Patrick O'Shaughnessy

One thing that you have to do well by definition, given you've started all these companies and all these industries, is know when to leave.

How do you know when a chapter is done?

I'd love to do a really quick tour of the businesses and something surprising about the business that you learned building them that people might not appreciate.

Maybe starting all the way back with oil business and your couple adventures there.

So I don't know what surprised people about me.

I really don't.

I think I saw somewhere that you would consider something like accounting as an area that you might go check out, but then decided against it.

And I'm always just so interested by why you might pass on something.

Is that a real example?

Did I have that right?

And if so, why did you decide not to do it?

Is there anything else about software versus physical technology in the software sense of incredible software businesses obviously have been built, but software can get disrupted by other software fairly easily.

Whereas disrupting United Rental or something, I guess it's possible, but it's not going to be done by a programmer in his closet.

I love the idea of think big and move fast.

I interpret it almost as a challenge.

That's something I can take and go do, try to do more of each of those two things.

Is there any other way that you would frame a challenge to those listening to live what obviously has been a very full life?

The thing that gives me joy is something that's happened today, which is I've done 400 of these.

I've not met someone quite like you.

You're this interesting combination of almost like John Collison's endless curiosity and optimism and energy with Frank Slootman's intensity or something like that.