The caliber of the founders that cross our threshold every day is truly staggering. Not only in their intellect, but also in their grit.

Nobody can predict the future. It’s important to have a certain self-awareness, an understanding of the limitations of our thinking. The realization that the happenings of yesteryear don’t necessarily foretell what’s next.

I spend almost all of my time with software companies. Software is a product for some of these businesses, but there are many more companies that are applying software to solve really important problems in enormous markets, like financial services in the case of Prosper.

One of my majors in college was Classics. Latin and Greek language and literature. I worked for a bit doing manual labor on an archeological dig in Greece. I wish I could say that my experience there somehow translates, but what it really taught me is that Indiana Jones is decidedly fiction.

The quintessential classical hero is Aeneas. He’s the embodiment of perseverance — that there are many ways the wind can blow you, but you can’t lose focus.

The consumerization of the enterprise is largely a failed promise to date, and it’s certainly not for a lack of effort. It's just a really hard problem to solve.

The sands of enterprise technology are shifting beneath our feet. All the way down to the building blocks. IT infrastructure is being completely redefined, and big businesses are both being built and being destroyed as a result.

Agility is the name of the game. Speed kills.

The next great software companies likely won’t look like much when they’re very young. Low or no-touch delivery models naturally require revenue to lag end-user adoption. But every customer that signs up is another piece of evidence of product/market fit and another rep for the company to improve product and improve customer experience.

People of my generation view the cloud as their primary option. There’s neither a migration nor a change in mindset required. It’s just a better way.

I grew up with an identical twin brother, Will. We played football together in college. We probably had 10 competitions every day for 22 years. People tend to ask me why I’m so competitive - I can’t think of any better explanation than that.

The foremost part of an investment that we need to get right is the size of the market. When the opportunity is larger than commonly believed, great investments materialize. Small markets breed mediocre companies.

We try to provide lessons from the great companies we’ve worked with to empower young founders who, thankfully, don't have any preconceived notions.

I think about a transmit/receive ratio — I try to keep mine as heavily weighted toward receive as possible.

Clarity of thought is a common factor in our great entrepreneurs. When they articulate their vision for the future, it seems almost inevitable.

There’s a great quote from Don Valentine when he was asked, “What makes for a great culture?” His answer? “Winning”. I wholeheartedly believe that.