Download: MP3 (76.7 MB)

My story begins with a computer repair business. I was in high school, and it was my very first business. I knew next to nothing about legalities, accounting, and taxes, but it was the perfect way to learn: diving right in.

The things I learned from this business carried me through the next several businesses. I’ve told my personal story in bits and pieces throughout the podcast, but I wanted to have a canonical episode that really focuses on the transitions between each business.

I zoom in on the reasons for going from one business to the next and review the lessons learned at each of them.

You’ll hear how I went from one to the next, and the takeaways that continued to serve me in all of my future pursuits. It goes to show that even if what you’re doing isn’t that thing you’ll do for the rest of your life, you have no idea how the things you learn will help what you do in the future.

Show Notes
  • Computer Repair
  • 11:13 I feel like I’ve told parts of my story a bunch in various places, but I wanted to zoom in on the details and focus especially on the transitions between the businesses.
  • 11:47 My first business was a computer repair business that I started back in high school. I was interested in a wide range of technology-related things at the time:
    • PDAs
    • Website development
    • Graphic design
    • Programming
    • IT
  • 12:11 I didn’t know how to program very well, and wasn’t sure how to monetize graphic design just yet, but I recognized a clear need for computer repair. Many, many people had slow computers, or wanted upgrades, or networking help.
  • 12:51 I would often go out to jobs without even knowing how to solve the problem and just figure it out, or research a solution until I knew how to solve it.
  • When you have an emotion tied to the motivation you have to learn something, you’ll learn it faster.

  • 13:50 If you have a girlfriend who is Japanese, you’ll learn Japanese much faster than if you just happened to decide to learn a random new language. It’s because you have an emotional motivation.
  • 14:03 In my case, the emotional motivation was fear, because I told the client I could solve the problem and they’re paying me to do it! But it was a good kind of fear—one that really motivated me to learn at an accelerated rate.
  • 15:00 Clients just want the problem solved.
  • 15:04 I’m learning marketing, how to deal with client, how to be personable, how to sell—I’m just throwing myself into all of this.
  • 15:15 I had about 20 credits towards a Computer Science degree but ultimately dropped out because my businesses were doing so well. I realized that experience was equal to education in both of the industries that I had businesses.
  • 15:30 I was in a band, but needed money to help pay bills. That’s what got me started with entrepreneurship.
  • 15:43 The computer repair business ended up doing really well. I was still living at home (I lived at home until age 21). This first business forced me to learn everything I now know about accounting and taxes.
  • 16:16 Focusing on the relationship with the clients I had, allowed my name to spread throughout their well-networked community.
  • 16:50 Increasing my rates from $35/hour to $50/hour was scary for me. But when I did it, no one blinked.
  • 18:56 The importance of learning to learn. Learning in and of itself is a skill. It’s something you have to develop.
  • Learning is the only skill that will continue to serve you for the rest of your life.

  • 21:51 That’s not to say other skills can’t serve you for a long period, but they all have various levels of degradation. They all have different expiring rates. They all have to be renewed and refreshed. Learning is, in itself, the refreshing.
  • 22:22 We often put timeless skills, like the skill of learning, secondary to other temporary skills. Great, you know how to use Photoshop today. The skill of knowing how to use Photoshop isn’t as useful as having the willingness to learn a new piece of software. What if Photoshop disappeared and you could only use something else: how scared are you to learn that? How unwilling are you to become adept and fluent at that new software?
  • 24:22 After a few years, I was getting disinterested and bored with the computer work. This was amplified by my stepping down from the band. With the music element out of the picture, I felt a creative void that the computer work was not filling.
  • 24:48 What I’ve determined looking back is that I have these two large, categorical interests: Logic & Creativity. It’s where those two overlap in a venn diagram format that I find most of the things that I’m passionate about.
  • Look to the two primary categories of things you’re interested in and try to find things where those two intersect.

  • 25:38 In my case, repairing computers was just the logical side. It didn’t really fulfill my love of being creative.
  • 26:36 But the things you learn now are going to lend themselves towards the thing you do later on. For instance, understanding Photoshop and being willing to branch out to Premiere, and then AfterEffects, etc., helps you develop the learning muscle. Each are facets to a bigger bigger picture, and many of the concepts from one thing to the next are similar. Even from video production to music production, you have similarities in layering and composition.
  • Freelance Graphic Design
  • 27:34 In the past, I’d experimented with design on the side. I hadn’t done any client work yet, but I gradually started to get more and more business clients for the computer repair business that also had websites. They needed web design and help with marketing and they often asked me if I did that kind of thing.
  • 28:20 So I used the computer repair business to transition into doing design work. I setup a different business name for it and started doing design on the side. I still maintained my computer repair business full time, but during my nights and weekends, I was now doing design work.
  • 28:44 These clients started referring me to other clients, which in turn boosted my computer repair work as well as requests for design. I started getting overwhelmed with all of the work requests in both businesses, but I was really enjoying the design work.
  • 28:59 Design, like music, falls neatly into the overlap of Logic & Creativity. The computer work was decent since it satiated one of my categorical interests, but it wasn’t nearly as satisfying as design was to me. Design allowed me to be creative and solve problems.
  • 29:36 At this point, I had 3 options:
    1. Keep turning down work
    2. Raise my rates
    3. Get help
  • 29:43 I decided on option 3, and brought on a partner to start up a web firm.
  • Web Firm
  • 29:47 My friend Brian was working as a developer at a local firm. I asked him over coffee if he was interested in starting a partnership web firm and he was. A few months later, we took the dive.
  • 30:14 This was also right around the time that I got married, so things were pretty crazy. Our first big task was to build out our own site. We also had some web work that I carried over from my freelance design business to keep us busy.
  • 30:19 We were working about 10 hours a day on average getting traction with the web firm. I no longer had the time to focus on my computer repair business. It’s continuing to flourish, even without me doing any advertising, just from all the referrals. It’s at this point that I hire a guy to handle all of the computer repair jobs.
  • 31:11 I somehow made time to take him to several computer jobs with me to familiarize him with the process, but very quickly had to let go of the reigns and focus on the web firm.
  • 31:31 While it was difficult to hire help and let go of control, I’m glad I was in such a tight position, or I’d likely be inclined to hold my employees hand for longer than I should have. Eventually, he went on to define the face of the computer repair business even more than I did—for the better.
  • 33:17 I was still running the computer repair business while I was at the web firm—so, handling things like invoicing, scheduling and accounting.
  • It’s super important to treat a partnership like a marriage.

  • 34:27 On the technical side of the partnership, I still owned the controlling stake of the partnership, because I started it (51-49).
  • 34:51 Collaboration was a really big thing I learned. Previously, I was a lone wolf and did everything myself. It’s hard at first to give up control, but the more that I did that, the more I saw that other people can really do things a lot better than I can. When you give up control, you enable other people to come in and help create a better end product—which is really what it’s all about. It’s not about your control of every aspect of the product, but the end product itself and the value of those results to the client.
  • 36:01 Coming from the computer repair business, I knew enough about business (registering businesses, handling taxes, talking with clients, invoicing, etc.), so when we started the firm, basically I handled everything that wasn’t development.
  • When you start a business, you’re going to end up spending 20% of the time time actually doing the thing you love. 80% of your time will be spent running the business.

  • 36:48 Don’t start a business because you love doing design. You have to love doing business.
  • 37:07 “How does that fit with what we talked about in episode e087—the excuse many people have of ‘I’m just not a business guy?'” (Related: e087 10 Myths Creative People Tell Themselves)
  • 37:42 If you’re running a business, you have to have a good handle on a ton of things:
    • How to talk to clients.
    • How to handle accounting.
    • How to do payroll.
    • Public speaking.
    • Communication.
    • Design.
    • Information architecture.
    • Etc.
  • 38:01 If you’re wanting to run a business yourself, you absolutely have to love business. If you want to run a larger company, that will allow you more freedom, you still have to be willing to do things yourself in the beginning (Related: w077 Growth Scaling Part 2 of 3: Hiring & Helping Hands).
  • 38:33 Ben: “I guess, the thing I don’t want to agree with is that you have to love business. I’d rather think of it in the sense that you love what you do so much that you’re willing to put up with some things that you don’t love as much.”
  • 39:06 Well, when you say “what you love to do,” you have to think about what you’re actually doing. When 80% of your work is running a business, what are you doing? Do you love that? If you want to do 80% design, then you need to work for someone else.
  • 39:39 This is why I encourage shifting your focus towards finding a love in business. If you want to run your own business, find something you love about business and focus on that, because that’s what will allow you to do design. As you grow, you can systematize, you can hire, and you can bring people on to handle different aspect of the business.
  • 40:18 Don’t delude yourself: If you’re going to start a business, you’re going to end up doing all kinds of stuff. You’re going to do customer support, you’re going to do shipping and fulfillment, you’re going to do client relations… all of it.
  • 40:42 Back to the story at the web firm.
  • 40:47 I had contracts when I was doing freelance work, but requirements were different. Our process was different. Our process had evolved, and our professionalism had evolved.
  • Professionalism is a journey.

  • 41:00 Your journey to being a professional starts whenever you start it.
  • 41:30 Didn’t get paid by the client? That’s your fault as the professional. Your contract should say what happens when the client doesn’t pay. You have to define those things.
  • 41:59 We lucked out: a prospective client we had was a lawyer and a judge. We sent him our contract, and being the OCD type he was, he basically rewrote our entire contract of his own volition. Of course, not all of it we agreed with (because much of the language was now in his favor), but we essentially got a bulletproof contract out of the deal.
  • 42:50 If you choose to look at every relationship as an opportunity, there’s almost never a client relationship you can’t learn a new lesson from. Usually you can find something that improves your process or helps you make your contract more bulletproof.
  • 43:10 “From what point are you 50% professional? When can you call yourself a professional?”
  • 43:19 The answer is, you can call yourself a professional whenever you want. You are a professional whenever you decide to be. The immediate moment you decide to be a professional is when you are a professional. It’s closing the gap between 50% and 100% professional that comes as a result of calling yourself a professional.
  • 43:42 The real gap you’re closing here is between what you are and how you act. You are a professional because you’ve chosen to be.
  • 44:39 Because professionalism is a journey, you’re either heading the direction of professionalism or you’re heading in the opposite direction. You’re either going towards it or you’re not. It’s a continual evolvement.
  • 45:17 The way you know whether you are a professional or not is determined by how you respond to problems and whether you see them as opportunities to iterate and improve yourself and your process.
  • 46:28 Another thing I learned while working at the web firm was networking. Building relationships within your industry is crucial. Reach out to people. Strike up a conversation and build a relationship. Meet in person, or connect on Skype. These relationships can grow online and eventually flourish when you make the in-person connection at a conference (you are making a point to go to conferences, right?)
  • 47:58 Having our portfolio and case studies written out was a really big catalyst for getting clients at the web firm. Writing those case studies and building that portfolio is something that has helped me all through my lettering work. Case studies are crucial. I know you’ve heard me say this a lot and you’re thinking, “Yeah, yeah… I’ve got a bunch of work on my website and it’s fine.” No. It’s not fine. You need to write case studies–otherwise, it’s just pretty pictures.
    • What problems are you solving?
    • What are you accomplishing?
    • Who are you trying to reach?
  • 48:35 These are the reasons people are hiring you. You need to preemptively answer those questions and you do that with case studies.
  • 48:46 We eventually came into one of our slow seasons with the web firm. We’d been doing this about 3 years at this point and my partner said he needed to get another job to pay bills. I told him I completely understood.
  • Lettering
  • 49:11 To back up a little bit, while I was working at the web firm an average of 8–10 hours a day, I was also doing lettering. From the beginning of starting the web firm back in 2010, I met Kyle Steed, who inspired me to pursue lettering just for the sake of the passion. I’d done lettering in middle school, but it was just a mild interest. He really inspired me to pursue art just for the fun of it.
  • 49:50 So I did. I just created lettering for fun.
  • I’m not exaggerating when I say I was spending 6–8 hours a day outside my day job working on lettering.

    I did this for 2 years before I ever took on a client, and before I ever sold a product.

  • 50:30 This is the part that I think a lot of people miss—or simply just don’t want to hear the part where I did this for 2 years before I got a bunch of exposure or made money from it.
  • 51:03 2 years into it, people started noticing and asking for my work on shirts and prints. They also wanted me to do custom commissions. What I did is I saved up all the money I made from doing client commissions because I didn’t need the money to pay bills. My bills were already covered by my day job at the web firm.
  • 51:21 I used all the money I saved up from commissions to invest in a large run of my very first shirt.
  • 51:51 This was about a 3-month period of production. After finishing with the manufacturing and packaging, I put it up on my site and it did really well. Fortunately, this just so happened to align with the hibernation of the web firm.
  • 52:10 This investment that I’d been working on for the year prior started to pay off. I had a lot of requests for client work with lettering that I’d been turning down because I didn’t have the capacity. When my partner decided to take another job, I was able to take on more of those requests in addition to selling the shirts to support myself.
  • 52:42 I continued to sell the shirts and make more shirts, as well as mugs and other products on top of that. I also started taking on more client work.
  • 52:51 At the web firm, we did web design and branding. So whenever my hand lettering work brought in jobs that were people asking for logo design, I’d say, “Right this way, sir. I work at this web firm here and we can handle your branding.” So I’d do the work and get half the money because it was a partnership. When we hibernated the firm, I was effectively able to make twice the money charging the same rate because I was now working on my own.
  • 53:34 “Sean, as the web firm was your day job and you needed it to pay your bills, did you ever compromise on quality/professionalism there so you could land a contract and pay your bills?”
  • 54:08 That was a really big deal. We were very big on staying professional and taking on the right type of clients. Eventually we came to this: We’re not going to compromise. There’s no way we’re going to make a long-term business here if we start by compromising. We need to be selective in the clients we take on or we’re not going to take them on. If this ends up not working out, we’ll move on to something else.
  • We weren’t willing to compromise on our values and we weren’t willing to work with what we felt was the wrong type of client.

  • 55:55 My love for learning and continual learning lead me to randomly decide to spend several weeks researching and understanding licensing. I can’t tell you why I did it, but I just felt compelled to expand my knowledge there. Well, in the next 3 months, I landed 3 contracts that utilized that knowledge.
  • 57:55 Many people do design work and transfer full ownership to the client. This is typically the default in most boilerplate contracts people use. However, thse underutilize the full power of licensing. by more thoroughly understanding the terms, I was able to craft custom contracts that enabled me to retain the ownership and permit selective usage rights for a fee.
  • 58:24 I ended up landing a contract with Las Vegas doing work for them for a good 6 months. When I quoted them for the work, it not only included compensation for the design work, but also specific usage rights for each design, in each usage case, and per month that it was used. This resulted in a 5-figure quote where I would have previously quoted something on the 4-figure range do to my limited understanding of licensing. I felt nervous, but they didn’t even blink at the number.
  • Phasing Out of Lettering Client Work
  • 1:02:34 I got to the point where I was working 12–14 hour days most days of the week just doing client work. This is early 2013. I got to the point where I was so booked solid that I wasn’t available for 2 months minimum.
  • 1:03:35 This is where Rachel Ray magazine approached me for a job—only they wanted it by next Friday.
  • 1:03:43 I was distraught. I was already way overworked and exhausted, but this was a big name client! “Isn’t that the point of a design career? To work with big clients? You’re supposed to take on big names! It’s what you do!” Everyone says that’s the epitome of arrival.
  • 1:04:12 I decided to take a day and think about it. I came to the conclusion that if they wanted to work with me, they’d need to pay what it would take to hire me right now in my current circumstances. I said, “First of all, I’m not available for two months, so doing this now would require a rush fee. Also, I would normally allot 3 weeks for this project and you want it in 10 days, so there will be an expedite fee.” I ended up quoting an amount that was 60% higher than the original budget they came to me with.
  • 1:04:52 To my surprise, they said, “Ok, we’ll get that over to processing.”
  • 1:05:02 I ended up working 16-hour days for 6 weeks straight to handle the work I had. This led to pretty severe burnout. This crazy season, in addition to wanting to build Learn Lettering, led to me deciding to phase out of client work completely.
  • 1:05:34 It’s extremely hard to say “no” to things (especially great opportunities), but saying “no” is the only way you can create time. It’s the only way you can focus. Since phasing out of client work, I have said “no” to some pretty incredible opportunities (including Oprah, Sprint, and certain clothing brands). It’s not easy, but I want to be able to do the things that are important to me—like this podcast and writing my book. The only way I can do that is by carving out time, and the only way to make time is by saying “no.”
  • 1:06:49 Sean: Ben, do you know why I say “no”?
  • 1:06:51 Ben: “So that you can say ‘yes.'”
  • 1:06:57 Sean: Right. I wanted to be able to say “yes” to the things that are important to me.
  • 1:07:07 Sean: Ben, you know we get feedback from people saying, “Sean makes a lot of really abstract, high-level points. I wish he told more stories.” People were asking for an episode like this, but I feel weird telling my personal stories—sometimes I think people just want the nuggets and the topic-driven lessons, but maybe people appreciated it. If you enjoyed this episode, let us know! Send us some feedback on it.