How I started freelancing

I’d like to tell you a story about how I started web development and freelancing.


In college I’d play computer games with friends across the world. We had a website to organize events and a forum to chat. It was fun but our website was always having problems. The webmaster at that time was also in college and he didn’t have the time to maintain it all himself. So I started to help out.

I had a background in computers but mostly on the hardware side. Fixing computers. Breaking computers. Re-fixing computers after my dad would complain that it stopped working after I ‘played’ on it.


While working with this webmaster I picked up HTML and PHP. The main reason I learned them was to fix problems.

Over time I became more interested in websites and programming then playing the games. My natural curiosity got the best of me and I started to dig deeper into computer programming.

Dot-com and entrepreneurship

At the same time I was learning about business and personal finance. I experimented with a few traditional business ideas. You see, this was right after the dot-com bubble burst so internet businesses were very much out of favor.

Side note: In one of my first classes there was a failed startup founder. He was only there for a week but from what I learned he started a company that was “worth” millions. Then the bubble burst and he was out. No business. No job. No prospects. Which is why he was going back to college. His story stuck with me.

Anyways. While I was teaching myself programming, I was learning the “textbook” way to run a business, while also experimenting with entrepreneurship on the side.

It was during this time that I decided I needed something with more structure than PHP for building websites. WordPress was just in its infancy and couldn’t be used for more than a simple blog. There weren’t any really good frameworks of “ready to go” PHP libraries. The only things out there were some heavy Python systems and this new thing called Ruby on Rails.

Suffice it to say that I tried Ruby on Rails and began the next stage of my programming journey. (One that continues to this day.)

Leaving California

Fast forward to 2007. My wife and I moved out of California to Oregon to start our post-college life together. As part of the move I sold my car. We wouldn’t be able to drive it, my wife’s car, and the moving truck up to Oregon.

(What we didn’t know if that we wouldn’t be able to drive my wife’s car up either. That’s a story for another day though.)

Once we moved up here, we became a single car family. I planned to re-learn how to ride a bike and use the great public transport system in Portland to go to work.

But instead, I wanted to do another experiment with entrepreneurship.

The Tiny Bet

I bet my wife that I could take half of the money from the sale of my car ($450), do “something”, and make back double that money in three months. Worst case I’d use the remaining half to buy a new bike and find a job. She agreed.

Thus started my freelancing business, which later was named Little Stream Software.

One little bet in 2007 turned into a freelance business that has keep me busy full-time, while earning more than I made as an employee.

Eric Davis

P.S. I’m telling you my getting started story to show that even without experience and outside help you can start your freelance business. Though it’ll go much better if you have a plan. Especially if it’s a good plan.

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