How I Started Watch Me Work

In the fall of 2013, less than a year after I started my video production company, CLEAVER, I took an idea to the Chicago Startup Weekend for Education and pitched it.

The idea was simple, at least on paper: a livestreaming coworking space for creatives. People could stream their work in real time and get automatically paired with others doing the same thing, so working alone didn't have to feel so alone. At the time, the idea of livestreaming your work felt a little crazy. But I was lucky. The idea got picked for the competition, we put a small team together that weekend, and we walked away with a business plan and third place at Startup Riot.

That was the beginning of Watch Me Work.

Check out my original LinkedIn post here: https://lnkd.in/p/gwcYy9v6

Building It Out

Over the next three years, I built out a team around Watch Me Work while also growing CLEAVER, and the two companies fed each other. Creative talent moved between them. Ideas moved between them. We joined incubators and accelerators, and the community grew to over 2,000 users who together created more than 60,000 livestreams.

We spent a fair amount of money making it happen. It never made a single penny.

But here's the thing. Watch Me Work never became the next big Silicon Valley unicorn, and that's okay, because it ended up being one of the best things I ever did for my video production work.

Why a Company That Made No Money Still Paid Off

Running Watch Me Work forced me to bring more people into CLEAVER. I brought my brother into the company, and between the two of us, we doubled our productivity and grew our team to more than ten people, right alongside a Watch Me Work team of about ten developers and volunteers.

It also became a constant source of creative inspiration for everyone working across both companies. New ideas, new energy, new ways of thinking about problems. That kind of cross pollination is hard to manufacture on purpose. It happened because I was chasing something I cared about, not because it was on a five year plan.

One of the things I love most about business is the ability to create something out of nothing. And the longer I've worked in this field, the more I've noticed a pattern. Some of the projects I'm most purely passionate about, the ones that never show up on a balance sheet, end up serving the paid work in ways I couldn't have predicted going in.

What About You?

I'd love to hear from you. What are some of the passion projects you've worked on over the years that you're most proud of? The ones that maybe didn't make money, but changed how you work, who you work with, or what you believe is possible?