Tiny Startup Camp

A tiny camp for making tiny startups.

November 10-11, 2012
Portland, Oregon

Free Ticket to TSC for your Best Boss Story

So, part of the allure of creating and running your own company/startup, is being your own boss. I’ve been my own boss on and off again for over 5 years, and non-stop for over a year and a half. It’s great. But whether you are your own boss now, hoping to be someday, or are starting next week at Tiny Startup Camp, we all have fantastic boss stories.

We want to hear them. And in our eternal gratitude, we’ll be offering up a free ticket to TSC for the best story. Hell, maybe even two tickets if the stories are good enough.

So, let us know in the comments you favorite boss story. They can be nice stories, terrible stories, stories of you quitting, stories of you pranking your boss, or stories of the words that came out of your boss’s mouth that made yours drop open. Enter as many times as you have stories.

Here’s one of mine.

One of my first professional jobs was working at a small car magazine. And over the course of the years, we’d taken and collected thousands of photos of amazing, old, classic cars. From photos of a 1964 Aston Martin DB5 to thousands of Corvettes, Ferraris of all years, and cars I’d never heard of that only had 2 in existence. The owner of the company loved this amazing database of images, and wanted a rotating display of all the images on a TV in the office. Now, keep in mind this was before LCD TVs, and so we had a big old 30-some inch CRT TV with a crappy VGA to RCA connector pushed from an old XP desktop publishing and rotating the images at all times in the office. It was cool, but not high def.

One of the problems with the database was that it was anything but organized. Hundreds of nested subfolders sorted by date, but not by the car type or make or model. So, we just used a image screen saver pointed at the top-level folder and told it to show random images. Which it did.

Now, when I left the company things weren’t at their absolute best between me and the boss. Nothing terrible, but we both acknowledged it was time for me to move on. It just so happened he wasn’t in the office on my official last day, so I did what any guy would do on his last day; saying goodbye to friends, and generally not working but packing up slowly… and I bought a six-pack of PBR.

After a few of said PBRs, I decided it would be fun to take a picture of me in every person’s desk, feigning that I was working hard at their computer/office, and taking a big swig of PBR in the process. 20 pictures later, I completed my tour of drinking.

Now, the fun part. I masked each of the photos’ names to match the naming convention used in our database, and went about littering the 50,000+ image database with my photos of me drinking beer in the office. I placed them all over and into the nested of nested sub-folders. I knew that these photos would never be found (keep in mind, at the time in this company, if something had a power cord, it was my job to fix it. Nobody there would ever have thought to do a search of the files sorted by date to find all my pictures… I just knew that was never going to happen).

SO, even now, years later, that database of images rotates through on a much nicer HDTV in their current office, and every once in a while, more often than you’d think, a picture of me on my last day, drinking a PBR and sitting in the boss’s chair pops up between Bentleys and Alpha Romeos, to remind him, you can fire me, but you can’t forget me ;)

your turn.

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  • e valentine

    I have about four jobs at any given time but one that I had for several years took me deep in the bowels of one of southeast Portland’s charming, two-level, brick, K-8 public schools. Though I am an educator, I moonlighted at this particular site just to help with the afterschool programs run by the city.

    My boss had been with the city for years and was nearing retirement. Now, in many respects, he was stellar at what he did, which was running afterschool programs: he hired some of the best teachers doing after school classes; he could remember which students attended what class ten weeks running.

    What he coudn’t do was anything tech-related. Anything. So, I quickly became the resident troubleshooter, tech support, InDesign expert, and Excel guru. Not because I am an actual expert at any of these things. It’s just that he was…not. In fact, he seemed absolutely impervious to any of technology’s allure. I can’t remember how many times he would get around to mentioning how exasperated he was by ‘how much’ his could wife check her email (which was, by the way, almost every night. In my world, once a night? That’s some sort of record.) But I gotta give the guy some credit. I mean, he was still able to get away with buying a cell phone that had prepaid minutes. He only needed about 100. A year. That’s impressive. And yup, I helped him buy it.

    Though I have plenty of stories about my time there, a classic moment was when he asked me about access to his Gmail account. See, sometimes my boss would ask questions about different things he had read on Yahoo or Bing (e.g. the newest Mac rumors, cloud technology, trends in online education). I didn’t know if this was one of those times. I mean, a question about access to Gmail? I was surprised he even had one. Maybe he was concerned about two-step authentication or he was trying to get his city email forwarded. But then, I watched as he proceeded to open up Internet Explorer, use the Bing search bar to type in “Gmail,” and click on the link on the first result page. “There’s gotta be a faster way to do this,” he said.

    So, I helped the guy. I showed him how to eliminate his extra steps. I explained about bookmarks (he had these, but he just didn’t think to create a new one). And his profound and sincere gratitude was almost as classic as the question itself.

    In a recent episode of “Parks and Rec” (which, ironically, is the city bureau my boss and I worked for), Aziz Ansari’s character is going through internet withdrawal after his court-mandated screen-free week. He catches a glimpse of his co-worker, Jerry, checking his email: “…When you check your email you go to Altavista and type, ‘Please go to Yahoo.com?’…God Jerry, you don’t deserve the internet!”

    My boss had the internet. He just didn’t get it.

  • B Rogers

    In 1994, I was working in one of New York City’s five boroughs as a children’s librarian for the public library system.

    I had only been on the job for about 6 months, but was almost immediately witness to a department manager that systematically created a great deal of artificial conflict between those she managed. She also took great pride in mediating those conflicts that she was, in large part, responsible for creating. There was also a mix of personal insults, unpaid overtime after it was approved, verbal instructions that were completed/followed that resulted in written reprimands, and other abuses experienced by all that worked in that department.

    In my first six months, turnover in the department was nearly 100%, as new hires would simply quit (or be fired) and seasoned veteran librarians would transfer out to other departments.

    Each year, the librarians and staff had to be recertified in a number of policies (e.g., inclement weather, security, sexual harassment). An all-hands department meeting was scheduled so that we could review the policies (my first review of them beyond my first day orientation). The department manager had asked if we had each read through the various policies, and wanted to know if we had questions about any of them. A quick review of changes in policies was discussed, and we were again asked if there were any questions. The policies were straightforward, so there were no questions.

    The department manager then said she wanted to “spend a little extra time” discussing the sexual harassment policy, and asked if I had read the policy.

    I said that I had read it, then she requested that I read it to everyone aloud. I said, “I’m sure everyone can just read it on their own.”

    Her response went something like, “Well, as the only male in a department with thirteen other women, I think it’s a policy all of us would like you to be particularly aware of.”

    I said, “I’ve read it, and I’m particularly aware of it, as I think you just said something wildly inappropriate in light of it.”

    I left the room, and went back to work. I was later fired for insubordination. No details were given beyond INSUBORDINATION.

    Three days later I was working for a startup company, and my career as a writer and content developer was under way. Six months later, the department manager retired early.