Nobody I've ever met likes asking for money. Whether it is a politician seeking election, a fundraiser working to cure cancer, a college kid trying to hit up mom and dad, an employee seeking a raise, or an entrepreneur trying to raise capital, everyone seems to hate the process. Yet it is a necessary thing for most people at some point in their lives.
Interestingly, some overcome this problem better than others. Politicians who win clearly do what it takes to raise campaign cash. The ones I have worked for in the past haven't liked it -- and some came up with every possible excuse to avoid it -- but at the end of the day they did enough to generate the money they needed to run for office and win.
And kids generally still have little enough shame that getting cash from their parents isn't that challenging. Successful entrepreneurs who have businesses that can't be bootstrapped similarly find a way to get it done if they are going to succeed.
Unfortunately, I frequently find that too many organized fundraising efforts lack good money asking skills. I have contributed to a number of charities, non-profits, schools, and campaigns in the past, and I have found that more often than not they don't do a good job of working to raise more.
For instance, in a recent election cycle I was never asked by a candidate for office to contribute to his campaign. I had contributed to this individual in the past, but never heard anything. Until he lost. And then I received the autoprinted campaign holiday card. So apparently my name was still on the house list, but I can't explain this glaring oversight.
Non-profits typically have been much worse. There are two that I give to that send me about one contribution request by mail every week. Yet there are others that I give to that rarely if ever follow up to ask for more. And there are a number with which I have a personal relationship either because of past giving or other connections with key individuals that fail to ever ask for any additional gifts. That's simply inexplicable to me.
It's not that I want to be hit up all the time -- I don't. But it would seem to me that even a once a year ask from some of these groups would be a wise move. And if they're overlooking the opportunity they have with me, no doubt there are countless others on their lists that fall into the same category. Imagine how much more good these organizations could do if they were more effective at fundraising.
And entrepreneurs aren't completely off the hook here. I deal with quite a few who are seeking angel investments in their startups. They're great about getting the first meeting -- most are pretty dogged about that. But most have a hard time figuring out how to follow up. Some do so very aggressively, but most seem to take a very passive approach.
One could chalk that up to belief in the soft sell. Or perhaps their belief is that any investor who is really interested wouldn't let a good idea just slip through the cracks. But if I were in their position, I would want to have a better sense as to where my funding request stood. Just a periodic check in email would be smart to see if a final decision has been made so that the limited resources of a startup can be better directed. And I can't speak for most angel investors, but at least in my own case the pace of my "first job" can often lead me to leave business plans on the back burner. It's not that I'm trying to ignore them or not interested, it's just there are only so many hours in the day.
Ultimately, the individuals and organizations that achieve the best balance between aggressiveness and passivity will do the best at raising whatever money they are asking for.
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