Pros and Cons of Working at a Startup (i.e. a 9-5? what’s that?)

Took a suggestion from a commenter to blog about the other side of working at a startup, that is, the positives of it; I wrote this late, late, late last night…fueled by Diet Cokes and Japanese strawberry gummy candies. I don’t really know the seedy underside of working for someone else in a startup, but I was able to round up some friends (and friends of friends) who do. I mean, we all know that working at a startup is exciting with a capital E!!! You know what I mean by excitement, right? “You get to work in a dynamic, fun and fast-paced environment!” Sweaty palms, ever-changing circumstances, not knowing if your next paycheck will be your last, doing things outside of your hired role, oh yes, this is VERY exciting. Hoping to glean some info on how to manage employees if ever I had enough money to do so; I gathered some interesting comments by plying these folks with some candy and my undivided attention. Quoted for truth:
“Yea, the founder thinks he knows everything. Even how to do my job.”
“My boss is really flexible; he changes his mind every few minutes.”
“I’m so happy I’m helping another person make their dreams come true. At $30,000 a year.”
“I’m the number 3 employee of the company. But I think I’m going to need health insurance soon.”
“We have office space. It just happens to be in the basement of my boss’s house.”
Ok, ok, sounds pretty bad, doesn’t it? But, the people I interviewed were smart and full of potential. Knowing that, the people who hired them - the CEOs most likely, are smart people too. And working with smart people is never a bad thing. On that note, let’s discuss the pros of working at a startup. You want to know how a business works? You want to see ideas come to life before your very eyes? Did you ever wonder what “business development” meant? Want to be a contributor instead of a cog? Well, working at a startup gives you that opportunity. That is, if you want it. The phrase “baptized by fire” comes to mind. It takes a very courageous and flexible person to weather the ups and downs of a startup. Maybe the company doesn’t go anywhere. Maybe the 0.25% equity stake you own means 0.25% of zero dollars next week. But imagine your next job interviews. Imagine not lying about how much you contributed and learned working at a startup.
Every company needs resourceful and tenacious employees. And startup employees have that times 10. You’re middle name is probably “Versatile”. Companies now want multi-talented employees who have some business sense and financial know-how. And you have that knowledge, because you probably had 50 different responsibilities. That, or you shared the same desk as the CFO. Do you know how to put the company first? Probably, because almost everyday in a startup is about survivability. So maybe the company went out of business - what did you take away from that? You were directly hired by the CEO (likely). In a way, you’ve already been vetted. Whether you were the technical lead or receptionist/payroll/cheerleader - hiring managers know that startups put tremendous energy into finding their first employees. They want very, very good people (for very, very low pay). But think of all the money you saved working from home because there’s no office space yet.
Conclusion: I definitely have to advise most job seekers who have some flexibility with their finances AND nerves of steel to give working at a startup a shot. Especially if you’ve always had a bit of the entrepreneurial bug - you’ll learn things they don’t teach you in business school, guaranteed. The best question to ask might simply be, “What is a typical day like?” Oh, and you might want to hang around for a day to see how things actually work before you jump in. But it will probably be worth it.

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