Surreal can't even begin to describe my first dev job. I'd never tell this story IRL, but this is an anonymous account so why not.
I was broke, living in a roach infested hostel in Waikiki after buying a one way ticket to Honolulu to surf, bum around, and not a whole lot more. Things had worked out great so far... until the money ran out. I was about a week from being homeless and living on the beach. Fortunately my brother was with me, and he had ended up landing a job as a tour guide for one of the big tour companies on the island. It so happened that the company was also looking for a web developer at the time, and my brother knew I had done a few small freelance projects in the past, so he recommended me to them for the position.
When I showed up for the interview, there was no white boarding, no engineers to talk to. At a small office in downtown Honolulu that also served as their tour bus depot, I met Diego, the Cuban-Hawaiian owner of the company, who was in board shorts and a t-shirt watering his banana plants. He took one look at me and hired me on the spot. Why? I had no idea at the time. But I'd find out soon enough.
Diego was obscenely wealthy. But Diego also turned out to be a swinger, and he and his Latin pop star wife had taken a real liking to me. What followed was a whirlwind of insanity. In between learning to write Javascript and PHP while working on our websites during the day, I was having wild threesomes, flying to Miami to stay in 5 star hotels, private flights to Maui and Kauai, staying in mountainside mansions overlooking the island, and generally living an absurd lifestyle. We ran practically every tour you could do on the island, and it was all free for me, so that meant beach houses to stay in, SCUBA diving (I ended up getting certified during that time), island excursions, every activity you could imagine. I even logged about 20 hours of flight training in the company plane.
We embarked on a complete rebuild of their reservation and online booking system. I knew nothing but a bit of HTML and CSS, but figured I could fake it and learn. The team consisted of myself and a couple of senior developers who had been contracted from the mainland. Our "office" was a converted attic above the bus garage. I didn't realize it at the time, but we were actually doing serious multimillion dollar e-commerce revenue. And I was able to save him a ton of money by switching out our payment provider on the fly during an outage of the existing one.
It all ended up going down in flames as he was, of course, an insane person. I was living in a high-rise apartment in downtown Honolulu that they had rented for me, and Diego flipped out after finding out I'd had other women up there. After he chucked my brand new fully loaded i7 MBP out of the 20th story window in a fit of rage, I knew I had to get the hell out of that situation. I bought a plane ticket to San Francisco, landed my first "real real" dev job, and the rest is history. Diego ended up getting taken down by a class action sexual harassment lawsuit filed by a raft of other employees, and forced out of his business. But I never held any ill will toward the guy, he was just a total nut.