In building organizations two of the toughest activities are raising capital and user acquisition. Since this is not a fun activity I have often tried to delegate it (up or down or left or right) but this usually does not work for me. In some cases I have found successful partnerships like working with CTNewsJunkie to build my voter guide app. Nobody would care about my voter guide if I just put it on my own site, but with a news organization behind it the voter guide gets much more use and it provides a useful tool for readers. The partnership works because in the end both sides win.
In my years of working in politics and non-profits raising money has been one of the most avoided activities. Raising money is a grind and I think most people do not wish to do it. It is especially hard to do with cold contacts. The rejection rate is high. So to effectively fundraise you need to get to know people with money and tell your story to them. So you go to lots of social events to get to better know people. Then you are able to ask folks for money when the time is right. It especially helps if you can show your traction or impact. People want to support things that are making a difference.
The result of this is that people who are good at these activities are worth a lot to organizations. I have found it especially challenging to find and recruit people who are good at these things. Even people who seem to have a bit of a knack for it, often prefer to do other work. I can empathize because I often feel the same way. When I have to choose between raising funds and building things, I would prefer to build things. But sometimes other activities have a bigger impact, especially when an organization is starved for talent in those areas.