Startups: Build Resilient Teams through Honest Expectation Settings

Founder: David Corcoran
Company: Digital Cowboy; Formerly Founder of Censys and TrustBearer
Stage: Self-Funded
Date Founded: 2013
Headcount: 1
Industry: Venture Development

William Shatner is one of my favorite actors. My wife and I had the chance to see him in Toledo before the great pandemic. So it was no surprise I was glued to the video of him launching into space and becoming the oldest person to ever reach the Karman line. It was almost serendipitous that I had just finished reading the book “The Martian” by Andy Weir (it was recommended to me by someone that said if you like the combination of survival, chemistry, electricity, and physics – read this book). As you watch Blue Origin ascend — the altitude and speed accelerate and as it gets higher and higher the acceleration is remarkable as the craft gets further from the surface of the earth. And while Blue Origin finally reaches its apex and starts falling back to Earth, other spacecraft would continue with the goal of achieving escape velocity so they can escape the Earth’s gravity.

As my mind usually does, a lightning bolt goes off and I start thinking about a startup’s journey. Startups are hard — really hard — and the beginning presents so many challenges just like that rocket launch. To credit my former tennis coach “everything is hard till it’s easy”. Duh, but there’s so much truth to that.

Talent is the lifeblood of every startup. If you can’t hire people you won’t survive. As a result startups portray an image of all the great camaraderie, perks, culture, and wins which serves to allure candidates. And this makes sense — if you sell a candy bar you are going to talk about how satisfying it is, not the 30 minute run you need to make to burn the calories. But just like the calories in that candy bar, an early startup isn’t all sunshine and roses and if you want to build a team that scales and succeeds candidates need to know the good, bad, and the ugly so expectations are set and people can self select out if it doesn’t fit their needs.

Work-Life Balance can be Challenging in a Startup

This is probably the biggest of the expectation settings that needs to be front and center. Lets face it, when you are a startup you probably have a dozen or more competitors some of which may be better funded and much further along than you. In order to achieve escape velocity there’s going to be some nights and weekends you are going to have to work. Hopefully this is the exception and not the norm but many times in the beginning that’s not the case. There is little to no role redundancy at a startup and many people are performing multiple roles for the first few years. If your startup is backed by venture capital they have clear expectations for you to double or triple in size every year or two. Your employees will have to be adept to change. Build fast, break things, and fix them at all cost. Change roles and get a new boss or directive every few months. If this environment brings a potential hire heartburn, it’s best to set clear expectations and allow them to self select out at the beginning. By setting those expectations clearly and filtering out the people who don’t fit that lifestyle — you will build a strong team that can weather the rollercoaster of events and emotions that occur in most startups.

So Why Choose the Startup Life if the Work-Life Balance is Challenging?

Some people join startups with the hope of cashing out on some generous exit. While that’s a fine outcome I would caution both the startups and candidates in overemphasizing that selling point — the odds are simply not in your favor. Instead, you join a startup for experience. You have the opportunity to witness how companies are formed and grow. You have the opportunity to rise and change roles in a fraction of the time it would take to do so at a large corporation. You get to work closely and see how the whole organization works, not just the microcosm you work in. And for an aspiring entrepreneur — it might just be your apprenticeship.