5 Questions to Answer Before Joining a Startup

Before making the jump, first assess where you are in your career. If you are just getting out of college, a startup would be a great place to begin your career. At the early stages of one’s career, it’s important to be open and explore different possibilities. Especially for anyone dubbed as the “millennials,” most young people these days will experience multiple career paths before settling on one. If you start at a startup, you’ll gain valuable exposure on how to run a business, and have multiple responsibilities. You’ll learn if you’re into marketing versus operations, or perhaps you will get excited about financial reporting. For people straight out of college, a startup is a great place to “startup” your career.

For others considering a jump into the startup world, they’ll likely have a few more years of experience. Some could be vice presidents in a major corporation and have been stricken by the “what-if bug.” What if I joined Facebook back in 2004? What if I took that plunge and taken on that lowly Operations role at a taxi company called Uber back in 2010? For experienced professionals, it’s not an easy decision, and it’s important to have the right framework before ditching your cushy corporate gig. Here are some things to consider:

Would you invest in this company?

For experienced personnel, a startup company will try to lure you with options or shares of their company. Often, this equity piece comes with a salary reduction. Even if you don’t get a salary reduction, you’ll likely take a hit in benefits. Most startups don’t have matching 401Ks. They don’t offer discounts at the local gyms. You won’t get a corporate card. Some startups don’t even have decent health insurance. So a chunk of your  benefits will come from those options they’ll dangle in front of you.

How would you value this company? Is their target market big enough? If they were publicly traded, would you invest in this company? As an experienced professional, especially for finance executives, it’s key to think like an investor.

Do you see yourself playing ping pong at midnight with this group?

Startups often lack enough personnel to handle all the responsibilities. This means you’ll be ask to take on more responsibilities than you’re used to. So are you ready to work more hours with less pay?

You’ll have a lot of late nights with your team at a startup. It’s a stop and sprint culture, meaning you’ll work on long hours on an analysis. Then stop to have a break and regroup with your team, usually in a game of table tennis or a session of Monopoly. Then right back into whatever analysis you were performing. If you don’t like the people you’re with, it’s going to feel like a long day as you grind through those long hours.

What stage is the startup?

The stage of the startup influences the amount of reward you’ll get for your time. However, a late-stage startup can also provide a more stable environment as they’ll likely have the typical benefits found in established companies. They’ll also likely to have more personnel to help with day-to-day activities.

Depending on how much risk you’re willing to take, it’s important to know what stage the startup is in.

What about family?

For experienced professionals, they often have a wife and kids to care for. At a cushy corporate gig, it’s easy to collect a fat paycheck to pay the mortgage, buy groceries, set aside money for the kids’ college education, and pay the monthly on the two cars parked in the driveway. Corporate gigs aren’t sexy and don’t have as much upside, but they are stable.

If you do decide to make that plunge into the startup world, you’ll likely have to sell your home and move to San Francisco or to New York. This means a return to the city (assuming you’re living in American suburbia), where it is more crowded and expensive to live. Are you comfortable uprooting your kids from their school? Are you comfortable letting go of those two Audi station wagons? Will your wife be okay with your late nights at work?

Even if you aren’t married, it’s still a big decision. Since you’ll likely live and breathe the startup, you won’t have time for living “La Vida Loca” on Tinder.

Where do you see yourself in five years?

It’s a staple question that gets asked in any interview. It’s so simple yet so applicable for anyone, pondering a move to a startup. It’s even more important for experienced professionals to know what they want to get out of the experience. There’s a reason people are attracted to cushy corporate jobs. They pay well. They pay the bills. You get a corporate card and an army of support to churn your reports.

But there is a certain appeal to work in startups. You’ll get to work on edgy stuff that can potentially revolutionize society. Jeans on Fridays turns into “Jeans Everyday”. There’s beer in the fridge at most startups. Finally, the most appealing part of working in a startup is to understand what it takes to run your own business.  If being your boss is a dream of yours, then a startup is good place to start.