I get interview requests from students almost daily. I do my best to personally respond to as many as I can, but I often don’t have the capacity to reply to all of them, especially when they are in-depth questions from students with short deadlines.

Since many of the questions are quite similar, I’m finally consolidating a lot of my responses that used to exist only in a bunch of different emails as a means of having a single source to point to.

If you have any questions not covered here, feel free to get in touch.

Jump to question:

What was the first thing that pricked your attention about the creative industries?

There are two categories of things that I love: Logic & Creativity. I have found that the areas in which I am most passionate are where those two concepts overlap. This accounts for my primary passions: Typography, Design, and Music. In music, we have rhythm, repetition, movement, underlying chord structures and chord progressions that are all vital to composing a comprehensible song. You can stray from these a little bit in some areas, but if you venture too far, you end up with a mess instead of a melody.

Letters share many similarly welcome constraints. While you can be creative in expressing letters, you can only go so far before they cease to become recognizable. As a designer, I always make it a goal for my lettering to first and foremost be legible. Some might argue that expression is more important than legibility. Personally, I think “what’s the use if someone can’t even read what you made?” In that regard, I tend to categorize my lettering more as design than art, though there’s certainly a little of both.

Can you talk a bit about your background, education, and how you got into design?

I was home-schooled growing up. My mom was a great teacher, though as I was the oldest of 12, there was only so much 1-on-1 time you could really get. This resulted in a lot of our education being very self-propelled. We were given the curriculum, but really we could go as fast or slow as we wanted to. I could see this being a good or bad thing, but for me it was very beneficial because it didn’t slow me down the way a traditional education likely would have.

I devoured every book in our house and then took to libraries. I think if being home-schooled gave me anything, it was an insatiable desire for knowledge and learning.

I got about 1/5 of the way through a computer science degree, but at that time I was already running two businesses. I recognized that in both industries I had companies, experience was equal to education.

I stopped pursuing the degree.

While my formal education ceased, my self-initiated education continued all the more and with renewed focus and vigor. I wanted to learn music production, so I spent 30 hours watching YouTube tutorials, and making things. I wanted to learn Adobe Premiere, AfterEffects, Photoshop, Illustrator, etc., so I simply did. I did this with each of my pursuits and businesses. From the first one I sold, to web design, and now lettering.

The internet is a phenomenal wealth of resources. The vast majority of information is freely accessible, and what quality material is available is very affordable. The internet merely amplifies what inclinations we already have. If you want to learn, there’s no stopping you. The sky’s the limit. If you want to waste it all away, there’s no cap on how long you can play video games, and there are enough cat gifs on Reddit to fill the rest of the time you have on this planet.

I always say if you go to school and didn’t learn to learn, you’ve learned nothing.

How do you like where you live? Would you ever relocate, and if so, where?

I live in San Antonio, which I wouldn’t say has much of a design community. I find myself traveling to Austin every couple of months to network and attend meetups with other designers. Austin is definitely becoming quite the hub for our industry, and I’m fortunate to live nearby.

I’m currently in San Antonio because it’s where I lived when I was at home. Several years after I was married and my wife and I settled here, my family ended up moving away for my dad’s job. There isn’t too much that’s keeping us here anymore. It is likely that we will end up settling in Austin in the coming years. However, my wife and I really liked New York City when we visited on vacation a year ago. We could definitely see ourselves living there at least for awhile, so we’re keeping our options open.

I’m an introvert, so location for the purpose of networking doesn’t seem like such a big deal to me, because I do not mind staying in most of the time. However, I know that it’s a very beneficial thing. If I lived in an area that had a strong community, I know I would enjoy taking advantage of that.

You seem to have a focus on lettering and your own unique style. Did you seek to specialize and how do you continue to grow?

It’s been a journey of trying lots of things and gradually honing my interests and focus. I think specialization is great. I think stagnation is not great. I always strive to improve my work, and I think the evolution of my “style” over the years depicts this growth.

I really never sought out to make a style. I just started creating. Eventually, you’ll find that you settle into something that you like. We all have tastes and personal preferences. However, I think it’s important to distinguish between personal projects and client projects:

I think we should always objectively serve the project goals. That often means turning down a client wants a certain style when it’s really not the best style for the job. You as the professional should be determining what style to apply in order to meet the goals effectively.

You’ll notice that my logos are all extremely unique. While I maybe arguably have a personal style, that has no place in a client project unless it just so happens to meet a specific need. The logos I design for clients are unique because the project goals are unique and the businesses are unique.

Client work aside, I think we should all resist complacency. I never want to be at a point in my design career where I feel like I’m not growing. Whenever I find myself in those places, I shift my focus. For instance, behind the scenes right now, I’m actually doing a lot of illustration! It’s been a blast to make a shift to something different to keep things fresh.

I may not post all of that work to my Dribbble, because I do largely want to respect the content expectations that are held by people that follow me, but that doesn’t mean I can’t try new things. On a conceptual level, I try to avoid boxes; putting other people in them, and thinking inside them myself.

What made you interested in pursuing hand lettering?

As a kid I thought I was pretty strange. I always found myself drawing letterforms throughout middle school and high school. My homework was littered with typographic illustrations. The artistic friends I had all seemed to draw cartoons, or paint still life, but for some odd reason I was drawn to letters. I just really enjoyed hand lettering.

In general, most people see words and read sentences to derive meaning. I saw letters as beautiful shapes and curves with forms full of beauty. It wasn’t until years later that I discovered that I had a love for what was known as “typography”. What a feeling of relief and excitement all at once! I discovered that not only was I not some strange person with a deranged affection, but that there were also thousands of others who shared the same love for type. The internet has a unique ability for making one feel less weird.

Was there someone in particular who inspired or mentored you, encouraging your career as an artist?

I feel odd saying that I never had any sort of mentor figure. I hear many others share that they had someone to help guide or mentor them, but that was never a part of my story.

I’ve always been very self-driven and motivated. The worthwhile things in life require discipline, so as one who very highly values those things, I came to love discipline. Whether it was learning piano, or teaching myself anything from guitar to design and typography, I trained myself to enjoy the process as much as the results.

I’m very long-term oriented. I like the slow-progressing steps toward vast goals. I suppose that’s what enables me to accomplish things because I see the big picture and don’t get discouraged by small defeats.

My family has always been supportive of my ventures. When I started my first business in early highschool, they were very encouraging. I thrive on words of affirmation (which can also be a weakness), so even if they never thought in their minds that I could be successful at it, the words they spoke were enough to fuel me.

What is the philosophy or driving force behind your designs?

Lettering is a form of voice for me. I’m a big proponent of doing what you love and I like exploring what that expression means beyond the cliche and helping others make it their reality.

The brilliant thing about lettering is that while it can be aesthetically pleasing in and of itself, it’s artistic appeal creates a platform from which you can speak any message you desire. I’m a very introspective person and I take lots of time to think and reflect. I letter my thoughts of positivity as a means of sharing encouraging with others.

My background in design has a heavy influence on my typographic work. I’m very objective about my design decisions and place a big emphasis on readability. After all, what good is a message if it cannot be interpreted?

Do you work by yourself, or do you have interns/employees that help you out?

It’s just me, however part of my business is selling and shipping the physical products in my online store. I used to spend many hours handling orders and shipments on top of my other work, but in recent years, I’ve been able to teach my wife to use the shipping system I have and she now handles order fulfillment completely, which is a huge help to me. We typically have new orders daily, so delegating those tasks really helps me get a lot more accomplished.

Did you think this was the direction of how your career would end up being?

I could have never envisioned it. I started out in music—I was in a band. I needed something to help supplement my income from the irregular gig schedule, so I started a computer repair business. From there, I got into design and freelancing web and graphic work in addition to my computer repair business. The freelance work got so busy, I ended up founding a partnership web firm which I ran for 3 years.

During that time, I still ran the computer repair business, but I contracted out the work so that I was only managing the business end and not having to go out and do jobs. Web design was my full time job (about 8–10 hours a day), and in the evenings and weekends, I began to pursue hand lettering (about 6–8 hours a night).

It was through this habitual and regular practicing during my free time, outside of my day job that my passion began to flourish. I built up a large body of work that started to garner attention. People started wanting custom commissions and asking for my work on tshirts and prints. I shifted from doing personal projects during my nights and weekends to using that time to work on commissioned projects. Since my web design day job was paying bills, I saved the money I made from commissions. I used it to invest in larger product runs.

For unrelated reasons, we ended up hibernating the web firm in 2012, and I took my lettering pursuits full time. Shortly after, I also sold my computer repair business. I wanted my efforts to be very focused. I’m now a full time lettering artist, but as you can see from my story, I could have never predicted it.

I always encourage people to start doing. Don’t worry about whether that thing is going to be the “perfect” thing. It’s probably not. But what so many people do is fixate on whether something will be the “perfect” thing for so long that they never start anything. They remain stagnant. It’s much better to start doing. What’s great is even when you find that something isn’t your favorite thing to do, it will lead you to the next thing.

What is your favorite project? Why?

My favorite project is usually my most recent one. I’m very much a perfectionist and am often pretty hard on myself and my own work. It’s usually not long before I look back and see something that can be improved or done better on a previous project. Rather than let this be a discouragement, I see it as a catalyst for furthering my drive to continue doing better with the next project. It’s a good thing. If I don’t see things to improve, it means my personal growth has ceased. I hope that day never comes.

What is your dream project or client?

Early on, I might have thought that working for a big name means you’ve really arrived. As time went on, I stopped seeing it that way. I’ve had the opportunity to work with names that just about everyone has heard of, and while they were some great projects, it’s not really what I live for. The right client respects your process and trusts you as a designer. This is how successful projects are enabled. When you insist on starting with that kind of foundation, it doesn’t matter who the client is: every project is a dream project.

You encourage your followers, listeners and readers to do double the amount of work they expect to need for their portfolio, then they are getting close. What kind of pieces do you think are vital to have in a portfolio?

A diversified portfolio is a strong portfolio. Remember that you will always play your best hits, that is to say that the work you display is the work you will get. If you no longer wish to do a certain kind of work, you should remove it from your portfolio.

If you are a designer, your portfolio should feature case studies that articulate the problems you solve, the project goals you meet, and the design decisions you make along the way. By displaying varied case studies, you are showing prospective clients that you possess objective design thinking skills that are beyond a mere aesthetic that is applied haphazardly to a project.

How do you balance your intense work ethic with spending time with your family, wife, friends, etc.?

When you are a freelancer, or you simply have side projects that you actively work on outside of your day job, it can be difficult to balance your time between work, family, and relaxation). There is a tendency to feel unaccomplished when you know there is an infinite amount of left to be done. Of course, this is and always will be the case. I find that by writing 3 things I want to accomplish the next day, and setting that note on my desk to be seen the first thing tomorrow morning helps me stay focused. I know the day was productive, because I accomplished those key tasks.

I also try to keep track of the other work that is completed during the day, even if it seems small. At the end of the day, you can look back on what you have completed and feel good about stopping work for the day.

Looking at your work, I have a sense that you are a man of faith. If this is true, what religious background do you have?

You have a good sense! I am a Christian. My personal values are often reflected in my work, though usually in an indirect fashion. I find that with this approach, I am able to speak messages of positivity to a wider, more general audience without making them explicitly “Christian” messages. I think people are more willing to listen when they don’t feel as if you are trying to sell them something, or push a certain label.

You stress doing what you love. What is the most satisfying part of your job?

The most satisfying thing is crafting something to the best of my abilities. In the beginning, these were usually self-initiated projects, but over time I learned to be selective in what clients I work with. The clients I choose to take on are very on board with my process and come to me solely for my expertise.

I was jaded early on in my design career because at the time, I did not know how to be a professional. It always felt like an uphill battle trying to convince clients that I was making the right decision or that I knew what I was doing. I came to learn that you can’t shove good design down someone’s throat.

So where do you start?

You start by ensuring the clients you DO take on are willing to invest in good design, and are willing to trust you based on your track record. You’re only able to be selective by practicing selectivity. You’re never going to get to that place unless you start paving the way by turning down bad leads. Your efforts should be spent pursuing good leads from the start rather than trying to convert bad leads.

Do a ton of self-initiated work until clients are practically knocking down your door to hire you based on the immense portfolio you’ve developed. My clients want the quality results I deliver, so I plainly explain that adhering to my process is how those results are achieved.

You’d be surprised how smooth it is once you get to that point. Since these clients are cream of the crop, there’s little-to-no friction in terms of me being enabled to do what I do best. They’re invested in my professional results and what I am able to deliver, and less about trying to tell me how things should be done.

It comes as no surprise that the work produced from these types of projects receives the greatest recognition and appreciation from a general audience when published.

What would you like to accomplish in the next 3-5 years?

I’m currently on the cusp of a very big transition. While I mentioned earlier that I used to take on custom commissioned work, I actually no longer do. I started slowly phasing it out in 2013, and have now completely phased out of client work. Certainly not for lack of demand. In fact, demand was so high, I barely had enough time in a day just to send polite decline messages to all of the inquiries I got. At peak times, I was receiving anywhere from one to multiple dozens of requests a day until I disabled the options on my contact form.

Why in the world then, would I stop taking on work when there was such demand? Well, as much as my services were in demand, what I also began to recognize was that the practice itself was also starting to explode. Yes, people wanted to commission me, and yes, people bought my products and enjoyed my work. However, what I began to realize was that my audience was largely comprised of people that wanted to learn how to do what I do. I was not not adequately addressing this need.

Throughout 2013, I worked on conceptualizing a developing a new section of my site, Learn Lettering. I wanted to go into extreme depth and detail on the finer points of lettering and typography. The difference between this and other tutorials, is that I would be producing a plethora of courses that not only explain the techniques and practice, but also the business side of things. These courses include education on things like design contracts, licensing, dealing with clients, and so on. It essentially takes someone from knowing nothing about lettering to not only mastering the craft, but also understanding how to apply those skills in a professional career.

After phasing out of client work, I dedicated months to designing and developing this new section of my site. I’m continuing to work on producing content for the courses, both in video, audio, and written tutorial formats. In addition to the course offerings, I’ve also been busy building the new Community section (currently in beta). This is a place where people can dialog on design, business, and professionalism, as well as get feedback and critique on lettering. In addition to the forum, Community members have access to a live stream of the podcast recording and live chat where they interact with us during the show. There’s a few other things such as a weekly video show for members, and monthly scheduled video hangout that are also in the works.

It’s a huge undertaking. It’s yet another leap of faith I’m taking, but I’ve acknowledged an educational gap in this niche and I think my response to it will be well-received. Every transitional stage of my career has been in the form of taking a risk, but it is always a calculated one. If this doesn’t go well, I can always turn back on the client work. Hopefully though, this will be my main effort from here on out.

I would say that is the current 6 months–1 year plan. To more pointedly address your question of what I’d like to accomplish in the next 3–5 years, I hope to shift my focus to more teaching, speaking, and writing. I have a couple workshops and speaking engagements in 2014 as well. The podcast takes up a lot of my time now. Preparation for shows has required a lot of writing, which I think has been positive habit-building exercise for me.

If all goes well, I’d like to write at least a couple of books. I think that is all quite reasonable within the next 3–5 years.

Where do you see hand lettering going within the next few years? Will it evolve more or dwindle down?

I have to say, I would not be making such a drastic shift to teaching if didn’t notice a huge demand for it. While lettering can be created through entirely digital means, hand lettering introduces a tangible human element. The slightly imperfect nature of hand-rendered forms provides a certain charm that is all too uncommon in the increasingly digital world. Everyone is familiar with pen and paper. Seeing something created with instruments that are very familiar allows the work to strongly resonate with a general audience. There is no veil of digital magic, there is only ink, parchment, and a steady hand.

There will always be an appreciation for the hand crafted. Email is undoubtedly more convenient, but you will cherish a hand-written card from someone to a much greater degree. People want to connect with humans. You can program human behavior, you can automate their actions, but we can still perceive the difference.

For now, there is no digital equivalent that quite mimics hand lettering. Technology may catch up to the point where we no longer use pen and paper, however the best custom lettering a type will always require the optical insight of a human. Those who want to make a more intimate connection with other humans will continue to value this craft.

Have your thoughts about the industry changed over the years?

Not really. Though I suppose I’ve come to notice more just how many people look for the shortcuts instead of dedicating themselves to practicing and honing a craft. I suppose it’s a cultural thing—the internet makes us want everything instantaneously, even if it’s something that only comes with time like expertise. It’s tough, because I want to help people by sharing my knowledge, but I also don’t want to feed the surface-lever “tips & tricks” seekers.

In the end, I think those who will work hard, will do it regardless, and those who will seek the shortcuts will always be so limited. My diligence is to offer what I can, in hopes that it resonates with people who will take it to heart.

What advice would you give someone just starting out with their portfolio and getting into client work?

You will not ever get to the point of being able to be selective in the kind of work you take on without having already made the choice to be selective from the start. There will never be a convenient time to say “no” to work, but the sooner you learn to turn down projects that are not a good fit for you, the sooner you will be in a position where the type of work you regularly do is the kind that you enjoy.

This goes against the common advice I hear from everyone else. I always heard people say that you have to take what you can get when starting out. This is simply not true. You don’t have to. It is a choice. It is not from a position of privilege that I speak. I’m able to be extremely selective in my client work because I’ve consistently chosen to been extremely selective in my client work—especially in the beginning when it was hard.

I have a number podcast episodes that speak directly to this: