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 […]

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 […]

“Startup 2.0″

Here are the slides from my talk on the impact of the current generation of emerging technologies on the startup, given at the Emerging Technologies in the Enterprise conference in Philadelphia yesterday. The event wrapped up today; by all accounts it was the best value in web technology conferences in recent memory, and I look […]

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 […]

“Tiger Team Innovation in the Enterprise”

I gave a talk today at the pre-conference CxO breakfast for the Emerging Technologies for the Enterprise conference. The group was great; so much discussion that we didn’t make it through all of the material I had planned.
As promised, here are the slides from today’s presentation. We talked so much about each point that I’m […]

Upcoming Podium Pontification

I’m going to be speaking at a couple of related events in March. The Emerging Technologies for the Enterprise conference on the 28th and 29th in Philadelphia has an interesting array of topics, centered around open source, lightweight architectures and Web 2.0, all with an enterprise twist. On the first day, I’m giving a talk […]

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 […]

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 […]