Five Lessons Founders Can Learn from Donald Trump

Honestly, it's difficult to think about anything else besides the election and this impending clown show of an administration these days--but I'd really like to get back to blogging about startups.  

Consider this post part of my own transition team of posts.

While the country is far from a startup, founders find themselves as essentially newly hired CEOs with a lot of uncertainty surrounding them.  This is the position Donald Trump finds himself in now, and by watching what he's up to, we can learn a lot of lessons around how to handle it (or how not to, mostly.)

1) Get to work.

Watching a President-Elect comment on every single SNL skit is like watching a founder who won't stop adding on to their fundraising around.  Fundraising feels good when it works out, especially towards the end when there are always a few more angels who want to squeeze into an oversubscribed round.  You need to come off of riding that high and put your head down and out of the spotlight for a while after that, and do some real work once you've got your fundraising win.

2) Hire people who create confidence, not the people you already happen to know.

Hiring should be a process--from Day One.  If you don't create a process that seeks out the best people from wherever they are today, how are you ever going to do it two years from now, four years from now, etc.  Eventually, you run out of people you know well--and frankly, most of these people aren't the best people for the job anyway.  Once again, this isn't exactly what's going on in the Trump administration and anyone who has built teams knows it's going to hurt his chances for success later on.

3) Stay positive.

Your competition is going to launch just before you or there's going to be some press saying how the funding cycle is done for your industry.  Maybe you'll get a bad review or two for your beta release.  These are all people you will need to convince and get the support of in the future, so while discrediting them might feel good in the short term, it doesn't help you win in the future.  Instead, why not listen to their criticisms fairly and double down in your efforts to win their support with action and results later?

4) Being a CEO isn't that glamorous.  

A lot of people start companies because they want to be their own boss or be in a fast paced environment, but most days, you won't feel like either of these things are true.  You're always lacking for resources or time, and you're not moving nearly as fast as you want.  The best companies build for the long term, and the job of the CEO is to create processes that effectively take the founder out of way.  So, if you're a developer, marketer or salesperson, you're going to have to reckon with the fact that you're now a manager.  Instead of building, you're taking meeting after meeting after meeting, and you won't be able to have your hands in everything.  

This is the job you asked for--so don't kid yourself what it's going to be like once you get into it.  Success can be a curse if you're not realistic about what it's like--it seems from the sobered expression Trump seems to carry around all the time, actually being President isn't nearly going to be as fun for him as running for the job.

5) Don't surround yourself with "Yes" people.

It's easy to live in your own little filter bubble, especially as a founder, or, apparently, as a President-Elect.  You can forget that there are lots of people who didn't think your ideas were very good--and those are the people who can make you a better founder, and who can make your company better.  It's easy to satisfy a small, vocal minority that feels like "everyone" until you need to build things that really scale.  Make sure you listen to a few skeptics along the way and really hear out what they have to say.