Thanks for saying what I'm sure a bunch of people were thinking! Strong disagree with this take :-), but I understand why you believe it!

First a point of clarification - I'm confident you think the 10% personal giving is less effective, but it's not 100% clear to me which 45% of my giving budget you consider to be reduced in effectiveness... I assume you mean the high risk, high return bucket? That's not how I view it; this is my budget for hits based giving, which in my view has very high expected value, comparable to the higher confidence, lower upside giving budget but with a different theory of change.

At core, I think one crux of our disagreement might be this: is it overall more impactful to optimize the expected value of individual donation decisions sequentially, or is it more impactful to optimize the expected value of all of your donation decisions collectively (i.e. your full portfolio).

I accept that giving opportunities are power-law distributed. But I'm relatively skeptical in my (anyones) ability to accurately assess where any one giving opportunity sits on that power-law distribution with high levels of precision beyond a certain threshold. I feel fairly confident I can identify and exclude bottom 50th percentile giving opportunities, but distinguishing between 75th and 95th percentile giving opportunities I'm less confident in.

That's true even when discounting for uncertainty... in practice there are so many assumptions built into a robust cost-effectiveness estimate, that reasonable people can defensibly land in assessments that are several orders of magnitude different from each other. That doesn't mean we shouldn't try! But it does mean we should have high levels of humility in our conclusions.

I make the decision to optimize my portfolio as a whole (with diverse theories of change, diverse risk profiles, diverse world views), which I think makes the expected value of my portfolio higher than if I viewed every donation decision in an isolated manner. Simply because there's less risk I put all my giving eggs in a basket that ended up being wrong because of a reasonable but minor assumption. 

Thanks Austin! I broadly agree with this point - hedge funds or mutual funds are the better analog for CG or GiveWell. I was trying to keep it simple for people who may not be able to immediately identify the difference between a hedge fund and an index fund.

I also agree it's often under appreciated in EA how much subjectivity and values gets baked in by the moral weighting that is fundamentally necessary to running a fund. I think GW + CG do that moral weighting in a reasonably robust and defensible way, but even then I know there are many places I personally diverge with some of their choices.

I feel torn on your final point - I'm someone who really values diversity of worldview, theory of change, risk tolerance, decision process, etc. So in my perfect world I'd really love it if more people deferred less and came to their own conclusions. That said, I don't know how reasonable it is to expect that... and it becomes such an easy reason to not give at all.

I suspect that practically there's a fairly direct trade-off between how easy it is to give (i.e. not having to do a bunch of thinking / work to come to your own conclusions), and how much ends up being given. And the marginal difference between a more thoughtful gift and not giving at all is fairly large. So my instinct that there's more value in pushing for the simplicity and scale of a well managed and strategic fund like GW, CG, GD or similar than there is in encouraging thoughtful diversification of gifts.

Hey Dan! Glad this was useful.

Sounds like you got what you needed from Claude, but to slightly expand if anyone else is interested...

Donating stock to DAFs: Fidelity Charitable, Schwab Charitable, and Vanguard Charitable all accept private company stock, including pre-IPO shares, though acceptance is case-by-case and depends on the company's transfer restrictions. Daffy has a dedicated private stock program (and extended it to all employees in 2024); Charityvest accepts private stock and a wider range of complex assets via a partner firm. The donor gets a fair-market-value deduction at the time of contribution (for shares held more than a year), and the DAF holds the shares until a liquidity event. This is the most common path.

Donation to charities directly: A number of large operating charities (GiveDirectly included) can accept private stock and hold it until they can liquidate - but most can't, so it's worth asking specifically.

The transfer-restriction question is the main one to investigate. Before any of this works, you need to confirm with your company that the share class you hold is transferable to a 501(c)(3) or DAF, and whether company consent or right-of-first-refusal applies. Some pre-IPO companies allow charitable transfers cleanly; others restrict them tightly.

It's worth taking a moment on the several good reasons I think it's worth donating stock even before an IPO or liquidity event. 

• Good tax math: donating appreciated shares directly avoids capital gains entirely and still gets you a fair-market-value deduction, so for early-employee or founder stock you're often able to donate 25–35% more for the same out-of-pocket cost than if you sold and donated the proceeds.
• Valuation upside: the charity captures the appreciation between now and the exit, not you-then-a-smaller-gift-later. And the deduction timing favors going early: appreciated-stock donations are capped at 30% of your taxable income per year, so a single post-exit gift often pushes most of the deduction into future years, while spreading donations pre-IPO lets you use them as they happen (often more valuable to you now than later post exit).
• To channel the original post - waiting for the exit is just another flavor of the delay trap; there are paths to start now.

Thanks again for commenting and glad this post could be useful!