Patrick O'Shaughnessy

What's interesting and unusual about you, there's basically nothing available about you on the internet.

You don't give interviews like this.

You seem to just be a heads down investor.

You could have long ago retired.

My sense from talking to some people on your team and talking to you is that you're working about as hard as you've ever done it.

What does a given week look like for you?

What would you say is the skill on the prospect side, evaluating a founder, a business, whatever, that you've most improved at over the entirety of Insight's existence?

So you today versus you in 95, 96.

more experienced at it.

Can you teach us some of that college-level math on understanding software businesses?

One of the things I think is so interesting about Insight is the ability to price different numbers, that it's not just that you're buying 95 plus percent gross retention and accelerating top lines or something like that.

You'll buy companies that don't have those metrics.

If I think about gross retention as one avenue of math to go down and that's algebra one, what's algebra two?

If you kept pressing on gross retention as an example of how you then keep digging into the business, how does it work?

What qualitative questions do you like to ask on the back end of the quantitative investigations?

So let's say you've got a company that has great gross retention.

How do you then continue to separate?

Does it stand to reason that you think for an SAP type company where the benefit of that long install process is very sticky, typically on the other side of it, that the right time to invest in those companies after they've gotten their install base, that's the better risk adjusted entry point?

Maybe you can walk through the one fund strategy that you've chosen to pursue at Insight, which is really interesting.

I'm especially interested in how in a fund that's $12 billion, it's worth your time to look at a $10 million investment or something like this.