The last couple of weeks have been odd—a mix of relief but also bittersweet. It's hard to leave behind a group of people you admire and enjoy spending time with. But I was also surprised at the amount of relief I felt when my time at ActiveCampaign ended. I guess I was carrying around more discontent than I consciously realized.

Regardless, it's been odd. I have had so much less to do, yet find myself busier than ever. Part of that was due to be my wife spending her annual time in Arizona with her folks. Even with older teens capable of doing so much for themselves, there's still a significantly higher workload caring for the home when one of us is away. And winter has not helped as February has brought more snow than the previous two months combined.

In all that activity, activity happening away from a computer, I've had a good chance to reflect on my last 20 years of working. And what kept coming up again and again is the people. My career truly has been blessed far more by who I know that what I've learned. And so I wanted to go through an exercise of recalling just who all the people were.

The timeline

Northern Health
I graduated college in 2003 and was immediately into the workforce. My schooling included a co-op program, so I was able to get right into some contract work at a company I worked for during my schooling. A nice option to have!

It only took a few months from there to get a full-time position at our local health authority as a member of the IT department. I followed a usual progression there, starting with telephone support, then desktop support, before finally getting into a multiyear, multi-million dollar project and doing more systems analysis and application support work.

But it didn't take long to grow tired of the grind and cyclical nature of a large, government-run enterprise. There are a lot of politics that make working at larger organization frustrating, so I found myself wanting something different.

Fusion Ads
During my 6 years at Northern Health, my wife and I had 2 children. Somewhere in that time, I started to dabble in web design and created a website for the grandparents to see pics of our kids (this was before Instagram and Facebook, even before Flickr). So I spent some fun years learning HTML and CSS.

It was also a time of appreciating what was happening with Apple and I eventually picked up a used G2 tower. I started reading blogs like Daring Fireball and Shawn Blanc and knew I wanted to—somehow— get into this space for my work. And two things truly led to that being possible: 1) starting my own blog (on Wordpress) and 2) Twitter.

I can vividly remember writing out 2–3 blog posts for my new WP install, then emailing Shawn about a typo in one of his articles. Seeing the domain of my email address, he must have checked out the site and subsequently linked to one of those first posts. All of a sudden, I had blog visitors! And I wasn't even ready for it.

That link from Shawn, as well as Twitter, led to some amazing relationships that eventually led to Fusion Ads. A business idea from a then 15 year old Michael Mistretta from the other side of Canada (his mom had to sign all our legal papers on his behalf as a minor). And a couple of months after launching that business, Loren Brichter asked if he could carry our ads for a free version of Tweetie for Mac. After that, the business took off and we had a fun four years.

Running Fusion was an amazing experience where I was able to talk to so, so many designers, developers, and publishers that I had spent the last 3–4 years following. Designers like Sam Brown, Tim Van Damme, and Elliot Jay Stocks. Bloggers like Shawn Blanc, Michael Lopp, and Rian van der Merwe. Fellow Canadians like Adam King and Pat Dryburgh. And best of all, brothers in Christ like Andrew Austin and Christian Ross (and a whole lot of others).

Some sample ads.

There was an almost sale (long story) to the Bold crew, where I got to spend some time learning how to splice PSDs and write front-end code with Noah Stokes, Garrett St John, and Sam H.

At some point, I did some freelance writing for several of Shawn's sites like The Focus Course, Tools & Toys, and The Sweet Setup. I got to meet Isaac Smith, Shawn's first direct hire and one of my best online friends (and hopefully, one day, IRL friend).

Why did we sell this business? Well, it was stressful … especially after Twitter bought Loren's business and with it, all the versions of Tweetie. But the ad business also felt like a race to the bottom, Michael was heavily invested in a Christian internship and pretty much out of the running of the business, and we all felt it was time for a change. We got a good offer from Todd and the Buy Sell Ads crew, and we knew it was the right time.

But it was an amazing journey that changed my career forever.

Campaign Monitor
After selling our business, I did some consulting at a local business while I considered my options. This consultancy had one major client and that was my old employer, Northern Health. It didn't take long for me to remember all the pains of the corporate life, so I decided to pursue full-time employment in the SaaS world.

And it was relationships with customers from Fusion Ads that helped me in this capacity. A lot of these companies used Fusion while they were still small or early stage, so I would communicate with a lot of co-founders. One of those was Dave Greiner, who co-founded Campaign Monitor. I eventually took a position there on the customer support team. And it was my first introduction to working with a larger remote team.

The culture and camaraderie at Campaign Monitor was fantastic. Most of the support team was remote, so we were a tight knit group that really loved working together. 10+ years later, I still talk to some of those folks regularly. Mathew Patterson (aka Mr Patto) was an excellent team leader who taught me a lot about what a people-first business looked like.

It wasn't perfect, but it was the best environment I'd worked in. But, after running bootstrapped for 10 years, the team took a massive funding round and things started to change. As well, it wasn't an environment where there was opportunity to stretch into different roles. And while I love customer support, working in the inbox/queue day after day can be tedious. So I stated to look for opportunities where I can focus more on the proactive side of the customer experience.

Along came the Director of Customer Success role at InVision (then CEO Clark Valberg was another founder who used Fusion Ads in the early days). This was a completely different environment, VC-backed and high pressure.

Suffice to say, it was a short six month stay that did not go as I expected. I believe the non-disparagement clause I signed has expired by now … but I won't go into details. But let's just say it was quite the opposite of a people-first environment. There were a lot of talented folks there who had success, but also a lot of talented folks whose experience was similar to my own.

In the long run, it was a good thing because it led to my next stop.

I still remember as I was in the middle of a job search, my good pal Christian Ross mentioned, “Have you considered Beanstalk as a place to work?” I was in the middle of the hiring process with companies like GitHub, Automattic, and Craft, but I had somewhat forgot about Beanstalk (and Wildbit, the company behind the product).

And guess what? Just like the previous two stops, Chris and Natalie Nagele were past customers of Fusion Ads. I checked out their site and saw they were hiring for customer success. Great timing. I spent that afternoon finding the right words to express my interest and sent it off. That evening, Natalie was in touch and we booked a call for the next day. The following afternoon, she was sending over an offer as I walked on my way to get some lunch.

(Almost) eight years later, I can say this was the best thing to happen to my career. Like Campaign Monitor, Wildbit had a very tight remote culture (despite half the team working from Philly). But at Wildbit, it was the entire team instead of just one function of the business. I joined the team in the middle of their annual retreat just as they were prepping the new office in old town Philadelphia.

I started just as they were building up the customer success team. And it brought so much experience in helping developers in their various experiences: version control and development workflows, deployments, and email. We spent several years building an app that would sit on top of Git. I had the chance to do support, onboarding and life cycle messaging, write UI copy, even write and deploy some production code.

It was an environment that encouraged everyone to wear different hats and try different things. Towards the end, we shifted from focusing on products to focusing on encouraging healthier business practices. We were on the forefront of a 4-day workweek trend and did that for 5+ years.

So it was hard to hear the news last year as the Nagele's shared about their decision to sell Postmark and walk away from the the world of SaaS. I had hoped Wildbit would be the last stop of my career, but also realize it was a long shot. 7+ years was already so much longer than people usually stay at a SaaS business. I walk away simply thankful for my time there.

In short: it was a blessing!


I'd be remiss to not mention the gift of travelling in these career stops. Although I was only at Campaign Monitor for 2 years, they were liberal in their travel budgets and I was able to visit Sydney, Australia, Fiji, Hawaii, San Francisco, Portland, and Whistler, BC in that time. Wildbit had annual retreats as well, and I was blessed to visit Orlando, San Antonio, and Chicago. We had some smaller team retreats as well, visiting Portland and NYC. I was able to take in one edition of both XOXO and Brooklyn Beta. And best of all, there's Philadelphia.

Oh, Philly—this was a city that does not attract you as you fly in. It's industrial, it's gritty. It's not always clean. But gosh, it grew on me. I was able to visit 5–6 times in my time at Wildbit and I had the chance to be there in all four seasons. And I fell in love with this town.

I love the Philly skyline

So many good places to check out. Menagerie Coffee—my fave café in all the world. The salted caramel shakes at Franklin Fountain. The Reading Terminal Market. Not to mention all the amazing architecture as the "birthplace of democracy". N3rd street.

The risk

I recognize this exercise comes with the danger of missing important people. Twenty years and 6 different organizations brings plenty of opportunities to meet people. So I very much did not list the hundreds of folks I had the pleasure of meeting or working with.

But know that I think of these people often in my day-to-day activity. And coming to the end of a role and having a little more time on my hands was a great opportunity to reflect further.

I'm not sure what's next, but I know whatever it is will be a chance to get to know more amazing people. I thank my heavenly Father who, in his sovereignty, graced my path with so many amazing folks.