SAFEs v. Convertible Notes, updated.

TL;DR: Still not seeing a ton of SAFE adoption, albeit a slight uptick. Convertible Notes still dominate outside of SV and pockets of LA/NYC.

Background Reading:

A recurring theme of this blog is that the advice and strategy you take for fundraising needs to be right-sized and contextualized for where you are located. Because by an order of magnitude Silicon Valley has the most startups, VCs, large exits, etc., the majority of the content available online for founders to educate themselves comes from Silicon Valley. A lot of it is very good, but a lot is also totally inappropriate for a founder in, say, Austin, Boulder, or Atlanta (or markets like them); where the dynamics between entrepreneurs and investors are fundamentally different.

Context matters. 

Y Combinator created the SAFE (Simple Agreement for Future Equity) a few years ago as an “upgrade” on convertible notes. It is a well-drafted document, but when you get down to brass tacks, a SAFE is basically a convertible note without interest or a maturity date. Purely from the perspective of founders, it is a fantastic deal. Most convertible notes are already slimmed down in terms of investor rights, and SAFEs effectively strip those rights down even further by removing the “reckoning day” of maturity.

The problem with SAFE usage for “normals” outside of Silicon Valley (and perhaps Los Angeles and NYC, which mirror SV much more so than other markets) is that it reflects the unique market leverage of the people who produced it: Y Combinator. Apart from YC itself, Silicon Valley already is an aberration among startup ecosystems. The concentration of seed funds and venture capitalists in such a small geographic area creates a level of hyper competition that is not even close to what is seen anywhere else in the world. And Y Combinator is, to some extent, the Silicon Valley of Silicon Valley. It takes competition among investors to an even higher level, where many founders can effectively dictate terms.

It’s therefore unsurprising that YC produced a security that effectively tells investors “Here are the terms. Thank you for your money. Talk soon, when we get around to it.” That’s a slight exaggeration, but it’s not entirely off base from how many investors I run into view SAFEs. And it should therefore also be unsurprising when investors outside of that environment respond with “Excuse me?”

So when founders I work with ask me if they should consider using SAFEs, my viewpoint can be summarized as follows:

  1. Only if you believe that all of your seed investors will accept them. Because if only your earliest investors (most trusting/risk-tolerant) will take them, they are not going to be happy about later investors getting real debt, and you will have to re-do everything.
  2. In 99% of cases, you’re better off just asking for a convertible note with (i) a low interest rate, and (ii) a long maturity date (24-36 months). For all intents and purposes, it is effectively the same thing, but will keep “normal” angels investing in “normal” companies more comfortable.

A conventional convertible note with a low interest rate and reasonable maturity period represents a balanced tradeoff: give us some trust and freedom to iterate quickly and get to a serious milestone (minimal restrictions), and in exchange we’ll give you a mechanism for holding us accountable if we don’t perform (maturity). A SAFE, however, reflects the expectation that investors should hand over their money and hope for the best. I rarely see angels or seed funds that use a maturity date to actually harm the company, but that doesn’t mean it’s unreasonable for them to expect somprotection if they aren’t getting the kinds of rights (board representation, voting rights, etc.) that equity investors would get.

Know thyself, and thy leverage. 

There is a subculture among certain entrepreneurs that acts a tad self-entitled to investor money; and I’m sure you can guess where that culture originated. I can say that as a lawyer who (deliberately) represents exactly zero startup investors. I always tell my clients, if I detect it, to snap out of it. You won’t win with it. If you aren’t the CalTech/MIT superstar in the room, then don’t take her advice, or follow her lead, on how to get a job. Persistence and hustle work best when combined with self-awareness and humility.

I have seen a slight uptick in SAFE usage, but it’s almost just a blip. Convertible notes still dominate, and for understandable reasons.  They’re investors, not philanthropists to your entrepreneurial dreams. See “Angel Investors v. ‘Angel’ Investors” for understanding how many Angels you encounter actually think about startup investing.

The truth is that SAFE culture, which reflects YC culture, is a broad reflection of the binary dynamics of how Silicon Valley approaches fundraising; touched upon in Not Building a Unicorn. Billion or bust. If you haven’t made things happen and my seed investment hasn’t 5x-ed into your Series A, I’m already moving on and focusing on the unicorn in my 30-company portfolio.

But if you’re not building a unicorn, that’s not how your investors think, and you need to act accordingly.

Maturity about Maturity. 

So if the idea of your convertible notes maturing scares you, well, entrepreneurship is scary. First, ensure it’s long enough to give you a legitimate, but reasonable amount of runway to make things happen. If your angels have given you 3 years to convert their notes, that’s a very fair amount of runway. I personally think less than 24 months is usually unreasonable, given the timeline most companies need to get real traction and attract more capital.

Second, there are mechanisms you can build into a convertible note to further help with hitting maturity. The most common and important is ensuring a majority of the principal can extend maturity for everyone; so if enough of your early investors still support you, you get more time. Extensions are very common.

Automatic extension, or conversion into common stock, upon achieving certain milestones – for example, upon raising an additional convertible note round, or hitting certain metrics – are another good option. Lawyers specialized in early-stage financing can help here.

The people who are the best at sales are also the best at getting into the heads of their buyers, and understanding their concerns. The same is true for founders “selling” to investors. It is not unreasonable for investors in high risk startups to expect some downside protection in the highest risk segment of a startup’s history, and that’s why so many angels and seed funds reject SAFEs. Give them what they want, while getting what you need. And don’t spend too much time listening to people who are experts in a world that you don’t live in.

Tiered Valuation Caps

TL;DR: Using a “tiered” valuation cap structure in a convertible note or SAFE can provide flexibility that bridges the gap between (i) what founders expect their company to be worth in the near future, and (ii) what investors are comfortable accepting now.

Background Reading:

This post assumes that, for a company’s early seed round, they’ve decided to use convertible notes or SAFEs; because the majority of startups do. SAFEs and Notes are optimized for speed and simplicity, with a cost of future uncertainty and dilution. They have their downsides, which are discussed in some of the above links.

Convertible notes/SAFEs are usually executed around times of maximal uncertainty for a company; the very early stages. For that reason, pegging an appropriate valuation can be very difficult for investors. The valuation cap has evolved into a proxy for valuation, even though by definition it is in fact a cap on valuation, and if things go south, the actual valuation at which the security converts goes downward with it.

Traditional valuation caps: downside protection for investors. No upside for founders.

When you think about it, though, the valuation cap structure is a bit one-sided. If things go badly, investors get a lower price. But what if things go very well very quickly? Under the standard approach, even if the outlook for the company dramatically changes (positively) within 1 month post-closing (which at seed stage can happen), the valuation cap is what it is.  Normally this is accepted as given, much like how when you close an equity round, the price you got is the price you got.

However, there are circumstances in which founders know there are potential serious milestones on the short-term horizon that would dramatically influence valuation, but they need to close their seed money now. Obviously, smart investors reward results, not promises; so they’re not going to budge on valuation just because the founders are confident they’ll hit a milestone in a month. Tiered valuation caps are a useful mechanism for bridging this uncertainty gap in seed rounds.

Tiered valuations can bridge the uncertainty gap, and give companies some valuation upside. 

A tiered valuation cap would look something like this (language simplified because this isn’t an actual contract):

  • If the Company achieves [X milestone], the valuation cap will be [A];
  • If the Company does not achieve [X milestone], the valuation cap will instead be [B].

Convertible notes and SAFEs are optimally designed for providing this kind of valuation flexibility. It is much more complicated to implement something like this in an equity round, which is why you almost never see it. Also, there are a number of other nuances around valuation caps that are too “in the weeds” to get into in this post, but that, depending on the circumstances, may make sense for a company. One example would be, if a certain important milestone is hit, turning the valuation cap into a hard valuation.

Standardization v. Flexibility

Something related to the above that is worth briefly discussing is why, despite there being many logical circumstances in which deviation from “standardized” startup investment structures makes total sense and would be acceptable to both sides of the table, founders are often encouraged to “move fast” and stick to the usual docs.

There is a mindset in parts of the startup world – and very much coming out of Silicon Valley – that promotes the idea that startup legal documentation should all be standardized and closed as fast as possible, with minimal fuss. The PR story behind that trend – the way it gets sold – is that it’s about saving companies money. Don’t bother actually talking to counsel on these “standard” things; you’ve got to stay lean and focus on “more important” stuff.  Sounds legit.

Of course, every heavily promoted story has incentives behind it. Who benefits from saying “nevermind with the lawyers; just close quickly?” Software companies selling you the automated tool that relies on inflexible standardization, for one part. Savvy investors (repeat players) who have a 10x better understanding (than you do) of what the documents actually say, for another. As I wrote in “How to avoid ‘Captive’ Company Counsel“, it is very amusing when, during high-stakes negotiations where small variances in terms can have multi-million dollar long-term implications, certain investors take such a keen interest in “watching the legal bill.”

Everyone’s favorite sucker is the guy who shoots himself in the foot, and then sings a song about it.

Always always remember: if you’re doing this for the first time, and someone else has done it dozens, the “let’s get this done quickly” mindset is definitely saving someone money; but it’s usually not you. If a few discussions with counsel could result in a 25% higher seed valuation, you tell me if that is “wasted” legal fees. 

There are times when the standard terms make sense, but there are a lot of times when they don’t. Companies not fully on the “move fast and break things” train should slow down and take advantage of some customization when it could have a serious impact on dilution. Good investors who don’t view you as just another number in their “spray and pray” portfolio won’t criticize you for doing so.

ps. for the best companies, the “standard” valuation in an accelerator’s convertible note/SAFE is almost always negotiable.

Do I need a PPM for my startup’s financing?

TL;DR: Legally speaking, probably not. Most tech startups never prepare one.

PPM stands for “Private Placement Memorandum.” You can think of it as the private company equivalent of an S-1, the long disclosure document that companies produce when going IPO. PPMs are lengthy documents that include risk factors, financial projections, business plan information, etc.  For a broad description of what a PPM is, see this article.

In dense startup ecosystems, PPMs are rare.

Startups in dense, more mature tech ecosystems like SV or Austin usually don’t even think of producing PPMs; nor should they. Assuming that they are taking the classic approach of raising money only from accredited investors, a well-made deck and a solid operating plan are often their core needs for closing on early money. Delivering an Austin tech investor a PPM would send an immediate signal that the founders aren’t being well-advised, which itself signals poor judgment in choosing advisors. 

Asking for a PPM signals inexperience.

In less dense ecosystems, however, I do occasionally encounter tech companies who are told by advisors, lawyers, or other players that they need a PPM to close on financing. FACT: The vast majority of tech startups raising money solely from accredited investors are not creating PPMs, and legally speaking, they don’t have to.  Most repeat ecosystem players consider PPMs a waste of time and money. 

One of the main reasons that startups avoid non-accredited investors and stick to accredited-only rounds is that the legal disclosure burdens are dramatically reduced, which means no need for PPMs. In healthcare, energy, and a whole host of other industries, using PPMs in private fundraising is very common. For this reason, if your lawyer is telling you (a tech startup) that you need a PPM, that’s often a good ‘tell’ that they lack experience in the norms of emerging tech financing. 

Exercise diplomacy with more traditional investors.

All of the above being side, I have also on occasion encountered more traditional investors who, because they do not regularly invest in emerging tech companies, ask startups for PPMs (because PPMs are more common in other industries).  All money is green and, particularly for early angel money, you need to be respectful of the expectations that angels bring to the table; even if they’re ‘off market.’

In these situations, it’s best to diplomatically let them know that PPMs are not the norm in the tech startup space, and that the company would prefer (as should they) to focus its legal budget solely on those things that are truly needed.   Asking a more traditional investor what specific information she/he was hoping to see in the PPM, and trying to address those concerns more informally, usually goes a long way to bridge the gap. Sometimes hearing directly from a Tech/VC lawyer about the norms of startup finance also helps. 

Founders outside of Silicon Valley can sometimes forget that most of the resources – blogs, articles, podcasts, tweets, etc. – on startup finance and norms are, in the grand scheme of things, a tiny bubble in the overall business market.  When anyone says there simply “isn’t enough money” available for startups in Texas, or markets similar to Texas, what they really mean is that there isn’t enough money flowing into tech companies. There’s tons of money floating around elsewhere. People who can culturally build bridges between tech ecosystems and more traditional business networks have a competitive advantage in the market, and are often the ones forging ahead building new companies, and even investment funds, while others run around in circles soliciting only the ‘techies’ of the market.

Why Notes and SAFEs are Extra Dilutive

Background Reading:

Outside of Silicon Valley, Convertible Notes are the dominant form of seed round security. In SV, SAFEs are much more popular. The difference between the two effectively amounts to interest and a maturity date. For larger seed rounds, however, seed equity is another possibility.

The point of this post is not to debate the pluses and minuses of any of the above structures. The optimal one is, as mentioned in the above-linked posts, highly contextual. However, founders should understand that while SAFEs and Notes are faster and simpler to close on (usually), they come with a cost in the form of extra dilution relative to doing a seed equity round at an equivalent valuation. The math is as follows:

Dilution when raising seed as equity

Pre-Seed Capitalization:

You want to raise a seed round with the following terms:

  • Round size: $1.5 million
  • Valuation (cap or pre-money if equity): $6 million

You end up doing a seed equity round, with a 10% post-money pool, but with the pool top-up added to the pre-money (as it usually is). Post-close capitalization looks like:

Key to understanding what’s going on here is how the Seed Equity price gets calculated. $6 million (valuation) / (5MM Common + 714,219 pool) = $1.05.  So the seed investors paid $1.05 per share for their shares.

A year or two pass, and it’s time to do a Series A. The Series A economic terms are:

  • Round Size: $2.5 million
  • Pre-money: $10 million
  • Post-Close Available Pool: 15%

After you do the deal math (explaining that is not the point of this post), the post-close cap table looks like this:

So the above is what dilution looks like after both (i) a seed equity deal of $1.5MM at a $6MM pre with a 10% post-close available pool and then (ii) a $2.5MM Series A at a $10MM pre with a 15% post-close available pool.

Dilution when raising seed as convertible notes or SAFEs

Now let’s replay the above steps, except instead of doing an equity round for the seed, let’s do a convertible note or SAFE round. We can ignore interest, which economically makes the SAFE and Note scenario exactly the same.

Pre-Seed Capitalization:

OK, now we do a $1.5 million convertible note or SAFE with a valuation cap of $6 million. Same numbers as the above seed round, except it’s structured as a convertible security instead of an equity round.

Because these are notes or SAFEs, there’s no dilution registered yet on the cap table. The dilution math is deferred until the Series A.

So after closing the $1.5MM, we’re now at the Series A round. Because we have notes/SAFEs, we’re required to do two calculations in this round: first we calculate the conversion price of the SAFE/Note seed round, and then we calculate the price of the Series A.

Repeating the terms of the Series A:

  • Round Size: $2.5 million
  • Pre-money: $10 million (VCs insist Note shares go in pre-money to keep their post-close % at 20%)
  • Post-Close Available Pool: 15%

After we run through the deal math, this is what the cap table looks like:

The conversion price for the Note/SAFE is calculated by $6MM (valuation cap) / (5MM Common Stock + 1,530,476 Pool) = $0.92.

Now let’s compare the Post-close Series A cap table between the Seed Equity v. the Seed Note/SAFE scenarios.

Seed Equity –> Series A:

Seed Note/SAFE –> Series A:

What’s different? The Series A got the exact same ownership, because that’s how VC’s approach deal math. They will adjust the numbers to ensure they get their %. However, the Common Stock has 1.56% less ownership, all of which went to the Seed round. And the reason for that is straightforward, the Seed got a lower price, because the larger pool (post-A instead of just post-Seed) was built into their conversion math. 

In this scenario, 1.56% is about $195K in Series A post-money terms. So the decision to do seed SAFEs/Notes instead of seed equity cost the common stock nearly $200K in Series A dollars. And that’s ignoring interest, which would put that past $200K if we’re talking convertible notes with interest. I also simplified the example by ignoring actual usage of the pool in-between rounds. A real-world example would’ve had a larger pool top-up at Series A, and therefore a larger dilution gap between seed equity and notes/SAFEs.

Conceptually the way to view this is that convertible notes/SAFEs, as currently structured, have a kind of strong anti-dilution protection built into them. And that’s apart from the more obvious anti-dilution aspect relating to valuation: that a valuation cap is just a cap, and the notes will convert at a lower price if your Series A is below the cap.

If I do a seed equity round, everything that happens to the capitalization afterward dilutes everyone, including the seed equity. There is a conventional form of (soft) anti-dilution protection (typically broad-based weighted average) in seed equity, but it is rarely triggered; only in down-round scenarios. When the Series A bargain for a larger pool and put that pool in the pre-money, the seed equity doesn’t benefit from it because their math already happened.

But in the note/SAFE scenario, the seed math is deferred to the Series A round. Anything that happens to the capitalization before that date gets built into the seed note/SAFE conversion math, so they’re protected from it. This is why the seed notes/SAFEs end up paying a lower price (92 cents) instead of the higher seed equity price ($1.05). The denominator in calculating their math is larger because of the larger pool. Lots of founders think that SAFEs/Notes only have harsh anti-dilution economics if there’s a “down round.” But that’s not entirely true. The scenario I described above was not a down-round scenario. SAFEs/Notes protect investors from dilution, much more so than seed equity, in every scenario.

If companies and investors, and in the case of SAFEs, Y Combinator, wanted to really make SAFEs and Notes more equivalent in economics to seed equity, they would allow for the capitalization, for purposes of calculating the conversion price, to be set in the security. In other words, at the time of issuing the SAFEs/Notes, we would say the capitalization is X, and that is the capitalization we will use for purposes of determining the conversion price, regardless of what the Series A negotiate for their option pool adjustment. That would not be hard to do at all.  The valuation would still float and be determined at Series A, as is part of the core “deal” of a convertible security, but that full anti-dilution aspect of SAFEs/Notes would be removed.

I have never seen this solution actually implemented in the market. Why not? I’m not sure. A lot of people aren’t even aware of this economic disconnect between SAFEs/Notes and Seed Equity, so it could just be lack of awareness. Hopefully this post helps with that.  But it’s also possible that it’s just part of the “deal” that investors expect for taking convertible securities. If you ask them to move fast and take minimal protections/rights in exchange for their money, part of the price is extra dilution.

Whether or not founders think that price is fair will obviously depend on the circumstances of their company.  The goal of this post was not to give an opinion on SAFEs v. Notes v. Seed Equity, because my opinion is that they are all good for different circumstances. They all have their positives and negatives. All I wanted founders to understand is that there is an economic price to using SAFEs/Notes. Make sure it’s really worth paying.

Angel Investors v. “Angel” Investors

TL;DR: The term “angel” investor has connotations that in reality don’t apply to a significant portion of early-stage seed investors outside of Silicon Valley. Historically, angel investors were very wealthy individuals who’d take big, almost irrational (from a risk-adjusted perspective) bets on entrepreneurs for reasons that go well-beyond a profit motive. Many “angels” that you’ll encounter as an entrepreneur, however, think and act in a much more self-interested, conservative manner; much like venture capitalists, but with smaller checkbooks. Both types are crucial to startup ecosystems, but knowing the difference is still important.

Related Reading:

One of the core reasons behind this blog’s existence is that the majority of legal/fundraising advice available to startup entrepreneurs comes from places (like Silicon Valley or NYC) that are dramatically different (in terms of access to capital and key resources) from the environments in which most tech entrepreneurs find themselves. That doesn’t mean at all that SV or NYC advice is bad or wrong. On the contrary, much of it is very very good and founders who look only to local advice will screw themselves – see: The Problem with Localism. But founders also need to understand the mismatches between the advice/culture they’re exposed to on the most popular podcasts, blogs, etc., and how things tend to work for normals.

One important area where I see the disconnect arise is in founders’ expectations in interacting with “angel” investors. The typical “angel” investor that you encounter in Austin, Houston, Atlanta, Dallas, or Miami does not look, think, or act like what Silicon Valley people have historically referred to as “Angels.” 

Classic Angels

While the full origin of the term “angel” investor goes beyond this post, in general very early stage investors were very wealthy individuals who, in addition to other activities, wanted to “give back” to the business community by making bets on promising entrepreneurs that no one else (rational) would be willing to make. Hence, their investments were “angelic.” While this doesn’t mean at all that Angels didn’t scrutinize their investments, or that that they acted completely out of charity (hardly), the term absolutely has (correct) connotations of motives that are much broader than just making a great return.

These classic “Angels” were wealthy enough that writing a $100K or $200K+ check barely moves their needle, and so they could take the risk of investing in a company with little more than a very promising team and an idea, and perhaps the very early beginnings of a product. If it fails, NBD. They’re doing it for the relationships, the excitement, and the chance at supporting something new.  I often see founders take very early money from investors that fit the classic “Angel” profile, but those relationships take a long time to build. They don’t spark over a pitch contest or business plan competition.

Anyone who says there isn’t enough money in Texas/the South is painting with way too broad of a brush. There’s tons of money floating around here and elsewhere. The core difference is that in Silicon Valley, the true capital-A “Angel’ money was created in tech, and therefore much more easily flows back into early-stage tech (because the Angels trust their judgment on tech teams/companies). Outside of that environment, much of the ‘Angel’ money comes from other industries (like Energy, Healthcare, etc.), and so much more relationship-building, selling, and (cultural) translation is needed to convince it to go into a tech startup.  Great t-shirts and a pitch deck won’t get you there.

Most “Angels”

In most other tech ecosystems (outside of SV), when people speak of “angel” investors they are often talking about successful individuals who, while willing to take on the risk of early-stage seed investment (which is great), are not so wealthy and altruistic that they’ll barely feel losing $100K-$200K.  That means that most “angels” seen in non-SV ecosystems are much more conservative in how they pick their investments (and will therefore have higher expectations), because to many of them angel investing really is about making a great financial return.

Classic Angel investors were/are generally very wealthy senior executives and business people with net worths well into 8 figures and above, who will bet on team, vision, and minimal traction (if any); so very early stage. The majority of “angels” that entrepreneurs encounter in their own ecosystems, however, come from broader backgrounds (lawyers, doctors, real estate, business owners, etc.) and are affluent/comfortable, but not quite the 0.1% (their angel investments are material to them), and they”ll often want to see clear customer traction, revenue, and a more mature product; and a lower valuation. 

Of course, there are far more “angels” than Angels, so I’m not suggesting at all that the more conservative, self-interested nature of typical “angel’ investors is bad or a problem. They are crucial to startup ecosystems. I’m not running around writing $100K checks on team+vision either. But the distinction between the two categories often gets lost on first-time entrepreneurs, with negative consequences.

You likely need a Pre-Angel Plan

So the net result of the above is that tech entrepreneurs outside of the most dense ecosystems like SV and NYC encounter much higher expectations from “angels,” and therefore (and I’ve written this in prior posts) pre-angel money, what is typically called “friends and family” money, is often essential to building something attractive to “angels.” If I encounter a founder team planning to start a company without a viable path to $50K-$200K in initial funds, either from their own savings, friends and family, or a classic Angel, that is very often a red flag. Not game over, but it is a concern. 

It’s certainly been done before, especially when the founder team is very self-contained and willing to work for nothing until there is real traction, but most companies will never make it to the “angel” investment stage (product, traction, revenue) without either bootstrap/F&F funds, or a classic Angel investor willing to make a big bet. Accelerators have helped with this issue by (often) being the first non-F&F money in and serving as a valuable signal to “angels”, and they deserve credit for that, but even getting to a point where you’re attractive to a top accelerator often takes some real cash.

In short: most angel investors are much more conservative, and have higher expectations, than the term “angel” suggests, because they’re in a different category from the classic wealthy “Angel” investors that give the term its meaning. Be mindful of that fact, and prepare for it in your early-stage fundraising strategy.