Startup Job Security: Calculating Risk Before Taking the Leap

By May 27, 2015Boomcast Blog

Is there such a thing as startup job security? Many startups have unproven business models and limited runway to figure it out, leaving job candidates wondering whether joining early stage companies amount to career suicide. For those who see this as a risky proposition, I submit that if you approach a startup career move as smartly as you should any other career move, job security isn’t as elusive as you may think.

You need to get to know a company before making any career move, startup or otherwise. Evaluating an early stage company requires more due diligence than evaluating a Fortune 500, of course, but that’s the price of entry. About a year ago I went through this process before making the leap to join Simpler, a startup with no customers, no revenue model, and no retirement fund.

Simpler’s founder, Alan Kane, had a track record of startup success and was being funded by investors that had backed him before. They were experienced as operators and investors in automotive software, the arena Simpler was getting ready to enter. They were in a position to make introductions to automotive manufacturers, dealerships, software vendors, and anybody else in the ecosystem.

I met with Alan. I talked to somebody else Alan was considering hiring to hear her perspective on the team and opportunity. I researched Alan’s previous startup experiences. I met with one of the investors. I confirmed that there was enough funding to last a year. I called a CEO from one of the investors’ other portfolio companies. While this took some effort, I was able to complete my due diligence in about 3 business days. By the time I wrapped up, my wife and I were confident that Simpler had a lot of ingredients for success.

After you’ve evaluated your chances of success at the startup you’re considering joining, evaluate your chances of success with startups generally. I submit that if you’re qualified enough to be hired by one startup, you’re qualified enough to be hired by another. While traditional job security is about a stable career in a single company, startup job security can be about a dynamic career in several companies.

Prior to joining Simpler I had been Managing Director at Quick Left, which had grown in size and reputation in the time that I had been there. I had experience working with software developers and making technical sales. I had gotten to know a lot of people in the Colorado startup community, particularly by adopting a give before you get mentality. These are all reasons I was valuable to Simpler. My wife and I realized that others would find me valuable too.

Fast forward to today. I’m actively interviewing Ruby on Rails developers to join our growing team. Many candidates wonder whether Simpler will still exist in 6 months as I did a year ago. We’ve got paying customers, additional investors, and growing momentum. I like our chances. I tell candidates about the thought process I used to evaluate Simpler a year ago and ask them to do the same.

I recognize that the type of opportunity that presented itself when I joined Simpler doesn’t come along every day. It was atypical in that not all startups have the same ingredients for success. That said, I had been patient and chose Simpler precisely because it was atypical. If you’re thinking about joining your first startup, I encourage you to find the right situation, do your homework, and have faith that the startup community will help you succeed, whether its at your first startup or the next. As it turns out, taking the startup leap doesn’t have to be as scary as it looks.

[author author_image=””]Bing Chou is an active participant in the startup community, moderating both Boulder and Denver Open Coffee Club. Prior to joining Simpler, he was Managing Director at Quick Left. You can follow him at @virtuallybing.[/author]
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