If you haven’t read the previous two articles about my IT jobs in Hawaii – they are here:

How I Landed My First IT Job in Hawaii

How I Landed My Second IT Job in Hawaii

Picking up where I left off… This dotcom supergenius, Cheyenne Ehrlich, contacted me by phone around lunch one day as I was working at IT job number two, Classic Resorts. I stepped outside the sales office and talked to him for about thirty minutes on my mobile phone. He’d found my resume on Monster.com. I was PERFECT for his project. He’d match what Classic paid. He’d give me a nice severance package if it all went in the toilet. I could come to work in my slippahs and board shorts if I wanted.

All he was saying was too good to be true, but I believed him. To say Cheyenne was smart, would be the most understated thing I’ve written in all of 2011. Oh wait, it’s 2012. Well – same deal. His mind was running like a hover-train flying across China.

Cheyenne had started an IT company from his university dorm room called, “clickthebutton.com” on the mainland. He got millions of dollars in VC funding and grew astronomically fast in less than a year. Cheyenne was not interested in running the company, so, once created he hired a bunch of people and he bailed out and moved to Maui where he lived in a killer little house on the mountain near Paia, where he got office space for me and another IT employee – Sonya, who coded.

Cheyenne had a few IT projects going on from Maui, Hawaii. As near as I could figure – I was to find new ways to place his shareware programs on other computers with drive-by downloads. The program downloaded to a computer even when the visitor just visited a site. Now, this was 2003, and what was allowed, and what wasn’t allowed – was always in dispute – but there were few laws about it. Cheyenne actually dropped software on internet surfers computers that scanned their computer for malware – and then told them if they had it. It was actually an amazing idea, but the implementation of it was obviously quite shady. On the other hand, many people – realizing they had malware installed, quickly purchased Cheyenne’s program to remove the malware. It was a win-win. Sort of.

Well, I tried very hard to increase Cheyenne’s reach with these apps. I worked 8-10 hours per day for months. I had many phone calls with him and some other staff in Wyoming I think it was. I usually felt like I was unable to do anything for the company because once I got something accomplished – Cheyenne had already moved on to something else – some other focus that became more important. I’d drop what I was doing and move toward that focus too.

Sonya, the only other person in our office was every bit as lost as I was. Or worse. The guys in Wyoming? They were all creating applications, so at least they had something tangible to work on. Cheyenne was a micro-manager that wasn’t available for days or weeks at a time as he ran around the world to Bhutan and other places. He was on numerous IT company boards and was trying to do (and doing) 60 things at once – always. He showed me his little T-mobile phone with QWERTY keypad and I watched as he banged out 50 words per minute – with his 2 thumbs. Not joking. He was running on high-octane JP-4 jet fuel, and the rest of us were drinking our vegetarian soy milks.

Cheyenne came back from a long trip and surprised us at the office. We hadn’t seen him for months. He fired me within 5 minutes and told me we had an agreement about severance, that he would honor – which he did. It was a bizarre, but well-expected ending to the strangest – most intangible, unexplainable IT job I have ever had in my life.

Last I checked, Cheyenne had a meditation business on Maui. I’m sure he is up to quite a bit more in IT though!

Such was my time in the IT industry in Hawaii. I am not a good IT employee. Never was. Never could be, I don’t think. I can consult – because those are short-term contracts where I can make a lot of changes and accomplish a lot – and get paid enough that it makes it worth it to me. I cannot, it seems – be employed in someone else’s company long-term.

There are IT jobs in Hawaii – you just have to put your resume out there and either they’ll find you or you’ll find them. There is a great need for IT professionals in Hawaii, but the rates are not always so competitive with mainland job offers.


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[Photo credit – flickr.com member, familymwr]