Fundraising is like dating

This evening, I was on a panel titled, "The Growing Gender and Race Gap in Seattle's Startup Scene".  I got to share the panel with some amazing people.  Then as I was on my ride home, it dawned on me that maybe, just maybe, the challenge with the whole not enough "minorities" getting funding (across the board from arts, nonprofits to startups), is that this game we are in is actually like dating.

Seriously, humor me for a minute.  

Fundraising is like dating.  There's usually two players in dating - one doing the pursuing, one doing the being pursued.  Sometimes you go back and forth in playing a role.  

MAYBE women (for example) are struggling to get funded because we (most of us) are not used to doing the wooing, like men are.  Maybe women have less practice and socialization with this.  Maybe?  Some of us are able to understand how to woo and attract very quickly.  Some struggle.   I personally love it.

Simple dating tips applied to fundraising:

1. Communicate, proactively.  Communication in person > communication by phone > communication by email/text > no communication at all.  Laziness typically won't win.  Find enticing ways to meet in person.  
2. Don't talk too much.  Embrace silence.  Ask good questions.  Listen.  Give them opportunities to ask questions.  Observe the room (and yourself).  Manage the energy, not data points.
3. Be interesting, and be interested in your date.  Ask good questions.  Offer something funny or insightful.  Ask about their children or if they like the newest Tesla updates.
4. Be dependable.  Show up when and where you said you will.  And on time, if not EARLIER.  I've noticed most (good) investors are really good about that.  Remember important dates (birthdays, etc.).   
5. Be very responsive.  Lead if you can to set the rhythm of communication.  If the other person sends a communication, like an email, do everything you can to respond quickly (under 2 hours best, under 4 hours acceptable).  Demonstrate that they are VERY important to you.
6. Be polite and respectful.  Say please and thank you.  Follow up after your date to recap that you enjoyed the conversation.  See if there's interest in doing another date or keeping in touch.
7. Compliment.  Notice the details of the person(s) you are in pursuit of.  Notice if they like sports or whiskey.  Demonstrate you appreciate their feedback or opinions.  Give extra kudos when they say or do something awesome.  Read up on them and compliment them on their latest press/news.
8. Study them.  Do they like meeting up during the day or evening?  Are they casual or not?  Do they lean forward or are they more laid back?  Do they prefer coffee or a beer?  Does ambiance matter to them or is it all business?  
9. Figure out how you disagree.  The precedent set on how you handle conflict with each other is important.  See if there are some benign topics you can try out together.  There will be some micro-actions or non-actions that'll be good cues on how this will go.
10. Tell them directly you want them.  Pursue. Find the right method that will match what they will respond best to and tell them you're into them.  Really go for it and woo them.  Close the deal.  Don't beat around the bush.  Make the ask.

Maybe it's a stretch, the dating analogy.  Let me know what you think.
​--Arry