In 2020, I not only turned 40, but I achieved a life-long dream of building a healthy, sustainable, and profitable business (Transistor.fm).
Here's the story of how I got here.
I started building things with computers in 1983 when my family got a Commodore VIC-20.
For me, computers opened up a whole new world of creativity and connection. By the time I was a teenager, I was heavily involved in the BBS scene. Bulletin board systems were really the precursor to the web the way we know it today. I was able to connect with people from all around the world.
The operator of Absolute Future BBS asked me to co-sysop his board when I was 13. This is when I started getting interested in marketing and business. Here's a line from my diary:
On the BBS, I mostly create artwork as well as some other tasks. With my help, we've jumped from 35 users to 236 (in 3 months!).
The BBS scene also showed me how independent developers could create and sell software online. I watched Seth Hamilton release Roboboard/FX. It was shareware, which you could download for free. But you could unlock additional features by paying for an upgrade (back then, you had to send a check in the mail!).
My buddy, Adrian, and I wanted to bring that big-city rave experience to our little town of 7,000 people.
It was 1998, and I was 17 years old. By some miracle, I still have the Word and Excel files we used to plan the event. Our budget was $1,232.48:
We ended up selling out the event and netted a nice profit ($1,000 I believe).
I didn't want to go to college at all, but my dad convinced me to get my Business Management diploma.
Initially, I got a job as a bellboy at a local hotel but then decided to quit and start a business. I was able to get a student business loan, and I bought a computer and a video camera. I called my new company Mediahead Productions.
That summer I started doing web design and video production.
After graduating, I became a manager with a non-profit. But my desire to run a business continued.
In my early 20s, I opened a skateboard and snowboard shop with my friend. I'd dreamt about it since I was a teenager. I was passionate about snowboarding, and I'd spent two years working on the manufacturing side. I was looking forward to earning a profit from doing something I loved.
Ultimately, I learned that retail is a hard business, with small margins. We tried to make it work for as long as we could, before closing the shop in 2005. (Those lessons ended up inspiring this post: Good businesses have margins.)
After losing the Real Deal, I was flustered. I had a university education in business, but I still didn't understand how to build a business that worked.
Then in 2008, I got a call from a guy named Gregg. He wanted to hire me to work at his tech startup, Mailout Interactive. I learned a lot from all three owners: Gregg, Mike, and Jon. They introduced me to this book by 37signals called Getting Real. I read the whole thing in a day.
I started going to tech conferences. I took a workshop from Mike McDerment, the founder of Freshbooks, called "How to build a Web app from A-Z.” I bought books and online courses.
On Sep 12, 2012, Kyle Fox sent me a DM that changed my life forever. It resulted in me changing my career, earning more money, meeting most of my current friends, growing an audience online, and (ultimately) building Transistor.fm.
Kyle asked if I wanted to start a podcast.
Initially, we thought it'd be a podcast about Product Management (we were both PMs at the time). But, it quickly became clear that we were both interested in building and launching our own products.
Podcasting opened up my world. Through the show, I was able to connect with the most incredible people. Many of these people became my friends.
These connections lead me to almost every opportunity that's come my way.
For example, I interviewed Sacha Greif, which lead to Nathan Barry, and then Paul Jarvis. The three of us did an episode together. Chase Reeves listened and reached out. One year later, he introduced me to Jon Buda at the XOXO festival.
And, four years after that, Jon and I started Transistor.fm together.
We signed the partnership documents in February of 2018 and officially launched on August 1, 2018.
Today, we serve over 10,000 podcasts of all types. Our customers include indie podcasters, small businesses, and enterprise companies. Current customers include Indie Hackers, Basecamp, VH1, ProfitWell, Ionic, and Laravel.
I cataloged our whole journey in this bootstrapping series.