Love the idea. Charity discovery is a big issue for donors and for charities alike. We (tech-based charities) are always working hard to increase awareness among donors in the tech sector.

Some feedback:

- Food for thought: Seems like your big hypothesis here is that social validation is the primary mechanism for unlocking new donors. Following in the footsteps of thoughtful giants. If true, it's worth considering whether you could more effectively test that hypothesis by putting the emphasis on the marquee donors rather than the charities they fund. AngelList does a good job of this with their Syndicates feature. For example, imagine Kyn could say "Donate like Zuck by funding these three up and coming orgs" or "Do Good like the Knight Foundation by donating to this portfolio of awesomeness".

- Confusion: Not quite clear what "watching" does.

- UX feedback: The donation process is a little unclear. Can you own more of the donation process, so it all stays on-site? If you can avoid sending donors off-site, you'll get a higher completion rate, and you'll also unlock the ability to add "also donate to Kyn" checkboxes on the checkout (DonorsChoose.org gets some huge % of their donors, I want to say 80% but I could be wrong, to leave that box checked, which results in a huge proportion of their annual contributions).

Great initiative and good luck. I'm excited about what you're doing.

You might want to checkout givewell.org, which does a very quantitative charity analysis.