Someone asked me the question today which many serial entrepreneurs have been asked, What would you do differently?”

The #TLDR quick answer is, “if you knew better, you’d do better”; the long-form answer is below for the more patient.

I think I am on my 14th startup now; I try hard not to count them all as there were several early failures and the scars still itch when closely examined.

What I wish I had known before I started my business(es):

1) Always do what you love, not what you think others will like
2) Always have an exit plan

My early failures were usually “great ideas” which I thought others would love. The issue is, if you come to the market too early, you go broke trying to convince others exactly how the idea is great. If you come to the market late, you miss the gold and only pick up the bronze (at best), or an “also-ran” yellow ribbon.

My later successes came from sharing what I was passionate about, and creating a system which was easy to run. Startups often have no income in the early stages, so if you are truly passionate about your field, your passion gives you fuel to run through the first dry months. If you also create a business which can be run part-time, it enables you to pursue other passions, or to easily sell the business to another party.

My initial startups were often 70hr/week monsters; my last three startups could be run in 24hrs/week or less. Guess which one is easier to stay motivated for, and guess which one is easier to sell?

Harness your passion. Create your system. Share what you love.