Ten jobs in five and a half years

Today is my last day at the company that I’ve been with for seven months. Earlier this month I was presented with the fantastic opportunity to run a small web-based software company. Elise, who is really excited about this opportunity for me, and upon my decision to accept the job offer asked, “So, what is this, something like your 10th job since Maly was born?”

She said this in a jovial manner, and I, of course, said, “No. This is only like my…” And then I saw her eyebrows rise as she watched it come to realization in my mind.

I’ve had 10 jobs in five and a half years.

1) The Drug Dealer

When Maly was born, I was running a small pharmaceutical-grade nutritional and wellness product wholesale company. This was a great job. My boss was great. He taught me how to run a business that maintained inventory. I managed a team who ran our fulfillment center, I learned strategies to cut costs, increased our margins, built a team who liked their jobs, kept our clients happy, grew revenue, and sold to pharmacists and physicians without having to get a boob job. I lost this job (and so did my entire team) when the company was sold to large pharmaceutical company.

The Dark Period

Then I entered a very, very dark period. Maly was but a few months old. I was happy to be a new dad, but having an infant added to the household made for some new stress. My dad died about a week after I’d lost my job. I was close to my dad and loved him very, very much. We had a new baby, my dad died and I was the unemployed breadwinner of our house. That’s why I call it the dark period. I was very isolated, confused and drunk.

2) The Organic Trail

A month later I was recruited by a little dot-com start-up in Austin. The owner was interested in me because of my accounting experience (I owned the P&L at my previous job). This job turned out to be three young adults working in the owner’s and her husband’s garage-turned-office (formally known as the husband’s mom’s apartment before she passed). One was hired for sales and advertising. The other for marketing. I was hired to manage ecommerce, financials and operations. What we all ended up doing was manually populating the website’s database with product photos and descriptions for $10/hour while our boss spent her days at Whole Foods and getting colonics. The economy and job market weren’t that bad at this point, so the three of us had options. I came into work on a Friday after having been employed for only 2 weeks. I politely and professionally told my boss that I just didn’t think the job was a fit for me and that I was going to pursue other endeavors. She was amenable to that and gave me a hug and an all-natural fiber cookie on my way out of the garage.

3) The Email Law

On my home from quitting the job above, I called my best friend in the whole world. I told him I’d just quit a job and that we should go get lunch and have a few beers. He asked if I might be interested in coming to work at the software company he was running. I didn’t have anything better to do, so I went to his office. It didn’t take long and I wound up working at this little software company. And we had lots of fun for a couple years, growing the client roster and revenue. Invariable the management structure at our company and at the parent company changed, and the overall company culture changed, and things just started getting ugly all around. It wasn’t a fun place to work anymore. We were losing clients and people weren’t happy anymore. I looked for another job and quickly found one.

4) The Spammer

I left my previous job to run the email program for a business-to-business lead generation company (a spammer). I was oversold (financially) on the job. It was a terrible job, but the coffee was really good. This company was listed on a world-renowned email blacklist, which completely shut down the facet of the business of which I was supposed to be in charge. After I started, the company was miraculously removed from this blacklist. And then 3 days after I started, they were blacklisted again (by nothing of my doing). It was a terribly toxic environment. Since the email operation was at a standstill, half of my team had to be terminated.

The Gray Period

Then I entered a brief gray period. A tree fell on my mom’s head (I can’t make this stuff up). So I rushed to her house during the middle of a Sunday night after she’d gotten stitched up and received a clean bill of health at the emergency room. Elise and Maly drove in the following morning so they could stay with my mom and so I could get back to my job. After making the long drive back to Austin, I was informed that my services weren’t needed any longer. I was effectively fired. That was a relief and a blessing. My boss was a tyrant and I was honestly fearful of my own and my staff’s emotional and physical well-being. I drove over to Starbucks after learning that I’d been terminated. Usually patronizing a Starbucks isn’t a memorable occasion. This time it was.

The Beige Period

Then I entered somewhat of a beige period. I had a lot of clarity, but I didn’t know what I wanted to do next. I couldn’t put my finger on what I wanted to do when I grew up. The creative juices were flowing. I did some soul searching. I read quite a few books. I enjoyed the downtime. I even wrote a hip-hop album that wound up being huge in Denmark.

5) My Own Business

I remember lying on the couch reading Jason Fried’s Rework, and that’s when I decided to try my hand at starting my own company. I worked 10-17 hour days for an entire month and started a little software business. I invested my own money (which was hard to do seeing how we were now living off savings and state unemployment compensation) and worked my ass off. And I had a total blast doing it. I was happy. I was motivated. I smiled and laughed a lot and sent screenshots of my software as it worked to my father-in-law and he said things like, “Wow! That’s fantastic!” and I’d pump my fist!

I started a software company in exactly 30 days. Three months later, I received my first sale. That, to me, told me I’d done it. I’d built something that was of value to someone else. That was, and still is, a great feeling. I’d never known a feeling like that (that I can recall) up until that point.

On October 17, 2011, my little software company turned a profit. It took me one month to build and less than a year in sales to be able to say that I started, own and operate a successful and profitable software company.

My “job” at the time was building Scrubbly, but I didn’t have an income. It was time to get real, be a man and support my family financially. I decided I wanted to try my hand at full-time, commission-based sales.

6) The Coupon Peddler

I don’t exactly recall how I came across the opportunity, but I was quickly and eagerly hired on as an outside sales representative for an Austin-based deal-of-the-day website (a Groupon competitor). It was a hot industry and I was ready to rock and roll and make gobs of cash. Come to find out, deal-of-the-day group buying coupon sites are a dime a dozen in an already overly-saturated market. Before even making my first sales call, my colleague told me she was on her way out the door the moment the next opportunity presented itself. She was already tapped out in her short-lived online coupon-peddling career. That wasn’t very inspiring or motivating. But I thought, “with one less sales person, that means twice as much business for me!” And then I learned that the competition required exclusivity in their contracts. I couldn’t work with a client who was already working with Groupon or Living Social. And Groupon and Living Social had already swept the nation. The only local client I could go after was Bubba’s Fresh Dead Bait and Discount Tanning Salon, and I just didn’t want to do that.

7) The Host

I don’t recall how I came across this next job either, but I was quickly hired on with a local web hosting company. My boss and I hit it off immediately. We met for barbecue at Rudy’s one afternoon and chatted for hours. He was like the father figure kind of boss and I liked him a lot. He was really leaning on me to drum up some new business. I think he was really leaning on me because he was having a really hard time drumming up new business himself. Neither of us had much luck generating an even lukewarm lead. I could sense that my boss was on his way out, and being a commission-only sales guy meant that I had absolutely no cash coming in until I sold something. And even then, it would take many months before I could build up enough residuals to cover my family’s expenses. I had the come to Jesus conversation with myself and realized that I need to get a real job with a steady salary and health insurance.

8) The Association

My father-in-law, who lives in Des Moines, IA (which is a French word for the Moines) has always touted a vendor that he’d used for a couple years. This software company provides database-driven websites and member management for non-profits and associations. They’re a really great, stable, profitable, service-oriented company and it seemed like a good place to plant myself. I looked them up and, sure enough, they were hiring. I submitted my application, was told that I was overqualified for the job I was applying for. I told them, “I don’t care, I want to work here,” and a week later I was sitting in a cubicle. And they even brought in kolaches on my first day. The people I worked with were great. Even the people I didn’t work with directly were great. The handful of clients I interacted with were great. The CEO knew everyone by their first name and he liked me. Everyone was just great. But I was bored out of my ever-loving mind at this job. I was hired to populate databases (again). I don’t know how I’ve managed to get myself into two database-populating jobs in less than five years. I’m not even a database kind of guy.

After around a month, I decided I was going to put some kind of plan into action. I really liked the company and the products & services that they provided, I just didn’t enjoy my particular job. So I started poking around internally to see if there might be another part of the company in which I could work. I’d also started putting my resume back out there and I let people know that I was casually looking for work. I began a correspondence with one of the Vice Presidents at the company and we were finalizing our plans to get together and put me on a path that would enable me to not only have fun at my job, but to also make a direct contribution to the growth of the company.

And that coincided with another conversation I began having with the CEO of the company that I’m leaving today.

9) The Agency

Over the years, both professionally and by my own personal doing, I’d gained valuable experience and knowledge in online marketing. That boded really well for me with this small agency that specializes in affiliate marketing. During our first phone conversation my boss asked, “did you read the job description?” to which I said, “of course! It’s right up my alley.” He then said, “You know you’re way overqualified.” And I told him that I didn’t care. I wanted to work there. It was a small company and I envisioned lots of room for me to grow. So he hired me just as he was moving to Austin to open up a new office. It was great timing. The company had previously been a virtual one with ~25 employees scattered about the U.S. I was going to be employee #1 at the company’s new home in the heart of Texas. I helped open the new office and hire the next 5 employees.

The job was great. The people were awesome. I really valued the work/life balance that I was afforded. All-in-all, I was happy, but I didn’t feel like I was doing much for my own personal and professional growth.

Then one morning I got a phone call from a friend. He said, “I have a buddy who needs someone to run his software company. I recommended you. You should be expecting a phone call from him.”

10) The New Job

I start that new job on Monday. On Halloween. It’s the job that I’m the most excited to take on since receiving my very first job after graduating from college over a decade ago.

Ten jobs in five and a half short years. I’d always thought that I’d grow up to be like my dad; that I’d graduate from college and work for the same company for 30-some-odd years.

My, how times have changed… and how I don’t really know any different.

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