You’re Young: Should You Work at a Startup or an Established Company?
Zak Slayback
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Let me throw in some other points and echo some of what you’re saying in a different way. This coming from someone who has worked in all types of companies.

Stability in established companies is a myth. The company may stick around but your job won’t,necessarily. What you want to know is if the company is growing and has a growth plan, regardless of what size the company is or how long it has been in business. Companies that have flatlined or are declining have very dark cultures and tough, anxious working conditions. Look at Buzzfeed right now, laying off a bunch of people, having missed numbers badly. I can name a number of established brands that are tanking, too (A&F, Victoria’s Secret, Blackberry, currently in the news but there are a bunch). Not a great place to work right now. Stability — and opportunity — comes with growth. Be highly aware of that.

You do need to think about your resume. Everyone needs to be a career entrepreneur in this age of widespread instability. Every role needs to add to the toolbox so that the next role/company can be a progression. Established/known companies are a plus for your resume early in your career. Says you’re smart and got through tough hiring thresholds. Plus, you will come across as more trained and in command of the fundamentals. If you start with a startup, be conscious of the impact you make if the company is not well known. Make sure you can dimensionalize your impact and can show how you have gone above and beyond to make sure you’re marketable. That’s how you overcome the potential downside of your last role not being highly valued to a prospective new employer if they don’t know much about your last employer.

When it comes to wealth accumulation, you make more at an established company because they can pay market rates and have great incentive comp. Unless you’re getting shares at the startup — and prospects are looking good for the company to be bought up or go public — you usually win at the established companies. Startup founders would be the obvious exception.

If you need or rely on coaching and direction then go to a more established company. Processes may be bad, but they at least have them. If you are inspired by the idea of being shown a seat and you are given some general business objectives to go achieve and then ‘call me if you need anything’ then a startup is for you. You have to be a real self-starter who thrives in white space and detests having a confined list of accountabilities. You enjoy making up for the gaps in thinking of the founders who have less time to tend to infrastructure in the face of real growth. Most of the resources go to servicing customers.

A few years ago I wrote an article about things to consider when you look at different types of companies (including family owned companies and others) as there are always positives and negatives for all. You can find that post here.

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