My Dream of Working Remotely

As you read this, I’m flying over the Pacific on my way to the Big Island of Hawaii for eight days. My incredibly gracious wife bought me a ticket as a Christmas/birthday gift. Besides the surfing, hiking to the lava, hanging out with friends and scouting for land, I plan to spend a little bit of time working remotely. It still blows me away how much life has changed over the past few years, and that I’m actually able to vacation in Hawaii with a viable business operating back home.

Five years ago

In April of 2007, my wife and our two children (we have four now), moved to the Big Island. Some of our friends were planting a church there and we had moved out to help. We lived there for 13 months, and it was one of the greatest periods of my life. I saw how relationships are more central to the culture in Hawaii. Time goes slower, and in general, everyone is more relaxed. The sun shines in Hawaii, and makes you happy. I would surf at least three times a week with friends. I could go on forever, but there is a reason why people are so healthy in Hawaii. It’s an incredible place.

In 2007-2008, while I was working for a company, building kit island homes, the housing bubble popped. After about six months, it finally hit the Big Island. It was like a delayed reaction, but all of a sudden new construction stopped. Orders for the kit homes had slowed to a crawl and the next thing I knew, I had been laid off. I was able to find temporary work fixing up a home up near Volcano national park, but that only lasted a month and a half before it came to an end. Facing relatively sizeable expenses and not much work, my wife and I decided we needed to move back to the mainland.

That was one of the hardest decisions I’ve ever had to make. I really loved the island, but there just wasn’t enough work. As we were leaving, I told our friends we would be back, whatever it took. I realized even then, that it would be an incredible place to work from remotely. I needed to come back to the mainland and set up some businesses that I could run from anywhere.

My First Craigslist Gig

Once we were back on the mainland, the first thing I did was jump on Craigslist and start emailing people that had posted jobs in the Gigs section. I still wasn’t ready to start my own business, or at least I didn’t think I was. I found an ad posted by a guy seeking someone to help him with a remodel at his house. Here’s what I wrote:

By the time the guy deleted the his ad later that day, he had over 100 response. After hiring me, he later said that my email stuck out because I was honest about my abilities. If you want to stick out from the crowd and get a job, land a contract or make a sale, just be honest. More often than not, people are looking mainly at what type of person they want to deal with, rather than only skill set.

After that job ended, I finally found a nice full time position working for a general contractor here in Portland building eight condo’s. When they were completed, I decided to venture off on my own and get my general contractors license. I wasn’t in love with construction, but I wanted to take some sort of step towards starting my own business. At the time, getting my license felt like the next step.

It wasn’t. I quickly realized that I didn’t have the passion or desire to spend the next ten or twenty years learning the trade. If I was going to be a contractor, I wanted to be a very good one, and to be good at it you really need to have a desire to spend a long time learning about all the styles of homes you would be working on. On top of that, contracting is not something you can do very well remotely. That definitely played a part in deciding to move on.

The Craigslist Business

It was December of 2010 and after meeting with my friends Chris and Jason, I started buying and selling on Craigslist full time. I started picking up anything I could make a buck on, and gradually moved to bigger ticket items. I finally settled on appliances as my primary focus. I had to work really hard, but things went well right from the start.

Almost from the first day of buying items on Craigslist I knew the business could be operated from anywhere. I needed the knowledge of a product category, a computer, high speed internet and a cell phone. I had the place I wanted to live (Big Island), at least for a decent portion of the year, the product (appliances), and Craigslist as the marketplace. All that was left was finding someone that I could teach the trade and could help run and partner with me in the operation.

Finding Peter

Finding a good worker is hard. Finding a good future partner is even harder. I was looking for someone that was hard working, loyal, honest, had attention to detail, mechanically inclined, strong and intelligent. They needed to be able to learn on the job, often times self-taught. This type of worker is also referred to as gold, as they are valuable and very rare.

Then one day I discovered Peter. I approached him a few times about the idea and he told me he was happy where he was at. About a month later, I tried once, and this time he was wrestling with what he wanted to do in life. We went out for coffee, I pitched him my vision and told him he could work on the side and test it out. He started soon after and I attest that he’s been all of the above traits and more. We’ve been working together for the past number of months learning as fast as we can about the appliance trade. He picks up appliances, cleans them, repairs them and delivers them. Basically everything on the ground, and he’s great with people.

Prepping for takeoff

Peter is working with me on the appliance thing part time, as he has a full time job during the day. This takes the pressure off us to produce big numbers while at the same time learning the trade. Each day we are getting closer to the business expanding to the point where the workload will demand two or more full time workers.

While I’m in Hawaii this week, we will continue to run the business, though much more passively. During down times, I will occasionally check for product to purchase and set up appointments for the right buys. I won’t be answering my phone very often, so we will have buyers contact Peter after he gets off work. The appliance operation will continue and will be in good hands.

I really hope this encourages you to know that almost anything is possible if you’re willing to work for it. To be where I am today has taken a lot of hard work, but it’s starting to pay off. Don’t be discouraged if your goals are taking longer than you expected. Just keep pressing on.