In Defense of Selling Out, or The Startup Badge of Honor

By Teddy Chesnut

There’s definitely a badge of honor worn by the founders and employees of startups.  They’re the underdogs.  The innovators.  The crazy people who say it can be done when others say it can’t.  They’re the 3am crew.  They can handle the highs and lows.  They breathe the business.  They do it because it is hard, and they just don’t care, because they can’t help themselves.  They carry around the weight of failure like a ball and chain, but they manage to fly anyway.  In the words of one entrepreneur, “when it’s raining, I feel every single f****ing drop of rain hit my face.”  To work in a startup is to live.  To die.  To be born again.

So who in their right mind would go work for a big company?  Only those who can’t take the heat, who don’t have the heart, who can’t handle the risk?  Sure, startups aren’t for everyone.  But there’s another set of folks who know they’ll end up in a startup someday, and instead choose to join a big company. 

I am one of those people.  I had an offer from a startup – a Boston-based software firm that just closed a $10 million Series B and wanted to make me the second in command on business development and strategy.  Instead, I’m going to be a lowly account manager for LinkedIn.  LinkedIn pays less.  I don’t have nearly as much equity upside.  And the startup was begging me to come back.  What the hell was I thinking?

Well, this is what I was thinking:

1) You only get one shot to build functional experience.  Joining a startup is often an exercise in flexibility.  “Thrives in the midst of ambiguity” is practically boilerplate for startup job descriptions, and what that really means is, “your job doesn’t actually have a description, you’re just going to fight fires and try to make sense of chaos.”  That process can be exhilarating, educational, and incredibly valuable- it’s how I spent 3 years before coming to business school.  But you really get one shot in your career to establish real functional expertise – the kind that people recognize, value, and ultimately try to poach you for.  A big company can offer that, and if you’re looking to become a functional expert who one day wants to get poached by a rocketship of a startup, then a big company might be for you.

2) It’s hard to find 5 great mentors in a company of 25 people.  Early in a career is when you develop a sense of the professional you want to grow up to be.  In a big company you can find a range of people – with different experiences, career paths, outlooks, and perspectives – to serve as role models and career builders.  One of the most attractive aspects of the opportunity to join LinkedIn was the fact that I met at least 3 people during the recruiting process who I was absolutely certain I could learn from – and more importantly, who shared my values.  These were people I would like to grow up to be like.  That’s tough to find if your co-founders are both 27 years old.

3) The whole point is to become a big company.  Any startup founder worth her salt absolutely disdains being a startup founder.  Sure, she’ll take that title for now, but what she really wants is to be the founder of a massive, profitable, sustainable enterprise.  How is she going to get from here to there?  Few companies make it by relying solely on their earliest employees.  When they face the inevitable challenges of scaling – formalizing processes and organizational structures, finding ways to maintain culture as hiring explodes, maintaining focus as competing priorities pull at the resource allocation process – it often takes people who have been there before to make it work.  And where do they often find the talent to take their now red hot growth-stage company to the next level?  Wherever young, aspiring functional leaders are killing it for the companies that have already grown to where they want to be.

In my ideal world, that is how it will work out.  Who knows whether it will.  But this I'm sure of: if I had listened to all the talk about the startup badge of honor, I would have convinced myself that I just wasn't cut out for it.  When in reality, that's just a bunch of talk.


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