I was talking to one of my former bosses tonight on Facebook and it just reminded me of some of the craziness surrounding the time when I worked for him. I have many stories about working there, but a few I’ll definitely have to keep to myself.

I was around 22 when I started working at his small Media and Advertising Agency. He only had 3 other employees when I started. Actually, I was never really hired. I just showed up with my laptop one day and just started making ads for some of their clients. I worked afternoons at Wal-Mart, so I went in there from 9-3 beforehand. After a few months, he started giving me a paycheck. And it was the most money I had made to date. I eventually was able to quit my job at Wal-Mart.

I was extremely happy to finally have a job related to computers and design. No more Wal-Mart, no more customers. It was exciting times. The company was on the bottom and we were moving on up. We had a perfect location next to the bank, post office, restaurants and bars. Everything was a quick walk away, and in 2002, banks and post offices were still relevant. If my friends and I decided to go out, we could always swing by the office at 2am, watch some tv and sober up a little.

Although things were good, the company experienced growing pains very fast. On pay day, the sales manager would race to the bank to deposit ad sales money before us, the production guys could get there. Even then, it was the luck of the drawl to see which one of us wouldn’t be able to cash our check. Eventually, the other two guys moved on. I hung on until the end, but at least I didn’t have to worry about bounced checks… for 2 months.

Ultimately, the salaried sales manager was sucking up the profits. He couldn’t keep his sales guys producing, so no money was coming in. In a last effort, the guy took payroll one weekend to a cas ino to try to save the company. Just like in ‘Empire Records’, he failed. I still remember that guys name.

I held on for a few more weeks, hoping I could help turn the company around. I got a new job at Kinkos to pay the bills, but I really wanted this company to succeed. I think I realized it was the end when I came in to work one day and my boss asked if I could help him move. When we had everything in my truck, I asked, “Where to?” and he replied “Back to the office”. Yes, my boss got evicted from his apartment and needed to move all of his belongings into the office. I actually stopped going in after that. I lost contact with him for about 2 years, thinking he would be homeless not too long after.

But, we did find each other a few years later. He is an idea man, and we always try to bounce ideas off of each other. It really is too bad things didn’t work out for us back then, because I think we could have had a great business today, 12 years later.