Look for new enabling technologies that create a wide gap between how things have been done and how they can be done.
I think because of the iPhone and the fact that we now have a ubiquitous internet, our creativity in the startup space is 10 times different. Every single industry, every single market, is going to be technology-driven in some way. There's an infinite opportunity for startups because now you can go and solve problems that previously looked like they had nothing to do with technology.
Every single industry is going through a major business model and technology oriented disruption.
Always look for these changing technology factors- any market that has a significant change in the underlying raw materials ...or enabling factors, is an environment that is about to change in a very significant way.
The best technology is aimed far enough in the future that it stands out, but close enough to the present that it blends in.
The business models in enterprise have changed pretty dramatically. A huge problem with enterprise software traditionally has been usually you sell to the customer and then they adopt the technology. The great thing about 'freemium' and the new way enterprise software is being sold is you get to try it first and then buy it.
Modularize, don't customize. Build a platform as opposed to building all of the custom technology and custom vertical experiences.
I tend to not discriminate when it comes to people I can learn from. Basically, if someone has built a meaningful business in software, technology or media, faced disruption and adversity, and overcame underdog status, I want to know how they did it.
The benefit to building a startup is that customers don't have the same kind of friction when they adopt new technology.
In a user lead model, users are bringing in their own technology... and you can build software then, around the user.
All we're really doing is repeating technologies that were tried 10, 20, 30 years ago... it's just that it was too expensive, too unusable, and we didn't have the enabling technologies to make it possible.
They can bring the technology in, then you can sell to the enterprise when they want to have better control, better security... you still have the same biz model as a traditional enterprise sw company, but the way to get into the company is through the end user.
Any time where the delta b/w what is possible and how things work today is at its widest, that's an opportunity to go build new technology.
I interned at Miramax and subsequently at Paramount because I was really curious about the future of entertainment - how were we going to get films online? While the inspiration for Box didn't come from that experience directly, it was very obvious that bigger businesses had a lot of slow processes and cumbersome technology.