If the depictions of startups in popular culture are to be believed, working for a startup is basically like hanging out in a clean version of a frat house basement. There are pool tables; ping pong tables; kegs that you can drink whenever you want! There are communal workspaces, free food and nap spaces. We have Nerf gun fights spontaneously every day!
And while some of that is true, sometimes — go check out Airbnb’s office in San Francisco for an amazing example of what can be done with startup unicorn money — the reality of working at a startup is a bit more… complicated.
“I’ve worked for a few startups now (Zirtual Inc. [pre-acquisition] for three years, WeWork for six months, and TrendKite presently for over a year),” Kristopher Louie, 27, tells Startups.co. “And they’ve all had a few of the same hardships: juggling many responsibilities with a high-degree of efficiency/fidelity (the ‘wearing many different hats’ rhetoric); preaching work-life balance but not always practicing it; constantly shifting processes; implementing workflows that are rushed; uncertainty towards future business practices; rapid scaling growing pains; and, the running joke with startups: Too many emails planning too many meetings and not having enough time to actually do work.”
Did you get lost in that list? Did you notice that there’s not one mention of free snacks? That’s because while working for a startup business can be incredibly rewarding, it’s also really, really, really hard.
I’ve been working with and for startups — and writing about them and talking to founders every day — for over half a decade.
I’ve been frustrated for a while now with the way the media depicts startup culture, so I reached out to my community to find out: What about working at a startup was harder than you thought it would be?
Here’s what they told me.
Probably the most well known hardship of working at a startup is the fact that the hours are seriously long. There’s a reason the startup world seems to fetishize youth, at times — and it’s not because they still have great skin. It because past a certain age (and I mean like, probably 25), most people just don’t have the energy or time to pour into a company like that.
On more than one occasion, I’ve seen founders and employees passed out on their communal desks while their team buzzes around them. When you’re trying to get your company launched, you expect to work 24/7. And you expect anyone working for a startup to do the same.
Job titles? HAH! A clear hierarchy? NOT HERE. Anyone who’s working for a startup can tell you that the disdain for “corporate” structure can be freeing, but all too often it causes more problems than it helps.
Guys, I hate to be a Debbie Downer, but there’s a reason companies have a chain of command. It’s called efficiency. And accountability.
“Basically, it’s harder than it seems at [my current startup] because it’s entirely run by Chaos Muppets with no understanding of what process is, why spreadsheets are more than pretty charts, or how to manage,” Jane,* an employee at a tech startup in London tells Startups.co. “I may have gone home and cried a little twice this week.”
Even more than youth, startups fetishize failure. The motto of “fail fast” can be seen plastered on walls from SOMA in San Francisco to coworking spaces in Columbus, Ohio. The part those signs leave out is the fact that some of that failure is going to be yours if you’re working at a startup.
“From a work perspective, I think one of the hardest things [about working for a startup] is that you’re simultaneously trying to do your work and figure out how your work should be done,” Katie, a freelance writer who works with startups, tells Startups.co. “There’s no process, no precedent, every problem you run up against is completely new. And you have to figure out how to solve it, and do it within a time frame that still gets the work out the door. I don’t think I realized at the time just what a heavy lift that is.”
Startups employees — and founders — have to “wear many hats,” especially early on in the company’s life. That’s because there usually isn’t enough money to hire a specific person for each specific job.
Some people thrive under those conditions, but before you jump into working at a startup, you should take an honest, long look at yourself and ask: Am I one of those people? If you’re not, you might want to reconsider your career move.
“[It’s a] the thin line between working to your maximum efficiency without stretching yourself too thin,” Kristopher Louie says. “Often I find myself taking on various responsibilities and projects that require constant resource/bandwidth management or things would fall through the crack, or even worse, I’d find myself so stressed and hating work.”
And, sometimes, those hats can be not only annoying but kind of offensive.
“The CEO asks me to manage her calendar like I’m her PA,” Jane says. “I’m a senior marketing professional.”
The startup life is not smooth sailing, by any means. If you need a lot of certainty about your life and your future — and there’s nothing wrong at all with needing that — then you shouldn’t be working at a startup. Just remember this statistic: More than two-thirds of all startups fail.
“Eric Ries defines a startup as ‘A startup is a human institution designed to create a new product or service under conditions of extreme uncertainty,’” Mauricio Palacio, CEO and co-founder of event management startup Eventtia tells Startups.co. “Living through this daily uncertainty, creating your own path, building your way through progressive and incremental iterations without knowing what the next day is made of is probably the hardest thing of working for a startup. But, ironically, this uncertainty is also what pushes you think and work harder to move your startup closer to success.”
Long hours. Located in expensive cities. (Usually.) Super high expectations for employees. You’d think that working at a startup would come with a nice, hefty chunk of change, considering how difficult it can be.
Unless they’re funded (and it’s estimated that less than one percent of startups get venture capital funding), startups are bootstrapping. That means they almost always running close to empty. In addition to office space, guess how they save money?
You got it — employee salaries. The gamble, of course, is that your company is going to go big, unicorn-style. But in the short term? It almost always means taking a pay cut.
Probably because working for a startup isn’t as easy as people think, turnover is a real problem for a lot of companies. Until a startup finds its groove, they’re likely to shed employees left and right. That’s the problem Jane is running into at her current startup.
“There was no marketing team for four months,” Jane says. “One hundred percent turnover in January, so my line manager is also brand new. The COO is brand new.”
Between the “wearing many hats” philosophy that’s so common for people who are working at a startup business (i.e. you do a million jobs, some of which you understand and some of which you don’t) and the fact that this is probably your founder’s first time managing a team, you can expect that there’s a lot of learning on the job.
Unfortunately, that often translates into no one really knowing what they’re doing — ever.
“It’s a big thinker — a visionary — who comes up with these ideas and then thinks they should also be director or whatever,” Sarah,* tells Startups.co. “But they have no idea how to manage at all or don’t trust people enough to do their jobs.”
For most startup founders, their company is their baby. They’ve invested everything — time, money, sacrificed personal life and relationships — into making their company work.
And while that commitment can translate into a great, supportive environment with the right founder, it can also mean that with the wrong founder, things can get very unprofessional, very fast.
Sarah* was working at a startup for two years, during which time the founder would do things like email her random GIFs while on coke binges, talk down to her and her employees in public-facing meetings and, one time, threaten to punch her in the face.
“It’s so personal for a lot of these founders,” Sarah says. “That clouds the vision.”
Sam,* 27, is an account executive at Justworks. He says that one issue he’s run into is the fact that some of his “benefits” end up looking more like manipulation tactics.
For example, unlimited vacations — which are a popular offering from young companies — can be used as “a guilt trip/ tactic for you to never take time off because it’s a ‘when you need it policy.’”
Another common one, especially for mature or funded startups, is providing food at work. On some levels, it’s great — you get “free” food every day! But it’s also a calculated decision by companies to make it possible for you to stay at work as long as possible.
Some companies manage to find that balance without being manipulative, but the culture at other companies can have employees whether a padded room is really less of a cage than a cubicle.
That rollercoaster startup life can wreak havoc on your emotions when you’re working at startup businesses.
One day everything is looking up! You have a verbal commitment from a top VC! You have steady growth! Your product has finally shipped!
And the next day, you’ve lost your VC, no one wants what you’re buying, and the company in China just got slammed with human rights violations.
“Morale in a startup is constantly changing,” Esteban Ochoa, co-founder and CTO of Eventtia, tells Startups.co. “One day you think you have everything figured out, you think you have the right market fit, the right pricing, the right product. Then suddenly morale is down, traction is not enough, tons of problems with the product, sales team, the market fit you thought you had is no longer existent.”
This is a long list of the potential downsides of working for a startup — and it can be daunting. But for hundreds of thousands of employees and founders, working at a startup is also the most rewarding thing they’ve ever done.
There’s a reason people keep jumping into this pool — and it’s really not about that potential $1 billion valuation. It’s about the satisfaction of creating something from the ground up; of working hard with real results; of a team that really cares about what they’re doing.
So, no, working for a startup isn’t all ping-pong and Kegerators. But for a certain kind of person, it can be a whole lot more.
*names have been changed per interviewee’s request.
is a full time blogger and digital nomad has been writing about startups, living with startup people, and basically breathing startups for the past five years. Emma is a regular contributor to Bustle, Startups.co, KillerStartups, and MiKandi. Her byline can also be found on Mashable, The Daily Dot's The Kernel, Mic, The Bold Italic, as well as a number of startup blogs.
Follow her on Twitter @MissEmmaMcG.