I’ve been in business long enough to have made some pretty spectacular mistakes.
And I’ve also gotten some things very right.

Here Are 3 of My Most Painful Lessons in Entrepreneurship:


  1. Not getting an office early.  We have a team that is all over the area.  Lesson Learned now:  Get the office early, and you can keep people accountable. Working from home sounds lovely. If you’re a boss, it’s not so great, because in practice, it gets abused.  I’ve seen plenty of evidence of people saying that they are being super productive, but when you look at what they actually accomplish, it is nowhere near what it should be.
  2. Failing to Get an Advisor. Lesson Learned: Get an advisor, and miss some pitfalls. Sure I have an MBA. And I have experience. A lot of experience. But an objective set of eyes is an amazing thing. I should have listened to my advisor on a few things much sooner than I did.
  3. Being too nice.  I’m not saying to be a real bitch. But sometimes people have taken advantage of the fact that I’m nice. Whether it’s taking time off from work, or not quite being as accountable as they should be, I’ve seen a few instances of this.  Lesson Learned: Draw the line, and call people on it when they cross it.

I’m also working through some other painful lessons, and the consequences right now. I’ll post those at a later date. But let’s just say, I should have known better, and I thought I could be nice and generous this time. It bit me in the ass, and continues to.