picture book work, just doing a little image here or there to market it, or doing a Facebook ad here or there, was just enough to keep it generating enough income during that time for me to do that work. It was really, really great, so.

Steve Folland:    Wow. Good for you, man.

Kyle Webster:    Thanks.

Steve Folland:    You're clearly very motivated.

Kyle Webster:    Motivated by fear, yeah.

Steve Folland:    I think you said earlier, "Not resting on your laurels." Although you did say that that's always been a dream, to do a picture book.

Kyle Webster:    Oh, yeah. And that's something that I just wanna do forever. I hope, if there's some way I can just do that, that would be my dream, to do nothing but write and illustrate.

Steve Folland:    So have we reached where you are now? If you see what I mean, 'cause you've just said that's about to come out. But I don't know, you might be able to say, "Yeah, but anyway, then I discovered that Snapchat filters existed," and ...

Kyle Webster:    Well there are a couple of things that I'm working on now. Well, it's funny you mentioned Snapchat, this is sort of similar, but I'm interested in starting to do some live streaming. And so I have to just see where's the best way to do that. And I'm doing Adobe Creates livestream soon.

Steve Folland:    Is that where you've contacted them? Or they've come knocking?

Kyle Webster:    No, no. They've offered me these opportunities, which is wonderful. I'm happy to say that one of the goals in creating these tools was to get on Adobe's radar, and I've certainly done that, and we've had a really great relationship. They even invited me to this absolutely inspiring summit a month ago in New York, with some other people who I really admire, some artists from around the world, who just do amazing things. We got to explore some new media things with them, and that was great. It was amazing. That's all, again, thanks to this brushes stuff, so.

Kyle Webster:    Yeah, all these things have happened that were never planned. At the same time, in some ways, I think you make your own luck by just being persistent with things. And it doesn't always pay off. I've had many, many times where I've thought of an idea, and I've thought, "Oh, this is gonna be the one. This is gonna be great," and it doesn't go anywhere. But I think if you just keep having ideas and trying to take them somewhere, then eventually, hopefully, something happens.

Steve Folland:    What would you say have been the biggest challenges of being freelance?

Kyle Webster:    Well there's just no guarantee that you're going to make it. Not that there's a guarantee you're going to make it if you have some kind of full-time employment, but there is that comfort when you have a job that you know you're gonna show up at a place, and as long as you do what's asked, more or less, and you're not rude and terrible to work with, you remain employed. And you get health insurance and whatever else, and you get a paycheck. There's something about that routine that is pretty comforting, and I think it can give you a little bit of peace of mind.

Kyle Webster:    But it's not for everyone. And I learned it wasn't for me when I worked at that design firm. I loved those people, they're all wonderful people, but the repetition of all that was getting me pretty down. So I guess the biggest challenge is not having that, but then in some ways, it's also the biggest benefit. It forces you to think a lot, and to be creative. And not to be boring, you know? It forces you to pay attention to the world, too. You kind of have to stay engaged. You can't really check out, you know?

Steve Folland:    No. It's all great. I'll tell you what, this feels like an epic long-

Kyle Webster:    I know, I talk a lot. I'm sorry.

Steve Folland:    No, don't apologize. It's brilliant. You know, the story of somebody's freelance journey, if you like, it probably takes about five minutes. Because it'll be like, "I left my job, and then I did this." Whereas you've continually evolved, thought of different ways to push it, which is inspiring.

Steve Folland:    So I always do this thing where I ask for three facts about yourself. Make two true, one a lie, and let me figure out the lie. What have you got for me, Kyle?

Kyle Webster:    Okay, so. Here we go.

Kyle Webster:    First one. Mick Jagger's roadie drove me to Montpellier, France when I was 21 and I was hitchhiking across the country.

Steve Folland:    Right.

Kyle Webster:    When I was 16, I was in a tuk tuk race with some friends in Bangkok, and we nearly got killed.

Kyle Webster:    And I once spent an evening, when I was in my 30s, doing figure drawing with Tori Amos.

Steve Folland:    Whoa. Okay. You were hitchhiking, and Mick Jagger's roadie just happened to stop.

Kyle Webster:    Yep.

Steve Folland:    And then just what? Told you, "Oh yeah, nope. I'm just on my way to meet Mick," or is there a ...

Kyle Webster:    No, I didn't know who he was. In fact, I was with a friend. We were two Americans doing an exchange that year in college, and we decided to just skip final exam week 'cause we knew were gonna fail, and decided instead to just hitchhike. And we had a series of rides, from Rennes, the northwest coast, on down to Montpellier, where another one of my friends was studying. And one of the people who picked us up was a roadie for Mick Jagger in the eighties.

Steve Folland:    You had a tuk tuk race when you were 16 in Bangkok, where you nearly killed yourself.

Kyle Webster:    Yeah.

Steve Folland:    Tuk tuks, they're like the motorized rickshaw....

Kyle Webster:    Yeah, they're three-wheel. They have one wheel in the front, two in the back, and a little. You sit with no seatbelt and no sides. It's wide open. And you go at the same speed as a regular car, flying down the highways in Bangkok. It's probably one of the most dangerous ways to travel. And we had two tuk tuks and asked the drivers, we had four of us, so two in each tuk tuk, asked the drivers if we paid them extra, if they would race.

Steve Folland:    And of course, they did.

Kyle Webster:    Of course.

Steve Folland:    And you ended up doing figure drawing with Tori Amos.

Kyle Webster:    Yep.

Steve Folland:    How?

Kyle Webster:    Well this is one of those weird situations where I was in Los Angeles. I'm almost never in LA, but I had a friend who had a friend, and they were just getting together for one evening of quote-on-quote, drawing. And one of these people who came, she looked familiar to me, and just was sitting and drawing like everybody else. And we had a live model, who was paid by the hour, just like you'd do for a regular classroom situation. And people sitting around sipping wine. And I kept wondering, "Is that Tori Amos?" And I never had the guts to go up and ask or anything, but when the whole thing was over, I did ask, "By the way, there was this woman who was sitting there the whole time and looked just like Tori Amos, and I love Tori Amos." They were like, "Yeah, that's her. And she comes to these things every now and again because she just loves to sketch."

Steve Folland:    Wow. You could have had an original Tori Amos picture, if you'd have been quick enough.

Kyle Webster:    Yep.

Steve Folland:    Unless of course that's a lie. I don't know. Um, tuk tuk, Mick Jagger, 16 year olds in ... Oh God, I don't know. Mick Jagger's the lie.

Kyle Webster:    That's the true one. Very cool French guy.

Steve Folland:    Okay, I'm gonna tag another stab. The tuk tuk is made up.

Kyle Webster:    No. So I grew up in-

Steve Folland:    Whoa, so hang on. Tori Amos never happened.

Kyle Webster:    Nope.

Steve Folland:    That was so believable. And to pick Tori Amos.

Kyle Webster:    I thought that would be the most believable. You know, why wouldn't someone come and do some figure drawing? Who knows.

Steve Folland:    But the tuk tuks was true.

Kyle Webster:    Yeah, I grew up overseas. My parents were overseas schoolteachers, and when I lived in Taiwan my last three years of high school, we went to Patpong, which is this very bad, kind of dangerous and seedy place full of sex clubs and things, whatever. We were 16, it was terrible. But really, just a lot of fun, and nobody got hurt.

Kyle Webster:    But yeah, we did this thing where we decided to race tuk tuks. And my friends who were in the other tuk tuk almost rear-ended a truck, you know, going 60 miles an hour, or whatever it was. It was not fun after that. We immediately thought, "Okay, let's never do that again. That was a stupid idea."

Steve Folland:    Man. Oh God, geeze. You've had a good life.

Steve Folland:    If you could tell your younger self one thing about being freelance, what would that be?

Kyle Webster:    Oh, that's a tough question, man. One thing I would say for sure is make sure you do business on paper. Have contracts signed for jobs. Make sure you read over any contracts that are sent your way for jobs, and just make sure you don't get taken advantage of, because I made a few mistakes early on with some rather large jobs where I wasn't paid enough, or I gave away rights I should have never given away. Things like that. So I would say, yeah, do your paperwork. Sounds a little too practical, doesn't it?

Steve Folland:    No, but we hadn't touched upon it, and it is an interesting thing to hear. I think probably, especially if you're doing something, like an illustrator, where you're creating something. Like you say, the rights to it. Being aware of that.

Kyle Webster:    Yeah, for sure. Everyone's trying to get something for nothing, so watch out. We have people send contracts all the time that are full of rights grabs, and it's important to be on the lookout for those. Especially when you're younger and just getting started, you have to just pay attention and don't be afraid to ask for more money, or ask the advice of someone who has been working longer and knows the value of what a certain kind of work is.

Kyle Webster:    I think it's always dangerous when we have, every year, a flock of new graduates going out into the world and illustrating, and then if someone offers them a nominal fee to do some work, they say yes right away because they're excited to get the work without actually wondering, "What a second, is that the right fee for this kind of work?" And what happens then is, you just basically, if you do it enough times, you just establish a new acceptable fee for what had traditionally been twice as much. And that becomes what art directors and other clients assume is the new norm, and that's bad for all of us.

Steve Folland:    Very true.

Steve Folland:    Kyle, it's been so good talking to you. Thank you so much for your time.

Steve Folland:    Don't forget to check out beingfreelance.com, where you will find a link to everything Kyle's up to, what with his illustration and his brushes, and more beyond. And reach out to him on Twitter. And by the way, as somebody who makes videos, I really like the way you use video as well.

Kyle Webster:    Oh, that's ... Thank you.

Steve Folland:    As a selling tool. It's both selling yourself and getting your personality across in your about video, for example.

Kyle Webster:    You know I did that because I wasn't in New York, and I just don't want people not to know who I am. And I found that regular boiler plate stuff on people's websites so boring, and it all sounds the same anyway. So I just thought, instead of having that little copy, you know, "Kyle's an illustrator who does this, this, and this," I'd make a video. And it actually wound up being far more successful than I expected it to be in getting me work, actually, or starting conversations with people who I work with. It was an eye-opener for me.

Steve Folland:    Good to hear.

Steve Folland:    Kyle, all the best being freelance, or being whatever the heck it is that you decide you are now, that is.

Kyle Webster:    Thank you. I really enjoyed talking to you, too, Steve. Thanks so much.

Steve Folland:    Wow, how about that?

Steve Folland:    I know it's longer than I normally do, but I hope you enjoyed that, and if this was your first episode then please do check out all of the other guests at beingfreelance.com. Hit subscribe so you don't miss out, because there is tons of value to be had in every single one of those guests' stories, I guarantee it.

Steve Folland:    In the meantime, you have a great week being freelance. Take care. Ta-ta.


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