Some Career Advice for Aspiring Tech CEOs

A shortened, better edited and with nicer pictures version of this post first appeared on TechCrunch. But if you want it in it’s full V1 glory read on …

You’ve never been a CEO but might like to be one some day. But how? Nobody sees you as a CEO since you’ve never been one? I wrote this conundrum and the need to take charge of how the market define your skills in my much-read blog post on “personal branding.”  If you don’t create the message about yourself, the market will. And if you want to be a CEO one day you need the messaging to reflect that.

The strange thing is that once you’ve been a CEO even one time the market will see always see you as a CEO but nobody really wants to give a new-comer chance.

Of course you could start your own company. For many people that’s the right answer. As I talked about in “Is it Time to Learn or Time to Earn” – overwhelmingly the best economics go to those that start successful companies. But not everybody has the right skills to build a highly successful and valuable startup from scratch. In fact, I would argue that most people don’t.

The decision tree for being a startup CEO begins with whether you can sustain 12-18 months of little or no salary while you define your market, do research, build v1 of your product, raise seed funding, attract your initial team, get your first customers and test whether you have initial product / market fit or enough momentum to be able to raise a large round of capital.  Even when you do sign-up initial customers it’s still not clear that your company will be a success and you’re still likely paying yourself under market rates.

Of course I’m not suggesting people shouldn’t start a company. If you can and if you want to – you should. I’m just pointing out that it’s not for most people.

For some aspiring to be tech entrepreneurs, I often suggest a two-step process, as I argued in this post that “The First Startup Founder You Need to Invest in Is You.” The punch line from this post was “angel yourself.”  It was meant both as a call to those writing angel checks into other people’s companies that they ought to think about putting that capital toward themselves either by becoming a startup founder or (and this was my real point) by taking an under-market salary in a company where they can learn the right skills to do it in the future.

Sadly most  people I meet these days would rather pile $20k of savings to be seen as an angel in somebody else’s startup than they would to take a $40k pay haircut (the pre-tax equivalent to $20k) to work for the hottest startup they could and have both the stock options and the career experience and networking that comes from working with amazing peers at …