The Quantified Self – Christian Rudder [Invest Like the Best EP.05]

In this episode, I speak with Christian Rudder, who is the co-founder of OK Cupid, a NY Times best-selling author (of the awesome Dataclysm), a data and math junky, and a musician. We discuss interesting and unsettling trends in OK Cupids dating data (age, race), artificial intelligence, the NSA, great books on the Civil War, and more.

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Please enjoy!


Books Mentioned


2:05 – Dataclysm: Who We Are (When We Think No One’s Looking) – Christian Rudder

27:23 – Civil War a Narrative – Shelby Foote

27:48 – Dune – Frank Herbert

28:06 – Look Who’s Back – Timur Vermes

28:37 – The Age of Miracles – Karen Thompson Walker

28:58 – Station Eleven – Emily St. John Mandel

29:14 – H is for Hawk – Helen Macdonald

30:21 – SPQR: A History of Ancient Rome

36:27 – Superintelligence: Paths, Dangers, Strategies – Nick Bostrom

44:35 – The Singularity Is Near: When Humans Transcend Biology  (44:35)

58:09 – Eating Animals –  Jonathan Safran Foer

Links Referenced

Christian Rudder’s band – Bishop Allen

Early member of SparkNotes

CEO and Founder of OKCupid

Essays on AI – Wait But Why


Show Notes


1:32 (First Question) – First an exploration of how Jeff Gramm (first podcast episode guest) introduced Patrick and Christian.

2:22 – Patrick questions about the transitions in Christian’s career

3:19 – Goes through his first few years out of school from creating his own startup, to baking bread, to eventually landing a job at SparkNotes

4:53 – Deep dive into SparkNotes

5:52 – The formation of Bishop Allen and OKCupid

7:12 – A look at the book Dataclysm and how Christian was able to sort through the incredible data buried within the dating site.

12:17 – First piece of data that they dive into, “Wooderson’s Law”, based on a character from “Dazed and Confused.”

15:15 – The idea of the Pratfall Effect and the role of variance in people dating

19:56 – Do people on dating sites say they want one thing and do another

21:22 – Exploring the trends in race and dating that show we are far from being a post-racial society

27:04 – Shift to some of Christian’s favorite books

29:59 – Christian explains how he finds new books

30:52 – Patrick asks Christian to explain his latest project which requires some background some famous math classes that are taught at Harvard, which are often a source of NSA employees.

33:15 – How corporations are using data versus how the government is using it and the privacy concerns of both.

35:20 – With big data comes bigger, smarter computers, which shifts the conversation to artificial intelligence.

39:09 – Can artificial intelligence take over creative ventures and completely replace the role of humans in the future?

40:40 – If more people are put out of work by artificial intelligence, will there need to be some sort of redistribution to ensure basic quality of life for all.

45:17 – What advice would you give to a 20-year-old looking to get into a data driven tech company.  Importantly, it’s not just about being able to collect the data, but how you analyze and use it afterwards.

49:27 – Breaking down the right and wrong people to go after the entrepreneurial lifestyle

51:39 – How do you know if you should continue to go down the road of an entrepreneurial idea?

52:53 – Looking into OKCupid and what each person’s role was in the business.

54:45 – Patrick asks Christian about being the CEO after serving in more of a creative role for most of his career.

56:32 – Patrick asks about some other entrepreneurial ventures that Christian might have up his sleeves, possibly something to do with animal rights and fair treatment.

59:08 – Other entrepreneurial ventures that are exciting Christian

Learn More

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