To Start Up or Not
I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying - Jeff Bezos
When first confronting a transition to tech, a confounding decision awaits. Do you pursue one of the big names? Microsoft? Google? Apple? Or is a start-up the right choice?
The question is not easily answered.
Established brands offer plenty of pros. Stability. Defined responsibilities. Name recognition. Higher base salary. Salable equity in the form of RSUs.
On the other hand, many of these companies are behemoths. They have their own bureaucracy. Risk and creativity can be dirty words. Some might feel similar to the government quagmire you’re seeking to exit.
So is a startup the right, first move?
Generally speaking, startups consist of smaller teams, particularly at the beginning. There’s no “that’s not my job” mentality. Everyone pitches. You can build on existing strengths while exploring activities usually outside your ken.
Also, you will have access to investors. This is a whole new ecosystem of opportunity.
The downsides of startups are not inconsiderable. That equity can go to zero. The company can go out of business overnight. Work-life balance is nonexistent.
These two articles provide further insight into how to explore the startup route:
30 Questions to Ask Before Joining a Startup
Startup equity is a complicated topic that is worthy of an entire book…you need to know that equity in this startup actually has a chance of producing a nice windfall for you…these questions should be asked after you've received an offer.
How to Choose a Startup to Work for by Thinking Like an Investor
Successful startups grow faster than they can hire experienced and qualified people to keep up with growth. This creates vacuums of responsibility, vacuums that existing employees who might be “underqualified” on paper can step in and fill. If you fill the vacuum well, you can keep repeating until you rise up to the highest levels of leadership of what will eventually become a public company.
Ultimately, as long as you clarify your goals, either choice is the correct one. Unlike the government, it’s not hard to make a change after a year or two. At the very least, your experience and skillset will deepen, thus opening even more doors.