About Me 0077: Making Money With Options

Startups ask me “How much money should I ask for?” The simple answer is the absolute minimum amount you need to make your plan work. Some entrepreneurs try to start with a huge number, hoping they can negotiate and close on a smaller one, while others understate their requirements, in hopes of getting their foot in the door with an investor.

Neither of these strategies is a good one, as both are likely to damage your credibility with potential investors, even before they look hard at your plan. Here are the parameters you should use in sizing your request, and be able to explain in justifying your request to investors:

Consider implied ownership cost. If your company is early stage and has a valuation under $1M, don’t ask for a $5M investment. The investor would be buying your company five times over, and he doesn’t want it. If your valuation is around $1M, you can validly ask for $200K-$300K, and offer 20%-30% of your company in exchange.
Type of investor. Angel investment groups usually won’t consider a request over $1M, while venture capitalists won’t look at anything under $2M. Amounts of $100K or less, are usually relegated to “friends and family.” Approaching any one of these groups with a funding request outside their range is a waste of your time and theirs.
Company stage. If your company is still in the “idea” stage, you have no valuation, so size your investment request on the basis of “goodwill” that you have with your rich uncle, and your business track record. Angels might be interested during “early stage” if you have a prototype, but VCs won’t bite until you have a product, customers, and revenue.
Calculate what you need, and add a buffer. Do your financial model first with the volume, cost, and pricing parameters you want. See where your cashflow bottoms out. If it bottoms out at minus $400K, add a 25% buffer, and ask for $500K funding. The request size must tie into your financials to be credible.
Investment terms. The most common case is an equity investment, but there are many terms that can impact what request size is credible. I’m talking about things like anti-dilution clauses, preferred versus common stock, valuation tied to later round, warrants, and bridge loan options. More restrictive terms reduce the credible investment amount.
Single or staged delivery. In many cases, a single investment request may be scheduled for delivery in stages, or tranches (often misspelled as traunchs or traunches), based on milestone achievement. Obviously, this reduces investor risk and allows a larger commitment, since they can limit their loss if you fail to meet key objectives.
Use of funds. Investors expect to see a “use of funds” list, and they expect the uses to apply only to your core mission. In other words, don’t tell investors that you intend to buy a fancy office building or executive cars with your funding. Even executive salaries should be minimal at this stage.
Projected return on investment. Most entrepreneurs skip this step, but it helps your credibility to include it. Estimate a return on investment (ROI) by projecting company valuation at exit, to show the investor who has 20% what he will get back for that initial investment. He’s looking for a 10x return, since he assumes only one in ten survive.

Obviously, determining the proper size of your investment request is a non-trivial exercise, but it’s one of the most critical factors for investors in making a decision to invest or not to invest in your company. You need to get it defensibly right the first time, because changing your request under pressure definitely will kill your credibility.

The days are gone, if they ever existed, when you could present an idea and a vision, and have investors throw money at you. Now you have to do your homework. Get busy, and have fun.

Marty Zwilling

Read more posts on Startup Professionals Musings »

Editors Note: Guest contributor Semil Shah is an entrepreneur interested in digital media, consumer Internet, and social networks. He is based in Palo Alto and you can follow him on Twitter @semilshah.

Reports are swirling that Twitter is in talks to raise $400 million, valuing the company close to $8 billion. It seems as if it was only yesterday that Twitter raised $200m from Kleiner Perkins. At the time of Kleiner’s investment, some pundits chuckled beneath their breath, claiming the old venture firm was paying up on price in order to claim a bit of equity in social networks, which they had been perceived to have missed.

Despite that laughter, it may be John Doerr, his partners, other Twitter investors, and their employees that share in the last laugh. In addition to the success of their niche funds, Doerr knew exactly the bet he was making when he hunted down this deal last December. In buying a piece of Twitter, one could connect the dots for the possibility that Doerr, with his deep knowledge of Google, knows something about a Twitter endgame that got his investment juices flowing. There have been countless blog posts trying to show that Google should buy Twitter. At the same time, other technology giants left hanging without any social data could perceive Twitter as an attractive acquisition target also, giving them a large network and helping circumnavigate many walled-garden sites filled with social, user-generated content. Can the company’s major shareholders help create competition for a Twitter deal in a very small market?

The roll call of Twitter’s investors is impressive, littered with the names of blue chip venture firms and consumer web celebrities, many of whom built their reputations largely through this one investment—and rightly so. With around 400 employees, half of whom are focused on engineering and product, Twitter doesn’t necessarily need almost half a billion dollars of additional financing to keep going. To date, it has been able to book some revenue based largely on the promoted tweet ad unit.

However, it has also been acquiring companies to help eliminate blind spots in its technology and product offering, to date spending more than $50M on purchases like Fluther, TweetDeck, and most recently, BackType. One could make the case that as the company continues to get the product back on track that a mix of housekeeping plus new acquisitions make sense to get the product to a point of stability. This seems to be what is happening especially under the product guidance of c0-founder Jack Dorsey, who came back but still is CEO of Square, and former Google AdSense guru Satya Patel.

That is, because right now, the Twitter product struggles just to be stable. For those that use Twitter’s native web site in the browser, it’s been considerably slower, possibly because the system is processing over 200m tweets per day. Sure, that’s a lot, but in those 200m items are a lot of loud, spammy, and inaudible (or inauthentic) accounts. For those trying to get a handle on direct messages (“DMs”), random old threads keep popping up when they finally load, which means they may be moving all DMs to a new server. @Replies are still not distinguishable from @Mentions, users haven’t been educated to make lists, and it’s very hard to search through favorites or old tweets. There are also more add-on options available per tweet via mobile than there is on the web, perhaps due to the fact that for those that use Twitter heavily, there are so many different clients from which to access the stream.

And therein lies the huge challenge but also Twitter’s massive opportunity. There has been much controversy about Twitter’s handling of its own developer community. For some, the lack of a clear roadmap has spooked people from investing in the space with time, money, and developer resources. For others, talk is cheap, and the reality that Twitter will have to eventually own every piece of the stack is obvious, so those that enter the fray must do so willingly.

Most recently, these tensions were brought to light when Twitter was seen to attack Uber Media and then subsequently acquired TweetDeck, or when Twitter decided to launch it’s own photo-sharing service in partnership with PhotoBucket (and thereby bypassing services like Twitpic and yfrog), or when it decided to get into the URL-shortening game, going so far as to re-shorten URLs that were already shortened by other services like bit.ly. As powerful and disruptive as Twitter can be in the real world, make no mistake that in its own ecosystem, similar forces are at work.

There has now been a good year of “bubble” saber-rattling in the technology world, and combined with today’s red-hot IPO market, Twitter needs to keep advancing its chess pieces forward. While the public demand for shares in Twitter may be huge, the reality is that the five-year old company not only doesn’t have the revenue acceleration needed to make this a viable option, but it’s product isn’t entirely set either. This latest $400m fundraising round may be an attempt to help fuel more product-enhancing acquisitions and, overall, to begin a consolidation of fragmented clients and services that currently survive solely on an oxygen supply from Twitter’s API. With each round raised and as its valuation goes up and up, the possible exit outcomes dwindle and the stakes get higher. The Twitter endgame transforms from chess into a dangerous game of roulette.

From my own personal viewpoint as a Twitter user, my sincere hope is that Twitter remains an independent, standalone company that eventually is publicly-traded. I will line up to buy shares. I view the Web through Twitter and spend more time on the service than any other, by a mile. And while I hope it will IPO, I have this sinking feeling that’s not realistic. This is not to suggest that Twitter is failing at finding and tuning all the best possible business models. They are doing an incredible job with only 400 people. It’s astonishing, really. Rather, it’s that the scope of all the potential opportunities is so massive, wide, and deep—from Internet, to television, to back-end analytics, search, location—that it may take a real partnership to transform these models into real revenue engines.

Who would be interested in Twitter should they continue to remain private and closely-held? Some make the case for companies like Apple, especially after its integration of Twitter into its iOS5 software. A company like Twitter could give cash-rich Apple a huge network to deploy its iAd advertisements on multiple devices, perhaps eventually even on television. Earlier this year, there was some chatter that Facebook may be interested, but they don’t (yet) have enough cash on hand to do this (though Facebook stock could do the trick). There’s always Microsoft, which certainly has cash on hand and an appetite to buy social communication services, recently demonstrated by its $8 billion acquisition of Skype.

This leaves one company, located in Mountain View, that many believe could be the perfect acquirer for Twitter, despite the fact it just launched its own social network, Google+, which is poised to launch brand pages, too. A possible Google-Twitter acquisition has been analyzed to death, so I won’t do that here, other than to say on paper, it makes a ton of sense. Because of all the bountiful seeds Twitter has planted around the world, the company best positioned to harvest those seeds (and turn a healthy buck while doing so) is Google, bar none.

But, as Twitter raises more money at higher valuations, and if an IPO is not likely in the near future, the number of possible outcomes dwindles. While an acquisition by one of the four companies listed above could be huge, both in terms of dollars and media attention, the real game would be to create enough competition among at least two of the four possible bidders to drive up the price and maximize shareholder returns. If Twitter uses the new funding to continue to fortify the product and also continue on a hunt for the best business models, it may give the potential acquirers information that leads them to think they may not be likely to extract profits from Twitter either.

By raising a whopping round, Twitter buys itself time but also elevates the stakes. Does Twitter putter along for the next few years and stumble upon a business model, enabling it to IPO? Does a giant like Apple, Microsoft, Facebook, or Google snatch up the company, or better yet, engage in a chess match with each other for the right to buy it for close to $10b or more, minting money for the company shareholders? Or, does Twitter start to slowly fade away, unable to reel in enough cash to keep the twittering machine humming? With the first option being a longshot, we’re down to two numbers on the roulette wheel. My money and my hope is on black: an acquisition.

Photo credit: Håkan Dahlström

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About Me 0077

Wednesday, August 3, 2011

Making Money With Options

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