It’s not that seed investors are smarter – it’s that entrepreneurs are

Paul Kedrosky recently speculated that there might be seed fund “crash” looming. Liz Gannes followed up by suggesting seed investors are a fad akin to reality-TV celebrities:

In many ways, what [prominent seed funds] are saying is that they’re just smarter, and as such will outlast all the copycat and wannabe seed funders as well as the stale VCs with a fresh coat of paint. But then — Kim Kardashian is the only one who can make a living tweeting. At some point it will be quite obvious whether the super angels’ investments and strategy succeed or fail.

Here’s the key point these analyses overlook: It’s not the seed investors who are smarter – it’s the entrepreneurs. Consider the case of the last company I co-founded, SiteAdvisor. We raised our first round of $2.6M at a $2.5M pre-money valuation. After the first round of funding, investors owned 56% of the company. Moreover, the $2.6M came in 3 tranches: $500K, another $500K, and then $1.6K.  To get the 2nd and 3rd tranches we had to hit predefined milestones and re-pitch the VC partnerships. Had we instead raised the first $1M from seed funds, we would have been free to raise the remaining money at a higher valuation. In fact, after we spent less than $1M building the product, we raised more money at a $16M pre-money valuation. We never even touched the $1.6M third tranche even though it caused us to take significant dilution. This was a very common occurrence before the rise of seed funds, due to VCs pressuring entrepreneurs to raise more money than they needed so the VCs could “put more money to work.” When SiteAdvisor was eventually acquired, we had spent less than a third of the money we raised. Compare the dilution we actually took to what we could have taken had we raised seed before VC:

Professional seed funds barely existed back then, especially on the East Coast. And even if they did, I’m not sure I would have been savvy enough to opt for them over VCs. I thought the brands of the big VCs would help me and didn’t really understand the dynamics of fund raising.* Today, entrepreneurs are much savvier, thanks to the proliferation of good advice on blogs, via mentorship programs, and a generally more active and connected entrepreneur community. For example, Founder Collective recently backed two Y-Combinator startups who decided to raise money exclusively from seed investors despite having top-tier VCs throwing money at them at higher valuations. These were “hot” companies who had plenty of options but realized they’d take less start-to-exit dilution by raising money from helpful seed investors first and VCs later.

Will there be there a seed fund crash? Seed fund returns are highly correlated with VC returns which are highly correlated with public markets and the overall economy. I have no idea what the state of the overall economy will be over the next few years. Perhaps it will crash and take VCs and seed funds down with it. But I do have strong evidence that prominent seed funds will outperform top-tier VC funds, because I know the details of their investments, and that their portfolios contain the same companies as top-tier VCs except the they invested in earlier rounds at significantly lower valuations.  So unless these prominent seed funds were incredibly unlucky picking companies (and since they are extremely diversified I highly doubt that), their returns will significantly beat top-tier VC returns.

* Note that we have nothing but gratitude toward the SiteAdvisor VCs – Rob Stavis at Bessemer and Hemant Taneja at General Catalyst. They offered what was considered a market deal at the time and supported us when (almost) no one else would.

Information security – are we experiencing a Pax Romana?

My last startup was an information security company — SiteAdvisor — that was acquired by McAfee, where I then worked for a while. I am no longer working in security, but have many friends that do and I try to stay in touch with what’s going on in the area.

The widespread sense I get is that we are going through a period of unusual calm, especially on the consumer side.   Instead of repeating the historical pattern where new types of threats emerge every few years, we’ve seen the opposite: threat types have actually gone away or been seriously mitigated. Spyware/adware is basically gone, as most of the businesses that were pushing it (yes, it was mostly driven by legal, US-based businesses) have gone bankrupt.  Spam has been mostly controlled, at least if you use Gmail or a good spam filter like Postini.  If you use a Mac you don’t have to worry about viruses or malware.  Mobile security hasn’t ever really become an issue, mostly because the telecom carriers (and now Apple) carefully screen the installation of 3rd party apps.  Identity theft is a real issue but not really something consumers can do anything about – most of it happens offline or through enterprise data center breaches.

On the enterprise and government side, things are more turbulent.   Distributed denial of service attacks using botnets remain almost impossible to defend against. There have been a number of breaches of sensitive consumer information and those will likely only get more common, especially as more information gets centralized in the cloud. Military and terrorist computer attacks also seem to be a likely future threat.

All in all, though, the good guys have been keeping the bad guys down.  This relative calm is generally great news for the computer users, but – let’s be honest – bad news for the computer security industry and venture capital investors.  As an investor, I’ve only made one security investment in the last few years — in a cloud security startup called Vaultive. Everything else I’ve seen seems to be trying to solve non-problems or rehashing solutions that were developed years ago.

Inevitably, the calm will end and new classes of threats will emerge. But for now we should enjoy the relative peace.

The challenge of creating a new category

One of the hardest things to do as a startup is to create a new category.  Bloggers and press have a natural tendency to “pigeonhole” – to group startups into cleanly delineated categories, and then do side-by-side comparisons, comment on the “horserace” between them, and so forth.

At my last startup, SiteAdvisor, we were at first consistently pigeonholed as an anti-phishing toolbar, even though what we did was help search engine users avoid spyware, spam, and scams, which (for various technical reasons) had almost no functional overlap with anti-phishing toolbars. My co-founder at Hunch, Caterina Fake, had a similar experience at Flickr.  Early on, people compared Flickr to existing photo sharing websites – Shutterfly, Ofoto, SnapFish – and found Flickr lacking in features around buying prints, sending greeting cards, etc.

Pigeonholing is one reason startups should actually welcome direct competitors.   It was only once a direct competitor to SiteAdvisor appeared that people started treating “web safety” as its own category (Walt Mossberg was the first one to legitimize the category with this article).

At my current startup, Hunch, being pigeonholed as a so-called Answers site is one of our main marketing challenges.  Hunch is a user-generated website similar to Wikipedia except, instead of creating encyclopedia entries, contributors create decision trees that help other users make choices and decisions.  For example, about 50 computer enthusiasts came together to create this decision tree about computer laptops that helps users with less expertise find the right laptop.  Hunch gets smarter over time as more people contribute to it.  So far, about 10,000 users have made 115,000 contributions to the site.  Last month, our third month after launch, over 600,000 unique visitors used those contributions to make decisions.

Many of the initial reviews of Hunch accurately reflected that Hunch is trying to create a new category of website.  Nevertheless, the tendency to pigeonhole Hunch as an Answers site remains. Answers sites allow users to ask a question and get back direct answers from other people.  There are many Answer sites including Yahoo Answers, Mahalo Answers, Vark, Answerbag, and ChaCha. These are all excellent and useful services – but have as much to do with Hunch as Ofoto had to do with Flickr.

There is no easy solution to avoid being pigeonholed.  All you can do is consistently, straightforwardly describe what you do, and then keep beating that drum over and over until the message gets through.

Understanding your market

Some startups become huge sensations without requiring any active marketing – YouTube, Skype, and Twitter come to mind. However, the vast majority of successful startups gained adoption through marketing:  PR, SEO, partnerships, paid marketing, and so on. My strong suggestion would be to hope for the former but plan for the latter.

Marketing is a huge topic.  Here I just want to make the point that, for starters, you need to figure out two things:   1) how information and influence flows in your market, and 2) when and where people use and/or purchase your product.

I’ll use my last startup, SiteAdvisor, as an example.  SiteAdvisor (now called McAfee SiteAdvisor) is a consumer security product.  Most consumers don’t learn about security products on their own.  Instead, they rely on their “family/friend sysadmin” (smartest computer person they know).  These family sysadmins read technical websites and magazines.  In order to reach this audience, we performed studies on data we had collected, which led to lots of coverage, which raised our profile and bolstered our credibility.

Now to when and where people buy security products.  Most people only think about security when 1) they buy a new computer, 2) they first get internet access, or 3) they get a virus or other security problem.  The last case is actually pretty rare, so most companies focus on 1 and 2.  How do you reach people at those moments?  Through “channels” – in particular PC makers (“OEMs”) and internet providers (“ISPs”).  (For public market people:  focusing on these two channels was McAfee’s big insight in the 2000′s and how they made a comeback versus Symantec who dominates retail).

Most people don’t talk to their friends about security products so it’s very hard to do mass word-of-mouth marketing.  (Exceptions would be the beginning of the spyware epidemic around 2001-2 when AdAware got super popular via word of mouth).  So you have to understand and pitch to these channels.

These observations are specific to consumer security, but every startup should have a similar theory of how to market their product.

Mail pile

Back when we were building SiteAdvisor, one of the things we wanted to warn users about were websites that sold or traded your email address leading to spam (you can see some of the bad stuff we caught in our old blog posts). In order to do this we created bots that crawled the web and signed up for every form they could find.  Tens of millions of forms.*

Some of these forms required a physical address, so we rented a post office box and gave that address.  A few weeks after we started, we got a call from the post office saying “Um, you guys better come down here and get your mail.”  What we found were crates and crates of junk mail.


As a result, visitors to our office were delighted to find a great magazine selection:


Eventually we had to build a magazine avoider algorithm into our bots because we started getting billed for all the signed ups!

This crazy little operation still goes on today.  The guys currently at SiteAdvisor (now McAfee) told me they recently received a lamb carcass in the mail (from a hunting advocacy organization).

*Yes, everything is recycled, and the ultimate goal is to reduce spam/junk mail, so we think net it’s a positive service.