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Three years in J-school prepared me for the job hunt and the demands of the 24-hour news cycle. What it didn’t ready me for was the evolving world of applying for jobs at and working for a startup.

Nearly two months to the day after I started my job as a reporter for KCFreePress.com, I left. While the details of my non-disclosure agreement don’t allow me to discuss the situation fully, I can say that I left after I felt that my ethics and credibility would have been seriously compromised had I continued to work for the company. That, combined with serious financial issues, made the situation unbearable.

I’ve been unemployed for a week, and between freelance work, interviews and the gym, I’ve done a lot of thinking about the job I left, and more importantly, the types of jobs I want.  I still believe that startups are making great waves in the industry and I wouldn’t hesitate to work for another one. My friends across the country staff some of the best: Publish 2, Patch.com, Pure, Texas Tribune…

When it comes to being a young journalist, joining a startup means having the chance to be part of the core of something new. As a member of a small team, you get to be a bigger player, gain more experience and ultimately make a large-scale impact. What’s really crucial is picking the right startup, making the right moves while you’re there and ultimately, knowing when (and if) it’s time to leave.

Here are a few things to consider if you’re looking to take the plunge into startup life, and some wisdom I wish I’d stumbled on sooner.

Get a reality check

If you’re at the ground floor of a startup, everything isn’t going to come easy. You work hard, then you work harder. You will do things you never thought would be in your job description. Chances are, if you’re a younger employee, you’ll be making a few copies and some coffee runs. Ideally, you’ll also be making some big contributions to the success of your organization.

Like in any job, managing your expectations is important if you’re on the team at a startup. You probably won’t be the next Mark Zuckerberg, but there are a lot of benefits toward being involved with startups:

• Learning: In two months at a startup I learned more about marketing, managing and self-sufficiency than I learned at more time working in a traditional work environment.
• Pride: If your startup is successful, you’ll have a ton to show for yourself. If it’s not, you still have a great skill set, and a rare experience to take to your next job.
• Influence: When you’re one of more than 500 employees at an organization, it’s tough to make an impact. Because startups are usually staffed by a few committed people, your voice matters more and you can have a bigger role in shaping the product.

The payoff and rewards of working for a startup are great, but they come with long hours, sleepless nights and no shortage of cheap, black coffee. That means when things get tough, you have to be your own ally in finding ways to make the situation work for you.  Think outside the proverbial box and find unconventional solutions to unconventional problems. Sometimes, arrangements don’t work out, but more often than not, you can find ways to survive, and even thrive.

Show me the money

Salary questions are one of the biggest sticking points of any job offer negotiations, but if you’re considering working for a startup, you need to ask a different kind of money question. Get an idea of what the company’s financial picture looks like before you accept any job offer, and make sure you’re comfortable with that picture before you sign anything. Guy Kawasaki, an Entrepreneur Magazine columnist, offers a couple questions you should ask before joining the team at a startup.

How much cash is in the bank?

This is a straightforward question. Now take this answer and divide it by the monthly burn rate. This will tell you how long before the company runs out of money. If the answer is less than six months, be cautious unless the company already has signed term sheets for the next round of financing. If it doesn’t, assume it will take at least six months before another round of financing closes.

When will the company achieve positive cash flow?

You should ask this question because you’ll probably be told that there are months and months of cash or that another round of financing is “looking good.” If the answer is years away, then you’re signing up for more risk because venture capitalists aren’t the most patient, loyal people. More risk is okay-it takes years to build a great company–but you should know what you’re getting into.

Check out the business model

Learn as much about the business model up-front as possible. If the company doesn’t have one, that’s a bad sign. From personal experience, I wouldn’t recommend signing on at any company that can’t guarantee operations (and your paycheck) for at least six months unless you’ve got another source of income or a nice nest egg to fall back on. The economy’s been fragile recently, and another bad turn could leave both startups and already-established businesses handing out pink slips.

Questions about money, finance and business models aren’t easy to ask and it’s often tough to get straight answers. Don’t let that discourage you from asking tough, uncomfortable questions.  Any employer who won’t respect your need to know isn’t one you want to work for.

It also doesn’t hurt to know who’s behind the dollars and cents at your startup. Do yourself a favor and do a quick background check of major financial backers. Each state has different laws when it comes to finding criminal and financial records online.  Be familiar with your state’s policies and make learning about your company’s finances as important as researching an investigative story.

If you find details that concern you – like unpaid taxes or a lengthy criminal record – ask about those things, and consult professionals you trust who can tell you if they’re small problems or potential red flags.

Find your passion

Partnering with a startup won’t work unless you’re passionate about the work, whether that’s a new news organization, marketing firm or a physical news product headed to the market. The best startups succeed because they’re piloted by several dedicated, invested people who are all working toward a combined vision.  If you’re half-heartedly going into this game, you won’t be able to make the sacrifices or do the work necessary to really  prosper.

Pick a startup that you find meaningful, with work that you can really throw yourself into. In my experience, I picked a hyperlocal news Web site aimed at bringing more local news coverage to Kansas City. While the site I worked for wasn’t the right fit for me, I’m invested in covering local news – particularly politics – for local communities. There’s a huge need there, and I think the right startup could take advantage of that need, especially in Kansas City.

Know when to fold

“By their nature, they are like lottery tickets for everyone, including investors and employees. The best situation is to get involved early or prominently so that you will share in the rewards if the thing succeeds.

Another note on startups: They can be helpful, even if you ultimately don;t score big, for all they teach you. Think about that. Also try to determine how well they are funded and how long they can go before they have to make money. If the CFO of this company does not have a handle on that, be afraid. Be very afraid …”

Grimm suggests all employees, given the economy, be in a “constant state of readiness” and show the new skills they’re learning and cultivating.  That way, if it becomes time to move, you’re ready and can offer value to a new potential employer.

So, should you stay or go? Be your own advocate and look for red flags, or non-negotiable situations, that mean it’s time to leave. Here are a few of my “non-negotiables”:

• If the lights are literally being turned off over your head, leave.
• If your paychecks are bouncing, or your employer can no longer compensate you reasonably for your work, leave.
• If your work has compromised your ethics in a major way, leave.
• If you are no longer getting personal or professional value from the work you’re doing, — and have made reasonable attempts to change that situation yourself — leave.

That said, before leaving any position, you should make sure you’ve done everything in your power to fix problems at your current job. Work with the people you work for to try to change your working environment before making the decision to leave it. It’s true that startups often offer less “wiggle-room” in terms of lessening responsibilities, but managers are often willing to make a few adjustments to keep a valuable member on the team.

Unless your situation has crossed a non-negotiable area for you (mine was ethics), stick it out until you are in a financially safe spot to move. Most people can’t survive without a paycheck, so make sure you don’t make a decision you regret.  If you’re thinking about quitting your job and want to get an idea of how it will impact your bottom line, check out Learnvest. It’s a great site that gives unbiased financial information, targeted at young women, and can help you plan to leave your job comfortably, before you actually jump ship.

About Juana

Political journalist. Social media addict. DC transplant by way of Missouri.

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