We don't know yet what will turn out to be the most important questions for nonprofits, so we just kept the subset of questions that seemed to apply to any project whether for profit or not.
I would suggest that this would be an excellent time for Y Combinator to consult with Holden Karnofsky of Givewell, which has done a large amount of smart investigation into nonprofits. Karnofsky is local to the Bay Area.
Caveat: Givewell tends to focus attention on nonprofits with well-validated, very-high-probability, easily-quantifiable effects which is not where one would expect the greatest expected value from daring new attempts to be located. Nonetheless I would expect that talking to Givewell would be very epistemically profitable if you are just venturing out into the nonprofit space.
We don't know yet what will turn out to be the most important questions for nonprofits
Evergreen funding source/s is (arguably) the definition of success, for any organization, profit or otherwhise, at least empirically. Competition for scarce resources is thus a key part of the game.
The CEO of MOMA (non-profit) has a salary approaching $2MM/yr. This is rationally viewed as a sales comission ($2mm/ on $XXmm in fundraising prowess) by the trustees. There is no other measure of 'productivity' at that order of magnitude for a "non-profit" organization (10x the statuatory salary of POTUS). Similarly, at non-profit universities. Both in the administration and elsewhere (multi-million dollar salaries for NCAA D1 sports linked with television contracts). Comparably, also the Clinton Foundation, per this recent note from the NY Times:
Worried that the foundation’s operating revenues depend too heavily on Mr. Clinton’s nonstop fund-raising, the three Clintons are embarking on a drive to raise an endowment of as much as $250 million, with events already scheduled in the Hamptons and London.
You accurately describe the trends, but I'm not sure those are positive trends. If these CEOs of nonprofits were indeed purely sales agents receiving commissions, fine, it's a rational ROI to employ them in a role like Vice President of Donor Relations.
But they happen to also be the CEO, formally in charge of the whole operation, and further tend to set the tone for that operation. Then you have the fundraising tail wagging the mission dog. As a result, some nonprofits (and universities) start to look more like weird corporations that exist to perpetuate themselves and their top staff, with some kind of mumbo jumbo relating to public service being an official goal but nowhere near the top of the priority list. An organization that exists primarily to perpetuate itself and pay its staff well is perfectly fine, but then it doesn't really have any business claiming to be a charity...
Similarly they dropped "How do or will you make money?", without replacing it with "How do you plan to you raise money?"
This is a bit naive. As someone who has worked a bit with non-profits, neglecting sales (and the whole "how do we get money in the door" part) of nonprofits is often what causes them to fail.
PG, assuming that you're as connected in the business world as I assume you are, I would recommend reaching out to John Wood, author of "Leaving Microsoft to Change the World" - http://www.leavingmicrosoftbook.com/ His book fundamentally changed my view on how successful nonprofits are built.
Awesome move! But from a data-gathering point of view, why not leave all the questions in. More questions more data!
Also, I find the "how do you make money" question still the most important. Sure a non-profit shouldn't focus on making money, but the more money it can pull in, the bigger its impact is and the higher the likelihood for success.