The game of risk

When evaluating new ventures, a lot of energy goes into thinking about the risks involved. I’ve been breaking things down into two major categories, and trying to consider those relatively independently.

The first, execution risk, has been well covered - I especially like this old post from Martin Tobias. In a nutshell, execution risk covers the […]

Math is cool again

A few weeks ago at the Emerging Technologies Conference at MIT, Ann Winblad made the comment, “Finally, math is cool again.” The comment stayed with me, as math has been an important part of virtually everything I’ve worked on - from InfoSec Labs in the 90’s, translating mainframe-era security models into methodologies appropriate for companies […]

Undervaluing web audiences

Fred Wilson posted yesterday about overcounting web audiences, highlighting a study on the topic put out by comScore.
The goals of comScore’s research, of course, is to make the case for panel data in accurately measuring audience. Fred’s conclusion is more general:
You cannot rely on your own analytics data. You need third party data as well. […]

Security on the Loosely Coupled Web

There is a growing trend in consumer web applications in which one site will ask users for their usernames and passwords on other sites. Using these credentials, a site will log onto the other sites to carry out actions on behalf of, and hopefully with the informed consent of, the user.
‘On behalf of’ logins
LinkedIn and […]

Enterprise Freemium: IT and the startup

I’d like to throw out an idea for discussion, especially as it applies to startups selling into the enterprise:
Small buyers of technology, acting early in the technology adoption life-cycle, are motivated by hope (hope == ROI, opportunity, etc). Large buyers of technology, acting late in the life-cycle, are motivated by fear (fear == risk of […]

New Enterprise Security Threats: Emerging Technologies

Each generational transition in IT, such as from mainframe to client server or from client server to web applications, has presented challenges to enterprise security. The pattern is clear, and will likely sound familiar to anyone working in IT through these last two major shifts:

The emerging technology is initially ignored as a lab project or […]

Could Digg create an AdSense for the long tail?

The long tail of content presents an interesting set of problems both for publishers and advertisers. Content in the tail may be seen only a few times a day; if the publisher has a small amount on content in the tail (one blog, for example), that content is:

Not valuable enough to the publisher to justify […]

New Enterprise Security Threats: SaaS

It has always been hard for the enterprise to address emerging information security issues proactively; usually these things end up dealt with by the majority of companies once a loss has hit close to home or regulatory attention has been brought to bear. I was lucky to be able to work with some very smart […]

Cart before the horse

When a company like Yahoo comes out with a cool new horse, it’s easy to get caught up in the technology and its potential, and forget about the product strategy differences between startups and big players.
Looking at the technically innovative startup pitches I’ve heard from this perspective, I can break them down into two […]

The Internet is flat

The Internet is central to the flattening of the world as described in Thomas Friedman’s book; I’d like to explore the idea that the Internet is itself being flattened in an entirely different way.

There is no question that the advancements in search have profoundly changed how users interact with the web. It can be argued […]

Swing for the fences

VC Confidential has an interesting post up today talking about Multiples vs IRR. The closing statement
So, next time you are trying to convince a VC about the merits of your firm, show them how they can make 10x capital on a realistic exit scenario (not how to get a 40% IRR).
reminds me of the importance […]

Rumpelstiltskin’s reporting interface

If Rumpelstiltskin sold a product to enterprise customers, he would quickly learn a lesson that we learned at my last company: no matter how fantastically his product could spin straw into gold, his sales would also depend on his product’s ability to display and report on every aspect of the spinning process. It doesn’t […]