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:

gig listing

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.


  1. Hey, Ryan,

    Interesting post! It leaves me wondering what your business plan is, though. From what I can tell, you work remotely from Hawaii, searching Craigslist and finding deals. What then? Do you call the seller and set a time and then relay the deal to Peter, and then he goes out and and gets the deal, cleans it, and resells it? It sounds like he is doing all the manual work and therefore most of the job itself. Does he get a bigger part of the profits as a result? Or is there more to your part? Another thing you emphasized in a previous post is that one of your greatest strengths was the ability to run out the door the moment you spotted and called for a deal. Peter is severely limited in being able to do that with a full-time job. Sounds like he is only available in the evenings and weekends. How do you compensate for that? And are you establishing yourself in the Hawaiian Craigslist community as well to pursue deals there?


    • Great questions! When buying appliances, and many other items, once you set up a time to come view the item, the seller usually honors the appointment. It’s different for free items. Every once in a while they will take a higher offer from someone else, but not very often. I scour the listings, find the good ones, contact the seller and arrange for the pickup. Peter picks it up, and prepares it to sell. I then do the posting of all the ads, and when I’m not on vacation, handle all the correspondence with the buyers.

      We both know how to do the repairs, cleaning, pick ups and deliveries. One of my main skills is finding the deals, vetting the sellers and vetting the appliances to limit risk on purchases.

      As far as compensation goes, he makes good money. As business continues to grow, eventually he, or someone else if he doesn’t want to, will start working full time. Right now I’m more than happy to do all the phases or steps of the work.

      As far as Hawaii goes, I’ll probably start up the business out there as well once we get a home there. I’m not sure when that will be yet.

      Thanks again for the questions!

  2. I came across your website and you really inspired me, I am 41 years old married for 17 years and I have a beautiful 13 year old daughter, I have been working in the ellectronics field for over 20 years and I was going to college to get my engineering degree, but like you I wasnt too excited to be an electronics engineer nor working for someone, working crazy hours , waiting for the 2 ercent raise every year and 2 weeks vacation a year, I am sick of the rat race , I am still young to make something big in this life, I sold and bought stuff from craigslist before and it works really good and I thought og being my own boss but I dont have capital to open a business, you really inspired me sir, I am goint to start my journey with craigslist and I hope to meet you someday so we can have a couple of beers, thanks for this awesome website, you just make my night, have an awesome day and God bless you my brother.

    • I love getting messages like this David. Let me know if you have any other questions and keep me posted on how your doing! Best of luck!

  3. Ryan, great story. I have been doing the arbitrage thing all last year via local retail stores, thrift stores and then selling on Amazon. I have sold a few things on Craigslist before, but never thought of it from a business stand point. I will keep viewing your blog for more great ideas. Keep up the good work!

  4. Ryan,

    You could manage your business remotely, as you mentioned, but you would probably have to replace yourself in the head functions, eg get a spotter/contact person to run the phones, and set up shop. At a low level you could probably rent out someones unused garage space. Also manage deliveries.

    If you gain a strong enough following, you may be able to consider sometype of consulting position, where you either command a fee, or a revenue percentage, since it appears you have a like minded audience. A consulting position COULD offer a much more flexible schedule.

    • I think I have been realizing that more and more over time. I think it’s definitely possible to operate remotely, but there would be a few challenges, especially with a larger operation, to give it the full attention that it could need. We shall soon see!

      I’ve started consulting more and more over the past few months. That’s been going well. I’m working on producing some resources to minimize some of the more repetitious parts of the training/coaching. Hopefully I will get those done soon.


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