The Good, the Bad, and the Weird.

A new newsletter following the journey of building a venture-backed startup

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The good.

The bad.

The weird.

The questions.

The answers.

The stories.

The reason?

The journey.

The Good, the Bad, and the Ugly is one of the greatest movies of all time.

The soundtrack. Ennio Morricone was neither good, bad or ugly, he was legendary (as you’d definitely know if you’re listening to the recommended song as you read).

The acting. Clint Eastwood in one of his most iconic performances of all time.

The final film in an incredible trilogy by an Italian director who was mostly unknown at the time, Sergio Leone.

Maybe it’s that innate young boy desire to be a cowboy at some point (either shortly before or after wanting to be an astronaut), but the soundtrack from the trilogy that this movie caps has often been the soundtrack as I spent countless hours, days, and weeks building my startups.

But The Good, the Bad, and the Weird is more than just homage to a great movie.

It’s a phrase that encapsulates a number of things that I believe, immovably, at my core as a founder. The Good and the Bad covers the natural course of building a startup. Some days are good, some days are bad, some days are an insane rollercoaster of both good and bad.

The Weird is something, especially in B2B startups, that I find missing across the board. Every software startup starts to feel the same. The same abstract shape logos, the same illustration styles, the same websites, the same marketing.

Take 5 startups in a competing space, blur out their logos in their materials, and 9 times out of 10, you probably can’t tell them apart.

Being weird, having a perspective, an opinion, an authentic human side, is still wholly underrated for the vast majority of startups.

I’ve been bootstrapping various startups and businesses since I was 17 (earlier if you count selling LEGO at 14), and before Commsor I wasn’t really involved in much of the traditional tech world. Maybe this is why I don’t find the rules and the systems and the general consensus advice very appealing. It just wasn’t in front of me when I started.

That lack of knowing the rules and the way things were meant to be done is a huge reason why Commsor took off in the early days. We had fun with what we were doing, we raised money without following the process investors always tell founders to follow. If you said “I have a crazy idea” in our Slack, a bot would auto respond with “Fuck it, I’m in. Let’s do it.”

Somewhere along the way we lost that weirdness and willingness to break the rules. It probably had something to do with raising a monster preemptive investment round, and suddenly feeling an immense sense of pressure and imposter syndrome.

I’d never been CEO of a venture-backed startup, let alone one with this many people, or with this much pressure from investors. I felt like I had no idea what I was doing (do we ever truly?), so I started building Commsor a different way than we’d started. I started following the rules. Reading the books. Watching the videos about how a company like ours should look and act and how I, as a first time CEO, should be.

It almost killed us.

In my next newsletter I’m going to dive into how exactly it almost killed us, what mistakes I made, and what I’d do differently if I could go back. But for now, back to the Good, the Bad and the Weird.

Over the last 6 months we’ve made sweeping changes to bring Commsor back to what made it great in the early days. These change unfortunately included a lot of bad. No one likes layoffs, cutting good people, having to change tack and take a morale hit. But sometimes that is whats necessary to bring back the uniqueness. The weirdness. The strong, unwavering perspectives.

If the good and the bad are the natural ups and downs we find ourselves in on the startup journey, then the weird is the unique things that make Commsor what it is, and not just any other startup.

All together, The Good, the Bad, and the Weird, as a phrase, represents a desire to build in public, to share the journey from all angles. My hope is that this newsletter acts as a place for me to reflect as we continue building Commsor, while sharing insights that others hopefully find interesting and, from time to time, insightful.

We’re about to launch two new products, Bronto and Matcha, and we’ve got a whole slate of weird ideas for how to build them, grow them and scale them. I’m going to document it all, and you’ll know what we try, why we tried it, and whether it worked or didn’t.

That might include basic shit, like paid ads, or new websites, or it might include weird shit, like 18 hour livestreams or other things that I can’t quite reveal yet.

It’s gonna be good.

Or bad, who knows.

Either way, it’s gonna be shared, and it’s gonna be weird.

Have a kickass week.


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