TL;DR: The default language of a Post-Money SAFE has the worst possible economics for founders in the vast majority of seed round contexts, because any future convertible rounds (that aren’t equity) force dilution entirely on the common stock (seed investors aren’t diluted at all – YC benefits significantly from this language in its own investments). A very small tweak to the language can save founders/common stockholders millions of dollars, and make the Post-Money SAFE fairer to the cap table.

Background reading: Why Startups Shouldn’t Use YC’s Post-Money SAFE

First, a very quick review of the high-level economic problem with the Post-money SAFE structure that YC promoted a few years ago; and which is only in recent quarters becoming more visible to founders as their seed rounds start to convert:

The stated value proposition of the post-money SAFE, relative to the traditional pre-money SAFE, was that it delivered investors far more clarity over how much of the cap table they were buying. If they put in $1 million on a $10 million post-money SAFE, they were buying 10% of the company today, regardless of what the current cap table looks like. This is actually a good thing. Clarity is great.

The hidden value proposition for investors of the post-money SAFE, and which has cost founders enormously by not understanding its implications, was an extreme level of anti-dilution protection built into the post-money SAFE. Any SAFEs or notes that you issue after the post-money SAFE round, but before a Series A, do not dilute the investors; they dilute only the common stock (founders and employees). This is the case even if the 2nd or 3rd round of SAFEs is an up-round with a higher valuation cap.

This was and remains crazy, and totally unnecessary in light of the stated purpose of post-money SAFEs; which was for investors to know what they are buying on the day of their closing. When you buy equity you are able to calculate the ownership you are purchasing at closing, but equity rounds virtually never, not even in the most investor-slanted deals, have full anti-dilution protection for post-closing investment. Why should Post-Money SAFEs give investors that? They shouldn’t, and this was an egregious (but in my opinion, deliberately obfuscated) over-step in startup financing template design.

We posted here a very simple redline (in track changes) of what needs to be edited on YC’s post-money SAFE to eliminate the terrible anti-dilution mechanics. Again, it’s worth emphasizing that this redlined safe still gives investors the stated benefit of the post-money structure, which is to know what % of the cap table they are getting as of their closing. What it changes is that it makes post-closing issuances proportionately dilutive to both founders and investors, just as they would (and should) be in any other kind of financing structure.

There are numerous different ways someone could draft a “fix” to this problem. I’m just posting a simple public redline so founders, lawyers, and investors understand the problem, and can either go with this solution, or craft a variant that works for their context.

A colleague of mine also designed a very helpful model (in Google Sheets) breaking down the mathematical (economic) differences between a typical pre-money SAFE, post-money SAFE, and our suggested redlined post-money SAFE. We know engineers in particular love seeing the numbers.

To give a high-level idea of the economic implications, assuming the following:

SAFE Round 1: $5M pre-money cap or $6.5M post-money cap ($1.5M invested)

SAFE Round 2: $10M pre-money cap or $12M post-money cap ($2M invested)

Series A round: $25M pre-money, $31M post-money ($6M new money), 10% post-available pool.

In Series A dollars (company value as of Series A closing), common stockholders lose $912,000 in moving from the traditional pre-money SAFE to YC’s preferred post-money SAFE. Fast-forward to an exit years later, and you’re talking easily millions or even tens of millions of dollars in lost value from simply changing the template.

Again in Series A dollars, common stockholders gain appx. $1.2 million in using the redlined post-money SAFE relative to YC’s post-money SAFE. The addition of just a few extra clarificatory words (which eliminate the hidden anti-dilution protections for investors) shift $1.2 million in Series A value from investors to the common stock; which again could easily be >$10 million by exit. All with just a few tweaks of language.

If this isn’t clear already: the stakes here are extremely high. And anyone suggesting that mindlessly using an investor or accelerator’s preferred templates is “saving” founders money (by reducing legal fees) is either hilariously uninformed, or lying out of their teeth. Tread carefully, and stay well-counseled.

Disclaimer: The model presented above is purely a hypothetical based on general math mechanics of SAFE and Series A rounds. The specific outcome in your company’s case will be dependent on the facts and circumstances, and you should always use experienced, trusted advisors to avoid missteps.