Should I quit my day job and work for this start-up?
July 18, 2013 1:04 PM   Subscribe

I've got a new job. I like it. But I've also ended up with a second new job - working evenings for a startup. Long-term, I need to pick one. Which?

I recently landed a new job in the marketing/PR space. I like it, and I like the people. The work's pretty good, though there's a fair bit of operational inefficiency and copy-pasting.

At the same time, someone I've known for a few months asked me to help out with the marketing/branding side of his start-up, which I do a few evenings a week. It's an exhausting schedule, but I like the work, and the sense of purpose it gives me. It's a reasonably established venture - not just an idea, but a company with assets. And it's a dynamic (if very small) team.

But I need to choose between the two, ultimately. Part of me feels I'd be stupid for turning down a role in a start-up, particularly as I can afford to take on the risk of it failing. Then again, I'm in my early twenties - maybe I'd be a fool for turning down a safe job with the prospect of promotion at a well-known agency, where I get training and support and perks.

Not sure what to do. Your counsel would be appreciated.
posted by anonymous to Work & Money (10 answers total)
If and when you get an offer at the start up, you can weigh your options.

Start-ups are gambles. You will either hit it big and if you get stock options before the IPO, you can cash out and buy a mansion. Or, it'll die hot death and you won't have anything.

Big risk, big reward.

Take the job with the start up if it comes with benefits, a larger salary and a better title. Which it should since you were there at the inception.

If you can't BETTER your situation at the start up, then don't do it. Once, having been at a start up, you'll get better projects and better experience, you can always go back to an agency at a higher level.

I'm a risk taker, so as long as I can do better by quitting one job to take the risky job, I might be inclined to do it.
posted by Ruthless Bunny at 1:09 PM on July 18, 2013 [2 favorites]

Why do you need to choose now? Are you able to execute all of your responsibilities at both jobs? What's the rush?

It's not a bad thing to work at a start-up part-time and also to hold on to a steady paycheck. That strikes me as the best possible situation you could be in, if you're someone who wants to be involved in startups.

The odds are that this startup will fail, and that's okay. From what I understand a lot of VCs like to see that people have been at several failed startups because failure is a good teacher. So I'd keep doing what you're doing until such time as the startup either fails or becomes sustainable enough that it looks like a surer thing than it does now. In either case the experience can only help you.
posted by gauche at 1:10 PM on July 18, 2013

Be aware that most employees make little or nothing from stock options even when their company is a success. There are a bunch of reasons for this, but don't expect to come away with more than a few hundred or thousands even if the company has a successful exit. That's not the reason to work at a startup unless you are a C-level employee, founder or investor. Startups are fun, startups can be liberating, but they probably won't make you rich.
posted by 2bucksplus at 1:11 PM on July 18, 2013 [1 favorite]

A few things to consider:
- Security and stability. How much does each job offer? How much do you need?
- Paycheck, obviously.
- What skills will you pick up at each job? Which will make you more marketable?
- Where do you want to go next? Is either setting better for getting you there?
posted by chickenmagazine at 1:21 PM on July 18, 2013

Nthing that working at a start-up is not a matter of living in a mansion or eating at Mc Donalds........

You know better than us about its funding, competition, etc., but if you feel reasonably good about all that stuff, why not sell the start-up folks on going full-time? If they're up for it, as you said, you can afford to take the risk so have at it.

(I've worked for start-ups that cratered, but subsequent employers in companies large and small have looked quite favorably on that experience.)
posted by ambient2 at 1:34 PM on July 18, 2013

You are in your early 20s; I vote adventurous startup. There is plenty of time for stability, so get as much different experience as possible. Just make sure the compensation meets your needs and that the company has sufficient funding.

And keep your eyes open, and if it looks like the company is starting to crater then jump ship asap. (executives leaving, clients leaving, no product actually making it out the door despite the "yeah us!" attitudes, cutting costs and perks etc.)
posted by St. Peepsburg at 1:44 PM on July 18, 2013 [1 favorite]

Be aware that most employees make little or nothing from stock options even when their company is a success. There are a bunch of reasons for this, but don't expect to come away with more than a few hundred or thousands even if the company has a successful exit

People should go in with their eyes open .. but this isn't really true.

Startups are high risk vehicles and you need to know what you are doing to evaluate whether going to a specific one makes sense for you. Without any of the details, we can't say one way or another (except that this particular startup is past the infant mortality phase - if by "assets" the poster means "revenue" anyway).
posted by rr at 1:57 PM on July 18, 2013 [1 favorite]

Like many others, I wouldn't get involved in a startup for the possible payout that can come from options. A startup and a large company can both offer different paths of promotion where one is not necessarily better than the other. Promotion paths at a startup are driven by growth, and -if- your company is at least moderately successful and -if- you are bright, talented and hardworking, you can expect to go from being a junior level person to manager to something like a director in the space of a few years.

With all of that said, startups can be a very intense experience and personal experience. The amount of real skills and career growth that you'll experience will be dependent on the management staff. Brilliant managers will impart to you lessons that you will never have a chance of learning within a large company, but horrible/poor managers will impart bad habits and waste your time. I've known a few people who had a title of "director" or "VP" at their little six or twelve person venture, but had the organizational skills of a peanut, and the title was obviously just a fig leaf of credibility. An established company with a good training regimen can give you some good habits that will be valuable to a startup later in life.

My general career advice for relative strangers making the choice between startup v. established company:

-- if you prefer structure, process, defined boundaries and consistent schedules: work at the large company. if you prefer making up your own job, a freewheeling environment and being a bit entrepreneurial: work at the startup

-- if you work in a field where name recognition of your employer is important and the big company has that: work at the large company. In consulting, for example, having an entry in your resume showing that you cut your teeth at a recognizable firm and -later- chose to go to a startup is a little more impressive than a list of places that nobody's heard of.

-- if you need a real HR department (ie. you're an immigrant needing a visa/permanent residency, you have health or family issues that require insurance coverage): work at the large company. if non paycheck benefits are the last thing on your mind: work at the startup

for me, I spent the earliest part of my 20s working IT at a couple of large banks, long enough to know that I didn't like the bureaucracy, but also long enough to learn about best practices and absorb the lessons of a bunch of guys who were older than me and had tons for formal training. I switched into startups in my mid-to-late 20's, basically taking a bunch of servers that were haphazardly organized and putting in some real administration and process in place. My career took off from there as I had quicker access to greater levels of responsibility, but I wouldn't have been ready for that responsibility if I just went into shops like that straight out of school.
posted by bl1nk at 1:58 PM on July 18, 2013 [3 favorites]

The only thing about the startup is that it sounds like not a full time gig. I think it would be not a great idea to quit a full time long term real job to do marketing for a startup a few hours a week.

I think if the issue is that this "a few nights a week" job is becoming more of a full time thing, and you'd be compensated accordingly, and it's a living wage that's comparable to what you could otherwise earn, take it! Work environment and feeling like you're a vital part of a team that's working towards something important is a huge thing, and I think it would be silly to turn down an otherwise good job out of some sense of obligation to some megacorp you otherwise don't care about.

On the other hand, if you've got a good thing going at the megacorp and are just feeling a little "grass is greener", and maybe romanticizing the idea of turning a part time marketing job into something more, and what if you could just do the one you like and not do the other blah thing? Just keep the consistent pays-the-bills good enough megacorp job.
posted by Sara C. at 3:11 PM on July 18, 2013

I'm in my late twenties and a senior engineer in a small company that behaves like a perpetual startup, as its always developing new products and experimenting with different ways of managing the company. Most other engineers I know work for established big companies. Obviously, this isn't marketing like you're in, so I can only offer my general impression of the two company extremes, and you'll have to fill in the snowflake details yourself.

My job can be very frustrating at times, but that's because of serious lack of structure in the company that only I seem capable of fixing bit by bit. Those are my own company's problems, but despite being tempted often, I have yet to pull the plug and go off to one of the bigger, more established companies where I would probably receive better benefits, better salary, much lower stress, and have access to a lot of knowledge already built into the company over the years from which to directly learn. That doesn't mean I won't quit at some point, but it always comes down to this question for me:

"Will I get pigeonholed and stagnant at the big company?"

From what I can tell with talking to my friends and family at those companies, the answer to that seems to be yes. At my current company, I have a ton of flexibility to learn a huge variety of things outside my nominal area, make creative suggestions, and develop and build systems that I think work best for the company. I've become kind of the ultimate engineering jack of all trades, and I'm mastering quite a few of them. My older sister is also the same type of engineer, and she has spent the past decade working for one big company in a narrow focus. She does not like her job, but what's worrisome to me is that I think she would have trouble finding another job if she quit. She's smart and has an M.S. unlike me, but her overall skillset is much smaller while her salary is much higher. She's always been about stability first and foremost, and while it's made her good money, now she's somewhat trapped because she's been pigeonholed this whole time.

You're young and you seem to like what you're doing with the startup. Here are a few questions to ask yourself then.

1) Does it seem like a fairly stable, decently-run operation where you won't have to be too concerned with loosey-goosey management or too many stupid, unnecessary day-to-day problems?

It doesn't have to be perfect, but it should not be chaotic. You seem to hint that this is the case since you call it a "reasonably established venture."

2) Will you be working with a team of COMPETENT people? This is just critical. If you can trust your coworkers and not feel that you have to check or redo their work, there's potential to do a lot of amazing things. Hopefully your team is flexible and receptive to new ideas.

It sounds like this may also be the case.

3) Can you work well without a lot of structure?

This is not an obvious answer, so be completely honest with yourself. I have a lot trouble working in an unstructured environment which is the unfortunately the very definition of where I work. I have to create my own structure and force myself to stick to it. It is hard. I am not good at it. What keeps me here is just the sheer potential for me to do things I would never be able to do elsewhere.

If you can answer yes to these three questions, I say go with the startup. Learn everything you can about everything you can touch and let the skills you've gained there speak for themselves if you have to find another job down the road.
posted by KinoAndHermes at 3:22 PM on July 18, 2013 [1 favorite]

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