Episode Details

I’ve often joked that this show should be called “this is who you are up against,” because I am so often having conversations with brilliant people across the investment landscape who are effectively my competition and yours. This week’s conversation fits that description because it gives you an inside view into how things work among some of Wall Street’s most competitive investment firms. My guest is Leigh Drogen, who has worked as a statistical arbitrage portfolio manager and who founded and now runs Estimize, a data company which works with some of the world’s largest hedge funds.

Our conversation centers on the massive shift from what we call discretionary portfolio management—basically stock picking—to a landscape that is increasingly dominated by quantitative investors of various types. We talk about how any investor might hope to earn alpha, and how doing so is harder and harder.

There are so many great stories in this episode, told by someone with the perfect career experience to know how the system actually works. After many episodes where I’ve been learning on the fly about topics like venture capital, permanent equity, or health, this episode marks a return to my world of quantitative investing. I think you’ll learn a lot, and that you’ll likely finish with an even deeper appreciation of just the type of investors that we are all up against. 

Books Referenced

Revenge of the Humans: How Discretionary Managers Can Crush Systematics

Links Referenced

The Undoing Project: A Friendship That Changed Our Minds

Force Rank (App)

Founder of Estimize Explains How He Plans To Disrupt The World Of Wall Street Research

Show Notes

2:45 – (First question) – A look at Leigh’s early career and how he got started in investing

3:13 – Revenge of the Humans: How Discretionary Managers Can Crush Systematics

8:04 – What happened when things stopped working towards the end of 2007.

9:35 – The proper dimensions to separate any sort of potential Alpha edge

11:15 – The traits that help a fund perform well

11:42 – The Undoing Project: A Friendship That Changed Our Minds

14:05 – Force Rank (App)

14:49 – How the scientific process plays into Leigh’s research strategies

19:18 – Explain what Estimize is and what it does

20:55 – How people are compensated for the estimates

23:33 – The scale of how many estimates they get per company

24:57 – Why you need to be part of this informational arms race if you hope to survive

28:30 – What happens if everyone buys Estimize data and the Alpha built into it goes away

31:04 – What has been the evolution in these hedge fund platform type companies

35:00 – If Leigh was designing a firm from scratch, what would it look like

37:25 – Understanding Numerai and crowdsourcing in funds

41:41 – What is an example of interesting data set that Leigh as come across

45:38 – What is the potential for a hybrid model between a quant only with a discretionary picker.

51:35 – How do you know when something is busted or broken?

55:33 – Exploring his most memorable individual day in his career – Flash Crash

58:16 – With all the algorithms and automation, will we continue to see more of these unfores