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Convertible Debt or Preferred Stock: which one is better?

The question of whether angel investments in early stage companies should be in the form of a loan that converts (usually at a discount) into the equity, and at the valuation, of the following (usually VC) investment round, or instead in the form of Convertible Preferred stock (typical of a venture capital investment round) is one which generates a lot of heat in entrepreneurial circles. It also frequently leads to disagreements and hard feelings between entrepreneurs seeking funding and the angels who may be in the best position to fund them. But in reality, the answer is very simple:

“Smart Money” does NOT invest in convertible debt. Period.

This is not a negotiation, or a matter of what is right, or a matter of choice, or anything else. It is simply a definitive, rational, factual statement.

But it does have one corollary, and one exception.

The multiple reasons that smart money (which includes venture capitalists, modern organized angel investment groups, and the leading independent angel investors) simply won’t (and shouldn’t) do convertible notes are amply and clearly spelled out by Bill Payne, formerly Entrepreneur in Residence at the Kauffman Foundation and generally regarded as the world’s leading trainer of angel investors. The primary reason, of course, is economic: the angel is investing at an earlier, riskier stage and therefore should expect a higher return than the VC, who is coming in when some of the risk has been removed, and after the entrepreneur has made the company more valuable using the angel’s money. For the angel to wait until the next round to value the company results in exactly the opposite: he or she takes the early stage risk and ends up with later stage valuation: a lose/lose proposition!

Another perspective on why convertible debt sucks comes from Furqan Nazeeri, a serial entrepreneur with EIR experience who is an extremely perceptive observer of the startup financing scene. He points out that from the side of the entrepreneur, doing a convertible debt round correctly is complicated, creates a perverse incentive for the angel investor to work against the company, and ultimately doesn’t make a big difference for the entrepreneur.

The practice of convertible debt had its heyday about a decade ago, when inexperienced angels found themselves getting hammered by VCs in follow-on rounds, and decided that it would be better to join them instead. Since then, serial angels have gotten a lot smarter, best practices in angel investing have been standardized, and a funny thing happened to all the serial angels who started out doing convertible notes: they found themselves losing money because of the poor risk/reward relationship, and therefore either (a) stopped angel investing, or (b) got smart and stopped doing convertible notes.

But wait, you say. I mentioned earlier that there was a corollary and an exception. OK, here they are:

Corollary: “Not-Smart Money” SHOULD invest in convertible debt.

Huh? Why? Because the primary trick to raising early stage money in a ‘priced’ round of Convertible Preferred stock is to price it to value it correctly! And this is the essential difference between ‘smart’ and ‘not-smart’ money.

Perhaps the single biggest problem we see with companies applying for funding to New York Angels is that they have done an earlier Friends & Family round that valued the company at a significantly higher valuation than we (the so called “smart money”) believe it is worth. In this situation, there are only three possible outcomes, none of which are good: (1) the entrepreneur won’t do a ‘down round’, so we simply walk away and don’t fund; (2) the entrepreneur does a down round, and poor Aunt Edna, who invested $50,000 of her retirement money, sees her investment lose half it’s value; or (3) the entrepreneur falls on his/her sword and protects Aunt Edna by taking the full valuation hit personally. Ugh.

In cases like this, the BEST thing the entrepreneur can do is take the unsophisticated money in a convertible note, because that way it will end up getting priced correctly when the smart money comes in. But one thing to beware: the next round investors, whether professional angels or venture capitalists, will be the ones to ultimately decide what discount the convertible note will get…regardless of whatever was written into the original note. In practice, few sophisticated investors will have a problem with a 10% discount, which will usually stand. And if there has been a fair amount of time between the note and the venture round (say, six months to a year, or more) a 20% discount has a decent chance of holding. But don’t bet the farm on the new investors accepting anything much more than that. If the note has, say, a 50% discount, it will almost certainly be eliminated, or, in a best case, factored into the lower pre-money valuation the VC offers.

Exception: Smart Money should consider a convertible note as a bridge to a legitimate term sheet, and should always have a backup price.

Bill Payne walks through these economics in detail, but in a nutshell, if a VC has already signed (or is thisclose to signing) a term sheet, it will be at a fixed valuation, so the angel bridge will be at a known discount to a known ‘correct’ price. In this case (a) the 10-20% discount is a fair benefit for the risk being taken (which is that the term sheet might fall through), and (b) if the term sheet DOES fall through, the angel now has debt, which is a better thing than equity to have when things go bad, which they will if the VC walks. Nevertheless, even in this case the convertible note should have a fallback feature of a set price, so that if the term sheet doesn’t happen the angel will STILL end up with an investment at a known, appropriate, valuation.

Note to angel investors: As Ben Franklin said, “experience is a hard school, but some will learn through no other.” Let me add one more piece of advice: no matter HOW iron clad a term sheet you think you are bridging to, NEVER make the bridge loan subordinate to other debt, and ALWAYS ensure that you are first in line (ideally, make the loan secured.) Don’t ask me how I know this.

So, there you have the definitive answer on convertible debt vs. preferred stock. It’s not hard. It’s not emotional. It’s just business.

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Reader Comments (2)

The point of choosing convertible debt is that it is paid first, as you mentioned. 10-20% is not a normal discount, that is really low. In many scenarios, evaluating the startup too early can harm the investor AND entrepreneur. There is still an evaluation, but the point is to leave the true evaluation to what an institution or venture group is willing to pay. I think in a lot of scenarios it leaves investors with security of getting whatever their dollar amount out first, protects dilution, and gives the founders the most incentive to reach the agreed triggers before conversion can take place.

September 21, 2010 | Unregistered Commenterhuh

10-20% may sound low as a discount (which is why sophisticated angel investors won't take it!), but in reality anything much higher than that (like a 50% discount) simply won't stand up when the next investors come along. So, yes, in the angel/venture/high growth startup industry, 20% is about the standard discount for a seed round convertible note.

March 6, 2011 | Registered CommenterEditors
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