I had an entrepreneur in my office that I've been working with for a few years. He's took a small angel round that I'm an investor in. The business has taken longer to get off the ground and in the last 6 months they're really starting to make strides. That said, the company is running out of cash and is about 10 to 15K per month from breakeven. Yesterday, he was in my office talking about raising 50K to get him to breakeven. I told him he should try to raise 200K so he can play for success. The terms of the 200K are going to be tough to the company and existing investors. The entrepreneur is doing all the right emotional things to make the company a success. He could easily throw in the towel and call it a "lesson learned". Instead, he wants to plow ahead. In the meeting, he told me he was committed to seeing this company through to success. In that moment, without knowing the terms of the deal, I told him that if he was in -- then I am committed to participating in this next round (personally and not as a fund). It was the right thing to do. And fortunately, I'm in a position to be able to do that. In that moment -- money equaled relationship and support. And fortunately for me -- I didn't miss the moment. There have been plenty of times where other friends I've worked with in the past have asked me to invest and support their ventures financially and for whatever reason -- I missed the moment when money equals relationship. This is a rare and important moment when even a little money gives the right emotional support and solidarity to help an entrepreneur. I suspect that this applies to famliy matters as well -- but tomorrow -- time willing, I'll write about instances where I have missed this opportunity...and how it bums out the asker as well as me.