The Best Place For An Online Entrepreneur To Live And Work

Surprise!  It’s not Thailand!  How’s one supposed to get friends and family to regularly visit you when you’re all the way out there?  Meanwhile, each time you want to return back to your home country, it’s going to cost you, or your business an arm and a leg.  For all sports fanatics except for soccer, you won’t be able to watch any of the latest!  Finally, it’s sad to say, but I think I’ll miss America’s health foods such as cheeseburgers, pizzas, and rib-eye steaks if I live abroad for too long.

I recently blew my tax refund on a 9 day, 9 night trip to Hawaii.  I’ve decided there’s no better place in America, and potentially the world than Hawaii, and I’ve been everywhere.  Even my beloved San Francisco, is a distant second.  With night temperatures in the low 70s, and day time temperatures only reaching the mid 80s, Hawaii has the perfect temperature for outdoor enthusiasts.

For the past two years, I’ve been pretending on each vacation that I’m retired, and working a fully location independent lifestyle.  Perhaps I’ll write about my other trips to Machu Piccu, Cancun, Hong Kong, Barcelona, and Malta.  But for now, I want to focus on where I think is the best place so far to balance work, life, and play.

Everything fun in Hawaii is free, or at most, dirt cheap!  Meanwhile, the Hawaiian time zone is actually ideal in dealing with everybody in the world.


* Body Boarding / Surfing. Everyday, I went down to the beach at around 8am to go body boarding.  The cost to park is $1 an hour, and I’d spend $2 bucks.  There’s nothing better than paddling out to were the surf breaks and riding a wave in.  The water is a warm 60 degrees, and there aren’t many people around.  Wave after wave comes, and everything is free once you buy your equipment.

* Hiking. In Oahu, there are literally hundreds of hikes one can go.  The mountain ranges are robust, and all hikes are free.  Some of my favorites are through the rain forest, where after a couple miles of a moderate ascent, you get to a water fall where you can go swimming or jump off cliffs.  There’s no cost to your hike except for the gas it takes you to get there.

* Tennis, Soccer, Football, Basketball, Softball. Hawaiian recreational parks are all free, and people play sports until 10pm when the lights are on and the temperature is cooler.  I played tennis twice, and shot some hoops for an hour another time.  The locals are friendly, and just want to have some fun.

* Golf. If you get the kama’aina rate (local rate), the public courses are generally around $20-25 dollars a round!  Not bad for 5 hours of trying to whack a small ball into a small hole.  I went golfing twice and shot a 82 and 86, after not playing for a year.  I still prefer the workout of tennis, but it’s absolutely beautiful to just walk a course with the mountains in the back and the beach in the front.


The Mainland: Because Hawaii is 2-3 hours behind the West Coast, and 5-6 hours behind the East Coast (depending on daylight savings), you have to get up early to correspond with your mainland friends.  I’m a morning person by nature and basically transferred over my normal 6am wake up time in San Francisco to Hawaii.  6am in Hawaii is currently 9am in California, and 12noon in New York City, which leaves plenty of room for correspondence.

Europe: 6am in Hawaii is 5pm in London.  I know how Londoners love to hit the bars come 5:30pm, so it’s important that I communicate with clients in the Europe and the UK first.  Ideally, I should try and regularly wake up at 5am Hawaii time / 4pm UK time, but I don’t think my body will be happy to regularly wake up at that time.  One of the main points of living a location independent lifestyle is so that you wake up whenever your body wants you to wake up.  6am works for me, and I’ve been able to close several advertisement deals at that time with the UK clientele.  Alternatively, I can “train” my European colleagues to respond to me by 11pm island time = 10am their time as well, so I can sleep in til 7am.

Asia: The Asian clientele is not yet developed as the US and the UK.  That said, I’m excited to see their growth potential in the coming years as Internet penetration and search become more prevalent as countries become more developed.  China and India account for roughly 2.5 billion, or a third of the world’s population after all!  At 2pm Hawaii time, it’s 8am the next day in China, Hong Kong, and Singapore, and 9am in Japan, Korea, and Australia.  2pm is a perfect time to deal with Asian clients after some poki salmon, kalua pig, laulau, and watercress soup!


My ideal amount of work a day is 2-5 hours vs. my normal 10-11 hours of day job work + 2-3 hours of online work.  I don’t want to be retired playing golf and surfing all day.  It would get old after a while.  Spice is the variety of life, and it’s important to keep things fresh.

Based on the various clients around the world, the ideal time for work is from 6am to 8am to catch Europe and the mainland, and from 2pm to 3pm to catch Asia if there is any business.  Perhaps one day, I will hire a virtual assistant in Asia who can keep an eye out for me while I’m doing other things.  However, if I was based in Hawaii, I wouldn’t have to.  Instead, the virtual assistant would probably be best suited out of Eastern Europe.

After 3pm Hawaii time, I’ll probably take a nap for 30 minutes to an hour, and then either go play tennis from 4pm-5:30pm or body board, depending on what I did from 8am-2pm.  Sunset is around 7pm in Hawaii.  This is the time to either grab a drink on the deck overlooking the beach, or have dinner.  Sometime between 8pm-midnight, I’ll spend another 1 hour corresponding through e-mail and writing a post for a total work time of potentially 2-5 hours.  Some days will be busier than others, but for the most part, if I can keep to the 2-5 hour a day work day, that’s fine.


For the experienced person with 10+ years of savings, a spouse, and potentially a family:

Because so much is imported to Oahu, Hawaii ranks as one of the most expensive states to live in.  A decent 3 bedroom, 2 bathroom, 2,300 square foot house will probably run about $600,000-$700,000 in a good location.  Right now, regular gas is at $3.97 with WTI oil hovering at $100/barrel.  Meanwhile, depending how much you eat and where, your food bill could cost about $600-$1,000 a month.

You can always rent a nice 2 or 3 bedroom apartment for $2,000-$3,000 a month.  Again, it’s all about to where exactly on the island you want to live, and how nice.  I believe life is too short to skimp out on good food and good living, hence I’m willing to pay up for quality and location.  The things I’m not willing to pay up for are fancy cars and fancy clothes.  All you need is shorts and t-shirt, and a beater to face the elements!

For someone experienced in their 30s and beyond, you should be able to live very comfortably on $4,000-$5,000 a month after taxes.  This equals around $60,000-$75,000 gross a year.

For the 20-something year old who is relatively unattached:

When I was 25, I was happy to live in a studio, and ecstatic to live in a 1 bedroom apartment in an average neighborhood.  If you are too, then you can easily get a studio-1bedroom for $800-$1,200/month in a good location.

For food, there are tons of cheap eats that will allow you to live off just $15/day if you eat out everyday.  That totals $450/month, which is probably at least a hundred bucks too much for you to spend.

Given you’re young, the outdoor recreation must call to you.  Once you’ve got your sporting equipment, surf board, and hiking shoes, everything is practically free.  I would say that as a 20-something year old, you can live a phenomenal life for just $1,500-$1,700 a month after tax.  That’s just $25,000 a year gross!  Not a tough hurdle, since I can make $18,000 a year working at McDonald’s if it comes down to it.


Given I’m in the veteran camp, my goal is to simply make $150,000 a year in net profits after tax (not gross profits) from my online business plus whatever other income I’ve created to live a comfortable life.  Passive income is a myth, except for the interest I generate from savings and CDs in my opinion.  Everything else requires effort.

I’m giving myself 5 years to consistently get to $150,000+ a year online.  It’ll be a fun journey with a lot of ups and downs.  However, I’m so looking forward to enjoying the journey, that by the time I get there, I’m sure I’ll have some new goals.

For those who are younger who want to work from a place such as Hawaii, making $25,000 a year online isn’t insurmountable by any means.  At the Yakezie Network, where we’ve assembled some of the best personal finance blogs on the web, we have a goal of in one year, increasing our incremental monthly income by $1,000 just through the Network alone!  I firmly believe that if you stick to your business, build your brand, network, and produce consistent content over at least two years, you will be able to get there.  It’s all about how much you want it!

Readers, have you ever thought about running a location independent business out of Hawaii?  If not, what other places in the world have you thought of, besides Thailand?  Do you believe making $25,000 a year is possible online after two years?  What are you doing to make it happen and blow that figure out of the water?




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Sam is the founder of Financial Samurai, America's fastest growing personal finance site. We believe in reaching financial independence sooner, rather than later. Slice through money's mysteries!


  1. Ivan says

    I’ve dreamed of living on a beach for a long time. Hawaii sounds great.

    However, I’m scared sh#tess of hurricanes :(

    Also, I eat lots and lots of fruits, does Hawaii have a good variety? This is the one thing I’m thankful for in Mexico City. All kinds of fresh foods dirt cheap year round.

  2. Sydney says

    Wow Sam I can tell you’ve given it a lot of thought. :) I’ve been to Hawaii a few times and loved it. Hiking is one of my fav hobbies and so are water sports. I was surprised how much poverty there is in some parts of the islands so I can see how having an online biz definitely has its benefits over traditional office jobs there. Although I’m sure doctors and people working in healthcare would do well there too. Do you think you’d ever get island fever if you lived there year round or is there enough variety between the towns?

    • says

      I’d get island fever, but the solution is to just fly to Asia or the mainland and explore for a month or two at a time to get my plane ticket’s worth. That’s the beauty of an online business. You can just run it everywhere and anywhere.

      Hawaii is absolutely amazing. If anybody ever goes there to visit, especially from the East Coast, they will be smitten and never want to leave. To me, Hawaii is a no brainer place to live and work!

      • Sydney says

        That’s true. Asia is pretty close and I bet there are a lot of direct flights out of Hawaii which make it even easier to travel.

  3. says


    An 82 and 86 after not playing for a year? Are you sure you didn’t just dream that score? Or is the Hawaiin weed really that good? :-)


    • says

      Maybe it was a 83 and an 85, but who is counting? :). The ground is much firmer in Hawaii, so my drives go 20 yards farther I’d 280-310 vs 250-275 ish normally. So it’s a nice pitching or 9 iron in on them 410+ par 4s!

  4. says

    Personally, I like the mobility of online income because I can do it anywhere. I am a bit more anchored to California because our (adult) children and eventually grandchildren live here. I am focusing more on statistics than a particular amount of money right now. This summer, I am making my big push with my writing and promotion. I am want to see how far I can go by the end of September.

  5. says

    Ok now I have to go to Hawaii! If only for the holidays.

    I’m currently in Shanghai, and it is a city I can recommend for both work and pleasure. You have everything available at Western standards, but you can live much cheaper if you choose to (the price range is huge). The best thing is the food.

    I’m only here for 5 weeks now, but could definitely imagine living here for a longer period.

    • says

      One thing I need to add though is that the internet censorship in China really can be a problem. Both facebook and twitter are blocked, so if you don’t find a way around this, that can be a big problem for online businesses.

      • says

        I totally hear you on internet censorship in China! Kinda nuts! Guess you’ll just have to get a Ren Ren and Weibo account right

        What a trip, living in Shanghai. What are you doing there? Shanghai is an exciting place!

        • says

          yes they have their own social networks here, but they are useless if you want to interact with an international audience.

          I’m in Shanghai because my girlfriend is on a work project here for a month, and I work online, so I decided to come along. I also love China a lot and have been here several times already, so it was tempting to go again :-)

  6. says

    Well I live in India and the benefit is that you can the conversion factor of Dollar to rupees make it really worthwhile living here even though it is not comparable to Hawaii at all. I know a lot Americans who live in Philippines and live only on online income again the conversion factor comes into play.

    Yes if you have to truly enjoy the online work and the life then I think Hawaii is the place to be in.

    • says

      Philippines is nice, and there are a lot of nice people, but it’s just a little too far removed for me personally. It’s cheap and if others like it, more power to them.

      India is definitely not a place I can see myself living for more than 1 year! Kinda rough!

  7. Stuart says

    Wow, Hawaii, it does look good, I like the isalnd I live on too, its Malta, central in the mediterranean, from here its really easy to get to anywhere with the great airline connections, and there is sun sea and sand too, oh, and fast internet connectivity! I have thought about a move, but dont want to end up always thinking the grass is greener…

      • Stuart says

        Hi yes, Valletta is the capital city, and a world heritage site I believe now too, I guess like you I am trying to put myself in the position I want to be in, as I work online promoting just about anything, and love it.

  8. Jeff @ Sustainable life blog says

    I do believe making 25k online a year is possible, though I know that with the amount of work I put into it, it’s a bit beyond my reach (for now). I’d love to live in hawaii as well, but I think I’d miss wyoming, even with the harsh winters. I’ve been to the islands twice, and wouldnt mind going back.

    • says

      I love Jackson Hole, Wyoming for it’s scenic beauty and more importantly, NO STATE TAXES! Can you imagine if Hawaii abolished state taxes as well? Everybody and their mama would move there in a heartbeat, especially from oven pits such as Texas and some parts of Florida! Jobs would be created, taxes would increase and all would be good except for traffic.

      $25k/year in net profits online after two years is a no brainer possibility. If a donkey like me can do it, anybody can!

  9. says

    Hawaii is one of my top spots to retire. I love the Island lifestyle. Did you try surfing? It is awesome. I only took one lesson, but will definitely take it up if we ever get to Hawaii.
    You’ll be set with 150k+ per year. I’ll keep working on it too.

    • says

      I did surfing, but for some reason, I love the convenience of body boarding so much more. Lighter, can throw into the trunk, carry around, etc.

      Hawaiian food is awesome! Laua laua, lomi salmon, haupia, malasadas, watercress soup, kalua pig, mangos, papaya and much much more!

  10. says

    I am actually surprised by the numbers you gave for Hawaii- 600k-700k for a 2300+ square foot house is actually lower than I expected. Maybe my dreams aren’t so lofty after all?

    Your days sound wonderful. I have not been been to Hawaii or ever seen a rain forest. There are so many things I have never done. Obviously you have been to many places and explored so much, I am envious!

    • says

      Just gotta book the tickets and make the commitment Kris! Your family will love it and so will you! You might even start wondering why you’ve been in Michigan for so long! Trust me, you guys will really like it.

  11. says

    Great article man. K and I are structuring Fifth&Brannan so we can spend 1/4 of the year taking Inspiration Getaways to places where we can unplug and just create (K designing, and me doing web stuff).

    We took an 8 day trip there last May (2010), and TO THIS DAY, we talk about that trip. Hawaii will be our first destination for our Inspiration Getaways.

    • says

      Awesome man! Then returning is a no-brainer!

      Yoour “Inspiration Getaways’ for 3 months at a time sound sweet. 3 months off a year could really be the perfect amount. Long enough where you can truly go and relax, but not too long where you get out of touch with the world.

  12. says

    For somtime i was working remotely which meant i could live wherever I chose! I should’ve thought about Hawaii – wasn’t too far from where I was back then, California!

    Definitely food for thought!

    • Sam says

      Hawaii is where Californians dream. But I gotta tell ya, I’ve been chilling in Laguna beach this past weeked, and it is awesome here! Kinda surreal actually. Only problem is that there are way too many people here!

  13. youngandthrifty says

    I tried to comment a few days ago but then I kept on seeing that I was “logged in as financial samurai”. Guess it was a weird temporary glitch of some sort.

    Anyhoo, I would love to live in Hawaii but I think I would be upset (at least for a little while) paying a premium for things like milk.

    I remember someone told me that there were 30 year fixed rates of 2.75% last year when I went. Amazing!

    Hey Sam, did you quit your day job?

    • Sam says

      Weird! That log in issue happened to me too, but with someone else’s account. Glitch in the matrix so it seems.

      Nope, haven’t quit my job yet, but have cemented a date of Feb 18, 2018 to do so as a goal! :)

  14. says

    Hawaii! Ive never been and want to go. Looks like we might be going there for our honeymoon this year. I went to Bali this year and I’ve read online the comparisons to Hawaii. Definitely have to see first hand. As for working remotely from Hawaii? Does sound too bad at all. :)

    • says

      Have a great honeymoon man! Bali is amazing, just so far away.

      If you’re quitting your job, is it possible to live off the Mrs by any chance? Would be nice for a while I’d think!

  15. Kristoph says

    I’m glad Sam wrote this post. I’ve been looking for an ideal location for entrepreneurs. I currently live in San Francisco and pay the “absurdly high real estate prices” but this is the place for tech entrepreneurs (VCs are very local people).

    I like it here, but I’ve never lived in one place for more than five years in my life and am always looking for the next place. My requirements aren’t too picky: 😉

    1. Cannot be a U.S. Airways hub city
    2. Has lots of young creative, inspirational people (pref. an entrepreneurial environment)
    3. Is a big city but has lots of nature at the same time
    4. Is clean
    5. Is trendy and/or has a great cultural vibe

    So far I’ve identified some cities that meet these requirements in some way or another: Montreal, SF, Calgary, Berlin.

    Any other ideas? I’m curious to hear what people around the world think

  16. says

    Wow Sam, awesome breakdown of island life. Looks like you’re a full blown Hawaiian. Got the pidgen going and all the local foods down, too! Would be great if we all could work online one day and catch up with everyone from amazing remote locations. What brought you out to Laguna and Newport beach?

    • says

      Haha, perhaps!

      Just visiting a friend down in NPB. First time, and I enjoyed it truly. Those guys have it great down there! Too bad, there’s just tons of people too. Hawaii is a little more peaceful if you just drive 30 minutes outside of Honolulu, there’s nobody!

  17. Hunter says

    Having flown over Hawaii several times travelling between Sydney & L.A. I can say with authority that it looks great from 40,000 feet. Thanks for painting such a complete picture Sam.

    • says

      LOL, nice mate! Maybe you can do a wrap of Sydney and LA as a place for an online entrepreneur to live and work! Love those places too… well, more San Diego/Laguna Beach area.

  18. says

    I love the way you detailed every bit of this post! Feel like going to Hawaii on a vacation! Yeah, will do that soon. I’m sure you’re loving it over there? :) Awesome post Sam! Thanks so much for sharing. Have fun :)

    • says

      No prob man. I was surely thinking about as much as possible, and any concerns or issues I’d run into pretending to be a lifestyler there. I guess the next step is to go there for even longer and discuss taxes, local rates, cable, cars, secret spots etc!

  19. Car Negotiation Coach says

    Sam I have to agree with you that Hawaii is probalby one of these best places in the world. Hiking, biking, waves, are all absolutely amazing. However, I will say I did not experience the same low costs as you…..easily my most expensive vacation ever and it seems like you must pay for every little thing, but what else can you expect from a place centered on tourism….but if I could afford it, I’d live there in a heartbeat.

    The location I’ve seriously considered working is Lake Tahoe. If I could convince my wife, I would definitely rent a house for the winter (they’re very reasonable for long stays) and work in the morning with the east coasters then ski or play poker every afternoon.

    • says

      I hear you loud and clear on Tahoe! In fact, I hear you so loud, that’s why I have a place there as I’ve envisioned myself spending 3 months a year there during retirement. I love Tahoe, both summer and winter. It’s magical man.

      My only dumb move is I didnt buy on the Nevada side, where there is no state income taxes! I probably couldn’t do anything about t anway as I won’t live there the majority of the year, but still.

  20. David says

    Sam… O’ahu is a nice island, but you can do better on housing costs on the other islands. Personally, I am looking to relocate from the Pacific Northwest to Maui. Much more kicked-back than O’ahu. Now it’s just figuring out what I’d do for a living to make it worthwhile. 😉 Or convince my boss to open a Hawaii office.

  21. Daniel Viitello says

    Wow I loved this post! Especially because my dad lived in Hawaii for 16 years and that is where he met my mom so I have heard hundreds os stories about living there. Unfortunately they decided to move to Texas to have kids so Ive never experienced life there.

    I have been running my online business for almost a year now and am currently doing at least $30,000 a month gross so I would say trying to achieve $25,000/year in 2 years is definitely achievable. On a similar note, I have been growing tired of life in Texas and am planning on taking my business to Miami come January. I wish we could go to Hawaii but cant because we ship physical products. (drop shipper I know!!) I think Miami might be a second best bet though.

    • says

      Hi Daniel, can you share with us what your net income per month is? Love to get a better picture of the bottom line. I love collecting anecdotes that making six figures is not as hard as people or the media might think. Thanks!

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