The Pre-money vs. Post-money Confusion With Convertible Notes

The other day, Mark Suster wrote a critically important post titled One Simple Paragraph Every Entrepreneur Should Add to Their Convertible Notes. Go read it—I’ll wait. Or, if you just want the paragraph, it’s:

I also have seen the problem Mark is describing. As an angel investor, I have never asked for a liquidation preference on conversion that is greater than the dollars I’ve invested. But, I’ve seen some angels ask for it (or even demand it), especially when there is ambiguity around this and the round happens much higher than the cap. The entity getting screwed on this term are the founders, who now have a greater liquidation preference hanging over their heads than the dollars invested by the angels. Mark has a superb example of how this works on his blog.

We’ve been regularly running into another problem with doing a financing after companies have raised convertible notes. Most notes are ambiguous as to whether they convert on a pre-money or a post-money basis. This can be especially confusing, and ambiguous, when there are multiple price caps. There are also some law firms whose standard documents are purposefully ambiguous to give the entrepreneur theoretical negotiating flexibility in the first priced round.

If the entrepreneur knows this and is using it proactively so they get a higher post-money valuation, that’s fair game. But if they don’t know this, and they are negotiating terms with a VC who is expecting the notes to convert in the pre-money, it can create a mess after the terms are agreed to somewhere between the term sheet stage and the final definitives. This mess is especially yucky if the lawyers don’t focus on the final cap table and the capitalization opinion until the last few days of the process. And, it gets even messier when some of the angels start suggesting that the ambiguity should work a certain way and the entrepreneur feels boxed in by the demands of his convertible note angels on one side and priced round VC on the other.

The simple solution is to define this clearly up front. For example, in the Mattermark investment from last year, I said “We are game to do $5m of $6.5m at $18.5m pre ($25m post).” When I made the offer, I did not know how the notes worked, what the cap was, or what the expectation of the angels were. But when Danielle Morrill and I agree on the terms, it was unambiguous that I expected the notes to convert in the pre-money.

Recognize that this is simply a negotiation. Tweet This Quote

In contrast, in the Glowforge deal, which Dan Shapiro talks about in his fun post Glowforge Completed its Series A with an Investor we Never Met, I was less crisp. I knew that Dan’s notes were uncapped with a discount and I knew his lawyer well, so I didn’t define the post-money in this case. Since the notes were uncapped, I expected them to convert into the pre-money. But I didn’t specify it. The notes were ambiguous and we focused on this at the end of the process after docs had gone out to the angel investors. Rather than fight about this, I accepted this as a miss on my part and let the post-money float up a little as a result. The total amount of the notes was relatively small so it didn’t have a huge impact on the economics of the investment but we could have avoided the ambiguity by dealing it with more clearly up front.

Recognize that this is simply a negotiation. In Mattermark’s case where there were a lot of notes stacked up, I cared a lot about the post-money. In Glowforge’s case where the note amount was modest, I didn’t care very much. And, while I care a lot about my entry point as an early stage investor, I’ve learned not to optimize for a small amount in the context of a pricing negotiation.

Fundamentally, it’s up to the entrepreneur to be informed about what is going on. Tweet This Quote

I think we are just starting to see the complexity, side effects, and unintended consequences created by the massive proliferation of convertible notes over the past few years. I’m pretty mellow about them as I’ve accepted that they are part of the funding landscape, in contrast to a number of angels and VCs who feel strongly one way or the other. As derivative note vehicles have appeared, such as SAFE, that try to create synthetic equity out of a note structure, we’ll see another wave of unintended consequences in the next few years. As someone who failed fast at creating a standardized set of seed documents in 2010, I’ve accepted that dealing with the complexity and side affects of all of the different documents is just part of the process.

Fundamentally, it’s up to the entrepreneur to be informed about what is going on. I hope Mark’s blog post, and this one, are additive to the overall base of entrepreneurial knowledge. And, if Jason and I ever write a third edition of Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist our chapter on convertible notes might now be two chapters.

This originally appeared on Brad’s blog.