Startup Experience and Your Career

Paul O'Brien
4 min readJun 9


With graduations upon us as the summer heats up our days, high school and college students are seeking the advice that gets them off to a great start in the next chapter of their lives. Increasingly, thanks to pop culture, media, and social media, seemingly everyone wants to be an entrepreneur or venture capitalist.

My Quora (a favorite Q&A platform where I advise) sense is tingling and an App I frequent, Fishbowl, put the question to me directly; with one of my kids on her way to college, here’s my take.

Does startup experience accelerate your career?

Without question. Not even open to consider debating it.

Startup work requires you do 3 things differently than a typical job:

  1. Constantly solve problems. Any problem. Something is wrong? Don’t ask for permission, don’t ask for help, fix it. Seriously, fix it, and *then* let someone know what happened and what you learned. Telling someone something is wrong without providing any help or solution, really just piles more on the endless list of work that needs to be done. Don’t misunderstand me, sure, let someone know, but weigh how much letting someone know or asking for help is a distraction, a priority, or something you can just solve. Solving it is valuable.
  2. Your job in a job is to keep the job, do the work, and maybe impress someone to get a promotion. Your job in a startup is to make sure the startup works, or you’re all out of the job. Follow that? Your experience working with a startup advances your career NOT because the startup succeeds but because it shows that you are able to handle the risk, work ethic, and burden of working somewhere you might not get paid, at all. In a job, you make a commitment to do the work and get paid for doing that work while in a startup, you have a moral and ethical obligation (in my opinion) to ensure the people you work with continue to have the opportunity to do what you all love.
  3. Take risks. #Startups don’t have the answers. There is no training, no operating manual, and no plan, at least not any that is right. If you’re seeking a manager or a boss in your #career, look to established companies, not startups. You won’t get promoted by doing what any “boss” says and you’re not getting much help doing your job in the startup because your job is to do your part: Create value, or get out because you’re wasting everyone else’s time.

I want to touch on that last point for a moment just a little more because in the startup ecosystem we get a lot of consultants, service providers, mentors, advisors, and even investors who *want* to help, want to profit in the process, and often have no business working startups. If you are not the type to wake up every morning and NEED to work on the startup, to accomplish something that creates value (not advice, strategy, or introductions but real value delivered by putting in the work), then do yourself and everyone a favor and remove yourself. You’re contributing to the failure of a venture and the demise of many other people because you are expecting a job where one doesn’t exist unless YOU make it.

In a nutshell, create value. Begging the question, if you have a job and, in your job, you do that and get paid for it, you’re not really *creating value*

Sure, you’re delivering value, but you’re also getting paid for that. So, good for you, good for the business, and everyone is happy. But you’re not creating greater value — even if you do more and get promoted (because that promotion is recognition and pay for the above and beyond you went).

Do good and keep your job. Do better and get promoted, maybe, next year.

Companies (in the sense of traditional job employer) don’t care about you. They have a moral responsibility to their shareholders, to be successful. So, you can advance your career, a little, if you go above and beyond (but not rock the boat) and get promoted.

Good for you.

But startup work is literally rocking the boat. Truly, rock the damn boat so we can see what happens… And now do something about that instability in our boat rocking: fix the leak, cover the edge that floods, create some balance… DO something, and god forbid, don’t just sit there and rock the boat while saying, “hey, this boat is tipsy.” To a startup, that skillset, which is unusual in people, is incredibly rare and hard to find.

You know who typically finds themselves rocking boats?

CEOs. Other Chief Executives. Founders.

Your skill at keeping a job and even getting promoted is nice, it is worth something. But the experience of WHAT IT TAKES to work in a startup is a unicorn among people, it’s invaluable (if you can really do it! And mind you, most people can’t, even if they try; but that’s not discouragement to at least give it a try)



Paul O'Brien

CEO of MediaTech Ventures, CMO to #VC, #Startup Advisor. I get you funded. Father, marketer, author, #Austin. @seobrien & @AccelerateTexas.