Treasure Island & The Side Hustle (2)

Treasure Island, 2018

A good side hustle must have a myriad of benefits; lucrative pay, flexible hours, and unique perks. The monthly Treasure Festival on Treasure Island provided all of these.

Even then, I knew that I would forever be changed by my experiences on the island and my days there would remain with me forever. Treasure Island was under construction and I became a part of the transformation and watched as the old crumbled and the new formed. For eleven months I drove the winding road off of the Bay Bridge down to the streets along the water.

Treasure Island had such a strange vibe at that time. Demolition crews worked to dismantle what was once a Naval Auxiliary Air Facility. The Air Force base had been built in 1941 serving as an air station during the war. Once useful and dignified it had succumbed to disrepair since its closure in 1991. In the years since development had became political and progress slow.

Many of the buildings were condemned with broken windows and paint so weathered to be almost nonexistent. In contrast, along the water tents and food trucks with portable grills and ovens sold food from every ethnicity imaginable. People gathered in the sunshine as a live band played on. Children danced in the streets as I walked through the crowds of people. I secured gates and stood at the vendors entrance where the food trucks parked. I talked to approximately 1,000 people per day. I wore my yellow fluorescent vest, a hat and sunscreen on my face and hands.

At four o’clock I would open the gates and begin directing traffic. As I stood at my post I could look out on the water and the distant cities of the Bay Area and think there is no place on earth more beautiful.

I worked two days per month. Every time I was there it was different and so was I. Boarded up buildings were demolished and sitting in a heap of rubbish. Entire blocks were bulldozed. Sections that were there the month before were corded off and entire streets disappeared. I was also changing. I willed myself to change, to catch up, and grow into my own life.

I had left my full time career in technology when my second daughter was born. I started a consulting business and worked part time doing small projects like websites and newsletters. Every few years I would return to my roots as a marketing consultant picking up full time contracts with Wells Fargo, Bank of the West, or other start ups. I would work short term contracts of three to six months. I had not worked a permanent full time job in 16 years. As a skilled project manager and technical writer I could have returned to this work. It would have been the easy way out, but instead I started a company and Ocean SF was my baby. Starts ups are difficult, but I had no idea how difficult.

I knew if I returned to corporate marketing I would remain there and Ocean SF would be a dream conjured on a sailboat and nothing more. I had been a dutiful wife, I had been a dutiful mother, and now it was time to be the person that I had always intended to be. The road ahead was treacherous in the same way Treasure Island had its shadow side. Crime was rampant on the Island, and not in a small way, it ranged from car break-ins to murder. My role as a security guard felt as improbable as raising 1.25M to fund an outdoor clothing brand. Yet, during that year I began both.

On my lunch hour I was reviewing my website with my drop ship management team. I stayed off my phone during my work hours as this was the type of job where you had to keep your head on a swivel. I took my responsibilities seriously; never taking my eyes off of my gates and the entrance I managed. Every half hour I would secure my parameter. This felt natural to me as my father was military and I believe we carry in our DNA inherited natural abilities. I stayed alert and got to know my coworkers, vendors and the many people who passed through my gate.

When I looked for my first side hustle my number one criteria was that it not involve a computer. As a writer and business owner I spent much of my life behind a screen.

The atmosphere at Treasure Festival was the perfect antidote to my grief and isolation. My husband had died fifteen months before leaving me in a precarious financial situation. I took on the Treasure Festival job, work in a distillery, and worked for a catering company serving food and washing dishes.

When I closed my first angel investment of $50,000 I did it sitting on the bathroom floor of an industrial kitchen in Oakland. I was wearing a rubber apron and peeled off my rubber gloves to answer my 11:00 a.m. conference call. I put that money in the bank and worked the next fourteen days straight washing dishes, serving at wedding receptions, bottling Gold Bar Whiskey and working at Treasure Festival. That was my fourth month on Treasure Island.

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