Ask Away: Why Should I Work for a Startup? [Part 1]

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SketchWelcome to Ask Away,’s new weekly column! Every Monday, we’ll pose an employment-related question to a group of experts and share their answers. 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?

“This is a question I face from potential hires all the time: ‘Why should I join a company that may or not make it?’ The answer is simple: upward mobility. Larger companies have larger budgets and will only hire you into a position you have been trained for and have experience in. Who will give you that first shot to get your foot in the door? Startups.

“At The Suit Depot, pretty much everyone came in at the entry level and worked their way up. We now have a manager, a Web developer, a head of SEO and marketing, and many more positions. All of these people would not have been qualified to get jobs at larger companies and would have been stuck doing the same thing for years. With our company, everyone is constantly learning and growing with the company. It’s hard to describe the energy in such an environment.”

-Marty Babayov
The Suit Depot

“I’m a big fan of the startup world and can’t imagine not working for one. I’m hooked. Startups are unique because they are fast-paced and exciting. You can see the impact of your work right away, which is incredibly rewarding. If you want to implement a new idea, it doesn’t take long to discuss with the team and receive approval. Startup teams are truly invested in their work — and it shows. This creates an inspiring, sky-is-the-limit environment that is extremely motivating.”

-Hannah Wright
Marketing Specialist

“There are some advantages to working for a startup, as opposed to an established company or large company. You come in and learn many things as the company is growing. It is new and exciting because there are no prior restrictions and [the company culture is not yet developed]. That can be very exhilarating.

“However, the disadvantages are many. The company is getting off the ground and may not have its corporate policies in place, and that can be risky. The company may be run by someone inexperienced. [They] will make some mistakes, and that can be a real problem. If it is a family-owned business, the owners may favor their children or relatives, despite their lack of talent. That may create dissension in the startup. Many startups have to play the learning-curve game: [people] don’t learn until [they] make a mistake, and it may be costly.”

-D. Anthony Miles
CEO and Founder
Miles Development Industries Corporation

“I left ‘large corporation’ with over 100,000 employees to be the 11th employee at a start up. My rationale: large corporations don’t care about individual growth. They look at the larger picture. You are just a statistic. Your growth and learning are dependent on you and your boss — mostly your boss. Things move slowly, decision-making takes eons, and you are left to fend for yourself.

Smaller organizations, on the other hand, empower you. So learning is exponential, decision-making and action are way swifter. Channels of communications are clearer and shorter. No red tape. And, they are flexible.”

-Ketan Pandit
Director, Marketing and Brand
Aureus Analytics

“Working for a startup, as opposed to working for a large corporation, means that each employee has more of a voice. If someone has great ideas for the company, they’re more likely to be heard thanks to the smaller number of total employees and the tighter-knit teams. These ideas are also more likely to be put into place than they would be at a more established company, as change is much easier to implement at the beginning of a company’s journey, before the mindset of ‘the way we do things here’ sets in and gets the business stuck in a rut.

“Working in a start-p also means more opportunity to create real change and disruption in an industry. Radical change rarely comes from within established companies, due to fear of reduced profits and a need to move fast. Startups offer the chance to be part of an industry shake-up that would most likely never happen in a larger business.”

-Rob Rebholz
Managing Director and Cofounder

“Startups aren’t for everyone. Job security, set hours, and guaranteed income may not be certain. For many a family man, a startup can be crippling to work for.

“However, for those who are a little less risk-averse — who dream endlessly of possibilities … and want a life where there are no limits — a startup has to be one of the most exciting businesses to work for.

“As a startup company ourselves, we find that every single day brings with it great rewards and possibilities. Each time we talk with clients, we walk away with new goals, reasons to work smarter, and a desire to achieve even more.

“While the financial rewards (and risks) can be great, the greatest rewards come from being counted as part of a tight-knit team, valued not just for the work I do, but also for the [ideas I contribute].”

-Gordon Hall
Flyover 18

“I have worked at a startup for three years, and it is definitely the best decision I have ever made.

“You should work for a startup because you get to have a direct impact on the business. You can also be exposed to all aspects of the company, which, if you are just starting your career, can be a great way to figure out exactly what it is that you want to do and are good at. Also, you’ll generally get some portion of equity, which means that the harder you work to make the company successful, the more your shares will be worth.”

-Scarlett Sieber

A lot of people clamored to share their thoughts with us on this particular topic. Stay tuned for part two, which we’ll post tomorrow!

Read more in How to Choose a Career

Matthew Kosinski is the former managing editor of