Unintended Consequences: When SAFE and Convertible Notes Go Awry




Andrew Krowne and I recently co-wrote an article in Tech Crunch, Why SAFE Notes Are Not Safe for Entrepreneurs. We’ve received numerous constructive comments, both privately and on social media, from attorneys, VCs, and CEOs who are well aware of the problem (including several who are experiencing it in real time).

This is a fundamental issue that does, indeed, boil down to understanding the post-money valuation of a company. But it is also a topic that many find esoteric and difficult to grasp.

To restate two core points of the article:

While there are proper uses of notes (to bridge the company to achieve a major milestone, or driven by insiders’ willingness to extend runway), there also are troubling and frequent improper uses (to postpone pricing equity until valuation is higher or to ignore the implicit message associated with being unable to find a lead investor to price the round on terms that the founders like).

 At its core, this issue points to the lack of understanding about the importance of post-money valuation by both entrepreneurs and investors. While VC deals remain marketed on a pre-money basis, sophisticated investors know that what matters most is the post-money (how much of the company will I own after all of the new shares have been issued). Unfortunately, what the CEO/founder forgets most often is that the notes have a multiplier effect in the post-money calculation; the more notes and the further the cap is from the new priced equity, the greater the variance between actual and nominal pre- and post-money valuations.

There is nothing wrong with using a SAFE or a convertible note in a startup if you know its implications. However, many VCs experience vexing discussions with CEOs, and many CEOs belatedly realize that this is because they made a mistake: issuing multiple series of notes at various valuation caps without actually sitting down and figuring out the pro forma post-conversion equity ownership.

This is not uncommon—and it is a problem precisely because the notes are being used improperly. The most serious unintended consequence occurs from “note waterfalls”— converting multiple notes that have multiple valuation caps.

Many entrepreneurs lose track of what they have been cooking up in the cap table. They do not recognize that they may have already contractually sold a meaningful portion of equity in their company.

When it comes time to convert the notes, these entrepreneurs face ‘sticker shock’ about their post-financing ownership. That’s only one result of mismanaged expectations dating back to when the notes were issued!

The following scenarios represent typical recipes for trouble:

  • Company X is early in business development, has a near-term need for capital to get through the next 3-6 months, and the management team has no understanding of how the equity should be divided up among its various constituencies (this includes option pools and what ownership stakes investors typically require at various development stages).
  • Company Y receives an offer from an angel or ‘unsophisticated’ smaller VC fund that is unwilling to lead and price the equity but wants to ‘invest now’.   The easiest way to do so is via SAFE notes, due to their simplicity, “available online” documentation, no major covenants established to protect the investors, no governance implications at the board level, etc. All of these items are postponed until the elusive priced equity round. “It’s going to be great!”
  • Issuing notes eases the burden of getting several investors to commit simultaneously and solves the ‘chicken-or-the-egg’ issue by creating a rolling close that financially benefits the earliest movers with more attractive financial terms. In contrast, there is limited benefit for being the 2nd investor or the 10th investor joining the syndicate of a priced round, so it is common for investors to wait to see “who else is involved”.
  • The CEO/founder often has leeway to influence or negotiate the cap value (especially when the headline cap is softened by a discount). This is very common when the company is still in its infancy and the valuation goalposts remain distant. A much larger problem arises when subsequent ‘series’ of notes are issued, especially if each successive series has a higher valuation cap. CEOs and unsophisticated investors very often start anchoring the caps to what they think the company could be worth, all without external validation. In these cases the caps can easily diverge from the true number at which a company could raise sufficient equity to provide at least 18 months of runway with no revenue (a normal VC round).

The bottom line: Startup CEOs/Founders need to do the projected capitalization table math on an as-converted, post-money basis from Day 1, before issuing any notes and modeling various possible future scenarios. It will be worth the time and effort.

Make sure you understand what you are doing now so that you are not negatively surprised in the future. Sound simple? Yes, and it’s a lot simpler than making your startup grow into a successful company. Now go do it.

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