Ask Away: Why Should I Work for a Startup? [Part 2]

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IdeaWelcome to Ask Away,’s new weekly column! Every Monday, we pose an employment-related question to a group of experts and share their answers. This week, we had an overwhelming number of responses, so we decided to add a second installment.

Have a question you’d like to ask the expertsLeave it in the comments, and you might just see it in next week’s Ask Away!

This Week’s Question: Why should anyone work for a startup  instead of an established business or major corporation?

“You’ve heard all the generic answers to ‘What are the perks of founding a startup?’ Perhaps: ‘I get to be my own boss,’ or ‘I get to create my own hours,’ or ‘My work also happens to be my passion project.’ As you might expect however, it’s not that simple. The real reward comes from the minutia of the startup life. Resolve a petty workplace quarrel over a proper pint. Relish in working with people who are smarter than you are and have been in your shoes. Take pride in listening to conflicting opinions, especially when you least want to do so. Never let yourself take for granted a small, collaborative work environment.

“Out of necessity, the startup life brings out traits you probably didn’t know you even had. If you can hold yourself accountable, are willing to put in long hours, and are looking to build something with a unified point of view, then you probably should have quit your dead-end job a long time ago.”

-John Hayes
Business Operations Manager and Founding Member 

“I worked in corporate America for 15 years at pharmaceutical and medical device companies. I enjoyed my job, loved interacting with my coworkers, had great benefits and income, and the hours were fairly predictable. If it was so great, then why did I leave it for a startup?

“In the summer of 2014, I was laid off. I decided to make a change and became a consultant/virtual assistant for some local San Diego companies and entrepreneurs. The main reason is that I wanted a more flexible schedule to be with my kids, I wanted to have more choice over the projects that I was doing, and I wanted to feel passion for what I was doing.

“In August, I met Jillian Darlington, the CEO and founder of the MomCo app. After spending 3 weeks with her, I knew that I had to be a part of MomCo. I believed in her, and I could see the value that the MomCo App provided to moms and small businesses. I knew that the work that I would do at MomCo would make a real difference and loved the idea of helping make moms’ lives easier. So, when faced with the choice between another job in corporate America and MomCo, I went with my gut. I decided to invest in MomCo and follow my passion of helping other moms.”

-Beth Bryan
COO and Cofounder,

“Company culture is different [at startups]. At Medigo, I have the feeling that my coworkers are friends, rather than mere acquaintances. There is less of the stale coffee-machine chat than you might expect at a larger company. People genuinely get along with one another and enjoying socializing outside of the office. Organized company events feel like a pleasure, as a opposed to a chore. That’s another fundamental benefit of working for a startup.”

-Andrew Cherrie
Country Manager, U.K.

“I would definitely recommend working at a startup. It may be scary job security-wise, but the experience that you get overshadows that fear. You get to see a company in the process of being built, and you have a hand in every element of the business. When people ask what I do, all I can say is, ‘Everything!’ or ‘I wear multiple hats.’ It’s always exciting to see our milestone achievements or to rework something to help its success.

“My response in a nutshell: It’s wonderful, but it’s not for the faint of heart. You will end up working more, but you’ll be more involved with a lot of decisions.”

-Natalie Tucker

“Speaking as an employee of a startup, I would have to say the ultimate benefit of working for one is the
opportunity to be irreplaceable and to gain invaluable experience. When you adopt early to a budding idea, product, or company and nurture its growth, you become indispensable when it flourishes. At a startup, you may not be hired to a specific position so much as you are taken on as a team member. Your contributions and dedication to a startup aren’t always rewarded monetarily at first, but seeing your creative input and valuable insights come to fruition in an environment where your unique perspective and abilities are fully appreciated is priceless.”

-Casey Fisk
Content Strategist

“Anybody can work for a startup, but it doesn’t mean that everybody should. As in any other industry, certain personalities are better suited for startup life than others. The broad appeal is the potential upside: the idea that the company could be acquired or, far less likely, go public, and the employees would stand to make decent money as partial owners. That’s a pretty universally appealing concept.

“But the key question is, does that truly motivate you? Are you the type of person who believes your actions affect outcomes, that you have the ability to make changes through both action and inaction, and that the work you do will help propel a company forward? That is only one aspect of the mentality of a person who might excel at a startup, but it’s an incredibly important concept to consider before signing up for the startup lifestyle.”

-Tina Lumbis
Senior Director, Marketing

“I sit next to the CEO. I make decisions that affect the company in big ways. Big companies move slowly. CB Insights has some wickedly smart engineers who respond quickly to client needs. We control our destiny. I believe in the problems we’re trying to solve here, and it’s up to us to figure out the best solutions.”

-Emily Veach
Community Manager
CB Insights 

“Small businesses have the time and resources to really care about their employees. For instance, eZanga celebrates the big wins in its employees lives. We’re given the day off to celebrate our birthdays, and we recently had a baby shower for our director of sales. You spend so much of your adult life at work, and small businesses want to make that enjoyable. Small business employees become a family of sorts, and they end up celebrating with each other like one. That’s what makes working for a small business such an enjoyable experience for me.”

-Megan Ingenbrandt
PR Specialist

“Do you like feeling like you are just a number? I don’t think anyone likes feeling that way, but at a large corporation, you usually get a nice little badge to remind you of that. People can make a decision about your future without having seen you in person even once. Corporations are mostly all about profits, and people come second to that.

“Do you like being challenged? Honestly, this is a matter of preference, because I have encountered many people on the other side of the coin that don’t like challenges. Some people prefer to have the same mindless task as a daily routine every day of their life. It makes them happy. If this is more of your cup of tea, corporations are right for you; otherwise, if you get easily bored and need to be constantly challenged, then maybe a startup is the best place for you.

“Do you enjoy constant meetings where there are a lot of good ideas but they are extremely slow to implement, if ever at all? Startups are living and breathing settings where things change at a rapid pace. They have to be this way; otherwise, they fail. If you are not someone that likes constant change, then startups might not be the best setting for you. If you do [like constant change], then you should fit right in.”

-Ramon Khan
Marketing Manager
National Air Warehouse 

By Matthew Kosinski