TL;DR: In an equity round, including seed equity, any post-closing dilution is shared proportionately between investors and common stockholders (founders and employees). This is fair. Assuming no shenanigans and the business is increasing in value, why shouldn’t dilution be shared? Convertible notes and pre-money SAFEs have a math formula that makes them more dilutive to founders than an equity round with an equivalent valuation, by “protecting” seed investors from some post-closing dilution. Post-Money SAFEs are even worse. The solution is fairly simple: “fix” or harden the denominator in the conversion price formula, instead of having it dependent on complex language and variables. This gives everyone the benefit of a “floating” valuation that is so valuable in convertible instruments, while making post-closing dilution mechanics equivalent to an equity round.
Broadly speaking, there are 3 main instruments being used by startups in seed rounds: equity, convertible notes, and SAFEs. From a historical standpoint, equity (issuing actual stock at a fixed price) is the default instrument, but for reasons of speed and flexibility (on pricing), convertible notes and SAFEs have gained traction in early rounds smaller than about $2 million in total funding (the number in Silicon Valley is a bit higher).
While glossing over a few nuances, the formula for setting the price of stock sold in an equity round is fairly simple: pre-money valuation divided by capitalization. The higher the valuation, obviously the higher price. But importantly, the higher the capitalization (the denominator), the lower the price. In equity term sheet negotiations there is often some (necessary) back-and-forth around what actually gets included in the capitalization denominator. For example, being forced to put any increases in the option pool is fairly common. Somewhat less common but still extremely impactful is being forced to put all of your existing convertible instruments (notes or SAFEs) in the denominator. In this sense, two startups can have the same “pre-money valuation” but dramatically different actual stock prices (price paid by investors) if they negotiated different denominators.
Pre-money Valuation: $10 million
Capitalization on your date of closing, including option pool increase in the round: 10 million shares
Math: valuation ($10 million) / capitalization (10 million shares) = investors pay $1 per share of preferred stock.
Simple enough. Fixed valuation, fixed capitalization, and you get a fixed price for easy modeling. Any financings (excluding down rounds) that happen after your equity round dilute the entire cap table proportionately. But the “math” for convertible notes and SAFEs is not so simple, and not as favorable as an equity round.
Convertible Note and Pre-Money SAFE Math (more dilutive)
In Why Convertible Notes and SAFES are extra dilutive I explained how the typical math of convertible notes and SAFEs makes them extra dilutive to founders/startups compared to an equity round. To summarize: because convertibles fail to “harden” the conversion math for the investors, convertibles allow seed investors to pack more shares into the denominator. Remember: higher denominator = lower price, which means the seed investors pay less and get more of the cap table even without changing the “valuation.” In an equity round, increases to the option pool after you close get absorbed by your seed investors pro-rata, but not so in typical convertible note math. Your seed note holders get “protected” from that dilution by including the pool increases in their denominator up until closing.
The fact that the denominator in convertible notes (and SAFEs, which are derived from convertible notes) isn’t fixed is actually a remnant from when convertible notes were traditionally used mostly for “bridge” rounds closed only a few weeks or months before a Series A. When your convertible round is truly a “bridge” for an equity raise in a few weeks, having your note investors get the same denominator as your Series A investors makes sense. But today seed rounds are being closed 2-3 years before a Series A. Keeping the denominator “open” for that long does not make sense.
So, keeping valuation constant, convertible notes and traditional pre-money SAFEs are more dilutive than an equity round because the denominator is larger. Why do startups use them then? Speed and flexibility.
First, given how early-stage fundraising and company-building has evolved, many (but certainly not all) seed rounds lack a true lead willing to hire their own counsel and negotiate hardened seed equity terms. Also, at the very early stages of a startup, pegging the exact valuation that investors are willing to pay can be difficult given the lack of data and track record. The valuation cap concept in Notes and SAFEs allows startups to set a proxy for the valuation, while flexibly allowing seed investors to get a lower price if the Series A valuation ends up in fact being lower than what was originally expected. Valuation flexibility (via a cap, as opposed to a fixed valuation) is a big reason why, despite the advantages of seed equity, many young startups still opt for convertibles. The ability to incrementally increase the cap over time, as milestones are reached, is also seen as valuable flexibility offered by convertible instruments.
Post-Money SAFE Math (even more dilutive)
A while back Y Combinator completely re-vamped the math behind their SAFEs, converting it to a post-money formula. See: Why Startups shouldn’t use YC’s Post-Money SAFE. Rather than setting a pre-money valuation cap, startups using the post-money SAFE are now required to set a post-money valuation, including all money they expect to raise as seed. YC’s stated reason for changing the math on the SAFE was to make it “easier” to model how much a company is giving to seed investors, but as discussed in the blog post, anyone who’s deep in this game and unbiased knows that claim is smoke and mirrors. The formula change made the SAFE structure far more favorable to investors (including YC) economically.
What was really happening was that because pre-money SAFEs had exactly zero accountability protections relative to seed equity and convertible notes – the maturity date in notes constrains the ability of startups to keep raising more and more rounds without converting the seed round into equity – seed investors in SAFEs were getting burned by startups raising SAFE rounds for years and years without ever converting. As an investor, YC itself was getting burned. So they changed the SAFE to be more investor friendly, benefiting YC and all seed investors.
But in the opinion of many ecosystem players, including lawyers focused on representing companies (and not the investor community), the change was egregiously one-sided. It effectively forces founders and employees (common stockholders) to absorb all dilution for any other convertible note or SAFE rounds that they raise after the post-money SAFE round, even if the valuation cap is higher. That’s an extremely high price to pay just for making modeling seed rounds a little easier. I have a better (fairer) idea.
“Fix” the Denominator in Notes and Pre-Money SAFEs (same dilution as equity round)
The benefit of convertible notes and SAFEs is flexibility and speed. They are simpler, and allow you to have a “floating” (flexible) valuation (cap) that helps companies and investors get aligned despite the uncertainty. This “floating numerator” is important and valuable.
But as discussed above, while the benefit of notes/SAFEs is a more flexible numerator (valuation), the benefit of seed equity math is you get a hardened denominator. That hardened denominator ensures that everyone (common stock and investors) shares pro-rata in post-closing capitalization changes, like future rounds and option pool changes. Everyone has appropriately-apportioned “skin in the game.” Another benefit of this hardened capitalization (denominator) is that it makes modeling the round easier. Wasn’t that what YC says they were trying to do with the Post-Money SAFE? Why not make modeling easier without hurting founders with harsher dilution?
So the “best of both worlds” solution is: do a convertible note or pre-money SAFE, but harden the denominator with the capitalization at the time of closing. You can even ensure it has an appropriately sized pool to account for expected equity grants until the next raise, much like you would in an equity round. Flexible numerator, but hardened denominator.
Making this change in a convertible note or SAFE is extremely easy. You simply delete all the language used for describing the denominator (the fully-diluted capitalization) and replace it with a number: your capitalization at the time of closing. Now both sides have the benefit of a valuation cap that adjusts if there is a “down round,” but a hardened denominator that allows everyone to model the expected dilution of the round; while ensuring that future dilution is shared proportionately between both founders and investors.
On top of being far more aligned with equity round economics (the default approach to fundraising), this approach can save common stockholders several percentage points on their cap table; a very high impact from just deleting a few words and replacing them with a number. When a seed equity raise won’t do, my recommendation is usually a low-interest, lengthy (2-3 yrs) maturity convertible note with a valuation cap and hardened denominator. As a lawyer who represents zero investors (all companies), I’ve felt that pre-money SAFEs are too company-biased, and post-money SAFEs are too investor-biased. SAFEs in general are also far less respected by investors outside of Silicon Valley than convertible notes are.
We’ve been explaining this issue to clients and investors and are happy to say that there has been a positive reception. We hope to see it utilized more broadly in the market over time. See: A Convertible Note Template for Startup Seed Rounds for a convertible note template that startups can utilize (with appropriate lawyers) for their seed rounds.
Do I expect all seed investors to adopt this approach? Of course not. They’re investors, and will naturally prefer something far more aggressive in their favor, like YC’s post-money SAFE. It all depends on context, character, and leverage. Nevertheless, founders should go into seed rounds with their eyes wide open about the significant economic implications of the various structures and formulas, and not give into any hot air about there being a single (air quotes) “standard” approach. Pushing misleading “standards” is a far-too-common negotiation tactic for getting inexperienced founders to mindlessly pursue financing strategies that are against their company’s interests.