Angel Investing | Learning the Art of Saying NO

I once heard someone say that the hardest part about angel investing is that you will probably have to say “no” 99% of the time. This aspect of being a responsible angel investor is especially difficult for me. I seem to have inherited this unhealthy sense of responsibility and always feel like I need to help everyone who crosses my path. This is both my best and worst quality, but I realize that in order to be a successful angel investor and maintain some sense of health, family balance and sanity (I am writing this after my third consecutive week of sleep deprivation), I need to improve my ability to say “no”. Here are some thoughts to help myself and similarly sleep deprived angel investors everywhere:

  1. No one likes a tease.  Due diligence is time consuming for both entrepreneurs and investors. The sooner the entrepreneur understands that an investor really isn’t interested, the better off they’ll be.
  2. Helping can be hurting.  I have certainly learned the hard way that not all startups are meant to be successful. Prolonging the unfortunate, but inevitable demise of an entrepreneur’s dream provides a false sense of hope. While it does temporarily delay them from hitting bottom, it also slows their bounce back up.
  3. If you just try it, it’s not so bad.  I’m always so worried that when I say “no”, it is going to be devastating to the person I am saying “no” to. Entrepreneurs are especially resilient and many can pivot from a “no” pretty quickly. Most of them don’t take it personally and if they do, it might be a sign that they don’t have what it takes to be an entrepreneur.
  4.  Saying “NO” in one place enables you to say “YES” in another. I try to remind myself that to be helpful, I need to stay focused on the companies that I am most able to help.
  5.  Your sanity is worth a “NO”.  By nature, I am an entrepreneur and, similar to many entrepreneurs/angel investors, I have the overwhelming drive to goal that can propel me to sheer and utter self-destruction. I try to remember that I have to take care of myself in order to continue to be able to help others.
  6. The easiest people to say “NO” to are often the last people you should say “NO” to. It’s easy to say “no” to the people you know best and care for you the most – your family, friends and close colleagues. However, these are often the people who have done and will continue to do the most to help you.

A wise and successful man (Rich Hoops) once said that his best and worst quality was that he says “yes”. I can definitely relate to that.

What do you think? Do you have tips for saying “NO”?


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