11 Things You Need To Seriously Consider Before Joining A Startup

Considering joining a startup? Looking for something different than the nine to five grind or bureaucracy of a large corporation? There's a couple things you need to know first.

Startups are hard. Working at a startup is equal parts addicting, rewarding, frustrating, and confusing. I should know, I've worked in senior roles at three different media startups in the last three and a half years and have some insight that should help you on your way.

1. Can you thrive in chaos but work towards structure?

Before jumping into startups I worked at major companies and publishers like Turner Broadcasting, Huffington Post and Business Insider. At Turner I joined to help launch CNNGo, which was a new property within Turner that in many respects was a startup, but within the mothership of a large company. At HuffPost, I joined right when AOL bought HuffPo, literally on the same day. At Business Insider I joined right as they were on the cusp of figuring things out with the brand and making a push internally.

This is all to say I had become accustomed to a bit of chaos before I even joined my first early stage company. Those experiences helped prepare me for what came next. They helped give me the context of what I believed worked and did not work when it comes to team structure, culture and expectations.

For those coming from a more rigid and already highly organized and segmented work background, the idea of the freedom and chaos of a startup can sound exciting and liberating. It is, but it comes at a cost. If you're coming in as a leader you must be prepared to embrace chaos and have a plan to implement structure and process that can scale.

If you're coming in at a junior level, you need to believe in and trust that your leaders have this plan and are providing you with goals along with the ability to explore what works within the framework of the brand mission.

Regardless, you won't always know what you're supposed to do and you need to be proactive and constantly experiment to succeed.

2. The people involved early ARE the company culture

Lets say the startup you're considering joining is 10 - 20 people. The entire team is handpicked by a few people. The company "culture" is only as defined as that small group of people have made it, whether they've been around for six months or two years. It is a different thing to work closely with a small number of people that comprise the entire company than it is to work for a department in a large corporation.

You will spend a lot of time with these people. Are you patient enough in dealing with different personalities? Do they check their egos at the door? Better yet, are you able to check your ego?

Company culture of an early stage startup is heavily defined by the founders. Who the founders are as people will tell you what the team will be like. Are they bros? Then expect environment to be bros. That's fine if you want that, but not so much if you don't.

There will likely also be a click of people who knew each other previous to the new venture, so if you don't know them then it's potentially like going back to High School and figuring out what table to sit at during lunch.

You have to be prepared to be proactive.

3. Sticky notes are bullshit

When you first walk into that office or co-working space and you're soaking in the setting and general vibe, keep an eye out for excessive use of sticky notes.

Are there whiteboards and walls covered with multicolored sticky notes with interconnecting lines pointing from keywords and mission statements?

It's bullshit.

The more sticky notes a startup uses does not mean the more creative or "startupy" it is. Sticky notes are colorful, but they're also a waste of time and will tell you if those at the company are spending more time writing on small paper squares and moving them around or actually getting things done. Just know that entire articles could be written based on making the proper use out of sticky notes in startups.

The harder a startup tries to look like a startup the less confidence it has in its own identity and those who are trying to give it an identity. Sticky notes and the like don't give a startup an identity.

In addition to keeping an eye out for excessive, dusty sticky notes, ignore the keg in the corner, the bean bags, the ping pong table or whatever else there is that looks like a startup. Put it out of your mind. Focus! A lot is at stake here.

It's the people, the product, the CEO, the investors, the revenue plan that matters.

4. How much do you know about the founders or CEO?

Do your homework. At an early stage startup, having faith in and trusting the founders or CEO is equal to if not more important that believing in the brand, product or whatever it is the startup is pushing for.

If for example this is the CEO's first foray into startups understand they're going to go through a learning curve and growing pains. In this case, you need to look to see if they've been an agent of change and forward thinking in previous roles. Do they have the endorsements of not just their peers but of previous direct reports? Do they spend more time talking at conferences and boosting up their profile than actual organizational and leadership experience?

A CEO of a startup absolutely must have experience in building teams and then managing those teams. If they don't have this experience they need to be smart enough to hire people who have those capabilities (and trust them fully) or have a co-founder than can. You need to make a judgment call, and to help you do this you need to gently inquire about the "past successes" of the founder or CEO. Some CEOs are just given money to start something but haven't the foggiest of clues as to how to get it done because they've never done it before.

If you can't ask directly, then ask around. Do some research. Is the CEO trigger happy and have a history of terminating employees at the drop of a hat? Expect that to be the case then.

Do you have confidence in the CEO or founder's ability to represent the company both to current investors, potential investors, the media, clients or possible clients and those in your industry? The founder and CEO is your pitch man or woman. They're the ones who are out there getting the company money to build, grow and sustain. Some CEOs are better at this than others.

Let's compare two different situations. One, a CEO is giving a large sum of money right off the bat by an investment group and four years to make it work without needing more investment. Two, a CEO has minimal and limited funds to work with by an initial investor that that requires other investors by the second year.

In the second scenario you must have faith in the CEO to secure investment early. In the first scenario you have to have faith that the CEO has the experience and capability in managing that investment money without overspending and hitting high burn rates. Because if that money runs out early or is spent too freely then that CEO has to go into full pitch mode or the company dies, so they must be capable. In each scenario there better be a good revenue generating plan in place. No exceptions.

When interviewing with CEOs for a startup role, I strongly advise asking the following questions of the CEO or the hiring manager:

• What are your earnings expectations at 1 year, 2 years for the company?
• How do you define a supportive and thriving company culture? What do you envision the culture to be like 2 to 3 years from now?
• What kind of people do you look for when building a team?
• What are the expectations for success with my role and what do you expect me to contribute to the company?
• Who are the investors?
• Who's on the board (if there is one)?

5. Make sure the startup has the right investors

Or at the very least are pursuing and targeting the right investors and not "random" money. Knowing who the investors are and their track record is incredibly important when considering the longevity of the company and the support it will have. You can have a successful brand or product, but if the CEO and product is not aligned with investor expectations then you're toast. This comes from my experience at Pixable. By all accounts we were successful. We pivoted a photo aggregation app into a media property geared towards visual storytelling with the millennial audience in mind. I came on at the pivot stage to grow it, and in under two years we hit nearly 10,000,000 unique views a month, high engagement rates, 50,000,000 video views a month on Facebook, advertisers on board for branded content, major publisher partners, and a revenue plan that would have had us making money.

We were shut down. Startups are hard. Pixable was bought in 2012 by a telecommunications company not based in the US. When they invested in it, they bought it for the photo aggregation app that it was. It wasn't working. So when the new CEO was brought in he rightfully recognized Pixable wouldn't survive as a photo aggregation app and decided to pivot. That's the point I came in.

The CEO was completely correct. Facebook ended up shutting off their API to third parties for personal photos and had we not pivoted it would have been game over right then and there.

Had I known what I know now, I would have considered this possible conflict before hand. The investors primarily worked in tech investment and not media, so there would forever be a disconnect in what we were doing and their expectations. This isn't to blame them as they did allow the pivot, but they were not in the best position to understand the market we pivoted into and what it takes to really make it.

I would have considered it, but in no way would I take back the position or the experience.

Additionally, if you're interviewing for a position at an early stage company and they're being shady about who their investors are and what their expectations might be, be wary.

6. Keep your grand plan to make millions in check

One of the main reasons people consider joining a startup is in the hope of eventually eventually making more money than they've ever dreamed of. Everybody has dreams of a startup going full on Snapchat or Facebook and making you millions, but the reality of it is much less encouraging.

Don't expect to make millions. Don't expect to make it big or make a dime over your base salary or bonus. The likelihood of a startup truly making it and you getting a fat payout are extremely rare and unlikely.

That's not to say that you shouldn't negotiate for all the equity you can possibly get. You absolutely must do this if you even want that chance at a payout, and you need to understand the right questions to ask before taking the job.

Where to start? Business Insider's Alyson Shontell's article "If You Want To Get Rich At A Startup, You'd Better Ask These Questions Before Accepting The Job" is a great starting point to asking the right questions.

Adding to Shontell's excellent guide, do not accept an offer if there's no equity they're prepared to give you right away on day one. If they tell you they'll have something in three months, don't accept. Why? Because you don't know if that three months will turn into six or never. It's a startup, things happen. Priorities change and unless you get something on the table in writing at the very beginning you're putting yourself in a bad position to negotiate later.

Equity can also be meaningless if you're not planning on sticking it out, which means that if you've misjudged the CEO, company culture or if it was the right long term fit for you, then if you took less salary in the beginning but more equity, you've just done yourself a disservice.

7. Have an exit plan before you even start the job

Because the majority of startups won't make you those millions, be prepared to not make those millions and to not spend summers on your mint new yacht.

So what do you expect to get out of the experience if you never end up with that money at the end? This is an easy one.

Startups are a fantastic opportunity for career growth and to gain experience that is more difficult to come by in corporation. This is the case even if you end up at one short term. You can still work it to your benefit.

You can get your hands dirty in a variety of ways. If you're hired as head of marketing, expect that you'll be doing more than what's in the job description and embrace it. If you're hired at an entry level position, do anything and everything you can and contribute where needed, as needed. You'll get promoted if you excel.

Have skills in mind that you want to acquire before you start. Will the startup provide you with the ability to try new things? Are you prepared to realize you're going to have to fly by the seat of your pants at times? But know that if you are prepared to learn then you'll grow. So even if the startup doesn't make it or if you don't make it at the startup, or a better opportunity comes along then you'll have expanded your skillset and hire-ability.

Case in point, when I left Pixable I wrote that post highlighting what the team accomplished and ended up getting multiple job offers. For the first time in my life I had employers coming to me. My former team went from interns to editors. Other staff went on to good roles quickly. The company didn't make it, but the staff did.

8. Do you want to be a leader?

Are you, or do you want to be, Alexander the Great or are you more of a Colin Farrell playing Alexander the Great in a movie type of leader?

If you're not already a leader, do you want to be one? The ability to grow at a startup is greatly bolstered by your ability to grow into a leader. When I've hired staff at startups I've always looked at the candidate and tried to determine their capability to continuously grow in responsibility, taking and incorporating feedback, their ability to handle failure and move on from it and their potential at currently or eventually being able to provide actionable direction to others. Those who sit on their hands and don't constantly engage and interact are those that will get the least out of being at a startup.

Uncomfortable with managing people? Be prepared to get less out of a startup. If you've no experience managing people but have aspirations to do so then a startup is a fantastic opportunity to get the chance to grow and manage a team, which in my opinion is absolutely invaluable when it comes to career development.

9. Established or new managers should manage their team building expectations

For those leaders already experienced in building and growing teams, its best to manage expectations and understand that burn rate needs to be kept in check. Team growth is something that should always be addressed as needs arise rather than filling holes that don't yet exist. For the established leader, this is an exercise in patience but a necessary one. Growth isn't equal to "hiring like crazy."

The Death Star wasn't built in a day was it?

It's exciting to build a team and to see it grow. It's exciting to come in and manage a team at an early stage, but it is also extremely challenging.

Just ask Orson Krennic.

"Bringing Galen back was a bad idea...maybe I shouldn't have shot his wife."

You must be prepared to work on process and establish goals that are achievable by your staff, to listen to them, to provide feedback and follow up on it even when you get too busy. This goes for a staff of two or 22. Don't try to build the Death Star in a day, work up to it. Raze a few ancient temples before going for the big enchilada.

If you can't do that, be prepared to lose people, and if you lose people at a startup then you're going to hurt the company much more than if it was an already established company with a reputation.

10. Working weird and long hours is mandatory, be prepared

It's thrilling to work late into the night on a shared vision or project and succeed. The sense of accomplishment you get from it is addicting and immensely satisfying. But so is the satisfaction you might get from attending your daughter's first day of school or spending time with your significant other or family.

There is such a thing as working smartly and not just working long hours because everybody else is. It is possible to have a life and work at a startup, but to do so requires a diligence in time management and organization that goes beyond your typical nine to five corporate gig.

For those looking at entry level roles at a startup, look for flexibility from your future manager. Yes, they'll want you to work long weird hours, but do you believe they'll also accommodate you when you need it? This is important.

For all of the managers and leaders at startups out there, don't drive your employees into the ground.

Burnout is a real thing at a startup at all role levels. Don't be complacent. Help your staff work smarter in addition to working hard. Reward them. Do what needs to be done and then some, but step back yourself from time to time and make sure you don't miss your daughter's first day of school, that family trip you were planning or that personal moment you need. Those things are important and when you're working at a startup it is easy to get completely caught up with "I'm doing this for our/my future" but miss out on the "now" of your life.

So that's a lot to think about...

There's a reason why those who really dig into startups end up working at multiple startups or even launching their own. They're the ones who are never satisfied and dream big. They look towards the future. They get a taste of "this is what a company should be like" and they want to try again and again. And eventually, they'll make it. You'll make it.

Consider all of the above when thinking about joining a startup but consider one thing above all else, does the startup give you an opportunity to do something you love doing? It sounds cliche, but I'll be damned if there's not truth in the tired old saying "love what you do and do what you love."

Good luck to you, find your perfect startup and don't give up.