A Reality Check for Anyone Eager to Work for a Startup

Guest Writer
Consultant, Entrepreneur & Former President of TrainSignal(acquired) & Former Chief of Staff, ContextMedia
4 min read
Opinions expressed by Entrepreneur contributors are their own.

About a year ago, the company I was president of, TrainSignal, was acquired. Since then people having been reaching out to me asking for advice regarding a career change. Everyone from accountants and real estate agents to baristas and retail employees have asked about joining a startup or starting a company of their own.

Almost every time I’ve told them to reconsider, that it’s probably not a good idea.

Related: Why I Left My High-Paying Job at LinkedIn For a Startup

I get it. They see headline after headline about some of the most outrageous startup ideas being funded or acquired for millions and millions. It is true that jumping into a startup has many allures.

Startups do not employ a lot of people, so every person counts. As a member of a small, committed team, your contribution really makes a difference to the success or failure of the business. You can see your impact day in and day out.

In almost all startups, there is no red tape to cut through to solve problems and implement new ideas. You will not have to battle or navigate a corporate bureaucracy. In startup-land, there just isn’t time for that kind of thing.

You will work in the trenches, right alongside the company founders. Often, early startup employees get exposure to the real movers and shakers in the industry. That is a powerful experience. You can build relationships that boost your career later, down the road.

Those are great things. And they are very appealing.

But, having been in the business, I can tell you, joining a startup is the modern day move to Hollywood to become a movie star. Those who make the career change will likely find reality doesn't live up to their dreams.  

Reid Tatoris, founder of statup AreYouHuman told me the other day, “…lots of people like the idea of a startup, but when they find out the large amount of work and the low pay, they are less excited. Basically, most people who say they want to work at a startup really want to work for Facebook.”


While the CNBC headlines are enticing, those looking to join the scene don’t see are the stories about founders who’ve lost houses, spouses, their entire life savings as well as the savings of their friends and family.

Those of us trying to be realists about startups talk about the “hard work.” Which means more than long hours. While working in a startup is grueling, it’s also often a baptism by fire. You will be expected to jump right into your work with very little training or direction. 

You also have to be a jack-of-all-trades. At startups, resources are limited so everyone has to wear multiple hats. One minute you’re meeting with a very well respected venture capital investor and the next minute you have to clean the dishes in the sink. You can't hide behind your job title.

Related: 10 Reasons Why You Shouldn't Join a Startup

Startups are pressure cookers. Don't let the casual dress and playful office environment fool you. New enterprises operate under do-or-die conditions. If you do not roll out a useable product or service in a timely fashion, the company is will fail. Bye-bye paycheck, hello eviction.

Which brings you to this fact: most startups fail. Even those with amazing ideas and visionary leaders don’t make it and, overnight, you’re out of a job. If you’ve been partly paid in company equity, as many startups do, you can find yourself in financial peril, and fast. I wouldn’t get too excited about having stock options and equity until it’s real. It’s real when it vests and you can actually sell it in exchange for good ole’ cash.

The reality is that most startups aren’t glamorous. It’s not for most people. Leaving a stable job, even one you find unrewarding, is long on risk and hardship.

Nonetheless, as I said, I get it. And I don’t mean to dump on startups. I love startups. I love the rush, the risk, the impact I make and I love the teams I get to work with.

But if you don’t love it, including the worst parts, take my advice. Don’t quit your day job.

Related: 7 Ways to Survive and Thrive at a Startup

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