Jan 7, 2016 · 13 min read

The path to a successful indie game: A complete history of my screw ups, false starts, and broken dreams.

I’ve failed at my plans so many times, it’s difficult to even catalog them all. I made a video listing some of these failures to start businesses, and accidentally left some out: there were so many, I forgot a few.
I’m going to try to compile a more complete list, with approximate dates, in this post. I’m not trying to beat myself up, I just want to make it very clear that any person who experiences success has experienced a metric ton of failure. These aren’t exactly chronological, because they overlapped, etc. but they’re roughly in the right order.

  • Tooth and Claw — When I was in high school, I really wanted to be a cartoonist published in newspapers across the country. Calvin and Hobbes, the Far Side, and Krazy Kat had a big impact on me, and so I was continually drawing up packages of comics to send to syndicates. My main focus was on a comic called Tooth and Claw, which I copied at Kinko’s, and wrote the letter to the syndicate before I chickened out. I just kept re-drawing, because the comics simply weren’t good enough to submit. This was not false modesty.
  • Beanie Mortuary — this was a strange one, and mostly a joke. My brother and I set up a website offering to hold funeral services for beanie babies. I secretly hoped that it would become a legitimate business, but we never pursued that. I’m amazed that the website is still live!
  • Voyages of the Hale-Bopp — I got to college, and almost immediately started drawing two web comics — one by myself, and Voyages of the Hale-Bopp with my older brother. The Voyages of the Hale-Bopp only lasted about 8 pages before I decided to focus all of my energy on my other comic. Why did I decide to quit TVOTHB? I felt overwhelmed. I had school to do, and I was drawing my other comic twice a week, and TVOTHB once a week. Ok, so I wasn’t exactly swamped, but with procrastination and all the important socializing and extracurricular activities, I felt like my life was soooper busy (ahh, the naiveté). Besides, I’d actually gotten some attention with my other comic, which drew me like an ant to a pile o’ sugar.
  • Lewis’s Life –– I had about 8–10 people who really liked this comic! CELEBRITY! It was a comic about a fellow named Lewis, whose internal struggles were made literal in the physical world, in the form of demons who would beat him up, and discourage him. It ran for two years, one comic weekly. It started out as a “I’ll just draw whatever stupid stuff I want to” side project, and ended up being my main project for two years. I made my first print-on-demand book, which a couple people (who were related to me) bought, I did POD T-shirts, which no-one bought, and I realized to sell stuff, you actually needed an audience. Ultimately, I got really bored with it, tired of drawing it, and delayed ending it because I’d found a modicum of CELEBRITY!, and I didn’t want to give that up.
  • Abstract art — I was burnt out after the end of Lewis’s Life, and I decided that I would throw people’s opinions to the wind, and just draw whatever the heck I wanted to, dagnabbit! Amusingly, this was the same process that got me into drawing Lewis’s Life. I painted abstract art in Photoshop, and found out that it was really easy to do! I’d turn on some high-energy music, and I’d just keep my hand moving. It was like meditating. I decided that I was supernaturally gifted, and started posting pieces on Deviant Art, where I had a few people who agreed with me! CELEBRITY! I decided that I was so good at Abstract Art that I would write an e-book on the subject. I was listening to “Six-Figure Second Income” at the time, whose core message was TURN ANYTHING INTO AN EBOOK AND YOU WILL BE DIRTY FILTHY STINKING RICH. I typed up my best Abstract Art tips, and made a lovely ebook, that was pretty much useless to everybody. Turns out there aren’t a lot of people looking for Abstract Art tips.
That title.
  • Artistic ADD — Suddenly, I was +5 inspiration! I had ended up hating Lewis’s Life because it wasn’t varied enough for me — I needed change, excitement, intrigue! I knew what to do — I’d start a blog where the subject of the blog changed every month — no, every week! I begin writing Artistic ADD, and I think I probably didn’t get past 10 posts before I quit writing it. But that didn’t stop me from setting up a website, designing everything perfectly, writing another ebook about creativity, and trying to sell it to the crickets who greeted my blog posts. Apparently I had to learn once again that a business needs customers. This one petered out pretty quickly.
  • Freelance Graphic Design, attempt 1 — I was working at a restaurant at the time, and I convinced them to let me lay out their menu, a process that included taking photographs with my little point-and-shoot, typography, and scanning the restaurant’s wallpaper (seriously) to use as the background image. I also designed some table tents, survey cards, and a miscellany of restaurant-related stuff. I made some decent money, and briefly entertained the idea of quitting and going around to businesses selling my mad graphic design skillz. I even nonchalantly told someone that I might quit over the summer, and “just pick up some graphic design work, you know, around town”. He was très impressionné. I chickened out, though, and worked at a seed company instead.
  • Anthologia — My wife and I worked with different artists online and compiled an art collection. It was called Anthologia. It was a hodgepodge collection of crazy drawings that we published through a print-on-demand service. We sold a couple, probably to the artists. It was kind of a boring experience (my main job was e-mailing artists who hadn’t send me high-resolution images), but at least the final product was…ok.
  • Winsome Vignettes — We moved on to selling tiny pieces of cartoon art, about 1"x2". They were drawn in ink and watercolored, and included a tiny frame, and handmade easel. They were pretty cool, and we also planned on selling prints of each piece. We sold a few of the tiny pieces of art on Etsy, even one or two to people we didn’t know! (CELEBRITY!) But pretty soon I realized that we would have to sell thousands of the tiny pieces of art to make any sort of decent business. Could we have expanded our product line or changed our pricing to help it make sense? Maybe, but I didn’t think about it at the time. Maybe today I would have brought them to Kickstarter, but instead we just pulled the plug, and I moved on to my next project.
  • AndHeDrew — I started blogging about productivity, creativity, and intentional living. A couple months after I started blogging, I had a post go viral, sending hundreds of thousands of visitors to my website. Awesome! I had made it, I thought. Internet famous! Of course, my website promptly melted down with all the traffic, and I had to spend time fixing that. Then I wrote an e-book in about a month, which was based on the internet famous blog post, and launched the ebook, sending a message out to all my adoring fans who signed up for my mailing list, and happily waited for the money to start rolling in!. . .after a few hours, nothing. Maybe I priced it too high? What was I to do? I panicked, and changed the ebook to “Pay what you want”, sending out a message to my followers, acting like that was what I intended all along. After that, I sold several copies (which was awesome!) and I definitely was sure that I had arrived. Now to plan my movement to full-time blogging! Easy, right?
  • AndHeDrew continued: TED, Bundles, and Here’s to the Weirdos — I remember having the conversation with Sonia — we’re so close. We were living on very little money as it was, and I was selling the occasional e-book with All I needed to do was launch a bigger product, and if I sold a few of them every month, we would be set! I could quit my soul-crushing job, and be a full-time entrepreneur! My excitement was ramped up even higher when I got my ebook into a couple of ebook bundles, and made something like $1500! I was wealthy. Success was just around the corner, I was sure of it. I gave a TED talk introducing what was to be my new “thing”: giving away 1000 pieces of art to random strangers. I patterned this big audacious idea on Chris Guillebeau’s “visit every country in the world” goal, and boy, was I excited about it. People really connected with the idea of giving away their art! I felt really good about being a TED speaker, and a semi-successful blogger, and it was awesome…until it wasn’t.
  • AndHeDrew starts to die— I worked hard on my big product, it was a course called “Here’s to the Weirdos”, where I interviewed a lot of people who I thought lived strange and remarkable lives. I included these interviews — text, audio, and video — with an ebook, and a bunch of goodies. It was amazing, and it was going to be my ticket into full-time self employment. I launched the course, and waited…and waited. In the end, not one person bought the course. This sent me into a pretty steep spiral, where I stopped blogging, stopped giving away art, and got fed up with the AndHeDrew blog. I was done with it. I was so discouraged, and I finally threw up my hands and quit blogging entirely.
  • Aprons — I remembered fondly the days when I draw Lewis’s Life, my second webcomic. I knew that I ended up despising the daily grind of drawing the same characters over and over again, but I was sure that I would totally love drawing a comic now, mostly because I was so tired of writing a blog. A webcomic seemed like the awesomest deal ever — I would just draw for a couple hours every day, sell prints and the originals, and watch the money roll in! This time I would market the webcomic better — I started drawing a comic called Aprons, which was about baristas and waiters. I figured that I could find out where these people hung out online, and since they were a very communicative community, I could get them to share my comics. It seemed to work! People loved the comics, and I shared and marketed them like crazy. It was a great idea, and I could find people to support it — but pretty soon, the old dislike started to creep in. Drawing the same people over and over again got really boring, really fast. I couldn’t find the joy of cartooning — it became repetitive and boring, and I found myself rushing through the drawings because they were just so crushingly mundane. I expected drawing cartoons to be different if I had an audience, but they weren’t. Despite the people who loved the cartoons a lot, I quit yet again.
  • Freelance Graphic Design, attempt 2 –– At this point, I was working two jobs and we were still having money problems. Ongoing health difficulties continued to nuke our budget over and over again, and I simply didn’t make enough. I started desperately reaching out to businesses offering graphic design work. I got a few clients, enough for us to limp along for a while, but it was terrible, terrible work. It’s one thing to design for friends and family, it’s another to work for a client that causes you to live in terror of the phone ringing. I hated every minute of my freelancing, it was stressful and terrible, but it paid the bills. I started looking for a way out.
  • Photographer ––My wife’s an excellent photographer, and at the time we also photographed a couple weddings together. We resolved to never, ever photograph weddings again. You can’t re-shoot a wedding if something goes wrong, and that’s a line we don’t ever, ever want to walk again. We promised each other that we’d never do another wedding.
  • Fitness Coach/blogger––I was worn out. I was tired. Tutoring, working at Starbucks, freelancing graphic design, photography, and trying to work on my own business when I had the time (ha!), oh — and also trying to be a good husband and father. I wasn’t getting much sleep, and I was stressed out and burnt out. I needed a way out. I started as a fitness coach, because I had an idea that I was going to test how fitness affected my productivity. I started measuring productive time and working out, but my life was so drastically out of balance that nothing was working right. I was trying to find a quick way to get out of the position I was in, and blogging is a long-term game, one that’s difficult to maintain if you’re barely holding you finances together and working too much and sleeping too little. It didn’t work out.
  • Indie Game Dev ––I started a fun side project with my brother and my cousin, which was a platformer video game. I loved every minute of working on that project — I did the art and a lot of the writing, and they did the coding. It was great work, but my finances were still falling apart.
  • AndHeGames: YouTube Celebrity –– at the same time, I started recording YouTube videos of my talking about video game design. I called the brand AndHeGames. I thought that this would be a great way to begin a marketing push for our video game. I also made small printable games to give away for free, again as a part of marketing my YouTube videos and our indie game.
  • Giving up the ghost — I was enjoying my personal projects more and more, but they were a long way from providing financial support to my family. We were drowning. We started talking about alternate solutions, and learned about a job that we thought would fit us well: houseparenting. We would work together, we would both be at home with our daughter the whole day, and I would have plenty of time to work on my projects, without worrying about immediate financial payout. We found a job in Ohio, which looked ideal. I quit making the indie game, quit giving away art (I’d only made it to 47 out of 1000) quit writing, quit making YouTube videos, quit pretty much all graphic design work, and we picked up to move to Ohio. My slate was clean, I had a messy past, but we were making enough money to live well and pay off debt — now I had the time freedom and freedom from financial pressure to figure out what I really wanted to do.
  • AndHeGames Continued — It was shortly before our move to Ohio that I discovered tabletop games, and the thriving community of people who design them. I didn’t think about Tabletop game design being a thing you could do, but I was instantly excited about it. Tabletop game design seemed like a great fit for me, in many different ways: I didn’t have to code, I already had the graphic design chops to put together the files, illustrate the game, and make it look very nice, and I could finish a project, and move onto the next one, none of the endless reputation that I’d found so frustrating in the past. Heck, I’d already been designing printable games to market my YouTube videos! I worked on a game about robbing a building, but after researching the cost/difficulty of manufacturing board games, I went back to the drawing board. I wanted to start my board game career out with a game that didn’t cost too much, that was easy to produce. I didn’t want to go to Kickstarter with a request for $40,000 — I wanted to make a small game that would only cost a few thousand. I thought to myself — hey, I’ve already made a few books, I know how to make a book. What if I made a game out of a book?
  • The Cloud Dungeon — I did game designer interviews at, and I worked on my game book. It was a creative, papercrafty game that you cut apart as you played. It was hopelessly wordy at first, but as I play tested the game I gradually trimmed it down and improved it. I had the great fortune to make a friend who runs local board gaming events, and he got my game into his events for play testing. It was pretty cool, and the game begin to develop. I started thinking about my Kickstarter, and as I set a goal to launch my idea in September. I set the goal for $2000, and for whatever reason, I raised $30,446. It seemed like a flash of lightening, a wet-behind-the-ears designer getting lucky and getting overnight success.

Although there was luck involved, the fundraising of the Cloud Dungeon was in no way an overnight success. Everything I’d tried and failed at over the years taught me what worked, and what didn’t work.

Looking back on all of the pain, missteps and frustration, I’m reminded by what the great Zig Ziglar said: “Failure is an event, not a person.” My life has showed this to be true, over and over again.

The clarity earned from years of failure meant that I was able to finally, finally find where my passion, talent, and the market converged, and that was well worth all of the pain and doubt.

Although I must admit, I’m still broken up about the Beanie Mortuary folding.


Andrew’s website is here. Buy The Cloud Dungeon Here.

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