Myths and Realities About Working at a Startup

Jeff Segal

Ever felt a twinge of envy reading about local startups in Crain’s? Seen The Social Network more than once? Finding yourself a little bored with your current gig—or in transition? Maybe you should consider working at a startup—even if you live in the suburbs and you’re old enough to remember the Bears winning the Super Bowl.File 28683

But first, you have to get past those common misconceptions:

“I’m too old.”

I was 46 when I joined my first startup. Having left a long career in options trading—with no real idea what to do next—I discovered opportunities there I might never have found anywhere else. When you’re part of a small team looking to do big things, you learn a new skill, a new technology or a new tactic almost every day.

And by the way, I wasn’t even the oldest team member.

“A third of our applicants are over 30,” says Brent Williams, Program Manager of Startup Institute Chicago, an eight-week program that teaches the necessary skills for working at a startup. “One of our real success stories is a 55-year-old who made the transition from print design to web design.”

“I’d have to live in the city.”

Yes, the nexus of the Chicago startup scene is River North, anchored by 1871 in the Merchandise Mart. And unless you live near the CTA Brown Line, it’s a pain in the rear getting there, never mind parking.

But you don’t have to go there to work there. It’s 2013, remember? Most startups have team members working remotely all over the city, if not the world. There’s almost nothing that can’t be accomplished online.

More than half my business is with River North-based startups, but I rarely stray into the city more than three times a month.

“I’d have to work 100-hour weeks.”

Some startup founders are famous for working insane hours and expecting the same from their teams. But other founders stress a more balanced lifestyle, and Williams says he rarely hears of startup employees working more than 60 hours a week.

Wait a sec. 60 hours? That’s a killer week!

Yes, it is. Startup teams work their tails off. But no one says you have to work full time.

My first startup job was 10 hours a week. Those hours multiplied as the company grew, but there were only a few weeks the work kept me away from my family. Now I contract part-time with startups and other businesses, but not more than 20 hours a week for any of them.

“I’d have to be tech savvy.”

Yes, but only a little. Williams points out that two of Startup Institute’s four curriculum tracks don’t involve design or development, and says, “We’re really looking more for business experience in a specific area. If you’ve had success in sales, you’ll probably do well in our Sales and Business Development track.”

If you can share this post with a friend through social media, you’re probably tech savvy enough to work at a startup.

“I won’t get paid.”

Depends what stage startup you work for.

Early-stage, pre-funding, pre-revenue startups can’t pay you because they have no money. But if you connect with one where you really like the concept, they might ask you to work a limited number of hours in exchange for stock options. These options will most likely prove worthless, but the experience can be invaluable—especially if you’re in transition. And hey, you never know about the options—Google and Facebook were startups once.

Later-stage startups, with financial backing and strong revenue streams, offer competitive packages. “Our graduates get full-time, well-paying jobs,” says Williams. “With benefits.”

File 28684“It’s just a bunch of slackers playing ping-pong.”

Not true! Foosball is just as popular!

Granted, your typical startup is a less structured workplace environment than you might be used to. People wear shorts and flip-flops, park their bikes in the hall and drink beer at their desks.

Unprofessional? Not businesslike? With major corporations now implementing the lean methodology principles pioneered by startups, you tell me.

All that goofiness is part of a culture that nurtures the hardest-working, most passionate, most productive people you’ll find anywhere. Maybe you should be one of them.


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Jeff Segal
True. Anyone who calls in five minutes before walking into the office gets what's coming to them.
Maxx Freedman
You didn't mention that we all have nerf gun fights 5 times a day.

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