How I Became a Indiepreneur

These are my responses to questions that Adam Clark send me for an episode of a podcast that I’m not sure he’s going to publish. I’ll update this post to include the audio file if he does.

Describe your path to becoming a indiepreneur?

My childhood was full of music and technology. My mother sang, played guitar and piano, and my dad always had computers around for the kids to use.

I started playing drums when I was 12, and always wanted to be a professional drummer. I went a little crazy after high school, and spent more time partying than I should have. When I was 22, I started looking at jobs that could be done on a laptop; I wanted to make money while touring with a band. I discovered web development and dove in.

I was also teaching myself audio engineering in my free time. I thought I could work in a recording studio someday. I loved listening to podcasts, and was a cohost on one for awhile. I saw Dan Benjamin of 5by5 post a job for an audio editor for his podcast network, and I thought that it would be a cool job to have. So I started helping people edit podcasts, and my best clients are still podcasts that I started listening to while trying to become a freelancer/indiepreneur.

Did you have an “aha” moment when you knew this was what you wanted to do?

Absolutely not. My only goal was, “make money with my macbook so I can tour”. After trying to be a front end developer for awhile, I discovered that I like the flexibility of being a podcast editor more. And I seemed better suited for it.

What would you say has been your biggest failure and what would you do differently if you could do it over again?

I don’t really think about things as failures. I just think about what has worked, and what hasn’t.

I regret spending so much time drinking and getting high, but at the same time, I learned that it wasn’t how I wanted to spend my time. Everything is a stepping stone to something else. As long as I’m alive, I’m going to make mistakes, and I think that’s ok.

I think anytime I’ve been selfish, or a jerk to someone; that’s a failure. So I try not to do that.

I do regret not writing more. That’s a failure, if anything is. So I’m just trying to do more of that, even when it doesn’t come naturally.

Have you had any mentors along the way and how have they helped you?

Absolutely. I can point to Merlin Mann, Dan Benjamin, Mike Monteiro and Sean McCabe as mentors; guys that have all had huge influences on my life and the way I think.

For drumming, my original teacher, Tim Fox, was huge. Also Mike Johnston has done amazing online teaching; he’s a super rad human that also rules at drumming and sharing what he knows.

For audio, Dave Pensado has been a great mentor. He does a show called Pensado’s Place, and I’ve learned a ton of things from listening to and watching his show.

Was there ever a point in your journey when you decided you had to take a big risk to move forward?

I don’t think there have ever been any big risks, just a lot of small ones. It was risky to basically get myself fired from my steady factory job, even though I wasn’t happy there, to go work part time at a sandwich shop and play drums in a rock band.

It was risky leave that job to be a full time drummer and take on freelance web design clients. That was a hard time, I didn’t make much money.

It was risky to apply to my first real front end development job, because my skills were still underdeveloped. I was lucky to work with a company that let me make mistakes and learn on the job, because there were a lot of things I didn’t know.

It was risky to quit that job to become a full-time podcast editor, although I knew that I had enough clients at the time to pay bills.

So it’s never been a massive leap of faith; more of just stumbling blindly from place to place, hoping that I make enough money to pay bills and keep moving forward.

How did you overcome self-doubt and fear of failure?

I’ve realized that I will make mistakes, and I’m at peace with that. As long as I’m honest with people about what my skills are, I’ll be ok. I try to under promise and over deliver, and not the other way around.

Do you believe that you have a purpose in life?

No. I do believe I can choose my own purpose.

If so, what is your purpose?

To enjoy life. To experience it with other people, and try to help other people with their experience.

What are 2 things that you regret?

Being a shitty boyfriend in past relationships. Time wasted being high or drunk.

What would you do if you knew you couldn’t fail?

I don’t worry about failure. I just go for it. So anything I want to try, I do. It usually involves just putting time in and trying to get better at something.

What are some of the things holding you back in life?

My wandering attention. My lack of commitment.

What is your definition of success?

Freedom to do whatever I feel like doing at that moment.

How does where you live impact your business?

I turned to the internet a long time ago. I had a hard time finding like minded people in my town (outside of Fort Worth, Texas), so I found my community online. It’s nice that rent is affordable here; I don’t live in a very nice house, but it made leaving a steady job less scary.

What does a typical day look like for you?

Wake up around 7am, make some coffee and a breakfast omelet. Jump on my macbook, start checking email or getting work done. Repeat until I want to take a break. Sometimes afternoon naps, sometimes hang out with friends or playing shows in the evening.

Some days I exercise, I lift weights and go on walks. I should be doing that more.

Is there anything new or different you’d like to try in the next 5 or 10 years?

Programming and touring across the US and Europe with my band. I’m also currently building a home studio to record music with my friends. I may also try taking on more responsibility, and running a company. Maybe have kids. Who knows?

What’s the best piece of advice you’ve ever received?

Show up and try not to suck.

If you could start all over, what would you do differently?

I can’t think of anything I’d change. I like how things have turned out.

If you could give a piece of advice to another indiepreneur who is struggling to take the next step, what would it be?

Just keep at it. Keep doing the thing you want to do, and pay attention to other people that are succeeding at similar things. They’ll often share their advice. Don’t beat yourself up for things you don’t get right, stay positive.