I received this email a couple of days ago from a guy I’ll call “Charles” to preserve anonymity. Charles is thinking about buying a business that seems to already be established and successful. I’ll respond to his email below in italics.Hello (not sure you said your name on the videos).

Just call me Peter.

I am contemplating moving to Oahu to buy a business. I just watched your 4 videos on YouTube. Good commentary. Thank you.

Sure thing.

I have been in the corporate world (though I’m not a corporate guy) for for over 20 yrs and am getting laid off for the 2nd time. I live with my family in MN and we’re headed into another intense winter. I’m an outdoors guy so I snowshoe and grew up skiing, but haven’t had the time in recent years. I have a boy in college and one finishing high school next year.

I am thinking a move to Hawaii will happen now or never in my life with this pending business opportunity. The business is stable and has been functioning for 25+ yrs. it is part of a larger distribution business on the mainland and the owner wants to start moving towards retirement. He is severing the HI business to sell it.

I think the idea of buying a business that is already working in Hawaii is one of the best ideas for getting into a new business in the state. When you’re just coming from the mainland you don’t understand what works and what doesn’t. Hawaii is like another country.

I figure work the business and Pay it off, then sell it in 10 years and move back to family property in WY to retire.

Sounds good.

I am an outdoors person and enjoy biking, motorcycling. Scuba diving, running, golf, hiking. and a few other things I don’t have time for.

I don’t mind the city, but love the outdoors and seclusion, so I don’t think living on an island would bother me. The business is based on Oahu, but stretches to the other islands.

I have been to Maui and Lanai, never to Oahu. I know they’re all different.

Remarkably different, yep. Oahu is set apart from the other islands just due to sheer number of people there and the infrastructure already built up all over the island. Lanai is in another class too. Maui and Kauai are quite different from each other too. 

I would leave my younger son and wife here in MN and let him graduate while I get use to the business. Then bring him over to the U of HI for college. He is a Biology nut and it sounds like the school is very affordable for residents, as well as being a good school (particularly for science). My older son might come over for grad school.

Do I sound like a good candidate?

You seem to be. As I said above, buying an established business is smart, instead of trying to start your own company in the islands. So many businesses fail. Have you looked at what will change when you take over the business? Agreements that have been in place for years can go away once the business changes hands. People that had agreements with the current owner, on paper or otherwise, may choose to change them when the business sells. 

There’s one thing that bothers me a bit. You haven’t lived in the islands at all before buying the business. Would it be possible to spend a lot of time there first? A few months or so? Hang around the business and meet the people that are working there? I’d want to do that if I was buying a business in the islands, especially one that stretches into the other islands. I strongly recommend reading my “Moving to Hawaii – The Good, Bad, and Ugly” book at Amazon. You can grab it for about $5. There is a ton of information there that isn’t in the book review video you saw at YouTube.

What area of Oahu would you suggest living in? I’ll be living conservatively until my son and wife move over, preferably a cottage outside of the city with a little privacy and decent access to Honolulu. I’ll likely ride a motorcycle mostly. I have a big V-twin bagger that I could ship over, but am thinking maybe a supermoto with a backpack for more mobility in traffic and on bad roads out of the city.

I know a couple of people that died on motorcycles on Oahu. I had one there myself. I must sound like “Debby Downer” from Saturday Night Live, but I don’t know that I would own a bike in Honolulu anymore. No, I’m sure I wouldn’t. Vacationing tourists aren’t looking for people on bikes of any sort. I saw and was involved in a few near-misses too. 

Back to the question. Personally, I’d live over Waimanolo way, Kaimuki is closer. Somewhere on that side of Diamond Head, not up the other way. Pali area could also work for me I guess. The traffic in town is nightmarish during rush hours and any special events. The view is also worlds better coming from Waimanolo way!

Timeline would be some time during The first couple of months next year.

Would enjoy any comments, suggestions, or comments.

Thanks – C.A.

Sent from my iPhone

I cannot believe you wrote all that on your phone! I hope you have a Bluetooth keyboard with it!