How Do You Run Your Startup As Headcount Grows?

brett fox
5 min readSep 5, 2019

I remember there were six of us after we closed our initial funding. Myself, my four cofounders and our operations manager Dave.

Two weeks later Sid joined as our design engineering director. Within two months we added three more design engineers bringing us to ten employees.

Picture: Depositphotos

We held company meetings every Friday afternoon in the large conference room next to my office. We had one row of cubicles (that we bought for $100) that everyone sat in. There was room for four more rows of cubes before we ran out of space which we would a couple of years down the road.

The environment at this early stage was intimate.

When you’re in a small team environment, you get to know everyone very well. That’s the beauty of a really early stage startup.

You should take advantage of this stage of your company’s development to build strong bonds with you and your team.

You’ll likely be in the process of recruiting and building your first product at the same time. There will be a lot of pressure (and there should be) to get the product out.

Don’t lose focus on the importance of your company culture. Bringing in the so-called “brilliant jerk” can have a devastating effect on your long term company culture.

And it’s oh so tempting to bring in the brilliant jerk who will keep your project on schedule. Don’t do it. The brilliant jerk will lay waste to your team in the process.

One of the things you want to do at this early stage is set up the meetings and processes for later.

At the beginning, we were mostly a bunch of engineers working on the various products we were developing. Everything was focused on getting these products out on schedule.

Thursday morning at 10AM, we had our weekly engineering meeting. We went over each product in development, updated the schedule as needed, and talked about how to help any engineer that might be in trouble.

Friday afternoon at 1:30PM was my favorite meeting, the Crazy Idea meeting. What’s a Crazy Idea meeting…

brett fox

I work with startup CEOs to help them grow their businesses . I built several businesses from $0 to >$100M. Learn more at