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Founder dilution

As founders of startups raise money from investors, their share of the company gets "diluted". This means the percentage of the company they own gets smaller and smaller. Last month a friend asked me the following question: "What do you believe would be a good equity position as a startup founder after a Series A? I don't want to be diluted too much.". This week, another friend who is in the process of raising money asked me if he should accept certain "preferences" from his potential investors in favor of a higher valuation and less dilution.

My answer to both friends was: "Well, euh, it's complex!". Because I get asked about this regularly, I decided to write a blog post about this. In this blog post, I'll discuss the dilutive effect of (1) of multiple rounds of funding, (2) reverse vesting, (3) options pools, (4) pro-rata rights and (5) liquidation preferences.

Raising Series A

Let's assume that we have a company, and that our company raised four rounds of financing the past five years:

Series A Series B Series C Series D
Pre-money valuation $4,000,000 $13,000,000 $40,000,000 $90,000,000
Injected capital $1,300,000 $3,250,000 $7,000,000 $10,000,000
Post-money valuation $5,300,000 $16,250,000 $47,000,000 $100,000,000
Dilution 25% 20% 15% 10%

"Pre-money valuation" refers to a company's valuation before it receives outside financing, while "post-money valuation" refers to the company's value after the capital injection. So, the post-money valuation is the sum of the pre-money valuation plus the capital raised. The pre-money valuation of your company, along with the amount of capital raised will determine the founders' dilution.

If our company raises its first round of funding (Series A) with a pre-money valuation of $4 million and the Series A investors were to commit $1.3M, the company would have a post-money valuation of $5.3 million. In the example, the Series A investors would receive 25% of the company ($1.3 million is 25% of $5.3 million).

Series A
Pre-money valuation $4,000,000
Injected capital $1,300,000
Post-money valuation $5,300,000
Dilution 25%
   
Founders 75%
Series A investors 25%
   
Total 100%

In an earlier blog post, I recommended a specific formula for deciding how much to give up to an investor in each round. For consistency, this post follows that formula. I consider this formula to be an ideal scenario, and recognize that most founders will be in a situation where they have to give up much more, or even be in a situation where they want to give up more. Don't get hung up on the actual numbers used in our example.

Option pool

You would think that in our example, the founders would be left with 75% of the company after raising their Series A. Unfortunately, this is not usually the case; investors will often insist that an "option pool" is created. An option pool is an amount of the startup's common stock reserved for future employees. Investors expect the employee option pool will equal 10%-20% of the company post-investment; they also expect these shares will be set aside from the founders' equity.

Let's say that the Series A investors' term sheets requires a "15% fully diluted post money option pool" to be setup. This means that the investors want 15% of the company, after the financing is closed, to be in an option pool that will be granted to future employees. The "capitalization table" of our company after the Series A would look like this:

Series A
Pre-money valuation $4,000,000
Injected capital $1,300,000
Post-money valuation $5,300,000
Dilution 25%
   
Founders 60%
Series A investors 25%
Employee option pool 15%
   
Total 100%

The bottom line is that instead of owning 75% of the company, the founders will end up owning 60% of the company, and the investors 25%. For the founders, the $1.3 million financing was not 25% dilutive but 40% dilutive.

As an entrepreneur, I think it is flawed to take the option pool out of the founders' equity; the option pool should be carved out after the financing and dilute both the founders and the investors. After all, future employees who are granted options after the financing add value to the post-money valuation of the company. I'll leave that gripe for another blog post but for the purpose of this blog post, the key take-away is that creating an option pool is usually dilutive for the founders and an important part of the negotiation with investors. The option pool size and the pre-money valuation need to be looked at together and can both be negotiated. Investors should price on the basis of a complete team needed to execute on the opportunity. If the founders have done a good job of hiring that team, the pool size should be smaller. If there are still a lot of hires needed to create a full team to execute, then the pool needs to be larger.

Reverse vesting

Stock options provide employees the right to purchase a set amount of shares for a set price in the future. To encourage employees to stick around, they don't gain control over their options for a period of time. This period is known as the "vesting period". Once the options are vested, they can be exercised. When you exercise the stock options, you buy shares in the company, usually at a very low price.

Founders are different from employees because they received their shares when they started the company -- they don't usually have stock options. To make sure that founders stay with the company, investors will set up a "reverse vesting" strategy. This is similar to "stock option vesting" except that it gives investors the right to repurchase shares already owned by the founders. The "vesting period" in this context measures how many shares the company can repurchase from a departing founder. The longer a founder stays with the company, the less stock the company can repurchase if a founder were to leave.

A founder who remains with the startup through the end of a particular vesting period -- typically four years -- will be fully vested and retain all founder's shares. The founder who leaves before the vesting period expires will most likely be diluted as the company repurchases some founder's shares.

Raising Series B

As our company grows and the time comes to raise a Series B, the expectation is that the valuation of our company has increased. Let's assume we used that $1.3 million well, and that the value of the company grew from $5.3 million to $13 million.

If we raise $3,250,000 additional capital in a Series B financing on a pre-money valuation of $13 million, then the series B investors will get 20% of the company. In the Series B, the founders, the employees (option pool), and Series A investors are all diluted. Often the new investors will require that the option pool is increased. Let's say they want the option pool to remain at 15% -- in this case, the founders, employees and Series A investors would suffer additional dilution on top of the 20%. In our example, the total dilution will be a little over 23%. The new capitalization table looks as follows:

Series A Series B
Pre-money valuation $4,000,000 $13,000,000
Injected capital $1,300,000 $3,250,000
Post-money valuation $5,300,000 $16,250,000
Dilution 25% 20%
     
Founders 60% 46%
Series A investors 25% 19%
Series B investors   20%
Employee option pool 15% 15%
     
Total 100% 100%

Pro-rata rights

It's not always as simple though. Investors will usually insist on "pro-rata rights". Pro-rata rights give investors the right to invest in a startup's future rounds and maintain their ownership percentage as the company grows and raises more capital. It is an important tool for early stage investors, as most of their investments fail. Pro-rata rights allow investors to "follow" the investments that are doing well. Their ability to double-down on winners is important to compensate for their losses. I believe it is fair to give early investors pro-rata rights; they are a reward for backing you early. But as I've learned, this is also where things get complicated.

At times, new investors don't want older investors to participate so that they can take more of the round. Usually, the new investors will insist that they put enough money to work so they can own a substantial-enough share of the company to make the investment worth their time and effort. In this case, the new investors will try to force the old investors to give up their pro-rata rights. Other times, the new investors want early investors to demonstrate their confidence in the company by participating in the round, and to show that they are not overpaying. To facilitate the "pro-rata dance" between investors, and to satisfy both the old and new investors, founders are often required to take more dilution and to give up more of their company. For simplicity, I ignored pro-rata rights in our running example, but founders need to be aware of how pro-rata rights can impact dilution in later funding rounds.

Raising Series C and Series D

Our company continues to grow and goes on to raise Series C and Series D:

Series A Series B Series C Series D
Pre-money valuation $4,000,000 $13,000,000 $40,000,000 $90,000,000
Injected capital $1,300,000 $3,250,000 $7,000,000 $10,000,000
Post-money valuation $5,300,000 $16,250,000 $47,000,000 $100,000,000
Dilution 25% 20% 15% 10%
         
Founders 60% 46% 38% 34%
Series A investors 25% 19% 15% 14%
Series B investors   20% 16% 15%
Series C investors     15% 13%
Series D investors       10%
Employee option pool 15% 15% 15% 15%
         
Total 100% 100% 100% 100%

In our example, the founders would end up with 34% of the company after four rounds of financing (assuming no additional option grants for the founders). As mentioned above, I consider that an exceptional outcome for the founders. Most founders will own substantially less at this point. For example, Aaron Levie, founder of Box, owned about 4% of Box when the company made its public offering in 2015. Zendesk founder and CEO Mikkel Svane owned about 8% at its IPO in 2014, and ExactTarget's co-founder owned 3.8% at the time the company filed its S-1.

Liquidation preferences

But there is more -- I warned you it's complex! When investors put money in your company, they will require the company issue them "preferred stock". Investors' preferred stock has various "preferences" over "common stock", owned by founders and employees. One of the most common preferences are "liquidation preferences". A liquidation preference helps investors make sure that they'll be paid before common shareholders when a company is sold, declares bankruptcy, or goes public. This is especially important when the company is being liquidated for less than the amount invested in it.

If our company was to sell for $75 million, you would think that per the table above, the Series D investor would make $7.5 million (10% of $75 million) and the founders would make $25.5 million (34% of $75 million). However, if our Series D investor negotiated a "liquidation preference" equal to their $10 million investment and the company is sold for $75 million, they will be guaranteed their $10 million back. The remaining $65 million would go to the other shareholders. This is called a "1x liquidation, non-participating preference". In the event the company sells for less than the valuation at the time of the investment, the Series D investors will make more than their percentage ownership, and the founders will make less than their percentage ownership. In other words, when your investors have liquidation preferences, your percentage ownership isn't always what it looks like on paper (or in a capitalization table, to be exact).

Sometimes, investors want "participation rights". In the case of "participation rights", the investors would be entitled to the return of their entire investment prior to the distribution of any proceeds to the common stockholders. However, the preferred stockholders would then also be treated like a common stockholder and would share in the remaining proceeds. If our company sells for $75 million, the Series D investors would get their $10 million out first, and then get their 10% share of the remaining $65 million for a total return of $16.5 million ($10 million + 10% of $65 million).

There is also a concept called a "multiple". Where founders and employees can get really hurt is when preferred stock owners have a 2x or 3x multiple. If our Series D investors have "3x liquidation rights, participating", they would be guaranteed $30 million back (3 times $10 million) and take 10% of the remaining $45 million. The founders would make $15.4 million. Instead of their 34% share, the founders only get 20%. So, before you agree to any liquidation multiple or participating rights, you should run a few models to understand how much you and the other founders will receive based on various liquidation scenarios.

Because of the preferences, the price or market value of common stock is typically much smaller than that of preferred shares -- especially in the early days. Because common stock is worth less than preferred stock, your percentage ownership is often meaningless. This is often evidenced either by a 409(a) valuation in the USA, or the market price of common stock when sold to a third-party. Preferences generally expire at an IPO, at which time preferred stock converts into common stock. At that point, common and preferred shares have the same value.

Conclusion

In summary, valuations, multiple rounds of funding, option pools, reverse vesting, pro-rata rights and liquidation preferences can all have a dilutive effects on startup founders. As a founder, it can be difficult to predict or plan how much dilution you will suffer along the way. As with everything, the devil is in the details -- and hopefully this blog post helped you be a bit smarter about raising money and negotiating term sheets. In general, I don't think founders should worry about dilution too much but that is a topic for a future blog post ...

From B2C to B2One

The Industrial Revolution, started in the middle of the 18th century, transformed the world. It marks the start of a major turning point in history that would influence almost every aspect of daily life. The Industrial Revolution meant the shift from handmade to machine-made products and increased productivity and capacity. Technological change also enabled the growth of capitalism. Factory owners and others who controlled the means of production rapidly became very rich and working conditions in the factories were often less than satisfactory. It wasn't until the 20th century, 150 years after its beginning, that the Industrial Revolution ended creating a much higher standard of living than had ever been known in the pre-industrial world. Consumers benefited from falling prices for clothing and household goods. The impact on natural resources, public health, energy, medicine, housing and sanitation meant that chronic hunger, famines and malnutrition started to disappear and the life expectancy started to increase dramatically.

An undesired side-effect of the Industrial Revolution is that instead of utilizing artisans to produce hand-made items, machines started to take the place of the artisans. Before the industrial revolution, custom-made goods and services were the norm. The one-on-one relationships that guilds had with their customers sadly got lost in an era of mass-production. But what is exciting me about the world today is that we're on the verge of being able to bring back one-on-one relationships with our customers, while maintaining increased productivity and capacity.

As the Big Reverse of the Web plays out and information and services are starting to come to us, we'll see the rise of a new trend I call "B2One". We're starting to hear a lot of buzz around personalization, as evidenced by companies like The New York Times making delivery of personalized content a core part of their business strategy. Another recent example is Facebook testing shopping concepts, letting users browse a personal feed of clothing and other items based on their "likes". I'd imagine these types of feeds could get smarter and smarter, refining themselves over time as a user browses or buys. Or just yesterday, Facebook launched Notify, an iOS app that pushes you personalized notifications from up to 70 sites.

These recent examples are early signs of how we're evolving from B2C to B2One (or from B2B2C to B2B2One), a world where all companies have a one-on-one relationship with their customers and personalized experiences will become the norm. Advances in technology allow us to get back what we lost hundreds of years ago in the Industrial Revolution, which in turn enables the world to innovate on business models. The B2One paradigm will be a very dramatic shift that disrupts existing business models (advertising, search engines, online and offline retailers) and every single industry.

For example, an athletic apparel company such as Nike could work sensor technology into its shoes, telling you once you've run a certain number of miles and worn them out. Nike would have enough of a one-on-one relationship with you to push an alert to your smartphone or smartwatch with a "buy" button for new shoes, before you even knew you needed them. This interaction is a win-win for both you and Nike; you don't need to re-enter your sizing and information into a website, and Nike gets a sale directly from you disrupting both the traditional and online retail supply chain (basically, this is bad news for intermediaries like Amazon, Zappos, clothing malls, Google, etc).

I believe strongly in the need for data-driven personalization to create smarter, pro-active digital experiences that bring back one-on-one relationships between producers and consumers. We have to dramatically improve delivering these personal one-on-one interactions. It means we have to get better at understanding the user's journey, the user's context, matching the right information/service to the user and making technology disappear in the background.

Acquia raises $55 million series G

Today, we're excited to announce that Acquia has closed a $55 million financing round, bringing total investment in the company to $188.6 million. Led by new investor Centerview Capital Technology, the round includes existing investors New Enterprise Associates (NEA) and Split Rock Partners.

We are in the middle of a big technological and economic shift, driven by the web, in how large organizations and industries operate. At Acquia, we have set out to build the best platform for helping organizations run their businesses online, help them invent new ways of doing business, and maximize their digital impact on the world. What Acquia does is not at all easy -- or cheap -- but we've made good strides towards that vision. We have become the backbone for many of the world's most influential digital experiences and continue to grow fast. In the process, we are charting new territory with a very unique business model rooted Drupal and Open Source.

A fundraise like this helps us scale our global operations, sales and marketing as well as the development of our solutions for building, delivering and optimizing digital experiences. It also gives us flexibility. I'm proud of what we have accomplished so far, and I'm excited about the big opportunity ahead of us.

Giving back and making money

It's not easy to build an Open Source software company.

Canonical recently has made a change to its intellectual property policy. The new policy prevents developers from distributing altered binary versions of Ubuntu. Users are still allowed to distribute unaltered Ubuntu freely, but if they make changes to Ubuntu, Canonical wants developers to either go through a review process or remove all references to Canonical trademarks, Canonical logos, and proprietary software and recompile the Ubuntu archive without any of those.

This change has caused friction with the Open Source community; many are not happy with these restrictions as it goes against the culture of Open Source sharing and collaboration. After all, Ubuntu itself is built on top of the work of hundreds of thousands of Open Source developers, and now Ubuntu is making it difficult for others to do the same.

Canonical's stated intention is to protect its trademarks and reputation; they don't want anyone to call something "Ubuntu" when it's not actually "Ubuntu". I understand that. That aside, many understand that the unstated goal is to make money from licensing deals. The changes affect organizations that base their custom distributions on Ubuntu; it's easier to buy a license from Canonical than to figure how to remove all the trademarks, proprietary software, logos, etc.

Jono Bacon, Canonical's former community manager, wrote a balanced post about the situation.

My thoughts? I understand Canonical has to find ways to make money. Most companies are downright greedy, but not Canonical or Mark Shuttleworth. I find the Open Source community "penny wise and pound foolish" about the situation.

I can relate because Canonical, like Acquia, is among a small group of Open Source companies that try to do good and do well at scale. We invest millions of dollars each year contributing to Open Source: from engineering, to marketing, to sponsoring community events and initiatives. It is not easy to build a software company on Open Source, and we all struggle to find the right balance between giving back and making money. This is further complicated when competitors choose to give back less or don't give back at all. Companies like Canonical and Acquia are good for Open Source, and helping them find that balance is key. Don't forget to support those that give back.

The post-browser era of the web is coming

At yesterday's Worldwide Developer Conference keynote, Apple announced its annual updates to iOS, OS X, and the new watchOS. As usual, the Apple rumor blogs correctly predicted most of the important announcements weeks ago, but one important piece of news only leaked a few hours before the keynote: the launch of a new application called "News". Apple's News app press release noted: "News provides beautiful content from the world's greatest sources, personalized for you".

Apple basically cloned Flipboard to create News. Flipboard was once Apple's "App of the Year" in 2010, and it remains one of the most popular reading applications on iOS. This isn't the first time Apple has chosen to compete with its ecosystem of app developers. There is even a term for it, called "Sherlocking".

But forget about Apple's impact on Flipboard for a minute. The release of the News app signifies a more important shift in the evolution of the web, the web content management industry, and the publishing industry.

Impact on content management platforms

Why is Apple's News app a big deal for content management platforms? When you can read all the news you are interested in in News, you no longer have to visit websites for it. It's a big deal because there are half a billion active iOS devices and Apple will ship its News app to every single one of them. It will accelerate the fact that websites are becoming less relevant as an end-point destination.

Some of the other new iOS 9 features will add fuel to the fire. For example, Apple's search service Spotlight will also get an upgrade, allowing third-party services to work directly with Apple's search feature. Spotlight can now "deep link" to content inside of a website or application, further eliminating website or applications as end-points. You could search for a restaurant in Yelp directly from your home screen, and go straight to Yelp's result page without having to open the Yelp website or application. Add to that the Apple Watch which doesn't even ship with a web browser, and it's clear that Apple is about to accelerate the post-browser era of the web.

The secret to the News app is the new Apple News Format; rumored to be a RSS-like data feed with support for additional design elements like images, videos, custom fonts, and more. Apple uses these feeds to aggregate content from different news sources, uses machine learning to match the best content to a given user, and provides a clean, consistent look and feel for articles coming from the various news sources. That is the long way of saying that Apple decides what the best content is for you, and what the best format is to deliver it in. It is a profound change, but for most people this will actually be a superior user experience.

The release of Apple News is further proof that data-driven experiences will be the norm and of what I have been calling The Big Reverse of the Web. The fact that for the web to reach its full potential, it will go through a massive re-architecture from a pull-based architecture to a push-based architecture. After the Big Reverse of the Web is complete, content will find you, rather than you having to find content. Apple's News and Flipboard are examples of what such push-based experiences look like; they "push" relevant and interesting content to you rather than you having to "pull" the news from multiple sources yourself.

When content is "pushed" to you by smart aggregators, using a regular web browser doesn't make much sense. You benefit from a different kind of browser for the web. For content management platforms, it redefines the browser and websites as end-points; de-emphasizing the role of presentation while increasing the importance of structured content and metadata. Given Apple's massive install base, the launch of its News app will further accelerate the post-browser era of the web.

I don't know about your content management platform, but Drupal is ready for it. It was designed for a content-first mentality while many competitive content management systems continue to rely on a dated page-centric content model. It was also designed to be a content repository capable of outputting content in multiple formats to multiple end-points.

Impact on publishing industry

Forget the impact on Flipboard or on content management platforms, the impact on the publishing world will even be more significant. The risk for publishers is that they are being disintermediated as the distribution channel and that their brands become less useful. It marks a powerful transformation that could de-materialize and de-monetize much of the current web and publishing industry.

Because of Apple's massive installed base, Apple will now own a large part of the distribution channel and it will have an outsized influence on what hundreds of millions of users will read. If we've learned one thing in the short history of the Internet, it is that jumping over middlemen is a well-known recipe for success.

This doesn't mean that online news media have lost. Maybe it can actually save them? Apple could provide publishers large and small with an immense distribution channel by giving them the ability to reach every iOS user. Apple isn't alone with this vision, as Facebook recently rolled out an experiment with select publishers like Buzzfeed and the New York Times called Instant Articles.

In a "push economy" where a publisher's brand is devalued and news is selected by smart aggregators, the best content could win; not just the content that is associated with the most well-known publishing brands with the biggest marketing budgets. Publishers will be incentivized to create more high-quality content -- content that is highly customized to different target audiences, rather than generic content that appeals to large groups of people. Success will likely rely on Apple's ability to use data to match the right content to each user.

Conclusion

This isn't necessarily bad. In my opinion, the web isn't dead, it's just getting started. We're well into the post-PC era, and now Apple is helping to move consumers beyond the browser. It's hard to not be cautiously optimistic about the long-term implications of these developments.

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