5 mistakes every startup founder SHOULD make

“It’s fine to celebrate success but it is more important to heed the lessons of failure.”  – Bill Gates.

Much digital ink has been spilled trying to caution startup entrepreneurs against making mistakes. Type “mistakes entrepreneurs make” into Google and you’ll find thousands of articles, sternly forewarning against the most prevalent pitfalls and errors that stand between you and your startup’s success.

But wait a second. How many times have you heard, “We learn from our mistakes?” As an entrepreneur and investor, I’ve definitely made some doosies — and if my experience is any indication, not only do we learn from our mistakes, but we learn much more from our mistakes then from our successes.

Then why try so desperately to avoid them? Call me a contrarian, but I’d argue that well-positioned mistakes can be quite worthwhile, and should even be encouraged.

So here’s a list of mistakes that you should make as a startup founder. Mistakes that are bound to happen anyway. Mistakes you will learn so much from that you’d best make them as early in your entrepreneurial journey as possible. I’ve also included some recommendations about what to do after you make each mistake.

1. Get screwed

It’s inevitable. Someone — your partner, co-founder, employee, investor, or any other character in your unfolding plot — will mess you over.

Someone will break your trust, violate a verbal or even written agreement, cut your compensation, try to steal your equity or destroy your whole company (or all of the above, if you’re me). Someone will do something stupid to scuttle your grand plan.

Accept the inevitable, steady yourself now for the oncoming blow, and just hope it doesn’t hurt too much or cause too much damage. A startup is usually an odd mix of people (ideas people, tech people, investors and others) thrown together by fate and circumstance in pursuit of a distant, moving target.

As clearly as you think you see that target and the path and step toward it, somebody else will see that path differently or may have a different set of scruples or incentives. That will create friction, and depending on the power balance between everyone involved, can result in someone — maybe you — getting screwed.

Post-mistake action

You’re thinking, “Why is getting screwed my ‘mistake?’ I didn’t do anything wrong.”

Look in the mirror.

2. Seek revenge

3. Tell people your venture is in “stealth mode”

4. Believe that “If you build it, they will come.”

5. “My favorite mistake”