Want to Know How VC’s Calculate Valuation Differently from Founders?

by Mark Suster on July 22, 2010

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Back in 1999 when I first raised venture capital I had zero knowledge of what a fair term sheet looked like or how to value my company.  Due to competitive markets we ended up with a pretty good term sheet until we needed to raise money in April 2001 and then we got completely screwed.  It was accept the terms or go into bankruptcy so we took the money.  Those were the dog days of entrepreneurship.

But the truth is that I didn’t really understand just how screwed I was until years later when I finally understood every term in a term sheet and more importantly I understood how each term could actually be used to screw me.  Things like “participating preferred stock” in legalese unsurprisingly never actually call out, “hey, this is the participating preferred language.”  We got a 3x participating liquidation preference with interest (not participating with a 3x cap, but 3x participating.  Ugh. I explain the difference later in the post or you can click through on this link above for an explanation).

Back then VentureHacks didn’t exist.  Brad Feld hadn’t written his seminal “term sheet series” and The Funded hadn’t yet been created.  And for some strange reason entrepreneurs didn’t share this information.  Other founders, “as a privately held company we don’t disclose our valuation.”  Me, “dude, I’m not a journalist.  I just want to figure out what a fair valuation is.”  I figured all the VC’s talked so we should. Duh.

I don’t feel that as a VC sneaking in nefarious terms into a term sheet that the entrepreneur doesn’t understand is a good way to build a long-term relationship nor to build a long-term reputation but this does happen and more frequently than we all would like.  I’ve started from day one trying to build total transparency into my process with entrepreneurs.

This starts with understanding how VCs and entrepreneurs often see valuation differently.  And no prizes for guessing which side of the table really understands the right answer.  I’m not sure I really even need to write this at length because Nivi absolutely nailed the topic in his article “The Option Pool Shuffle.”

When I went to raise money in 2006 I thought I knew every term in a term sheet but somehow I still got a bit duped by the option pool shuffle.  I had several term sheets and one of the leading term sheets had an option pool of 40% in it.  I couldn’t understand why they wanted so many options until a friend pointed out that this just lowered their “true” pre-money valuation (they also asked for some sharp elbowed terms in the deal).

I turned them down.  They were nonplussed.  They couldn’t understand how I could turn them down when they considered themselves the leader in my field and they had worked so hard to get the deal.  I told them that True Ventures had stuck to their brand name and submitted a totally clean term sheet.  No gotchas.  No option pool shuffle.  No hidden terms.  So they agreed to match True’s term sheet.  I thought to myself, “OK, they were willing to F me when they thought I had no idea what I was talking about . Now that I do they’re willing to accommodate?  Gee, if they treat me like this in good times I wonder how they’d treat me in bad times!”

So to make sure it never happens to you, as a loyal reader of this blog and hopefully an occasional watcher of This Week in Venture Capital, I recorded a video session with my colleague Kelly Hwang on how VCs calculate valuations and he’s created a cap table spreadsheet you can download from DocStoc to plug in all of the terms and you can watch the video here and/or read the text summary below.

How VC’s Calculate Valuation: We walked through a standard deal where you raise $1 million at a $3 million pre-money valuation leading to a $4 million post money valuation.  The math works out that the investor owns 25% of the company post deal ($1 million invested / $4 million valuation) and assuming 1 million shares, each share would be valued at $3 / share ($3,000,000 pre-money / 1 million shares = $3 / share).  Investors own 25%, the founders own 75%.  NOTE: In the video I talked about how VC’s and entrepreneurs decide the total number of shares at the first major funding round and why it’s often a high number.

But this example above is all entrepreneur math, not the VC’s.  The VC assumes you’ll have an option pool.  That’s normal.  You’ll need to hire and retain talen to grow your company.  Those options need to come from somewhere.  The more senior members you have (say you already have a CEO, CTO, VP marketing, VP Biz Dev, VP Products) then the less options you’ll need and vice versa.  Industry standard post your first round of funding will be 15-20%.  I say “post” funding because you’ll need more than this amount pre-funding to get to this number after funding.  We walk through this in the video.

So taking the same fund raising round and assuming that the VC wants the options including before he or she funds (and before is totally standard) then the math works like this: Assuming a 15% option pool post funding then you need a 20% option pool pre funding (because the pool gets diluted by 25% also when the VC invests their money).  So your 100% of the company is down to 80% even before VC funding. Normal.

The VC’s $1 million still buys them 25% of your company – it’s you who has diluted to 60% ownership rather than 75%.  The price / share is actually $2.40 (not $3.00), which is $3,000,000 pre-money / 1,250,000 shares (because you had to create the 250,000 share options).   Thus the “true” pre-money is only $2.4 million (and not $3 million) because $2.40 per share * 1 million pre-money outstanding shards = $2.4 million.

Note that the term sheet you get will still say, “Pre-Money = $3 million” and there won’t be anywhere in the term sheet that says “true Pre-Money” or “effective Pre-Money” – that’s for you to calculate.  So let’s start calling the term sheet listed pre-money valuation as the “nominal” pre-money valuation.  Luckily you all now have the spreadsheet to download that will calculate both for you.

Term Sheet Overview:

The second most important economic term in the term sheet other than price is “liquidation preference.” This states how the proceeds from a sale or dissolution of the company will be distributed.  Investors will always want to get their money out of the company before founders, which in the case where the company is sold for a low price is fair.  You almost certainly will have liquidation preferences if you raise VC so don’t worry about having them.

But not all liquidation preferences are equal – we discuss all this in the video – some can have a “multiple” on top of them such as a 2x liquidation preference, which means that investors get 2x their money before founders get anything.  In an early round of investment where there is not an extremely high price relative to normal valuations this is anything but benign.

More likely what you’ll see if you have an aggressive term sheet is “participating preferred” stock.  This means that investors get their money back AND they get to share in the proceeds.  If you’ve raised $6 million in total and still own 40% of the company and sell for $10 million (not a great outcome but it happens) then with participating preferred investors would take $6 million off the top and then 60% of the remaining $4 million so the founder’s take would be $1.6 million (.4 * $4 million) and not $4 million. Note that it might be even less than $1.6m because liquidation preferences often have interest calculated on top of them.

VC’s in early rounds will argue that “participation” is simply downside protection and if you sell for a lower price they should get more of the proceeds.  While true, the problem I have is that any terms you have in your early stages will certainly be asked for by future investors in your later funding rounds so all of these terms pile up when you’ve been through 3-4 rounds of funding over a 5 year time frame.  And by the time most companies get to an exit (which despite what you read on TechCrunch about all the high-profile early exits the most realistic case is still 8-10 years) often the founders own very little of the economic upside.  This is a shame.

Privately some early-stage VC’s talk about participation helping them to “juice their returns” on smaller exits.  This is silly talk.  I don’t imagine any VC seriously makes money by having tons of small to mid-sized outcomes and therefore “juicing” to me is delusional. I think VCs make money by investing in 20-25 deals and finding 2-3 outliers that drive extra-ordinary returns.  And those are often done by the best and smartest founders who have enough knowledge to know which VCs are juicers and which aren’t.  You reap what you sow.

I also won’t say there is never a time for “participating preferred” but it tends to be in later-stage rounds and particularly in the case where the founders are getting an exceedingly high valuation relative to the norm.  In those cases there are all sorts of mathematical reasons why participation might make sense.  These are edge cases.

But for founders stuck in this negotiation about participation or not with VCs the most standard compromise is “participation with a cap” which is usually set at 2-3x their investment.  This means that participation truly only applies in downside scenarios and once your exit outcome is above a certain price investors would still be better off converting to common stock and not taking their preference.  I prefer to see no participation but this is a good compromise if you can’t get a straight 1x liquidation preference.

After valuation in the video we went through Liquidation Preferences, Board Seats, Protective Provision, Voting Rights, Drag Along Rights, Redemption, Anti-Dilution and a few other key terms.  We spend a lot of time on them in the video but frankly we could have done a 3-hour session.  If I get demand from people after this video to do a deeper dive on term sheets we will.  Heck, maybe we’ll even invite a lawyer on to do it with us!

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  • Curious investor
    Quick Question:
    For the option pool, are there stipulations on who those options go to? i.e. can the board issue those future options to the current management team?
  • You should write a (book or 2) and go into teaching, at least as an 'adjunct'...
  • Bhagya4
    Good one Mark. What a treasure of good advice for entrepreneurs!
  • Susan Morgan
    There is a great tool for computing the complete waterfall analysis of distributions (including options, warrants, management/bonus plan carve-outs ...), for ANY and ALL values of merger or acquisition sales. Go to www.equilytics.com, and download the "Sample Spreadsheet" there for an example of the MergeComp Analysis.
  • Piyushp
    Great post, Mark. You are a real hero who is providing valuable information to people. It's not that this information is not available anywhere but providing in way which people can read in 5 minutes and understand easily is rare to find.
    If an investment firm is asking for more than 1x liquidation preference, I will prefer to put a clause where they cannot make more than 20x returns. Higher the liquidation preference, lower the maximum return. I guess this is very reasonable. If you are looking for limited risk you deserve limited returns as well.
  • justfunded
    Thanks, just going throught the same process and your account matches our experience.
  • Mark, I have a question that might be trivial about the second sheet of your spreadsheet (incl options).
    If options are added in order for the VC to calculate the option dilution before investing, shouldn't the cash paid at the exercise time by the option holders (the strike price) be included (on top of the negotiated entreprise value) in the valuation to a) reflect the true value of the exercise and b) reduce the dilution for the founders by including both sides (dilution compensated by extra cash) of the option equation?
  • paul s germo
    Outsatnding post - makes those of us who are seeking capital - a little nervous and much more aware. Thanks for your integrity.
  • Howard
    Great Stuff Mark! I raised NO money for my first start-up. My 2nd Start-up, now 6 years old, was primarily funded by Venture money and OH! (ouch!) what a difference in my daily mindset and fundamental approach to business. I am an operator and like many entrepreneurs, neglected some critical subtleties in deal terms, hoping it all will take care of itself (or my attorney would) in my zeal to get on with building business. This is a must read primer for all thinking about VC raise. thx
  • Awesome post Mark. Question about the option pool: What happens if you don't end up using all the shares allocated to the option pool? Say you use only half of them. Does the other half default to the founders?

    And would it be correct to say the term sheets offered by angel/seed investors tend to be light weight like YC's and cover only some of the main terms you discuss?
  • You should check the dilution calculator at HackFwd: http://hackfwd.com/dilution
  • Hi Mark
    A friend of mine from SVB turned me on to your blog this morning. This post was exactly what we were talking about this morning, great coincidence. I will definitely have to read all your posts.

    I am glad to hear you had a positive comment about True Ventures.
    Regards,
    Baha
    KRAASecurity.com
  • Hey Mark, great post and very helpful. Is it safe to say much of this applies to Angel investments as well?
  • Most angel deals have less terms attached to them. But if angels are asking for a huge number of rights normally associated with VCs - run.
  • hi Mark,
    I am from Canada, I must tell you that I found your post extremely useful. How VC work has been such a hush topic nobody talks about it and everyone is doing the guessing game.

    I will make sure you post gets to all the entrepreneurs sites in Canada.

    EDUCATION is critical and the more we have the better Entrepreneurs and future leaders we become.

    Look forward to reading more post from you
    Oscar A Jofre
    Founder, President/CEO
    BoardSuite Corp.
  • Thanks, Oscar. And tell them to watch This Week in Venture Capital where every week we try to demystify things just a little bit more.
  • kris
    Request for the next show: options.
    How do VCs make sure the option pool won't be increased after they've done the deal?
    Who decides what the fair value is in between 2 rounds?
    A few examples of what employees get would be nice.

    When I started watching the show I was like oh no, spreadsheets and a business guy who never started a business ... am I supposed to listen to this?
    However, I'm glad I ignored my allergy and I listened to the entire show.
    You should definitely do more shows like this, it's a good resource! Thank you.


  • From a legal perspective, there are typically 2 ways that a VC can ensure that it has a block on whether the options pool is increased, and usually one or both are included. The most straightforward is to require a specific vote of the preferred stock to increase the pool. The other, which is more complicated to explain, essentially says that any increase to the pool with the consent of the preferred stock would trigger "anti-dilution" protection -- a topic too complex for a blog post comment, but suffice to say it is something that dilutes the common stockholders and is not desirable. From a practical perspective, you want the Board to be in agreement on actions taken such as increasing the option pool, so if you ever get to the point where you are looking at the legal ramifications then you probably have bigger problems.
  • kris
    require a specific vote to increase the pool ... is that done very often?

    When you don't get permission, it could sort of make it difficult to find good employees.
  • Thank you, Kris. Yeah, I'm going to cover options on TWiVC.
  • kris
    Thanks.
  • Hi Mark, great post and video. Kelly great job!

    If Venture Hacks coined the phrase the "Option Pool Shuffle", can I coin the phrase the "Preference Giveaway"?

    The "true" or "effective" valuation of the common stock is actually less than your spreadsheet calculates because it assigns an equal value for preferred stock as it does for common stock. As we know, preferred > common (as the name implies ;) and should be reflected as such in the cap table. The formulation in your cap table (and every other cap table I've seen on this topic) "gives away" these preferences for free, which I would argue is not accurate.
  • For 409a valuations the IRS agrees with you. Generally, I don't. It's true that preference stock has more "rights" associated with it and therefore more "value" - sure. But in terms of how the pie gets sliced the preference itself doesn't impact returns other than specific rights (like participation, PIKs, etc.). And each of these can be quantified individually.
  • Susan
    Years ago the Council for Entrepreneural Development in RTP,NC had a course taught by local entrepreneurs called FastTrac. Kauffman Foundation sponsored it and they taught all sorts of things like this and some patent law. They modified it over the years and I believe put it out for other groups to use.
  • Great post. Entrepreneurs who have delivered good exits can and should negotiate fair (even advantageous) deals. Everyone else ends up taking what they can get (if they can get any investment at all). As a result, "normal" terms reflect a strong bias towards the investor. Appreciate your stand against participation (at 3x entreprenuers should run screaming from the room).
  • In April 2001 that was all I could get!
  • As an entrepreneur, I can't say good enough about this post. Great learning.Definitely make the 3-hour TWIVC with lawyers and all :)

    I just wonder one thing: KISS, could these things just be simpler, plain flat terms?

    If these terms were "flattened" to a simpler, non abusive form, VC's money would consequently be worthed differently due to the risk they had to take but it would remove complexity from the process and have "money on the table" as the variable to discuss.

    I'm newbie on this subject so I am not sure if it make sense... Could it be?
  • I've come to realize that all terms exist for a reason. Somehow at some point in the past some company had a situation that required each term. So they stay. But the key is to KISS especially in the early stages of companies.
  • Susan Morgan
    Great post. I am both an attorney and entrepreneur, having started two companies, and worked for 10+ years as a corporate attorney focused on entrepreneurs, startups and private companies (currently: Of Cousel to Scott Walker - at Walker Corporate Law Group). I am also an adjunct professor at Golden Gate University, where I teach a course on "High Tech Startups - Business and Legal Issues" (course is cross-listed with Law and Business/Management Schools). A significant portion of my course focuses on this topic - teaching law and business students how to understand VC financing terms and term sheets, and their implications.

    I have looked at a lot of books on this subject, and the one I use in my class is by Alex Wilmerding: "Term Sheets & Valuations". It's paperback, affordable, and understandable by the uninitiated. And it does a pretty good job of going through the "gotchas". (No, I do not receive any renumeration for recommending the book - I have no economic interest here). This stuff is hard enough to learn (and a real challenge to teach), so I thought I would throw out this resource, in case anyone was interested, or found it helpful (particularly, for the entrepreneurs).

    Cheers!

  • Thank you for the book recommendation. Much appreciated.
  • Great post and video. I wish I had seen it when I was learning all this years ago. I posted it on my blog too.

    Here's another great resource for learning about term sheets. Justin Fishner-Wolfson's Term Sheets 101 presentation:

    http://www.slideshare.net/dmc500hats/term-sheets-101-by-justin-fishnerwolfson-founders-fund
  • Dig deeper, dig often.
  • Thanks for your post. I know how hard it can be to describe as accuratlely and simply something that is, I guess, really obvious for you now.

    I wanted to know if things work in the same fashion with Business Angels or are there some major differences (option pull included in pre-money valuation (?) & liquidation preference (?))

    Thanks a lot,
  • Please dive deeper on term sheets. I really like your perspective being from both sides and still feeling some of the pain from not understanding your eariler terms.
  • Michael_RightSite
    Mark -- this is the most helpful post on understanding the basics of VC deals that I have seen yet. I would like to find out more, but I think you may have put me off of VC funding forever.
  • No reason to be put off. There are great VCs out there. I'm just pointing out that you need to be educated about how valuation and term sheets work. And triangulate enough with other entrepreneurs to find out who the good VCs are.
  • Great post. VC Experts has some excellent data on the terms and valuations venture funded companies are getting at www.vcexperts.com . They also have a new web application that can show entrepreneurs the effect certain terms will have on their ROI at liquidity.
  • Cool. Thanks for the link for people.
  • LV
    Here is a link to an article that they posted that follows your post. http://vcexperts.com/vce/news/buzz/archive_view.asp?id=925&referrer=buzz&mail_id=buzz1126
    We currently use the company analysis tool that modeled this, and it is amazing.
  • How would this conversation change when the founders have put in cash and/or already have a meaningful revenue stream? What would that mean for the preferred-ratios in particular?
  • When founders put in money it gives them more leverage in the negotiations but never more than having competitive investors wanting to put money to work. If you have a meaningful revenue stream you have huge leverage and deal structures will be totally different.
  • ariel
    Can you quantify meaningful revenue stream. If you are 1-3 months post a beta launch and you have revenues from 5-10 trial customers (assume its a B2B sale) -- is that leverage?
  • Thanks! That's what I figured.
    Can you elaborate a bit on what exactly will change in the deals in that situation?
  • After reading this post I got great understanding of the VC company evaluation. Thanks.
  • sigmaalgebra
    Shuster's blog post describes a sad situation:

    The post makes venture capital look like an effort to get something good out of dirt pit, cock fighting: Dumb because nothing good comes from there -- get a lot of blood in the dirt and torn feathers and maybe some money changing hands in a zero-sum game and nothing good.

    Why am I reminded of the Wall Street remark "I could teach my dog to be an investment banker in a weekend"?

    Or if we list everything important in venture capital in large type on one side of a 3 x 5" card, how much room is left over on the card?

    Or once again, as we can conclude from a recent entry on this blog, that I reference below, at this time in venture capital we see an old 'business model' being pursued blindly, refusing to wake up and see what is going on, and spiraling down.

    Good things have happened and can happen in the economy but not from cock fights.

    Here there are too many people losing and too few gaining. Let's consider four major cases:

    (1) The limited partners MUST want gains from venture capital because from a table at

    http://www.bothsidesofthetable.com/wp-content/uploads/2010/07/university-endowment-losses.jpg

    in

    Both Sides of the Table

    What’s Really Going on in the VC Industry? What Does it Mean for Startups?

    by Mark Suster on July 16, 2010 at

    http://www.bothsidesofthetable.com/2010/07/16/whats-really-going-on-in-the-vc-industry-whats-it-mean-for-startups/

    commonly university endowments are down 25% from 2008 to 2009; from the financial news fixed income interest rates are low from overnight to 30 years; and we all need to see future inflation is a concern meaning that the real interest rates now are likely negative.

    (2) The general partners MUST want gains because apparently about half of the partners are about to look for different jobs; as in the blog above:

    "I was at dinner with a large LP and mentioned that I had heard the industry would shrink by 50%. She laughed and said, 'Our predictions are for a much larger drop.' Gulp."

    Big Gulp, indeed.

    (3) The entrepreneurs, of course, want gains.

    (4) And the US economy needs to get MOVING again.

    So, as in

    What’s Really Going on in the VC Industry?

    these are "The worst of times."

    It's also "the best of times"; let's see four points:

    (1) Hardware. Now can buy, for about $200 each, a 4 core, 64 bit, x86 family processor with a 3.0 GHz clock, a 2 TB SATA hard disk drive, a motherboard with bells and whistles, about 8 GB of main memory, and a nice tower case and power supply. With three hard disks for reliability, that's a total of $1400.

    Can do a lot of computing with that. A spare bedroom with two 24 x 48 x 72" wire shelf units full of such tower cases can serve enough Web pages and ads per year to be a significant business.

    One of the last of the 'water heater' mainframes had a clock of about 150 Mhz; so the speed is up by a factor of roughly 80 and the price, electric power, software cost, etc. are so much less they are lost in the old roundoff error.

    AMD and Intel just reported record quarterly earnings -- people ARE buying computers.

    (2) Infrastructure Software. Lots of Unix based software is free; the basic Microsoft .NET software is free, and the Microsoft BizSpark program will provide more software for free to new businesses for a while.

    (3) Bandwidth. Internet bandwidth is growing and prices are falling, e.g., can get 15 Mbps upload speed (that used to be 10 T-1 lines) for $55 a month. Can put 100 Gbps on one wavelength on an optical fiber, maybe dozens of wavelengths on one long haul fiber, dozens of fibers in one cable, etc.

    (4) Internet. The Internet is one of the more important steps up in civilization: The 500 million users of Facebook is maybe twice the US population of computer users and means that about one person in 13 on the planet is on Facebook; Technorati has long since been tracking over 100 million blogs; the tree cutting media, TV, and ads are all moving to the Internet.

    The Internet is growing: E.g., as at

    http://www.avc.com/a_vc/2010/06/ad-spend-trends.html

    in

    Ad Spend Trends

    is a graph by Hal Varian and from Fred Wilson:

    "But what this chart says is that over that past decade Internet has gone from nothing to 5% of all the ad spend in the US.

    "That is the most bullish signal about investing in the Internet that I have seen this year. If you include audio over the Internet (what radio becomes) and video over the Internet (what TV and cable become) in the Internet line, then I bet Internet will someday be over two-thirds of the ad spend."

    Web 2.0 should be a license to print money for the limited partners, the venture partners, the entrepreneurs, the advertisers, and people looking for good jobs and a rich flow of nitromethane into the engine of the US economy.

    Beyond Web 2.0, higher economic productivity from computer-based automation should be spreading all across the US and then being sold to the rest of the world for whatever they have to trade -- I'll take one of Chambertin, one of Montrachet, and two tickets to La Scala, thank you!

    From "the worst of times", there's a SERIOUS problem, and we need to look at it. Let's consider one entrepreneur typing in software for a Web 2.0 project. In this we should keep in mind the example the Canadian Web site Plenty of Fish as at:

    http://highscalability.com/plentyoffish-architecture

    So, there is one guy, two servers, ads just via Google, and $10 million a year in revenue.

    Continuing, apparently what is on the 3 x 5" card are five 'stages': Angel, Seed, A, B, and C.

    Okay, in more detail, especially for the entrepreneur, there are project 'milestones':

    (1) The early plans that convinced the entrepreneur to pursue the project.

    (2) Completion of the crucial work in the plans.

    (3) A Web site the VCs can "play with".

    (4) A live Web site with users -- might take $2000 in hardware.

    (5) Ads, say, 10 per second at $0.10 RPM for

    0.10 * 10 * 3600 * 24 * 365 / 1000 = 31,536

    dollars a year in revenue.

    (6) 100 ads a second, and users and revenue per day growing quickly.

    (7) Profitability (doesn't take much revenue considering just one entrepreneur running a Sub-chapter S-corporation).

    (8) $1 million a year in revenue.

    (9) Ads, say, 100 per second with good ad targeting for $4 RPM for

    4.00 * 100 * 3600 * 24 * 365 / 1000 = 12,614,400

    dollars a year in revenue.

    Okay, in this list, let's consider two 'milestones' S1 and S2 where:

    (i) Milestone S1 is the latest the entrepreneur can still use equity funding and, to get venture funding, is willing to get into a cock fight, work for a Board that doesn't understand the work and can fire him, and get a lot of lawyers involved.

    (ii) Milestone S2 is the earliest a good venture firm is willing to offer significant funding.

    It does very much look like in the most important cases S1 < S2 by 1 or several milestones. That is, the latest the entrepreneur is willing to take the money is one or more milestones short of the earliest a VC is willing to invest the money.

    Here's the rub: About the smallest S2 can be for significant venture interest is when the Web site has gone live and the number of users is significant and growing. Everything the entrepreneur did before that point has value $0.00 on the 3 x 5" card. However, by then, assuming the project is as planned, the entrepreneur is also likely within just a few months of being profitable enough to fund growth just from revenue until revenue is above the Plenty of Fish $10 million a year at which time the entrepreneur already has in his bank account more money than from a Series A. Then he has no Board and little need for lawyers; he spends no time entertaining a Board that doesn't understand the work; he keeps his bookkeeping and tax returns simple; he needs no 'option pool'; he need spend no time on 'negotiating', 'term sheets', or dirt pit, cock fighting; he owns 100% of the company with no 'vesting' schedule; and there is no Board that can fire him.

    Here's another point: As we know from Facebook, there are more than 500 million Internet users out there.

    Well, for a Web 2.0 site, there is some number, say, n, of Internet users that, once they hear about the site, will become users. Okay, what fraction of Internet users is n? Well, if the site has grown fairly quickly to, say, 100,000 unique users a month or 25 million ads a month or some such, then we are beginning to estimate that the fraction is significant. Or, if you will, imagine a survey that asks Internet users if they have heard of the site. Maybe when extrapolate from the survey sample, the number that have heard is 1 million. So, the 100,000 is 10%. Then we guess that we are close enough to a simple random sample and estimate that the site could get 10% of all Internet users. Now we're talking over 50 million unique users a month and a significant business. Net, an early 100,000 is an important 'sample' that extrapolates to something significant.

    Well, both the venture partner and the entrepreneur can see this sampling and extrapolation.

    The next question is how fast the growth will be? For that can set up a little differential equation: time t, users per day y(t), users now y(0), total eventual users b, so that for some k, we have y'(t) = k y(t) (b - y(t)). The solution is left as an exercise (hint: it is in terms of some exponentials).

    So, the k is essentially a 'viral coefficient' that says how fast people who have heard of the site tell people who have not heard of the site. The solution is an S-curve, really the 'logistic curve' that once saved a now famous company. Should be able to estimate the viral coefficient.

    Doing this calculation, the entrepreneur can begin to guess when the 'big bucks' will start.

    So, with the extrapolation and the S-curve, the entrepreneur might conclude that waiting a few months, less time than he'd need to get a VC check anyway, he should just ignore venture capital and pay attention to his business.

    So, venture capital is not looking for deals like Plenty of Fish (which stands to have its revenue continue to grow). So, instead, venture partners are reduced to looking for much less good deals where both sides are reduced to some dirt pit, cock fighting. Bummer for everyone (except maybe the lawyers).

    If the venture partners were doing well, then they might not be concerned. But on average, they are going out of business. They need to do better. Cock fighting over bad deals looks like bad business, and it is.

    The situation is too close to private equity investing: For the value of a company, just use obvious criteria, say, from accounting. Then, look for owners just desperate for some cash due to, maybe, a nasty divorce, loss of a key employee, too much in fast women and slow horses, some family member who wants a few million dollars in cash to build some monument to ignorance. Such investing is dirty business, bottom fishing and not innovation or a way to move the economy forward. The economy needs buyers of last resort, but it's still not nice business.

    Above I outlined the problem, serious for nearly all concerned except possibly for a site like Plenty of Fish, and we should not expect that to be the only future for Web 2.0 or computing.

    Now I move on to the solution:

    Get venture capital out of the dirt pit of cock fighting, off the 3 x 5" card, past the Mother Goose story 'The Little Red Hen', and somewhere into the 20th century, hopefully the 21st century.

    In particular, essentially everything important in innovation should be clear enough at milestone (1) above. For this, two changes are needed:

    (A) The entrepreneurs need much more definite, solid planning. E.g., as in the blog post with a talk by Eric Ries

    Founders 2010 #9: Conditions of Extreme Uncertainty

    July 21st, 2010

    at

    http://www.feld.com/wp/archives/2010/07/founders-2010-9-conditions-of-extreme-uncertainty.html

    entrepreneurs need to dumpster the planning with such "uncertainty". It did appear that Ries had fun running down the entrepreneurs telling them that 90% of them would fail. Ries embarrassed himself: What is important is the conditional probability of success given a solid plan; that should be much higher than the Ries 10%; and the Ries statement indicates that he doesn't see that it is possible to tell in advance what solid plans are. Ries thinks the work is just throwing wet stuff against the wall to see what random 10% sticks -- ignorant, destructive, disgusting.

    Instead, right there in milestone (1), entrepreneurs need to know quite definitely what the heck they are doing and build a solid, rational case. Right: Can't do that in a 'foil stack' of 12 foils in large type or six foils, etc. And if all the venture partner wants to do is glance at a few foils and 'play with the Web site', then they are ignoring nearly everything that is important and, in a biomedical analogy, looking at the color of the pills and the label on the bottle and, for a project with any content, ignoring the important aspects of the content -- just SUCKS for everyone concerned.

    Referencing this blog, at

    http://www.avc.com/a_vc/2010/07/terms-term-sheets-and-terminal-value.html

    Fred Wilson posted

    Terms, Term Sheets, and Terminal Value

    and emphasized that what really matters is "terminal value". Right. But starting with an early milestone, for people without some golden intuition seeing that far into the future takes serious, solid work, MUCH more than just a short 'foil deck'.

    Is such planning possible? Yes, and else we in the US would all be speaking German, Russian, or Chinese by now. E.g., essentially everything important in US national security for at least 70 years has been from solid planning, just on paper, at essentially just milestone (1): The proximity fuse, radar, radar jamming, passive sonar, spread spectrum radar with shift register sequence encryption, .... And except maybe for DARPA projects where high risk was accepted, the failure rate has been lower than admitted for venture capital. Beyond technology projects, for operational projects the US WWII effort in Europe -- North Africa, Sicily, Normandy -- emphasized planning in fine detail with essentially 100% success. E.g., in the first 55,000 allied troops who landed at Normandy, about 10% were injured and about 3% died. 'Failure' would have been getting thrown back into the sea, and that never came even close to happening.

    (B) VCs need to be able to read and evaluate such plans and, then, DO that effectively. Reviewers at DoD, NSF, and NIH can; likely some biomedical VCs can; Web 2.0 VCs should also.

    Else entrepreneurs with poor plans and VCs with just 3 x 5" cards will be forced into dirt pit, cock fighting where nearly everyone loses.

    Many entrepreneurs with good plans will take the path of Plenty of Fish.

    However, this path is still not good for many of the most promising founding CEOs: The model assumes that the founder takes the project from the first plans all the way essentially to first revenue and, for a good project, within a few months of significant revenue, just with his own checkbook. So, this approach tends to rule out as venture funded founders the most experienced mid-career people with families (not me!). Instead, if the project is good with, say, $500 million estimated market capitalization within a few years, then for venture capital to play hard to get and to refuse to evaluate the project early on when the entrepreneur had to is bad for nearly everyone.

    I am reminded again that not everyone can get rich. Instead, it is too common for people to snap, like the alligators in the pit in the movie 'Romancing the Stone', at any short term food.

    It looks like information technology venture capital will morph more into private equity where they invest mostly in 'special situations' and not in the mainstream of the future of computing or the Internet.

    Guys, this is SERIOUS. We need to start actually thinking and do better.

    For me, I want nothing to do with dirt pit, cock fighting and entertaining a Board that doesn't understand my work and can fire me, and with my vesting schedule has a big fiduciary reason to do so, and am learning more about what to do with my project from the Plenty of Fish example, $1400 computers, and ad arithmetic than from VC blogs.
  • Ivan Gaviria
    Mark,

    Great post. For those who are still learning about this stuff, I'd also recommend the chapters on "The Term Sheet" and "The Exit" in Jeffrey Bussgang's book which are written in a similarly accessible style and give some additional color and perspective on these issues.

    Two small comments - I'd tweak the cap table in that model spreadsheet to have more like 6-8M shares for founders instead of 1,000,000 so that in a typical Series A deal you are landing on a price per share below a buck. While you can always play with splits and such to move the price per share, you should expect your common stock valuation (for option pricing purposes) to be somewhere in the range of 15-30% of the Preferred Price and so it makes for more attractive option pricing to have a bit lower A price than $3. Also, there is a funny psychology around options. Even super smart people who understand perfectly that 1% = 1% seem to prefer a job offer with 100,000 options over one with 10,000 options.

    Regarding the comment about carve-out plans, I'd also remind people that carve-outs are essentially the company's agreement to pay mgmt bonuses which corporate liability gets paid ahead of liquidation preferences. As such, they are compensation and taxed as ordinary income (as opposed to capital gains on the sale of your founders' stock). Something to keep in mind when you're trying make apples:apples comparisons.

    Lastly, I'll differ a bit with you on the comment that most lawyers don't tell founders how to negotiate these provisions or what is market or how they can get screwed. If that is the case, people are STILL getting the wrong lawyers. The VC world is a specialized place where you need advisors who know their way around and don't just understand the terms but have seen how they play out in real situations in up markets and down. I don't want to start another thread on how to pick lawyers as there are many resources out there. I think it's pretty simple, just get list of the clients and a sampling of the deals; those two things will immediately let you know if you're shopping at the right place. Then it's just an exercise in checking references and seeing who feels like the best fit.



  • There are great lawyers out there and the best ones walk entrepreneurs through the details. Still, I have never seen a lawyer calculate voting percentages of preferred stock and walk entrepreneurs how these could possibly be used as veto power in certain scenarios and/or describe how different investors might see financing events differently going forward depending on fund size, etc. Lawyers do much - but there is much more to do.
  • philsugar
    I can give you one at DLAPiper that definitely does.....he has a large practice.
  • I'm curious Mark: VCs reserve the right to be paid the first, but shareholding has two aspects: participation in returns and the control of the company. How would VCs react to a suggestion that okay, they can have liquidation preference, even preferred, but their shares only bring half as much (or some other factor) votes as the common shares owned by the founders?

    Edit: Ah, and one more thing. Usually, are the stocks in the option pool common, or in any way preferred?
  • If a founder wins the voting battle, it's typically the opposite -- they have shares of a separate class of super voting common stock (e.g., 10 votes for each share of common). But in my experience they need to have huge leverage to win that battle, and at the early stage most do not. I think Google has this.
  • Matt, thanks for the answer. But are those super-voting stocks instead of the common, or in addition to them?
  • Options are always common.
  • Great post, hugely helpful.
  • Mark, this is an excellent post, thanks for sharing all the gory details and for creating the DocStoc spreadsheet to help us first-time entrepreneurs out.

    I'm an entrepreneur based out of Bangalore and although much of what you write about applies here in India as well, I wonder if there's enough knowledge about what kinds of terms are offered by VCs in India.

    Thanks again.
  • thanks, Ravi. Although I've worked in India before I really don't know how the VC environment works there relative to the US. Sorry.
  • Phil Black
    Hey Mark,
    Great post and I appreciate the nice mention you give to True. As the author of the True Ventures term sheet that you mention, I would add that it was an easy decision for us to make in presenting you with that term sheet. We were a new firm back then, but we have always said that we wanted to create a venture firm that Founders could trust. You had an excellent option in selling the company at that time which you took, but it has been a real joy to see you "on the other side of the fence" as a venture capitalist who is not afraid to shine a bright light on the issues that are important to Founders. It's great to be a co-investor with you.
    Phil Black
    Co-Founder, True Ventures
  • Thank you, Phil. As you'll remember it was a hard decision for me but having been through the wash out of 2000/01 I felt like I had seen the movie before.

    I appreciate the kind words. And it's been great to watch you guys go from being a startup fund to being one of the go-to places for young entrepreneurs. Like First Round Capital, I've never met a True CEO who hasn't raved about their positive experiences working with you guys. Not sure even the best known Silicon Valley VCs could all say that.

    And, yes, fun to finally be working together (even if not yet announced ;-)

    Mark
  • indus
    Great stuff. Well narrated.
  • Good thing to keep in mind is that while option and valuation are intimately related as you point out, from the entrepreneur's perspective it's better to get a higher valuation than a lower option pool, because the VC bears the entire effect of the higher valuation. The VC would rather have the lower valuation with the lower option pool, because when they increase the pool post-money, they are only pro-rata diluted. Also, if those options are never actually granted, the dilution was not actual dilution. Great post, by the way. It's good to have this information in the open.
  • philsugar
    I agree that the options shuffle is just a valuation issue, but there is one thing that I never liked and that is that while the option pool comes out pre-money when the money for the options come in, the post money people share that money.

    I.e. if you have a company that is valued at $10M and issue 15% options, when the company sells the option holders have to put up $1.5M. That should only be split by the people that essentially paid for those options.
  • word.
  • NY Media Exchange
    Thanks for the post...like many entrepreneurs, I got screwed by guys who have done this a million times. Keep up the great work.
  • Hi Mark

    Nice post, thanks. It's nice to see someone (partly) on the other side of the table who gets it and wants to say so publicly. I also liked Nivi's post. I ran into the above issues when writing code ~7 years ago to manage an options plan, and it has bugged me ever since.

    Fred Wilson posted about this subject back in November, and received lots of comments. Here's one of mine http://www.avc.com/a_vc/2009/11/valuation-and-option-pool.html#comment-22043449 which I still stand by (it's as you say above).

    The wriggle to avoid (what seems to me to be) clear and unambiguous thinking and alignment of interest in this issue is for the VC to argue that the options pool is implicitly priced into the deal, and that's just the way it is. I don't like that line of argument, as I find it *much* less explicit. It feels like a post-facto rationalization of something that has always been wrong. The way to fix it is to do it properly, with sunlight and clear examples. So.... thanks. I hope my examples in Fred's post seem clear too.

    Too bad we didn't get to meet when you were in Barcelona (Tyler Crowley sent an intro). In the meantime, we managed to get funded http://blogs.fluidinfo.com/fluidDB/2010/05/24/anatomy-of-a-funding/

    Terry
  • Yes, sorry we didn't meet. I was there for an MBA reunion so it was hard to sneak away.

    re: your comments on Fred's blog - I'm afraid I don't agree. When I put $3m to work for 25% of your company I don't expect to then get diluted by 15% afterward to create an option pool. I expect that the founders did this when then set up the company. But it's important to me that the founders understand this rather than being tricked.

    re: funding - congrats. Hope all is going well.
  • Hi Mark

    Funny to see you disagreeing :-) But I think we're talking about different things. I agree with your comment - if you're putting in X in exchange for Y, you shouldn't be then hit with the surprise creation of an option pool. The fact that the option pool is going to be created should be known and factored into the price you pay.

    My issue is with other things that seem clearly wrong / awkward with the standard process. I gave a couple of simple examples in the comments that follow on that thread in AVC in case you want to read more. E.g., the company gets sold an hour after a financing, before any pool stock is issued: who owns that pool stock? It should very clearly be the property of the original team, not shared with the incoming investors who didn't pay for it, but the argument from the VC world is that they own a percentage of that pool stock too. Sorry if this seems unclear, the example I give is clear & simple. The whole arrangement is just far clearer and simple when the pool is created after the financing is closed. Then everything is aligned.

    Terry
  • Agree to disagree on this one ;-)
  • Shafqat
    Great post... We just raised our seed round, and posts like these (especially Venture Hacks) meant we were absolutely prepared to discuss all of these details with our investors. Understanding the option pool shuffle was probably the biggest win we had - and Nivi's post brilliantly guides you through the process of negotiating the option pool (hint: show a reasonable hiring plan!). I can tell you that it works.
  • Yes, it does. And Nivi deserves a medal of honor.
  • Excellent post!

    I'm glad to be starting my entrepreneurship life during a time where open communication is deemed best for all. The VC/entrepreneur blog world is an unbelievable resource.
  • I generally agree with everything you've said, but I want to press one point and get your opinion on it. As I've tried to explain in my blog, I think there is a case for 2x non-participating in a small, but growing angel niche where I exist. Namely:

    > decent probability >=50% of never needing to raise VC money
    > very small round, <=300K, so the aggregate preference is low (600K max)
    > no interest or other economic terms (dividends, etc.).

    I think in that case the follow-on risk is much lower because there may not be VC and if so, you can argue that the aggregate is low enough you can start from scratch. The ability to argue that is of course dependent on leverage and situation, but I don't think it is a complete non-starter as everyone reflexively says.

    From the investor side, it does protect against the small exit case, which is way more prevalent in this niche. And in particular for the smaller new angel investor, who can't go into 30 deals and get that outlier, in the small exit they make a modest return to enable them to make more angel investments. That is, it doesn't move their overall portfolio IRR needle, but it enables them to get to 15-20 deals instead of 10-15, which a) may get them to that more of an outlier and b) allows more entrepreneurs to be funded.
  • Gabriel,

    I've read your stuff on many occasions and normally agree with most of what you say. But I'm diametrically opposed to this point. Here's the reason: your "harmless" 2x ("it's only $300k so only $600k in liquidation preference) makes the next round investor ask for the term and then the B round asks for it. It snowballs. I would encourage you to rethink your position.

    Entrepreneurs: start with a clean term sheet and fight like hell to keep it that way from day one until exit (or at least through the A & B rounds).

    Mark
  • What would you think if the next financing was carved out? That is, if there is no financing it is 2x, but if there is, it falls back to a "clean term sheet?"

    On your first point, just to press a bit harder, if they raised 10K and it was 2x that would be harmless, right? So there is a sliding scale so-to-speak, where the amount does matter. Maybe it causes everyone to ask for it, but the retort of it being a small amount does carry some weight. You make it seem that every VC would unreasonably dig in on that point regardless of the amount of preference.

    I realize it is tough to think in my shoes given that you're seeing and funding stuff that by definition requires more financing.
  • Kai Mamand
    You are asking the entrepreneur to take on lots of downstream complexity (for the 50% of entrepreneurs who will need to raise on follow-on rounds) for a fairly small amount of money. If I were raising <= $300K and you asked for a 2x non-participating beyond ending the negotiation I would encourage my friends to avoid meeting with you so as not to waste their time i.e. you are killing your deal flow.
  • Al
    Mark, I don't think anyone took you up on your offer to do a deeper dive - but I know it will be extremely helpful so please do a deeper dive. Dave Young, Scott Alderton or Scott Walker would all be great choices :)

    Al
  • Thanks, Al. Will do.
  • philsugar
    I really agree with you on the participating preferred. I know that you have to look a terms from a purely dis-passionate viewpoint, its all a numbers game, just run the spread-sheet.

    I can't get my head around participating preferred. You want your cake back and then you get eat it to? Sorry that one I really just take personally. Also some of the "control" issues that get floated I really take personally. As somebody points out if the entrepreneur fights they can't be enforced as it will kill a deal.

    And yes I agree there is an edge case where the founders raise a ton of money at a high valuation and take a bunch off the table, but if you're in that position you better be getting some better advice than here.

    Which brings up a point. I'm sorry but everyone that says I wish I read it before seriously must have had a bad lawyer. Sorry. Mine went through this me right up front with three scenarios..low, medium, high exits....here is what is going to happen.
  • Roko
    This episode was very informative and unfortunately SAD as well.
    For a group professionals who's entire existence depends on investing in innovation, it is just disheartening that you guys fail to innovate within your own environment.

    With this many rules and fine prints it is as if investors are not frankly trying to help companies succeed. Please invest in simplifying the investment process, the language, eliminate the fine prints.

    Mark, you seem pretty different so you should be one of the guys leading this change in the industry.
  • thiernofall
    This episode was very informative and unfortunately SAD as well.
    For a group professionals who's entire existence depends on investing in innovation, it is just disheartening that you guys fail to innovate within your own environment.

    With this many rules and fine prints it is as if investors are not frankly trying to help companies succeed. Please invest in simplifying the investment process, the language, eliminate the fine prints.

    Mark, you seem pretty different so you should be one of the guys leading this change in the industry.
  • I think many guys have started. YCombinator, Foundry Group, Union Square, Founders Fund, etc.
  • Great post. I wish I had read it 4 years ago.
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