Hawaii Business Owners - would love to connect

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April 21, 2026

by a searcher from Missouri State University in Santa Rosa, CA, USA

I'm actively evaluating a business acquisition on Kauai and trying to get smarter about Hawaii's unique operating environment — Jones Act logistics, GET vs. sales tax, PHCA health insurance requirements, labor market on neighbor islands, permitting pace. Would love to connect with anyone who owns or has owned a business in Hawaii. Happy to share what I've learned in return, which is a work in progress. DM me or reply here. Looking forward to participating in this community. Thank you.
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Reply by a searcher
from Massachusetts Institute of Technology in Captain Cook, HI, USA
Hi Dennis, I live on Big Island for 5.5 years now. I don't own a business here but I did have a business here under LOI last year but walked away from it. I'm actually about to close on a biz in Pennsylvania but I'm still going to live here. I'd be happy to chat if you'd like, I've learned a lot from living here and from the deal I had here in terms of things like labor (it's iffy) a permitting (it takes forever). Kauai is a tiny market in general but depending on what you're doing and your goals can work
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Reply by an admin
from Massachusetts Institute of Technology in Portland, OR, USA
^redacted might be able to help here. Press @ to tag someone else! :-)
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