10 Years at Directive

This month I celebrated my 10th year working at Directive. Since this is my longest commitment to anything, I figure I’d reminisce on a few of the milestones and lessons I’ve learned. It all started, surprisingly, about ten years ago…

It was May, 2007. I lived in the Town that Made Pepto Bismol Pink. I had been seeing a few jobs at the time; we’ll call it “working around.” Nothing serious – it was totally casual. Being a college graduate in Norwich, New York put me at a disadvantage – I was a slice actual pizza in a world of Little Caesars and it made employers nervous. It turns out I was overqualified to stock shelves and wrangle shopping carts and nobody wanted to sign the checks for someone with those college smarts. I turned back to Oneonta, hoping that my diploma would have more value there.

I had been selling Rainbow Vacuums door-to-door for a couple months. Then I spent another month working at a really shady electronics store that was already in the process of going out of business and needed to offload a bunch of outdated rear-projection, standard-definition, big screen televisions when everyone else was already buying LCD and Plasma in HD. I didn’t know what I wanted to do, but practicing annoying sales-pitch tactics gave me some semblance of perceived confidence while standing around an abandoned sales floor listening to Madagascar play on 40 TVs on loop all day gave me time to brood.

At night, I would work on self-employment ideas, ranging from photo editing services to drawing webcomics. My parent’s home wasn’t very conducive towards anything like that; my mom consistently urged me to get a job as a bank teller or a packer at the dog food factory. To be fair, she didn’t know how a graphics art degree was going to pan out as a career for her oldest son, but fully supported her youngest when he announced his goal to become a dolphin trainer in upstate New York and run a roadside ice cream stand on the side. I wish I were making this up. No, instead I’d work on my computer until 2 in the morning, trying to come up with cases as to why one would want to get their photos retouched. My mother would barge in and accuse me of doing drugs because that is what people who use the computer in the middle of the night do. This is taking me back to a really dumb place, so let’s tread further along.

With a stack of resumes, I was leaving my name all around as a guy who could basically do anything on a computer. This wasn’t true, but I was naive enough to stand behind that claim. I did know my way around; I knew how to build and maintain a PC, and I figured anything else could be faked and Googled (which I’ve learned since is 100% accurate). To get interviews, I used the same processes I developed selling $2000 vacuums door-to-door. I put the pressure on my follow ups and I was consistent. I’d drop by businesses every few days, check to see if they had a chance to look over my resume, and ask if they had any questions. Looking back from the perspective of someone who plays a role in hiring employees, I was an annoying little shit, but even annoying little shits make an impression.

One business I was interested in was a print shop in Oneonta. I had walked in to drop off my last resume, but something was going on with the staff, and nobody was available to help me. Next door, in the same building, was another company, and it wasn’t clear by the logo or company name what they did. I did a quick Google (well, back then using a smartphone was slow and arduous, so it wasn’t exactly quick) and found out they were an IT company. I dropped my resume off, got a call back, and got a job as a level 1 technician with the idea that I’d get my feet wet with some web and graphic design (I had examples of comics and digital artwork). My IT experience consisted of building my own computer, troubleshooting when things went wrong, and fixing the computers of friends. I did have a weekend job being the tech in the 40 machine Mac lab that other computer art majors used, but honestly all I did was watch anime on the 322 inch projection screen and post on my LiveJournal.

And the rest is history. Ten years ago I started working at what was called DTi at the time as a guy who swaps out power supplies and network cards. I was one of four employees.

2007, As a Level 1 Technician

I have a lot of interesting stories from this era of my career, mostly involving blocking porn, accidentally coming across porn, and removing that certain flavor of malware that only seems to come with porn. One of my first on-site jobs involved taking a big box of printer parts (fusers, actuators, motherboards, and who knows what else), and replacing them out of a network printer until it worked again. Maybe that sounds more complicated than it was, or I’m just really good at winging it, but that thing was ready to spit out a hundred copies of War and Peace when i was done with it.

I learned to deal with people and keep them in the mood I wanted. Things can go wrong, and good news isn’t always going to be doled out. Sometimes you need to accept it, keep moving, and not be afraid to get out of your comfort zone.

Recap of the Stuff I Did:

  • Checked to make sure things were plugged in and powered on
  • Swapped out computer components
  • Removed viruses and malware
  • Configured desktops, laptops, network printers, and other office equipment
  • Managed and monitored backups
  • Ran Cat5 and DB9 wiring
  • Figured out how to get the Windows 98 Second Edition Dangerous Creatures theme to work on a Windows XP machine (that’s a long story)
  • Some very light Windows server configurations


2008, As a First-Time Web Designer

I didn’t learn a lick of HTML in college. There was no formal course at first, and once there was one, it was already pretty dated. I learned the most messing around with the back end of my various blogs, so to say I knew what I was doing was a farce at best.

Fortunately, I was able to start small. We weren’t designing a lot of new sites at first; instead we were just making minor tweaks and performing SEO on old Microsoft Frontpage-based sites. I suppose they weren’t old at the time, I’m just dating myself. This opened up a whole world for me, and while I’d never get super fluent in HTML or CSS, I quickly got comfortable with it enough to make changes without breaking stuff. I fixed broken javascript, built little microsites, and learned how to clean up all the junk code that Microsoft Word vomits into an HTML file when the client tries to use Word to make changes to their homepage.

I played around with content management systems; Expression Engine, Drupal, WordPress, and Joomla. I messed around with web-based desktop environments. I got a chance to play with e-commerce systems, blogging platforms, cpanel, and even industry-specific platforms. I also had the opportunity to experience working with people who had great ideas (and with that, some pretty cheeseball ideas). There is a lot to take from the experience of convincing a paying customer that their logo doesn’t need to take up the full width of their browser, or that they probably don’t need to put a bunch of random flash games on a vacation rental site.

This was about the time social media platforms started to become a viable outlet for businesses, and I built out presentations and materials and other resources on how small businesses could leverage Facebook and Twitter.

It wasn’t long before we started to grow. I was helping us expand the web design side of the business, and all the while we were switching IT models from a traditional break/fix support model to a Managed Services Provider (MSP). For everyone outside of the channel, the difference is break/fix waits for a customer to call with a problem and then charges to fix the problem, where an MSP charges a monthly rate to keep computer problems from happening in the first place. The MSP industry was still young, but IT companies were quickly jumping into this more proactive, recurring revenue-based model.

Recap of the Stuff I Did:

  • Used Front Page to barf HTML span tags into websites in order to make changes to the words on the page
  • Used Microsoft Expressions to barf HTML span tags into websites in order to make changes to the words on the page
  • Assisted in the design of, and project management for a handful of websites (we were launching about 1-2 per month)
  • Learned Joomla, WordPress, ExpressionsEngine, and several ecommerce applications
  • Wrote website proposals
  • SEO’d websites
  • Wrote the book on Facebook and Twitter marketing for small businesses before everyone and their mom was calling themselves a “Social Media Guru” in their Twitter bios.


2009, As a Director of Business Development

During our growth in 2009, my position changed. My focus shifted further away from tech to and more exclusively towards the marketing side of things. We were focused heavily on making it easy for our clients to switch over to the proactive MSP model, and we had a developer working on building an integration between our new website and ConnectWise (a system many MSPs use to manage clients, support tickets, and billing). This is where things got interesting. The integration was leaked at a ConnectWise peer group and it was very well received. We quickly named it, commercialized it, and went viral in the IT/MSP Channel.

Website projects were coming in faster than we could build them because we filled a major need for IT companies that use ConnectWise. We worked on projects for channel vendors as well, ConnectWise included. These few years lead to a lot of growth, and there were many lessons to learn. There was stress to overcome, all-nighters to trudge through, and mistakes to learn from.

I did a little bit of everything during these years; SEO, project management, consulting, content writing, social media marketing, web design, web development, PR, and even sales. Somewhere between all the challenges and the variety of responsibilities I had, I gained a serious consciousness. Not that I took myself too seriously – that would be a messy suicide. No, instead I started appreciating hard work and the results that came from it when you started to figure out what you were doing.

Recap of the Stuff I Did:

  • Pulled many all-nighters
  • Found unconventional ways to consume caffeine (caffeinated hot chocolate!)
  • Once went temporarily blind from stress (or maybe caffeine consumption?) but it only lasted about 7 minutes and hasn’t occurred since.
  • Helped develop a service around establishing a strong social media presence
  • Storyboarded and starred in a music video that people in the IT channel talked about for years (sadly it’s been pulled from YouTube)
  • Gave webinars, lunch and learns, and presentations to local business owners
  • Worked my butt off


2010, Causing Mayhem

By now, it was clear that we couldn’t build websites fast enough for people who wanted our ConnectWise integration. On top of that, building a great website, even with a content management system, was extremely complex. Sticking with standards and constantly changing best practices and quality controlling the hundreds of thousands of little moving pieces was a bear, and we didn’t want to make it cost prohibited. Partnering with other companies to handle the websites while we focused on the integration wasn’t panning out, so we decided to roll out Project Mayhem.

Project Mayhem was designed to be the ultimate website for IT companies. The goal was to have everything an MSP would possibly need for their website baked into a customizable, easily deployable package. New websites would no longer need to wait months for content or picking a design or prototype phases. Each site would be standalone and easy to deploy on virtually any host. Most importantly, each site would be fully customizable and easy to manage through Joomla, while we handle the back-end maintenance.

This was another huge win, and we were rolling out websites rapidly. I had written the content, built most of the processes, and in no time we were launching more websites in a month than we were able to in a year just a year before.

Our notoriety helped us go viral and fill the pipeline. Channel vendors flocked to us. We had to announce a temporary client freeze at one point, and it still didn’t slow the sales. We weren’t perfect back then and still had a lot to learn, but despite all that, things were exploding.

This become most evident to me when we attended Joomla Day in Washington D.C. Joomla (an open source content management system – think of it like an operating system for managing your website) had a very large community even back then, and held events for developers and Joomla users to meet up. There were panels, courses, and presentations by developers who we recognized just from using their software. What stood out was when the President of Open Source Matters (the non-profit behind Joomla) gave up the podium for his panel to our CEO so we could humblebrag about what we were doing with our integration (which was already turning into a marketing automation platform) and our website rollout processes. I realized how much we rocked, and how we had answers for challenges that others were just recognizing.

Recap of the Stuff I Did:

  • Built the ultimate prebuilt website for our industry
  • Managed projects
  • Build and enforced processes
  • More webinars, sales, and proposals than I’ll ever be able to remember
  • Went to Joomla Day DC in 2010, came back with a big head
  • Ran breakout sessions for IT company owners about marketing and social media
  • Started writing IT industry blog content that would eventually be used by hundreds of companies


2012, As a President

During our Christmas party at the end of 2011, I was named President of Directive. What used to be three other people turned into a team of several dozen, celebrating our growth and prosperity with steak and tequila. In just five short years we went from being a local mom-and-pop computer repair company to a multi-headed beast.

It wasn’t always perfect. There were hardships. There were conflicts. There were stressful days and angry emails, incompetence and betrayal, and hardest of all, customers that just couldn’t be pleased. Despite all of that, for the next several years, hard work and an eagerness to take on more proved to make me happier and more fulfilled.

Even though I had new responsibilities, I found it very rewarding to roll back my sleeves every so often. Writing content, planning marketing campaigns, and light front-end website stuff remains a nice little outlet when I can fit it in. I was still doing a lot of sales and consultation, but left the HTML and CSS to those were far less prone to breaking things. Although I miss the smaller, quick-fix achievements, I’ve learned to appreciate the accomplishments of my team almost as much.

I’ve always felt that a leader should get the last pick from the box of donuts. Take care of the people under you first, then worry about yourself. Although I’m not always the best listener, especially when I’m extremely excited about something, I am very empathetic. If you can sate someone’s emotional bank account consistently, it’s much easier to present hard truths when needed. Through encouragement, respect, and honest admiration, a leader can build a buffer that dampens the blow of Messianical rabidity. These days, I think folks call this radical candor. I wish I had known, I would have written the book on it.

If you were to ask me, without warning, what keeps me motivated, I’d probably say something like “I built this city,” but there’s more to it than that. I’ve still got much to learn and figure out, and I think, beyond all else, that’s what keeps me so engaged. That doesn’t mean I’m infallible, and don’t need a long weekend and a skin of wine every so often, but to me, a big part that I enjoy is knowing that I can always keep tweaking the dials.

Recap of the Stuff I Did (and Still Do):

  • Helped establish and maintain company culture, which, as it turns out, some people just don’t like being happy. Life lesson.
  • Edited and helped write thousands of blog posts
  • Drew a monthly single-frame comic for the IT industry
  • In 2013 I was put on a list of the world’s top 250 MSP Professionals by MSP Mentor
  • Wrote content used by hundreds of businesses
  • Wrote the IT playbook for business owners and CIOs
  • Wrote lots of scripts for videos
  • Helped write marketing campaigns and consult businesses on their marketing
  • Performed all kinds of fancy-pants administrative stuff
  • Constantly strived to drive people to be the best they can be
  • Never took myself so seriously that it compromised who I am
  • Very rarely was a dick

It’s been a wild decade, and I’m not done yet.



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