To Participate or Not (Participating Preferences)

When I wrote my first post on the structure and financial components of a typical venture capital investment – where I described Liquidation Preferences – I alluded to the concept of participating preferred as a maligned and typically hotly negotiated issue in many venture capital investments. In this post, I’m going to try to explain the notion of participating preferred (referred to hereafter as PP), how it works, and its financial and emotional impact on a deal. I’m not going to take sides, but rather try to give a broad perspective on it.

First – some history. I first encountered PP when several of the angel investments that I did in 1994 and 1995 matured to the point where they raised a round of institutional venture capital. Since I was living in Boston at the time, most of the VCs looking at my angel deals were east coast firms. In every single case, the initial term sheets each of these companies received included a PP feature – a “double dip” as my east coast lawyer called it. When we pushed back on the PP, we were told that all east coast term sheets had them (our lawyer told us it was negotiable, but that it was definitely an east coast standard request). The PP survived several of term sheet negotiations, but not all of them.

My east coast-centric world changed significantly after I moved to Colorado in 1996 and started doing venture capital. Because of geography and investment focus, I ended up working on more stuff on the west coast. There, I rarely saw a PP feature and was told flatly that PP was “an east coast term.” As the 1990’s marched on and the bubble started to build, I rarely saw a PP – even the east coast guys had dropped it from their standard term sheets.

After the bubble burst in 2001, PP was back – and this time on both coasts. Suddenly every term sheet I saw had a PP feature in it, regardless of the stage of the investment, type of business, or location of investor. It had once again become “a standard feature”, although it was now bi-coastal (or – more accurately – a red-blooded American term.)

So, with this as background, and before we dig into the actual mechanics of a PP, lets first recognize it for what it is – an economic feature in a venture investment. It’s not a standard term, nor is it something that is evil and should never be part of a deal. Unlike a liquidation preference which is rarely negotiable with a VC, a PP is almost always negotiable. There are even cases where it economically disadvantages an early stage investor who insists on it in the deal from the beginning. Importantly, there is not a consensus among investors on when a PP feature is appropriate in a deal and each firm approaches it from their own, unique perspective.

A PP is the right of an investor, as long as they hold preferred stock, to get their money back before anyone else (the “preference” part of PP), and then participate as though they owned common stock in the business (or, more technically, on an “as converted basis” – the “participation” part of PP). It takes a preferred investment, which acts as either debt or equity (where the investor has to make a choice of either getting their money back or converting their preferred shares to common), and turns it into something that acts both as debt and equity (where the investor both gets their money back and participates as if they had converted to common shares).

To illustrate, let’s take a simple case – a $5m Series A investment at $5m pre-money where the company is sold for $20m without any additional investments being made. In this case, the Series A investor owns 50% of the company. If they did not have a PP, they would get 50% of the return, or $10m. With the PP they get their $5m back and then get 50% of the remaining $15m ($7.5m), resulting in $12.5m to the Series A investor and $7.5m to everyone else. In this case, the Series A investor gets the equivalent of 62.5% of the return (rather than the 50% which is equivalent to their ownership stake). The PP results in a re-allocation of 12.5% of the exit value to the Series A investor.

Obviously, this can get much more complicated as you start to have multiple rounds of investments with a PP feature. A simple way to think about how the economics of a PP works is that the total dollar amount of the preference will come off the top of the exit value (and go to the investors); everyone will then convert into common stock and share the balance based on their ownership percentages. For example, assume a company raises $40m over 3 rounds where each round has a PP feature and the investors own 70% of the company. If this company is sold for $200m, the first $40m would go to the investors and the remaining $160m would be split 70% to investors / 30% to everyone else. In this case, the investors would get a total of $152m, ($40m + $112m, or 76% of the proceeds – 6% more then they would have gotten if there was no PP.)

If you sit and ponder the math, you’ll realize that a PP usually has material impact on the economics in low to medium return deals, but quickly becomes immaterial as the return increases (or – more specifically – as the ratio of the exit value to invested capital increases). For example, if a company is sold for $500m, a $10m PP re-allocates a small portion of the deal ($10m of the $500m) to the investors vs. the $40m of $200m or $5m of $20m in the other preceding examples. As a result, a PP usually only matters in a low to medium return situation. If a company is sold for less than paid in capital, the liquidation preference will apply and the participation feature will not come into play. If a company is sold for a huge amount of money, the PP won’t have much economic impact, as the preference feature of the PP becomes a small percentage of the deal total. In addition, in essentially every case, PP’s don’t apply in an IPO where preferred stock (of any flavor) is typically converted into common stock at the time of the offering.

As PP started showing up in more deals, some creative lawyer came out with a perversion on the preferred feature called a “cap on the participate” (also known as a “kick-out feature.”) In this case, the participation feature of the PP goes away once the investor holding the PP reaches a certain multiple return of capital. For example, assume a 3x cap on a PP in a $5m Series A investment. In this case, the investor would benefit from their PP until their proceeds from the deal reached $15m. Once they reached this level, their shares are no longer counted in the cap structure and the other shareholders share the remaining proceeds. Of course, the investor always has the option to convert their shares to common stock and give up their preferred return (but participate fully in the proceeds). Put another way, at a high enough valuation the investor is better off simply converting to common (in the current example at an exit value above $30m).

Participation caps, however, have a fundamental problem – they create a flat spot in most deal economics where the investor gets the same amount across a range of exit values. If we stay with the example above and assume a 50% ownership for the Series A, the PP would apply until the exit value reached $25m, at which point the investor receives $15m in proceeds. Between $25m and $30m, the investor would continue to receive this same $15m (this is the flat spot – it doesn’t matter whether the exit value is $26m or $29m, the investor would get $15m). At exit values above $30m, the investor would convert to common stock and take 50% of the proceeds (i.e., their as-converted share of the proceeds would exceed the $15m cap so they would be better off converting to common and taking this share of the exit value). This is an odd dynamic, since the common shareholders are clearly not indifferent to exit values in this flat spot, but the investor is (and consider a case where this flat spot was much larger than the one in the example above). Any way you cut it there is misalignment, at least for a range of outcomes, between the investor and the rest of the shareholders.

Another perversion is the “multiple participate”. In this case, the investor gets some multiple of his participate off the top of the transaction. For example, a 3x multiple participate on a $40m investment would mean the first $120m would go to the investor (and then the remaining proceeds would be distributed to the investor and the rest of the shareholders). This type of PP only appeared for a short while when investors were doing recapitalizations without actually going through the mechanics of recapitalizing the company (more about this in a future blog post).

Interestingly, there is a case to be made that PP in early financing rounds can actually end up disadvantaging early investors. The math on this gets complicated very quickly, but if you assume that every subsequent investment round has at least as favorable terms as the initial round (i.e., include a PP if the first round does) and that subsequent rounds include new investors there are many cases where the initial investor is actually disadvantaged by the existence of the PP (they would have been better off to have not put it in the initial round and because of that pushed for its exclusion from subsequent rounds). It’s counterintuitive, but it actually works out this way in a number of very common financing scenarios.

So – if PP simply relates to economics, why is it a term that brings out such emotion in entrepreneurs and investors alike? A close friend of mine who is an extremely successful entrepreneur recently told me “I’ve walked on every investment deal for any company that I’ve run that even smelled of multiple dips of participation – and spit back in the direction the term sheet came from!” We debated back and forth a while. For example, I asked him “would you take $5m for 33% of a company with no participate or 25% of a company with full participate?” He responded “I would go find a deal where I gave up 26.5% without a participate” which, while an emotional reaction, ironically reinforced my point that it was just economics. After pondering this term over the years, I’ve concluded that participating preferred is one of those terms that creates real tension between the entrepreneur and the investor – it forces the acknowledgement by the entrepreneur that a moderate return is not a success case for the investor and at the same time forces the investor to acknowledge that in those moderate cases they believe it is fair to receive a greater percentage of the proceeds at the expense of the entrepreneur.

  • Ralph Clark

    One point that should be made about preferences (both regular and participating) is that they typcially disappear on a qualified public offering. A qualified IPO is usually defined as a minimum pre offering valuation and offering size. The reason for this is LP and PP are all about the economics of downside protection when a non ipo exit does not result in an acceptable favorable return for investors so they get some compensation or return as a “lender” in addition to their participation if it is PP.

    The PP becomes an emotional issue when VC’s use it not so much for downside protection but as a way to juice returns even in high valuation merger exits. Instead of dealing with the up front valuation expectations by establishing the appropriate pre-money valuation many investors try to juice the returns in this backdoor way. The problem is this can create really perverse incentives once mgmt and employess catch on and are presented with the option of an exit via an ipo (no PP) or merger (with PP). All things being equal and depending on the size of total liquidation preference they will be naturally incented to drive to an IPO exit which may not be the right thing for the company. That is why PP’s are almost always recut/reneogiated on a merger deal in order to get the proper alignment between investors and management. In most situations this negotiation can happen in a constructive way but sometimes based on how much the PP was relavant in the IRR calculation of the investor it can be pretty messy.

    IMHO, PPs should be used for downside protection and therefore a cap is appropriate. If investors want it for return enhancement they should deal with the economics throught the front door on the pre-money valuation so there are no surprises when you are looking to a non ipo exit.

  • Dave Jilk

    Boo hoo, horror of horrors, a cap on the participate creates a MISALIGNMENT and a FLAT SPOT in the return for the investors! Why is this misalignment a concern, when the BIG OL’ LIQUIDATION PREFERENCE flat spot (at $0.00) for the common doesn’t seem to keep any VCs up at night? After all, this misalignment can create real problems, where management has every incentive to run the company against the wall rather than throw in the towel when it’s clear that success is unlikely and return the remaining cash.

    Besides, the flat spot is easily remedied. The liquidation preference could phase out as the participate scaled up. Then there is no flat spot, the investor gets above-share returns for lower proceeds. Hmmm, you could even have the common’s share start at dollar one, in a very small share, and increase monotonically over the range of proceeds — this would solve any number of “alignment” problems.

  • Dave Jilk

    I had more to say in my first comment but was interrupted by a beautiful woman.

    I find it interesting that you use the term “perversion” to describe capped participates and multiple participates. That’s a highly emotionally laden term… yet these are just further twists on what is, after all, just economics.

    Further, in my experience, VCs get very EMOTIONAL about the idea that their cash should have a liquidation preference. Why is that? Investors in an IPO don’t get a liquidation preference, and their money is just as green.

    One other technical point: a capped participate can also be viewed as a “multiplier preference” where the common shares in the return above a certain point. As companies started to fall apart during the later stages of the Internet bubble, some investors turned the screws and insisted on a 2x or 3x liquidation preference. Again… just another economic term… liquidation preference doesn’t need to be tied to the cash. A capped participate is just a variant on this that allows the common to get some return sooner.

    I still like my idea of a phased-out liquidation preference with the participate. Has this ever been tried to your knowledge?

    Feld Comment: I didn’t intend “perversion” to be an emotional term. Unfortunately, I can’t support that with an dictionary.com definition since – other than the sexual references – it’s apparently a “a change to something worse; a turning or applying to a wrong end or use” (I always thought of “pervert” as “weird” – guess I’ve got to modify my internal dictionary – but than again, I have trouble with then and than). So – no emotion intended (even though it appears it slipped out – I’m sure I’ll get called a pervert the next time I propose a partipating preference cap.)

    The base liquidation preference (not the participate) is more than an emotional point for VCs – eliminating it is a non-starter in 99.9% of the cases. It’s a longer discussion as to why this is the case – I’ll save it for a later post.

    I thought I talked about multiplier preferences in a way that was generalized enough. It can apply whether or not there’s a preferred preference in place. It’s typically used when one or more of the existing investors don’t participate in a financing and the investors (or the company) is unwilling to do a recapitalization. Multiplier preferences are intended to “punish” investors who chose not to participate in future rounds – if all investors participate then they are usually unnecessary. However, there are lots of unintended consequences associated with them, including the obvious situation where there is a dramatically increased preference over the common shares. Again, a complicated situation that I’ll try to explain in a future post.

    One of the big challenges with all of this stuff is that the capital structure of a company can quickly become very complex which makes it very difficult to (a) understand what is going on, (b) create a situation where all parties are appropriately motivated on a going forward basis, and (c) set up an end-game situation where everyone feels like they shared appropriately in the risk / reward situation. Hopefully some of these posts and ensuing discussion will help with that.

    • DaveSF

      "VCs get very EMOTIONAL about the idea that their cash should have a liquidation preference. Why is that? Investors in an IPO don't get a liquidation preference, and their money is just as green."

      Why do you compare a very risky early stage investment with PP to an IPO? I don't see the relationship.

      Investors like PP because it prevents a misalignment, where founders have an incentive to sell at zero investor profits. It also allows investors to be less brutal about valuations, since a wash-sale still produces profits for them.

      Consider the scenerio where the author's example of a $5M investment at $5M premoney is made, giving investors a 50% equity stake. A year later, the company sells for $10M. Without PP, the investors just made a zero-interest loan while founders make $5M. With PP, the investors would receive their $5M back and both parties split the $5M "return" at $2.5M each.

      As the author mentioned, there is a valuation number at which the investor return on a given deal works out the same. For example, the above scenerio at a $3.75M pre-money puts the investors at 75% equity and the same return on the $10M sale. What this does _not_ equalize, is the incentives if the founders wish to sell at $7M, which is again a wash-sale for the investors but profit for the founders.

      I can see an argument for less than 100% participation, but founders walking away with all the profits on a wash-sale doesn't seem fair. PP allows the investors to fix this mis-alignment problem at sale values between the investment amount and at or just above the post-money investment valuation. As the author pointed out, once the ROI increases, the PP term diminishes.

  • Dave Jilk

    “Non-starter” — just a euphemism for an emotional issue! Hmmm: Would you rather have 33% of a company without a preference, or 25% with a preference? Isn’t it just economics? I’m pretty sure most VC funds don’t have this as a restriction in their charter.

    But I’ll look forward to your post.

    You didn’t comment on whether a participate with a “phased-out” LP would work or has been tried.

    I agree with your a, b, c that are the goals of a good capital structure. I think what your “entrepeneur friend” was trying to tell you is that participates do not satisfy (b) and (c) for the entrepreneur (or, at least for him) — and I would add that for line employees (but probably not management) they do not satisfy (a) either.

    Feld Comment: While I wouldn’t ever do an early stage deal without a liquidation preference, I’d still rather have 25% with a liquidation preference than 33% without a liquidation preference (I’m assuming you mean a simple liquidation preference rather than a participating preference.) Here’s a challenging situation – assume 33% without a preference (the entrepreneurs own 67%). The investment is $5m in a company that has never made a profit. On the day after the investment, the entrepreneurs decide to liquidate the company. Since they own 67% of the company, theoretically they can do this and take 67% of the newly invested cash.

    Fundamentally a venture capital investment – especially an early stage one – has strings attached – one of them is that the investor has some downside protection. A liquidation preference is part of this downside protection. The participate is a more economically aggressive version that combines the downside with improved economics on the upside. If you don’t like the notion of the strings, then venture capital is probably not for you.

    Regarding a phased out liquidation preference – this is certainly a valid approach to get rid of the flat spot. I’ve never used it nor have I encountered it, but it’s an interesting, albeit potentially mathematically complicated, approach to bridge the gap between a capped participate and a full participate.

  • Dave Jilk

    Fun debate.

    Be sure to realize that I think liquidation preferences are a completely appropriate mechanism for early stage investors.

    The point I am trying to make (perhaps sarcastically) is that the downside protection that VCs want is ultimately just an economic provision, just as the participate is just an economic provision. You could get terms that economically balance the lack of a liquidation preference, but you wouldn’t, because that’s not the way you like to do things. Similarly, your “entrepreneur friend” could get terms that balance a participate, but he won’t, because he doesn’t like to do it that way. In both cases, it’s more about what “feels right” than the actual economic analysis.

    In the end, it’s really all just a negotiation, and the posturing about what’s “fair” and “appropriate,” and “reasonable” is all just posturing. The goal (and responsibility) of the VC is to balance getting as high a fraction of the return as possible back to the fund, while making sure the entrepreneurs are motivated enough to make the company successful (i.e., the size of the pie and the slice of the pie). This is a tricky business and not one that I envy.

    Your example of the day-after distribution is easily fixed by covenants and governance provisions. The lack of a liquidation preference doesn’t mean there are no other strings attached.

    The real message of a participate, and although you make the point I think it is easily lost on first-time entrepreneurs, is that the reason VCs invest is to aim for a very high return. This can create many disconnects between the investor and entrepreneur after the investment:

    ENTREPRENEUR: There are a bunch of customers over here who need our technology.

    VC: That’s too small a market. Ignore it. Go for that longshot over there.

    This seems irrational to the entrepreneurs, but it’s not irrational — it’s a high-risk, high-return posture. Instead of saying to the entrepreneur “the participate is a standard term and we believe it’s justified”, say “that’s in there so that every day you wake up and realize that you’re not getting much money out of this unless it’s a huge success.”

    I know that YOU have this conversation with people, but I don’t think most VCs do.

  • http://www.iskela.com/flowoftime/archives/000155.html Flow Of Time

    Term sheet negotiations

    If you think that a ‘double dip’ refers to dining and you are raising funds you better read Feld Thoughts…

  • http://www.qumana.com/blog/_archives/2004/8/28/131637.html Qumana Blog

    Man has Venture Blogging come a long way since…

    I pulled this quote from Venture Blog not so much about its topic, but about how blogging has opened up …

  • http://www.qumana.com/blog/_archives/2004/8/28/131637.html Qumana Blog

    Man has Venture Blogging come a long way since…

    I pulled this quote from Venture Blog not so much about its topic, but about how blogging has opened up …

  • http://www.qumana.com/blog/_archives/2004/8/28/131640.html Qumana Blog

    Man has Venture Blogging come a long way since…

    I pulled this quote from Venture Blog not so much about its topic, but about how blogging has opened up …

  • Michael Platt

    I agree that PP is an economic vehicle designed to increase the return to the VC, and as a result, should be considered in light of the valuation placed on the company.

    However, I’m not as intellectually troubled that either “capping” or eliminating the PP feature misaligns management and the VC.

    It’s important to note that “flat spots” are associated with the return curve of at least one of the securities in any company with a liquidation preference. If a flat spot was the problem, in and of itself, the only way to solve for this is to remove the liquidation preference entirely. For example, a “flat spot” is created on the return “curve” for non-participating preferred too. However, since the flat spot in NPP is created with the first penny distributed beyond the liquidation preference, many VCs object that the entreprenuer actually makes money (assuming a nominal purchase price on founders’ shares) by a sale that marginally exceeds the liquidation preference, while the VC only receives a return of capital.

    The primary purpose of creating a PP with a “cap”, as perverted as that my sound, is to better align the interest of the common and the preferred in a potential sale that exceeds the liquidation preference with an average return, while maintaining for the entreprenuer the stretch goal to earn their way back to the the position of “equality” that would be acheived if the company were to go public.

    If the VC accepts this as valid compromise objective, this additional incentive requires one to move the flat spot on the return curve associated with a non-participating preferred further to the right, immediately following the “cap” level in a capped liquidation preference. It essentially creates an economic “accelerator” for the entreprenuer for a job well done. I don’t see anything “weird” about that. To say anything contrary, would be darn right un-American. For those who don’t recognize it, the last two sentences are merely humor, not true emotion.

  • http://gruia.blogware.com/blog/_archives/2004/9/2/134359.html Technology Futurist

    The Return of the Participating Preference Option in VC Deals

    Brad Feld’s blog (Feld Thoughts) is a great source to learn quite a bit about the VC world.  In a recent pos…

  • Jason Mendelson

    Interesting and good read.

    I�d push back that it�s �not a standard term� as I don�t really know if anything (outside of reg rights and some sort of preferred of return) is standard.

    Furthermore, I think the flat spot in the capped participation usually helps out the common, so I don�t get too caught up in it. What is more interesting is with a capped PP, every new preferred investor (Assume same capped amount and up round) takes money away from older preferred (even assuming pro rata involvement), to the point you�d be better off having no capped participation.

    That is why you see sometimes the capped number going down as valuations go up.

  • http://odnt.typepad.com/new_dog_old_trick/2004/09/venture_financi.html new dog old trick

    Venture financing T’s and C’s

    Feld Thoughts: To Participate or Not (Participating Preferences) Brad Feld is one of the six or seven venture capitalists that I know of who also write very interesting weblogs. If you are at all interested in venture capital and how

  • Ann Onimus

    You could also go with a “no double dip” where the investors get their original investment returned and the the common gets their pro-rata share, and then they split the rest. This way they get theirs first in case the deal is not too sweet, but they aren’t double dipping.

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