Ask Wahoowa: Startup vs. Big Company – Which is Best Right After College?

We ask dozens of U.Va. alumni for their thoughts on this polarizing question.

This is the first post of Ask Wahoowa, where we put U.Va. students’ questions in front of HackCville’s alumni network and ask for their feedback. In this post we’re kicking things off with a hotly-debated question – what’s best to start in after college, a big company or a startup? (Answers were selected for print out of a larger pool, and were slightly edited and condensed for clarity.)


Start in a Big Company

Both require different skill sets, so you need to pick the right one for you. I liked being able to cut my teeth doing big-company tasks, and getting familiar with what it’s like to be in a “real” workplace. I  worked my way from the front desk to a marketing position in less than four months. I fought for my salary. I met some coworkers and bosses who are now my lifelong mentors. And, thanks to one of these mentors, I found my current startup opportunity.

There’s always time to jump ship and join a startup when the timing is right and your resume shows real dedication. When I’m looking at resumes & hiring for my startup, having too many six-month stints is a red flag. Connections are everything and I made those connections at the “big company” level.

– Kaitlyn Houk Witman


Go to a big company first. You get to learn how to be organized and prioritize conflicting tasks and assimilate data. Pick up the good habits and learn how things work in the corporate environment. After a few years you’ll be ready to take that learning to a startup where there is a lot more ambiguity and a lot less time. If you’re efficient at the basic things and know how to quickly settle on a process – abilities the big company experience teaches you – it leaves you with more time to focus on innovation.

– Sukanya Ragunath


Start in a Startup

My first work experiences following college were all in startups of sorts. One was a corporate art firm that worked out of two offices – one in New York and one in London – but the company only employed about twelve people in total. My second experience was in a young independent school that was less than twenty years old. These small, personnel-driven work environments were open to change and innovation simply because they still saw themselves as works-in-progress. As a result, I was able to participate as an engaged and vocal member from my first days on the job. I was given opportunities to lead and develop new programs because everyone had to do so in order to ensure the success of the organization.

– Marie Reed


Startup! You’ll get to wear more hats, build real products without bureaucracy, and (often) help people. Most new hires to big-co’s go to underwhelming teams because internal people move off of them. You have to be more critical of the personalities when joining a startup, the extremes of a bad CEO and a good CEO will impact your day-to-day much more. It may take a couple times to find the right type of company for you, but my suggestion is to look for humility and great people you can learn from.

– Olex Ponomarenko


Take risks while you’re young, before you have a family, before you have responsibilities, kids, a mortgage, etc. So, I would say a startup. You’ll see a lot of failure, but the lessons you learn from failure are often much more powerful than the lessons you learn from great success… The truth is that great success is often a mixture of impeccable timing & luck…

– Zee Rahim


It Depends

Totally depends on what area you are in and what goals you have. If you are focused on developing as much experience as possible, as quickly as possible, then I’d say working at a startup is best. Starting at a well regarded “name brand” company can add substantial credibility to your resume, especially in a consulting role or select finance roles.

– Andrew Kennedy


Generally speaking, you’ll have more varied roles in a startup, whereas, in a big company, you will likely have narrower responsibilities. There are good startups and bad startups just as there a good big companies and bad big companies.  Figure out what criteria (e.g., flexible hours, stability, collaboration) are important to you and make sure the company meets most, if not all, of them.

– Elise West


Do whatever you’re most passionate about at the time! There’s no one right method as they both advance skill sets in different ways. I enjoyed my path from big company to startup though 🙂

– Jason Fishman


There are merits to both. I started my career with Bank of America and spent two years in a terrific training program, had access to excellent mentors, and the opportunity to see how an established company operates. I would not trade that experience for anything – however, I also knew I wanted out of the constraints that a large organization imposes.

Having started a “startup,” we loved hiring young college grads because we could mold them while teaching them our culture and our approach to doing things. Some excelled in this environment, others needed more structure. If you can work in a far less structured environment, I think you can learn a ton working in a startup and, while you will likely be paid less, you will have much more access to company leaders and decision making.

– Mickey Millsap


Instead of thinking about whether it’s a startup or a big company, I’d suggest evaluating opportunities based on learning, impact, brand, and compensation. Those factors are relatively more or less important to each individual, so you should find out how important each is to you and evaluate opportunities on that basis.

– Rohan Wadhwa


It definitely depends on the kind of work you would like to accomplish and the nature of the startup. On TV, I took a very unusual path and after interning and freelancing for a local Charlottesville TV station, set my sights on CNN. This is unusual because most in the TV industry remain at the local level for a few years before applying for positions at the national level.

Since the change, I’ve found I work much better in a larger, more competitive environment with an established structure whereas someone else might thrive in the atmosphere of trial and experimentation startups must cultivate. Remember how you worked alone and in groups in college and then make sure to fully investigate the workflow of positions that interest you.

– Shelby Rose Folmsbee


Your first job does not need to be the job of your dreams (or even the first job on the path to the job of your dreams). Choose a job that will be challenging, interesting, and give you a lot of responsibility and the ability to grow. Depending on your interests, that could be a startup, a Google, or a huge consulting company. It is important to have the confidence to try something and reevaluate.

– Siggi Hindrichs


Joining a startup versus a big company is largely a question of, “what will I be learning?” and, “who will I be learning from?”

– Spencer Ingram


Honestly, it depends on what you want to do in what industry and personal preference. I personally started at a little bit of a larger company (PBS), and would probably only want to transition to a later-stage/larger startup as my next career move after this. I’m still earlier on in my career and seek a design team and mentor that only slightly larger companies can offer.

Once I get to the point later on in my career where I’d like to take a flagship role and am comfortable being the first designer/only designer/one of two designers where they truly need to establish a design culture and the design direction moving forward, a small startup would make more sense. I also find experience at a larger company can open more doors. That being said, I’ve had several friends and colleagues successfully transition from either large company to startup or vice-versa at some point in their careers.

– Trisha Cruz


Doesn’t matter. Put yourself in the highest intensity environment you can where you’ll surround yourself with the smartest people you can find, and where you can learn a lot very quickly. Then leave after 18-24 months and find another equally intense, but different, environment. Stagnation is the enemy of progress.

– Weston Reynolds


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