Six tips to prepare for startup life while working at a big company

By Amanda Herson

Few successful founders drop out of college, found a successful company, and stick with it for their careers.

Most entrepreneurs are going to have some period of time working for someone else.

Here’s how to make the most of it if entrepreneurship is your long-term goal.

Fuzzy projects, like launching a new territory, or working on a skunkworks initiative, are often avoided by corporate strivers. The lack of clear success metrics can stall career progression, but they’re great prep for future founders. Prove that you can ‘run through walls’ and have someone who can sing your praises.

You want to have legitimate experience thriving in atypical reporting structures, without the benefit of procurement and distribution support. “Intraprenurial” efforts that demonstrate hustle and grit are much better than rote corporate projects.

HBS professor Howard Stevenson described entrepreneurship as “the pursuit of opportunity beyond resources controlled.”

Prove that you can make things happen without a corporate structure — it can be a charity, professional organization, or even a blog. You don’t need a huge exit to have credibility.

NB: This isn’t like resume padding in high school. Don’t start something for the sake of starting it. Ideally, this activity will overlap with the subject matter of the startup you hope to lead.

Short stints at employers is a red flag in all job interviews, but this behaviour weighs heavily in VC estimations. Startups are generally long slogs and investors like to see some evidence of ‘sticking it out’.

Sometimes moves must be made for personal reasons, but try to log some multi-year stints to demonstrate you can stick with an idea for an extended period, see complex projects through to completion, etc. Demonstrate a thirst for growth and genuine curiosity.

Try to find roles at companies where you’ll be able to meet folks who could make good co-founders or early employees.

Even if you already have a group of like-minded people with whom you’d like to build a company, choosing roles, where entrepreneurship is common, is beneficial because you’ll pick up more info through osmosis.

Even if you can’t found a startup on the first day of your career, you should try to gain experience in the market in which you’d like to build a startup. It’ll allow you to learn the industry, build a network, and get paid.

VCs generally look more favorably on founders whose prior work experience informs their startup. Some are able to make the leap, but years spent in an industry do tend to confer an “unfair advantage” that entices investors.

There’s an old joke that the toughest addictions to break are gambling, smoking, and a weekly paycheck. Getting funded is harder than it looks and your early salary may not match your Google comp package.

Many founders are locked out of entrepreneurial opportunities because their personal burn rate doesn’t provide the flexibility to go without salary for six months while fundraising, or to live on the reduced sum a seed round will allow for a year or two.

Our mission is to be the most aligned VC for founders at seed. #ProudInvestor in @Uber @TheTradeDeskinc @Buzzfeed @Cruise @Diaandco @PillPack @SeatGeek & more.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store