Feedster was not the first company I raised money for but it was the first time I raised money from true silicon valley investors. I vividly remember Scott Rafer taking me around all the different angel groups, individual investors and Sand Hill Road. One of those investors was Dave McClure of 500 Startups fame.

Dave was one of our angel investors the the one that I felt personally responsible for. So, after the awful day that I was let go from Feedster, I remember sitting in my apartment in Indianapolis and having to call Dave around 6 pm on a cold fall night and telling him that I was gone and I couldn't look out for his investment any longer. He took the news far better than I expected and wasn't even angry or disappointed with me much to my surprise. His actual concern was how I was taking everything. Looking back at this, I can now see it a little differently:

  • We were just one of many investments that he had
  • The amount wasn't all that large
  • Preserving the relationship with the entrepreneur is more important; they'll do something else

So here's what Dave McClure taught me:

Not everything works out. And that's ok.

Relationships matter. Keep relationships strong no matter what.

Now I don't think I've talked to Dave in years at this point but the truth of it is that I'm still impressed by how well he handled this and I still remember it vividly. And If anyone ever asked me if they should take Dave on as an investor, I'd answer "Yes; a thousand times yes."