We Are Moving Back to Hawaii


Why not now? I was finally able to ask that question this past summer. I looked over at my wife one evening and asked her why not now? I told her that I thought we could make the move. Our goals had been reached. A smile quickly came over her face, and I knew that our lives would soon be changing again.

Those of you who have been following my journey through this blog will know this is a big deal. When my family and I moved out to the Big Island 7 1/2 years ago, we thought we were moving for good. We had sold all our possessions and bought one way tickets to our new life out on the Big Island. I quickly got a job, began surfing, we moved into a great neighborhood, made a lot of friends and were loving life. Then the housing bubble burst and utterly flattened the job market on the island. I lost my job and we ended up moving back to Portland to try and start over.

We arrived back in Portland in debt and discouraged. We moved into an apartment within a few weeks of being back and had zero furniture. We borrowed a futon from some friends to sleep on, and we ate our meals on the floor. I got a temporary job helping someone remodel their house for a month from the gig section on Craigslist of all places.

This job led to another construction job working for a contractor building a group of townhomes. I learned a lot at that job, and it was a good experience that lasted almost 2 years. But at the end of it all, our debt had continued to rise. This was especially discouraging as we had been back for over 2 years and we were not even close to being in a position to go back to Hawaii to visit.

An entrepreneur can only go so long working for someone else before something deep within them drives them to venture out to try something on their own. It was at this point that I set out to start a business. I ended up choosing to construction mostly because that had been where I had spent the majority of my time working over the past 3 years. So I got my general contractors license and I was in business!

In the end, it wasn’t the business that I wanted to pursue long-term. So I quit construction. I had no clue in the world what I was going to do. I had no money, tons of debt, a mortgage (we had gotten into a house) and a family to support.

I got behind on all my payments and was at rock bottom. The day I was going to walk away from all the debts, I sat down for coffee with my friend Jeremy and told him my plans. Like an army general, he ordered me to make my next mortgage payment and to bust my tail 16 hours a day if that’s what it took to make my next payment. Later that week, I met with my friends Chris and Jason and the Craigslist business was born.

It took off right away. Within a year I had seen the opportunity to get into the appliance business and charged right in. I started this blog, started reading business, investing and financial books and started rapidly paying down our debt. Almost three years to the day that I had met with Jeremy, we paid off 25k of credit card debt and became debt free.

Over the past few years, I have been focusing on figuring out ways to add value and earn money that isn’t location dependent. I started consulting for people that were interested in starting up their own appliance business. That went so well that I ended up building ApplianceSchool (now Tradeskills.io) for people to learn the appliance trade.

It’s been this side venture, as well as a few others that are really making it easier to move back. We built ShirtSchool and are working on a number of resources to help people learn various trades. I’m excited to continue working on these projects amongst a growing Tech community on the Big Island, including Hawaii TechWorks. Startups can be built anywhere now, so why not the Big Island?

We are planning on moving out this winter sometime, but there are still a number of unknowns. Currently, there is a lava flow charging straight for the beautiful town that we used to live in. (Check out LavaTracker for the latest information on the lava flow) It could end up going through the town, cutting off the main highway and ultimately changing life out in that area forever. But that’s a minor obstacle. Never give up!  Where we will live on the island and a few other details might be up in the air, but our family returning is not one of them.

The night before we left the island in 2008, a bunch of our closest friends gathered together to say goodbye. That night was tough. Our friends shared favorite memories, things they appreciated about our family, and things they were going to miss once we were gone. I was overwhelmed by how much I didn’t want to leave. But there were two things that made that night especially hard. First, I hate saying goodbye. The reality that I wouldn’t see my friends for a while hit me all at once. Not many things will cause my eyes to leak like having to say goodbye to friends. Second, I couldn’t see how we were going to make it back, even for a visit. It was in that moment that my friend Don walked up to me, and in complete confidence told me that we would back. Don wasn’t looking at our circumstances when he made that prediction. He was looking at our hearts. Don was right. We are going back, lava and all.

I also want to thank you all. I’ve received a lot of support and encouragement from readers of this blog over the years. I started this blog to help encourage others who might find themselves in similar situations in life that I was in. But I’ve  received an enormous amount of encouragement myself and have had the pleasure of communicating with many of you. So thank you!

I’m going to continue to write on this blog about Craigslist, business, making money, education, learning the trades, raising and educating kids and I’ll soon be mixing in some stories about island life! I have already begun work on starting up an appliance business on the island.


  1. Awesome Ryan!

    That is such great news to hear, and I am so pleased for you and your family!
    You are inspirational in the things you have overcome, and your optimism, hardwork, persistance, and determination.

    Trust in the Lord with all your heart, do not depend on your own understanding. Seek God’s will in all you do, and he will direct your path. Proverbs 3:5-6 🙂

    • Lisa, thanks for your kind words. We have rested on those verses in Proverbs many times, and they have extra weight to us now with the lava coming. It could have a big impact on the Island, but there will still be people there and life will go on!

  2. We just visited the Big Island this summer and it was gorgeous! We missed the lave flow and hurricanes by like 2 weeks. Congrats on your move, wish we could be in the same position!

  3. Thanks for your words, posts, and inspirations. I’m glad you are getting back to a place where you and your family want to be. Compared to other people I follow, I seem to actually relate best to you. Your craigslist experiences are something that I would like duplicate but still have my hesitations. I look forward to reading more while you wrap up your Portland Chapter and start a new Big Island Chapter. Thanks Again

  4. Hey Ryan…I’m a longtime lurker, first time poster, and fellow Oregonian and surfer. Super stoked to read about this new turn of events (and a little jealous). Good for you guys. Stoked you’ll continue to blog!

  5. Ryan, congrats to you and your family on the move!
    Will you continue to actively buy and sell appliances in Hawaii? Or just work on the startup/tech side of things? Are you earning income from anything other than appliances, shirts, metal and the school websites these days?


    • Hey Mike, I’m still buying/selling appliances here in Pdx, and am already in the process of getting an operation going out in Hawaii. Like I said with the lava, it’s interrupting things a bit for people out there right now, so that’s going to be delayed. But yeah, I will be doing appliances at least on the side until my boys are old enough to get into themselves. I also enjoy the interaction with people, the physical work and it keeps me sharp as far as the school goes.

  6. Congrats, Ryan! I too may move to Hawaii one day. It’ll be interesting to see how Craigslist is out there, and look forward to the future posts on it. You’ll really enjoy making pickups and deliveries in your truck shirtless with the windows down in the sunshine. Just a thought here, maybe buying and selling surfboards can be possible out there if you need a little extra cash flow.

  7. Life is short but GOD is good and he is blessing you cause you have blessed so many thanks for letting us in your world its great to see what can be done when you have a goal and with hard work see it unfold before you CONGRATS

  8. I’m not into surfing or any other water activities but. I always wanted to live in Hawaii. A few years ago I looked into finding a job out there but that didn’t pan out. I also heard that the cost of living is higher than anywhere else in the USA. So, I felt that moving there was not an option. But, your blog has given me hope once again. Thanks and congrats on finding your niche and your impending move back to Hawaii.

    • Thanks Vicki. It’s all about where in Hawaii you live. Certain parts are way more expensive than others. The Big Island can be relatively cheap in certain areas. Food and electricity are both very expensive out here, but there are ways to combat that. Where there is a will there is a way. Work: you either have to bring your own job, or look a good bit before you come. Or bring a skilled trade that has demand everywhere. Hard, faithful works are in demand anywhere. Never give up hope for what you really want to do!

  9. So inspiring story! You are so brave! I am thinking about moving to Hawaii for about a year and I still am hesitating. I have a few friends there, who already took this step and they are extremely happy now. I think I need a little more time and I will leave everything here. Thank you for the inspiration!


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