Simon Walker Lettering Artist & Designer

Simon Walker is a lettering artist and designer based in Austin Texas. You may recognize Simon’s charming lettering work on labels like Modern Times Beer, on book covers like the latest by Brené Brown, and other exciting places. Simon’s custom lettering has a charming hand-drawn quality to it. It’s a classy and rugged style that I love.

Interview by Cesar Contreras

Cesar: Pencil or pixel?

Simon: Pixel.

Cesar: I would imagine pencil with you, man. How do you start your work?

Simon: I think probably for everybody it’s a little bit of both. I’m sort of known for the fact that I don’t have a lot of … For example, I was recently asked to contribute some work to a book – I think it’s a French book, somewhere in France – and they wanted to see some process work for some work that I’d done. If I do any process work, it’s mostly on the computer, but if I do any pre-sketching or anything like that it’s usually really crummy, really bad.

Cesar: So just a really rough sketch.

Simon: I sketch super briefly just to prove to myself that I have an idea that’s going to work – that I can do what I want to do, that’s in my head. Once I have that, there’s no refinement done with pencil or pen, or anything else. The other thing that I kick myself for is even though these are usually crummy sketches, I should hold on to a few of them, just because people do ask from time to time, but I don’t. I tend to just kind of recycle everything, so what I’m left with at the end of the day is my finished piece and very little else. I do all my refining with my mouse.

Cesar: With your mouse?

Simon: With my mouse.

Cesar: Not even a Wacom tablet or anything like that?

Simon: Yeah, no, nothing like that. It’s second nature to me now, I draw better with a mouse than I do with a pencil.

Cesar: Have you ever considered starting to use a tablet at some point? Have you tried it?

Simon: No. Well, you know, to be fair to people who do use a tablet I obviously haven’t taken the time to properly learn it.

Cesar: It’s a learning curve.

Simon: Exactly. I just don’t have any reason to because what I do works so well for me.

Cesar: It just works for you.

Simon: Yeah, it’s a muscle memory thing, it just is what it is now.

Image by Modern Times

Cesar: Definitely man. Tell us a little bit about yourself. You’re a hand lettering artist, you create typefaces, you do a lot of amazing lettering. Can you give us a brief history of where you started off? Any background you’d like to share with us?

Simon: I’m going to show my age here a little bit. We moved to the US from England when I was 15, and this is back in 1988, so I’ll let you guys do the math. That meant that I spent a lot of my formative years in England, during the 80’s when, in England, hip hop was starting to become a big deal. I was into a lot of different types of music, but me and my friends loved that whole scene, everything about it.

Cesar: What were you particularly into?

Simon: It was primarily the music, and music is still of course a big part of my life, but the fact that it came with this graffiti aspect, the break dance stuff I got into a little bit.

Cesar: Were you a breaker?

Simon: I tried to be, I thought I was. I was more nerdily into doing the robot and stuff like that, probably than I was into popping and locking. I did a windmill once and kind of hurt myself and said that’s not going to happen. I let that go, but the graffiti thing was super, super fascinating to me from day one, and still is. I still look at graffiti artists and think man, this is some of the best.

Cesar: Did you ever try tagging yourself?

Simon: I tried it once, and I think that’s a whole other skill set. I think that most of the guys that are good at what they do, they do start with pen and paper, they figure it out beforehand. So that part of it I was into, I just used my pens. I was into kind of calligraphy at the same time, kind of simultaneously.

Cesar: Like classic?

Simon: To some extent, I didn’t get too heavily into it. My parents recognized that I was enjoying it and they got me a set, and it probably wasn’t a particularly professional-level set, but I got into it for a while without really realizing where I was heading with it. I was into lettering very early on. I think what I really loved about graffiti was that you could take recognizable letter forms and sort of warp them and twist them into art, and to the point where they become so abstract they’re illegible. And yet somewhere deep inside is a message, is a word, there’s some sort of communication there beyond just the visceral, visual aspect. Loved that about it.

Cesar: So, was it at that point that you decided to start drawing letters?

Simon: Yeah.

Cesar: Did you get into some other parts of design or illustration?

Simon: Not at all. Well, illustration, yeah. I was always drawing from a young kid.

Cesar: Was it for the most part letter forms?

Simon: Yes. Again, the way you can draw a relation between graffiti and what we do now is it’s all about ligatures. It’s all about taking a letter and turning it into something else, or finding some sort of a cool connection between two parts of a word. You know?

Cesar: Yeah.

Simon: So, I was doing that really early on, not really knowing what I was doing. So that laid the ground work.

Cesar: So, why the move from the UK to the States?

Simon: My dad was an engineer, he worked on aircraft’s. In England during that time they just weren’t making as much money as they were here. So, he tried to get a job in a few different places, even Canada at the time. San Antonio, Texas was the place that finally bit, so that’s where we moved in 1988.

Cesar: What part of England were you in?

Simon: The south coast, a town called Bournemouth. Not too many people have heard of it, although they do have a major league soccer team now.

Cesar: Oh, I thought you were going to say baseball!

Simon: No, not major league. I don’t have the terminology.

Cesar: Football. The proper word.

Simon: Football, exactly. Premier league.

Cesar: Did you know you wanted to become a letterer or a designer?

Simon: Not, not at all.

Cesar: What do you consider yourself nowadays?

Simon: Yeah, I would say primarily a letterer. Although, I’m absolutely a designer, I always will be. I just don’t get called to do much straight up design work anymore.

Cesar: You did at a point, right?

Simon: Yeah, that was my career for a long time.

Cesar: As far as education, was there any particular place that you went to learn technique? Are you self-taught?

Simon: No. The whole lettering thing sort of fell by the wayside over the years. I would occasionally dabble, just for fun. During my early college years I was really thinking I was going to do something else, I was going to be a meteorologist or a chemist. I was really into science, I was really into all that kind of stuff. I recall taking one look at the meteorology curriculum for A&M, which was a good school for meteorology, and I just instantly knew that was not the life for me. I just wasn’t going to be able to do that.

Cesar: Why?

Simon: All that math and chemistry, and all the physics. All stuff that interested me, but I just knew deep down that … I mean, I was fairly academic, it just didn’t fit somehow. It just wasn’t for me. But, right around the same time I was taking my art class, I was taking a drawing class, Drawing II I think it was.

Cesar: Just an elective?

Simon: It must have been, yeah. It wasn’t the first class, it was one of the later ones. But for whatever reason, and again it’s all kind of vague now, for every project I would always integrate type in some way. Just because I was always motivated by posters, album covers, things like that. So, if I drew something I wanted to put a message underneath, I wanted to come up with some sort of a phrase to match it. Not for any deliberate “this is what I want to do. I’m a designer,” I didn’t know what that was. It took a teacher to tell me, “Hey, you realize what you’re doing is graphic design,” and I literally said, “What’s graphic design?” He opened that door for me, told me about a couple of schools that taught graphic design. UNT, University of North Texas in Denton was one of them, and that’s where I ended up. Since Denton was so close to Dallas, I found a job in Dallas, I was already kind of familiar with the area.

Cesar: What was the job?

Simon: What was the job? First job was a place called Tractorbeam, which is a pretty badass studio, they’re still doing some pretty cool stuff. Worked there for a year, they did some advertising. They primarily did, at the time, branding, but they sort of dabbled with advertising, I think they do a little more advertising now. They try to be a one-stop shop for that kind of thing. Moved after about a year to Square One, which is an advertising agency, which I don’t believe they’re around any longer.

Cesar: Was it also in Dallas?

Simon: Also in Dallas, yeah. Stayed there for a couple of years, kind of got myself entrenched in the ad world.

Cesar: How was that?

Simon: You know, it has its ups and downs. I was never particularly interested in advertising, but it was a more stable environment, better pay than your average small design shop will pay. Then I had a friend who worked there who moved down to Austin to GSD&M, here in Austin. I don’t know if you’ve heard of them.

Cesar: No, what is that?

Simon: That’s another advertising agency.

Cesar: Oh.

Simon: Yeah, a pretty big place, they’ve been here for a long time. Which was an amazing move, I stayed there for 12 years.

Cesar: When did you decide to make the move from working in advertising to whatever was next? I’m assuming it was lettering.

Simon: It’s funny because the whole thing happened over such a long time. It was so sort of osmotic. It’s just kind of like how did that happen? I just kind of fell into it. There’s one client in particular … I was doing a lot of freelance, I was developing a little bit of a following with my regular design work. What I was really into, and still am and still love, was the traditional sort of logo type design work where you would come up with some sort of an icon, some sort of an image that stood for the brand. Then you would find some font, I loved fonts, still love fonts, find a beautiful font to match it up – and that was what I was really into, especially if it got kind of conceptual and especially if you could find a way to take the initials and kind of work that into the imagery in some way. That was what I was loving to do, and still do. I don’t get asked to do that anymore, I do lettering, that’s pretty much what I do.

Cesar: You were doing a lot of that.

Simon: I was doing a lot of that kind of stuff.

Cesar: This was freelance?

Simon: Well, freelance and of course it worked into what I was doing in my day-to-day job too, but primarily freelance, yeah. That was really starting to take off, and it was starting to take off right around the time that Dribbble started up, and Pinterest. I was posting my work on Flickr, I didn’t have a website at the time. I knew I needed some way to put my work out there.

Cesar: This is before the Super Furry days?

Simon: Yes. [Laughing]

Cesar: Which I love by the way, man. I still dig it.

Simon: I don’t really quite embrace it the way I used to, I’m never quite sure how I feel about it, but it’s still my name on Twitter.

Cesar: A part of history. Keep it man, keep it.

Simon: I don’t think it’s going anywhere. There’s nothing I can do about that. Not to make a long story even longer, but it did come from the Super Furry Animals. I was listening to them at the time and I was having a discussion with a friend about how I like the band, and he looked at me and said, “You’re a super furry animal.” You know I had the long hair and the beard, and I was like that’s fine, okay. Right around that time I signed up for Flickr and because I couldn’t come up with any other name I came up with “Super Furry,” and that’s why that stuck.

Cesar: It was available.

Simon: Yeah, and it was available, exactly.

Cesar: So you were doing logo type.

Simon: Yeah. No custom type work at the time, not very much anyway.

Cesar: So you were just picking fonts that you were into and finding some icons or some emblem, and you were putting them together making them work.

Simon: Yeah. Which is, again, an art form that I still love, still appreciate. I love a good logo, that kind of a logo. Custom lettering was starting to sort of become a new thing at that time. I remember telling people …

Cesar: This is around when? Like approximately what year?

Simon: I would say between 2005 and 2010, somewhere in there I guess probably. I was doing mostly logos, I was doing illustration too. I was on Threadless a lot, I got a couple t-shirts printed on Threadless. I was really heavily into illustration, getting my vectoring skills up to par. And occasionally, even on Threadless, did some custom lettering but didn’t think of it as custom lettering. It was more just art, like if you needed a word that needed to be created in a custom way, that was just part of the art, it wasn’t anything beyond that. I had a client come to me and ask for a custom lettered logo, and he showed me a few examples of what he liked. I often credit him with really launching my career, and I’ve written to him and since told him thank you, because I did not believe it was something I wanted to do, or that it was something I was really good at.

Cesar: You just didn’t see that at the time.

Simon: Not at all. What he was asking for was slighting more sort of font-style custom lettering. The kind of stuff that I was doing was a lot more free-form. When you’re designing letters that feel like they’re from a font system, there are a lot more rules that come into play, it’s a totally different practice. It was really, really hard, and it wasn’t good. It really wasn’t.

Cesar: The final product you don’t think was good?

Simon: The final product, no. Funnily enough, I have a lot of that process work that I did for him, and I’ve shown it online. I have a Skillshare class and I actually showed a couple of them.

Simon: Yeah, which I’ve taken.

Cesar: Oh, well there you go.

Simon: It’s so great.

Cesar: Oh, thank you.

Simon: That’s a whole nother story, but I showed a couple of those on there just to show people, hey I started out pretty rough too.

Cesar: Right.

Simon: It was a real struggle to get to where I’m at now. I try to put it all out there. I have no secrets, I’m not one of those guys who is like “no, I’m not going to tell you how I do that.” If you want to know, no worries.

Cesar: That’s great, and I’m glad you’re bring that up because I don’t think there’s any point to keeping any secrets.

Simon: I don’t either, that doesn’t make any sense.

Cesar: I mean, if someone knows another person’s process or style or way of doing things it doesn’t mean that they’re going to take that work from them.

Simon: No, exactly.

Cesar: They’re just going to do their own thing, whatever they learn they’re going to make it their own.

Simon: Absolutely, yeah. If someone’s going to rip you off, they’re going to do it anyway. It doesn’t make a difference.

Cesar: Exactly. If they do, what does it matter?

Simon: What are you going to do?

Cesar: At some point, the originator is going to be credited.

Simon: Yeah. Well the amazing thing about our community is that it polices itself so well so I don’t even have to worry about it. If someone rips off something that I’ve done, I find out about it really quickly, which I really appreciate. There’s not often much I can do about it, it’s not worth my time or money, for the most part, to follow up with these people. It’s kind of on them. It would depend on the level of thievery that happens. I could imagine there might be a situation where I would have to pursue it legally, but it hasn’t happened yet.

Cesar: You were saying that you have a long career history, especially with the advertising world. You’ve done a lot of design, and then you slowly transitioned into, I don’t if you consider this but, hand lettering.

Simon: Yeah.

Cesar: You say that it’s really thanks to this one client that wanted a particular letter form.

Simon: It jump started that part of my brain, it really did.

Cesar: That was kind of your moment, you were like “I can do something with this.”

Simon: Yeah. Even though it didn’t turn out, I enjoyed it. I enjoyed the challenge and I thought, well I want to try this again, I want to do more.

Cesar: So this client never used it?

Simon: No, he did. He ended up using one of the logos that I came up with, and it wasn’t horrible.

Cesar: It wasn’t one of your favorite.

Simon: Not at all.

Cesar: Not something that you’re like extremely proud of.

Simon: No.

Cesar: Just something that got the juices flowing, you got everything going.

Simon: Yeah. It made some sort of connection with stuff that I had already done, it was starting to come together, but it was a whole new discipline, a whole new level.

Cesar: So, how long would you say that it took you to get to this point? That’s a tough one to really think of. I’m glad you’re sharing this with us because, whoever is listening to this, you’re proving to us that it takes a long time.

Simon: It does, yeah.

Cesar: You don’t instantly … There are some exceptions but …

Simon: There are, I think it’s possible. There are people out there who naturally have it right off the bat.

Cesar: Right.

Simon: And I’m not sure exactly why that is.

Cesar: You know what? I was having this conversation with someone, young designers are just killing it out there. They’re doing great, they seem to have it down.

Simon: They’re still in school, and they’re better than I ever was at that age.

Cesar: We don’t think about the fact that some of them have been doing this since they were 10, 11, 12. I have a nephew who is really into computers, and the guy’s talking about Node.js, JavaScript type stuff. This is a 12 year old, I’m like are you kidding me? I don’t even know that.

Simon: That’s still creeps me.

Cesar: People who have had access to computers at a very young age, and have taken advantage of it …

Simon: Well, they’ve also had a lot more resources. Back in the day, I had to have a subscription to Communication Arts and Print Magazine to be able to see what was going on in any real way in this world that we’re in.

Cesar: Exactly, yeah.

Simon: So now it’s all out there. Kids are learning design in high school now, and it wasn’t in high school when I was there.

Cesar: Now they have programs where they have the whole Adobe Suite, and they can just play around with it and figure things out.

Simon: Yeah, it’s a different world.

“It takes screwing up and it takes sucking for a while.”
– Simon Walker

Cesar: I’m glad you’re sharing it with us though because I love your work.

Simon: Thank you.

Cesar: You have solid, beautiful typography, in my book, you’re one of the top typographers/lettering artists out there.

Simon: I’m glad this isn’t on camera, I do blush. It does happen, a pale skin red head. There’s nothing I can do about it.

Cesar: Seriously though, man. I’m glad you’re sharing this because I had no idea that it took you so long. I thought this guy’s been doing it forever. Just the simple fact that you’re saying that it took you from this point, over a span of years, to get to where you are right now. That’s great man, I appreciate it.

Simon: Yeah, it takes that time. It’s so hard not to sound cliche when you’re giving advice, when you’re talking about how to do what it is that we do. It really does take time, and it takes screwing up and it takes sucking for a while. Just muscling through it, and it wasn’t easy. That’s definitely what I did. As I often tell people, for all the work that I have out there, there’s twice as much that I don’t show anyone, that is awful, that is really bad.

Cesar: Have you ever considered showing any of it?

Simon: Well I did, on my Skillshare class a little bit. I think I would, for the right reason I would go back.

Cesar: Where do you draw inspiration? Where do you get your ideas? How does it all manifest itself?

Simon: As with anything artistic, it’s a matter of continuing to do it. I think for people who don’t do what we do, it is kind of like, how do you keep coming up with new ideas, new things? Because I think from that state-of-mind, from that way of thinking, it’s like surely you would run out of ideas at some point, how is it that you can keep doing it? I think the way that the creative brain works is that if you keep doing it, that’s what makes the ideas come. I think if you stop, that’s when the ideas stop too.

Image by Austin Eastciders

Cesar: What’s an example of keeping on doing it? Do you mean like daily?

Simon: I’m not talking about being religious necessarily about it, but if you got downtime, work on something of your own making. That’s something I’ve been really open about in the past too. There’s a lot of work out there that I’ve done that people are very familiar with that I did just for me, just to exercise, just do something new, something I’d never done before. I think that’s really important. If you’re between projects, invent one, I mean why not? You’re your own client, it’s the best possible way of doing it.

Cesar: Sometimes when you invent something, you see a lot of those redesigns and re-branding and that kind of thing, and it seems to work.

Simon: Yeah. Talking of Threadless, there was a guy called Olly Moss, you know that designer?

Cesar: Yeah. Firewatch was like his big project?

Simon: Yeah. Well back in the day, in ’04/’05 when I was on Threadless, he was a young up and coming designer at the time, and he was submitting a lot of stuff to Threadless too. He obviously developed an interest in movie posters and just started creating them for himself, and now does posters for all these movies.

Cesar: They’re amazing.

Simon: He does legit work for them. So that’s a great example right there.

Cesar: I remember those Star Wars posters were iconic. Olly Moss right there, man.

Simon: Yeah, I know.

Cesar: How does living in Austin influence your work? Does it influence it at all? Or kind of draw inspiration from different things?

Simon: Yeah, definitely.

Cesar: What kind of things?

Simon: Specifically?

Cesar: Yeah.

Simon: I don’t know about specifics, it’s just the vibe. You know, being in a creative community. It’s interesting because I work alone now, I work at home on my own, but I still get together with my old buddies from GSD&M and other places, just because getting in those communities, getting back to that feeling is good. I don’t necessarily need to be around people to do good work all the time, but again, you got to reconnect.

Cesar: It definitely helps.

Simon: It does. For the 12 years I was at GSD&M working with all these amazing people, and again, that sounds so obligatory and so fake, but it’s not, it’s so true. They’re amazing guys, they really were, love them to death. That feeds you in a big way, hugely inspirational, still are.

Cesar: So, you were just talking about working on your own for the most part. You usually just work by yourself. What are the kinds of challenges that you come across?

Simon: I may have to come at this question from the other end because I have so few challenges, creatively, now that I’m working at home. It’s just a situation that really works for me and I know a lot of people who have tried it and it doesn’t work, especially if they have families, they have kids and stuff. I tend to thrive in that kind of environment. There’s been times where we’ve had a lot of kids in our house, we had foster kids for a while that would come and stay with us. It would be nuts, it would be crazy, they’d be like running behind me and knocking into me. It was fine, I loved it.

Cesar: All while you were working?

Simon: Yeah, I was totally cool with it. I’m not going to say every sort of home situation is conducive to that for me, but in general it’s incredible. Working for yourself and working from home, obviously there are challenges but it’s not usually creative ones, it’s usually about getting paid, obviously. That’s probably the hardest thing.

Cesar: Do you manage all your invoicing and all that?

Simon: No, no. I couldn’t do that. I have a guy who does that for me, he is worth his weight in gold.

Cesar: Do you recommend people do that?

Simon: Yes, if they can, absolutely. I don’t have to answer emails or anything, it’s all taken care of. It’s beautiful.

Cesar: So is this is a rep?

Simon: He would not call himself a rep, that’s not a term he likes. He would say he’s my studio manager or business manager. He answers my emails, he talks the money, I don’t have to talk about it. I just have to say yeah, that sounds great, let’s go for it.

Cesar: And he gets a cut from that?

Simon: Yeah, exactly, he takes a cut. And honestly, I would pay him more if he asked, I really would. He’s amazing.

Cesar: How can someone search for a studio manager?

Simon: Well I don’t know, he kind of fell into my lap through a friend. I wasn’t even necessarily really looking for that at the time, but just expressing how difficult it was to manage all of what you were just saying, all the emails, all the invoicing, all of the phones calls, everything.

Cesar: And this person just offered his services to you?

Simon: No, but I heard about him through Dana Tanamachi. He works with her.

Cesar: Is she also in town?

Simon: She’s not, I think she’s in Seattle now I think.

Cesar: Okay, cool.

Simon: But yeah, I had a quick conversation with her and she just talked the guy up and said, hey, look, try it out, see if it work. It works for me. And sure enough, it was such a load off, it really turned my whole career around, it really did. But, I was still working at GSD&M at the time actually, and that was a big part of the problem. I was really working two jobs, not intentionally. My financial situation at the time, without going into too many details, was such that I couldn’t quite make the transition. I couldn’t give up one or the other, but I’m not a workaholic, that is not my bag. My free time is super important to me, and I was working nights and weekends and that was not going to last. Something had to give at some point. So, I found out about him, didn’t even really know that that kind of thing was available to me. Once I figured that out, I haven’t looked back since.

Cesar: So, you would recommend, for any freelancers out there, to have someone that takes care of that sort of thing for sure.

Simon: Most definitely. Unless, some people would rather manage it themselves, they’d rather not have to pay for that. They can do it, it’s not for me. I’m not a business guy, it’s just not my thing.

Cesar: So you’re right, you have no challenges.

Simon: No, I have so few. When I’m struggling to come up with an idea, and that happens of course, that happens all the time, there’s nothing more intimidating than an empty screen or an empty page at the beginning of a project, I can just take off. I can take a walk, I can watch a movie, I can kick back, it’s a beautiful thing. So the pros definitely outweigh the cons.

Cesar: You were talking about music earlier, how deep do you want to go into music, man? Do you play music?

Simon: I don’t play music, no. I play a little harmonica, I learned some blues harmonica way back in the day when blues was still kind of cool.

Cesar: I love the blues, man, are you kidding me?

Simon: No, I still love it too.

Cesar: Do you credit music to giving you some sort of inspiration for your work?

Simon: I do, but I couldn’t tell you how that works. I just know that it’s a part of my creative process definitely.

Cesar: One of your daily things.

Simon: Yeah. I’ve often told people, I can talk about music much longer and in more depth than I can about design.

Cesar: Nice.

Simon: Yeah, it’s a far more integral subject for me in my day to day.

Cesar: What are your favorite tools? What tools do you use on a daily basis for work?

Simon: My mouse, my keyboard.

Cesar: Illustrator? Photoshop?

Simon: Yeah. It’s 95% Illustrator, 5% Photoshop maybe.

Cesar: That’s where you put your finishing touches?

Simon: Yeah, depending on what you’re trying to achieve with the visuals.

Cesar: Tell us about your typical work day. What does it look like? Is it even typical?

Simon: Yeah, it is and it isn’t.

Cesar: Do you have sort of a daily ritual? A daily routine?

Simon: Ritual is too strong a word, no. I take care of the dogs, I walk the dogs in the morning. I love that, that’s the first thing I do. It’s hard to love right now, because even first thing in the morning, it doesn’t matter what the temperature really is, it’s going to be 75-80 degrees. I come back gross.

Cesar: It’s like 200% humidity.

Simon: Yeah, a 10 minute walk and it’s shower time after that usually. But then after that, I ease into my day, I really do. It’s going to make a lot of people crazy to hear it, but 10:30ish perhaps.

Cesar: That’s when you start working?

Simon: Yeah, give or take. Depending on when I get up. I actually don’t try to extend that out, I am kind of an early bird; it depends on the time of year. Like right now, my kid’s not going to school, she’s out of school, so we wake up a little bit later. It’s a little bit of a later start for these few months. Still, between 9 and 10, I would say, I’m up at the computer.

Cesar: That’s not bad.

Simon: But once I’m there, I’m there all day long.

Cesar: For how many hours approximately?

Simon: I try to put in close to 8, so I’ll work until 6 or 7. But again, it’s super flexible.

Cesar: As far as projects go, how many projects do you work on at a time? Do you have multiple projects at a time?

Simon: That’s super varied too. I mean, I’ll have three or four projects at once, and then I’ll have none, not one for a week, which is when I work on fonts, which is when I work on whatever other endeavors I’m kind of into at the time.

Cesar: Tell me about some nightmare scenarios when it comes to clients, and not getting paid?

Simon: Not getting paid, yeah. I don’t have to mention any names of course, and I won’t, but that is of course one of the most difficult things to adjust to. Of course, when you’re going from regular paychecks twice a month, to sometimes you’ll go two months or more, without a paycheck. I have two outstanding clients right now, who haven’t paid in over a year. We’re talking about reputable clients, reputable businesses for which the work was loved, the relationship was good, they were invoiced promptly and here we are a year and a half later, and they still haven’t paid.

Cesar: These are two clients?

Simon: It’s two, yeah. Two that I can name right now. They’re not the first to have waited this long. I would say there’s a lot about this that I will admit that I don’t understand, which is why I have a business manager who I know works his ass off to get me paid. It’s his money too, it’s in his interest, so he does a lot. Outside of engaging a lawyer every five minutes, and having that extra expense, it’s hard to justify spending a lot of money going after someone for $1500, you know what I mean? Give or take. So yeah, it’s tough. As far as I can tell, there aren’t many laws protecting freelancers out there.

Cesar: I don’t think there are any at all.

Simon: So you can put on your invoice “must be paid within 30 days,” where they’re just not going to care. They’re going to pay you when you’re good and ready. Seems like the bigger the business, the bigger the corporation, the bigger the client, the longer they take because they have to get you set up in a system. So, God knows how many desks your paperwork is sitting on before they get around to actually cutting you a check. So that’s tough, yeah. A lot of times you feel like you’re just working for play money, you know? It’s like oh, this job’s for this amount, oh okay sure, I got nothing better to do, I guess I’ll work on that, and maybe within a few months we’ll get paid. So on average I would say you get paid anywhere from between 3-6 months. It takes about that long from invoicing most clients.

Cesar: Between that time, what is the kind of stuff that you do to ensure that you’re getting something?

Simon: My first experience bringing in passive income, which is what I’ve learned it’s called, was working doing my class for Skillshare. That was huge.

Cesar: How long has that class been going for?

Simon: I want to say it’s been a couple of years now at least. I forget, but I still get a check from them every month, and it’s not huge. Of course it started out bigger and it kind of gradually decreased, but it’s pretty steady now. And again, it’s not enough to maintain me, it’s not enough to sustain us as a family, but that in addition to the fonts that I’ve worked on, so far that’s all I have going right now. It’s as much as I can do to work on one font and get that out the door, but I do have plans for other things. I’m considering doing portfolio reviews and things like that, like one-on-one for kids just getting out of college, or out of college, either way.

Cesar: At the university nearby?

Simon: Wherever. It could be online, it could be someone in another country. If it’s in person, if they can get here, great. I haven’t quite figured that all out yet, but it’s something else I’m going to do. But yeah, passive income is huge. I would love to get into selling products, but it’s just another thing to get to.

Cesar: I would buy in a heartbeat.

Simon: Oh well, thank you. That’s good to know. I just love some of the things I’m seeing out there too, people doing iron on patches and enamel pins and stuff like that. That’s all really cool, I would love to get into that.

Cesar: How many in your family?

Simon: It’s just me, my wife, and my step-daughter. Three of us, plus a bunch of animals.

Cesar: The dogs you mentioned earlier?

Simon: Yeah.

Cesar: Have you ever considered doing your own courses?

Simon: I have.

Cesar: Similar to Skillshare but your own thing?

Simon: Skillshare have even come back to me wanting me to do another class, but at this point in time it would feel disingenuous of me to put another class out there and ask for more money from people when I put everything I could think of into that first class. You know what I mean? I just don’t know what else I could bring to it. I did have one fleeting idea, which didn’t quite come to pass, which I guess I could go into that a little bit.

Cesar: Yeah, if you’d like.

Simon: I was going to do a case study, and I was going to do Austin Eastciders, I was going to do them as a case study and actually involve the guy who started the company. Interview him on-site, and just get a lot of that sort of client-relationship thing as a part of it. That’s definitely something to learn from on both sides, I think, how to make a good client relationship work.

Cesar: You were considering to do that for Skillshare?

Simon: For Skillshare, yeah. And for reasons I won’t go into, that didn’t pan out. I might consider doing something like that again one day, sure. For now, I’d need a really good reason, like this is something that has value for people. Otherwise I just feel like I’m taking money because I know people would buy it, and that just seems wrong to me. I’m going to wait.

Cesar: You were mentioning that you’re working on some typefaces currently.

Simon: Yeah, I have two in the works right now.

Cesar: Can you talk about them?

Simon: Yeah. Well, one of them is another script and, as a lot of people listening may or may not know, for reasons I’m not going to go into right now, Eastcide was pulled from sale, which was unfortunate but had to be done. I really felt like I owed people another script, so I started developing a new script. It’s coming along really well, I’m really pretty happy with that. I have a San Serif too, it’s sort of a condensed, bold San Serif font, which pairs really well with a good script. I’m kind of hoping to release, not together, not as a package, but you could look at them that way once they’re out there.

Cesar: Oh, I’m excited.

Simon: They work together really well.

Cesar: That sounds really rad, man. This is one question that totally slipped my mind, but I wanted to ask you, are there any particular letterers, or artists that you look up to, and kind of look back for inspiration? That you just really look up to and you’re like, man, this is where I want to get?

Simon: Yeah, but you know what? My mind goes blank, I’m terrible with this kind of thing. It really does, I just blank out. My all-time hero would be Herb Lubalin, I’d look at his stuff all the time. I think what’s beautiful about what he does is that his stuff isn’t perfect. Do you know what I mean by that?

Cesar: Absolutely.

Simon: If you really look at it, it’s kind of wonky. It’s kind of like, why did he do that? But it works, and I love that. I’m a bit more of a perfectionist than I think he perhaps was, which I’m not saying I’m better than him, my God, by any means. I’m saying that usually when I put something out, I’ve really, really, really thought about every little aspect of it. But, when an imperfection does creep in, when a slight irregularity does come into it, I think that’s part of the beauty of custom typography. When it’s really good it’s not so rigid and font-like that it looks like somebody just typed it in. But yeah, I love him, I love his stuff. There is of course one another guy, Spencer Charles and, his now wife, Kelly Thorn.

Cesar: Kelly Thorn too?

Simon: Yes, they’re both just agonizingly talented, just really, really cool. They both started their own thing together, I think it’s called Charles&Thorn, they have their own website now. They just created a font, which I believe will be coming out on Lost Type also. Two of the nicest people I’ve met in a long time in the industry, for one, which almost makes me hate them even more, but I don’t, I love them both very much.

Cesar: Double the talent.

Simon: Yeah, they’re a force to be reckoned with, for sure. As someone who feeds off of, as we all do, we’re inspired by other people, it’s hard not to want to rip them off.

Cesar: Take a little bit from them.

Simon: Take a little bit of what they do, yeah. Perish the thought, of course.

Cesar: You mentioned music earlier, what about any musicians? Any particular music?

Simon: I don’t think saying this is going to make me seem any different to most people these day, but I like my music, and my beer, and my movies to be different almost every time I listen to it, or take it in, or drink it, or whatever it is. I don’t have a lot of people that I say I go back to over and over again. What I love about what the Internet has done for music for me personally is it’s sort of like virtual crate digging. You can get online, you can go to some blog, some music blog, something really obscure, and just find this incredible music that just disappeared for 10, 20, 30 years, no one’s heard of it, and all of a sudden oh my gosh, it’s another new discovery. I love that about music. There’s a lot of new artists I love too, but I love digging up old stuff from the past.

Cesar: Anything come to mind?

Simon: Well the band that always comes to mind is one that have been a little dormant lately for the last couple of years. I know they’re busy, but they’re not busy with their own band, it’s a band called The Bees. In America they’re called A Band of Bees, for legal reasons, so they have two names, they have to call themselves A Band of Bees here in the States. Everything about their vibe, and everything about the music that they make fits so well with just my state-of-mind, it’s really kind of hard to explain. Obviously they’re not for everyone.

Cesar: Are they from the UK?

Simon: They’re from the UK, yeah. They’re a UK band. I just think they’re incredible, I just love their musicality, their approach to what they do.

Cesar: So all of the members from that band are doing their own thing?

Simon: Yeah, they produce and DJ and do all the stuff that most musicians do. They’re pretty well known in the UK, but over here they just never made a splash. I guess it’s possible they still could. There’s always that part of you that wants to know about the band nobody else knows of, of course. I would love them regardless, but it just so happens that very few people have heard of them, but I’m happy to plug them. They’re an incredible band.

Cesar: Nice. Favorite beer?

Simon: Yeah, again, I can’t say I have one.

Cesar: At the moment.

Simon: Alright, favorite beer. This is going to sound wrong, but I really want to be clear about this, I love the beer that Modern Times is doing. Now, yes I did their logo, I get that, but I’m never just automatically biased toward my own clients, never. If they weren’t good, I wouldn’t mention them. You know what I mean? I just wouldn’t have any time for it. They’re the only client that I occasionally work for beer, I still do it.

Cesar: What?

Simon: Oh yeah. They’ll ask me for a t-shirt design or something, and I know I could ask them for, not a lot of money, but I know I could make some money off of that, but I’m like, just send me a case of whatever’s new. They’ll send me …

Cesar: A keg…

Simon: Oh, I wish. That would be nice, but no, they’ll send me 12 big beers, like the fanciest, baddest new stuff that they’re coming out with, and it’s all good. They’re just so, so good at what they do.

Cesar: Before we wrap it up, do you have any parting advice you’d like to give?

Simon: It’s stuff that you’ve heard a million times before, but it’s a cliché because it’s true. Just keep doing it, if you’re no good that doesn’t mean you’re going to stay no good, it just isn’t because I was not that good. It’s perhaps fair to say that I had some ground work laid because I did dabble, and had since I was a kid, but in terms of the real deal, it took me a while, but for whatever reason, I was determined to figure it out. The more you do it, the more you train your brain to see what’s wrong and what’s right about what you’re doing. It just happens, it just happens, it will come together. And, don’t sleep. Invent projects for yourself, pick your favorite project, pick your dream projects and do it and put it out there.

Cesar: That’s some of the best advice. Simon, man, appreciate you being on the show.

Simon: You’re welcome, absolutely, a pleasure.

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