Patrick O'Shaughnessy

I thought it would be fun to begin with a weird but interesting question for our past conversations, which is...

If you could go back in time and think about the original SoftBank Vision Fund, which was $100 billion, huge fund.

Of course, everyone was talking about it.

Who knows what will end up happening with it?

The story is still not fully written.

But if you could go back in time and you were fully personally in charge of deploying that $100 billion fund, how would you have approached that problem?

It's a lot of money to put out the door in a couple of years.

How would you have done it personally?

Obviously Insight has raised some of the largest funds in our industry, 10 plus billion, 20 billion.

What size would you set a fund, a hundred billion or some other number, if you wanted to do today in 2025, the thing you just described, how big would it have to get so that you were actually competitive?

Today's tougher.

So if you were to size a fund today,

for the best possible risk-adjusted return, where like fund size dictates the strategy, where do you think you would size it?

I think we're pretty close.

We don't lose sleep over that not being our core strategy.

What do you make of this?

You were an investor in the big Databricks round and Anthropic more recently.

What do you make of the late stage private markets today?

It's gotten so interesting and crazy relative to when you started Insight.

Maybe a fun thing before we get into insights strategy specifically is to talk about your day and your life as an investor.