My life at Obie - from scrappy startup to acquisition

As I reflect on Chris’ post about the past 6 years at Obie, I think that he, Kristen and Alex would find my POV of the Obie journey, oh I don’t know… cathartic. 

I met Chris and Alex via the tiny but ambitious #HamOnt startup ecosystem. They were clearly leaders in the region for young founders, always volunteering their time to host events and engage with anyone that shared their own dream of starting a high-growth company. Among the many posers (ie. the ones who always couched their startup dream by corporate job backup plan - Chris and Alex had no such thing), they sold me on their grit very early on. 

On the back of some early product market fit traction, they raised a pre-seed round to fuel growth. They thought I’d make a decent candidate and the timing was right for me. We didn’t stress much about my job title, but we figured that I could contribute in a vague Ops type role. I could code enough to help with some lightweight tech and build prototypes, help with any financials and just had a general passion to do whatever it took to pull this “little engine that could” up the mountainside. In my head, this wasn’t a job, it was a mission. We had, at most, 18 months to raise another round based on solid PMF, get acquired or die trying. 

It's hard to imagine what it's like to work for a 4 person, growth-stage company. It’s not for those with a weak stomach. It’s a harrowing journey. It’s probably the worst place for a guy with a young family to be for the sake of financial security and mental health well-being. But my support system was steadfast. My kids beamed with pride that their dad worked at a place with a cartoon beaver as its mascot. Imagine the look on my wife’s face when I told her I wanted to leave my stable banking career to be a startup cowboy. But she celebrated my second career with a reassuring “giddy up” and the comfort of knowing that I’d never been happier. 

When the pandemic hit us, we literally cancelled all of our big growth plans for the year and things were looking very bleak. I walked home one day and I told my family that it was done and the company was going under. But days and weeks passed, and Obie didn't didn’t die. Times were tough but slowly our “remote enabling” tech found a home with customers that needed it more than ever before. The light at the end of the tunnel appeared and even though I expected at least a couple of paychecks to bounce, they never did (Chris and Alex still haven’t told me how many they missed themselves in those dire days).

In my eyes, with small teams like the Obie Four, success is ultimately about the people and their ability to contribute something that, when combined like a recipe, makes an amazing result. Here is how I saw our individual contributions to making something magnificent. 

Chris always held the purse-strings and made the final decisions, but I loved our frequent debates on where to spend our very limited cash on hand. 95% of the time, he was in favor of spending and I was always trying to save money lengthen the runway at all costs to give us another day to figure everything out. He taught me that even with the bank account teetering towards overdraft, that we always had to make bold moves because this was our one shot. Chris is FEARLESS, and to me, that’s the DNA of a true entrepreneur and a born leader. 

Alex humored my 10-years-too-late (maybe more?) programming chops as I loved to get into the code for any growth-related projects. I simply cannot fathom how Alex could build and maintain an enterprise-grade system on his own and still have the time to mentor me. I’m sure he was crumbling underneath his skin with the weight of the world on his shoulders, but he never revealed it to me, which I found incredible. Alex was the herculean WILLPOWER that would relentlessly propel us to viability. Even when feats seemed impossible, he rarely broke a sweat, grit his teeth and shipped code. 

Kristen, in many ways, was the MECHANIC of Obie - she understood everything that was going on under the hood, if you will. Kristen patched all of the wounds borne by Obie as he fought for relevance in the absurdly competitive knowledge management software landscape. She had to deal with the arguably the most challenging parts of the Obie day-to-day - delighting customers and prospects. She surely never signed up to be anointed the public face of a startup with her smiling mug emblazoned on all of our sales & support channels, but she sure took the ball and ran with it. Only someone with special powers can do what Kristen did, especially with the three of us in tow. 

As for me, I always viewed myself as the GLUE. Not a particularly great glue, but good enough. Every early-stage company needs some kind of glue to keep things from falling apart from a lack of resources. It's partially cultural glue (someone that strives to build camaraderie), but mostly it's just a role that encapsulates the will to pick up the slack, wherever that may be. Was I particularly gifted at writing? No, but I wrote a hundred blog posts. Nor was I bred to be in sales, but would grind as an SDR whenever I had some spare time to try and drum up leads. I was proud to be the glue - it's a special role that I treasured because of its uniquely short lifespan in companies that struggle through early stage growth. 

What do you get when you combine these ingredients? You get a fearless engine with unbreakable willpower that is held together by some cheap glue and a mechanic on board fixing things as they break on the fly, that miraculously defies all odds and gets acquired for millions of dollars. That’s pretty awesome if you ask me. I’d do it all over again, given the chance. One day, I’m sure we will. 

A few takeaways for those trying to replicate the magic of the Obie Four: 

1. Agree on the important stuff. The team doesn’t need to agree on everything, just the stuff you’re working on. Each one of us has little in common, except for Obie. We almost always fight about everything except for the company, which feels great.
2. Cast a big shadow. Before I joined, this was the biggest looking three person company I had ever seen. Everything looked professional and the team projected as though they were a lot bigger than they were - and that starts with the collective ambition of the team. 
3. Trust your gut. The entire startup journey is about collecting valuable information along the way. Sometimes you haven’t found what you need to know yet and you have to make a decision because the clock is ticking. When in doubt, go with your gut, particularly when choosing the team, customers and partners.

To all those that helped both me and Obie along the way - thank you, and we'll see you down the road, but first a stop at the Llama Farm.