Mismanaging entrepreneur's expectations

The job of a CEO is to manage the expectations of employees, investors, and the board.  I learned to do that pretty well (I think). Now that I'm a full time investor -- I need to learn that my job as an investor is to manage the expectations

  1. first, of the entrepreneurs we want to do deals with,
  2. second, the investors in Founder's Co-op and
  3. third, the broader entrepreneurial community

I don't think I've done a good enough job of number 1 and 3.  Today, in particular, I found myself in a conversation with an entrepreneur in whose business I had wanted to invest.  I had previously told him that we were going to invest in his business contingent upon customer diligence.  As time wore on, the economy (or credit) crashed and I got more familiar with his company's position, I ultimately decided that it would be better if Founder's Co-op didn't invest. That change in investing position -- while very common in all sorts of business deals -- always sucks from the entrepreneurs perspective.  I need to do a better job at this!  If the entrepreneur I spoke with today on the phone is reading this --please accept my apology -- I know I fucked up in our communication.