Show Notes:

[00:01:32] – (First Question) – An exploration of how Jeff Gramm (first podcast episode guest) introduced Patrick and Christian

[00:02:22] – Patrick questions about the transitions in Christian’s career

[00:03:19] – Goes through his first few years out of school from creating his own startup, to baking bread, to eventually landing a job at SparkNotes

[00:04:53] – Deep dive into SparkNotes

[00:05:52] – The formation of Bishop Allen and OKCupid

[00:07:12] – A look at the book Dataclysm and how Christian was able to sort through the incredible data buried within the dating site

[00:12:17] – First piece of data that they dive into, “Wooderson’s Law”, based on a character from “Dazed and Confused”

[00:15:15] – The idea of the Pratfall Effect and the role of variance in people dating

[00:19:56] – Do people on dating sites say they want one thing and do another

[00:21:22] – Exploring the trends in race and dating that show we are far from being a post-racial society

[00:27:04] – Shift to some of Christian’s favorite books

[00:29:59] – Christian explains how he finds new books

[00:30:52] – Christian explains his latest project which requires some background some famous math classes that are taught at Harvard, which are often a source of NSA employees

[00:33:15] – How corporations are using data versus how the government is using it and the privacy concerns of both

[00:35:20] – With big data comes bigger, smarter computers, which shifts the conversation to artificial intelligence

[00:39:09] – Can artificial intelligence take over creative ventures and completely replace the role of humans in the future?

[00:40:40] – 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

[00:45:17] – What advice would you give to a 20-year-old looking to get into a data-driven tech company

[00:49:27] – Breaking down the right and wrong people to go after the entrepreneurial lifestyle

[00:51:39] – How do you know if you should continue to go down the road of an entrepreneurial idea?

[00:52:53] – Looking into OKCupid and what each person’s role was in the business.

[00:54:45] – Patrick asks Christian about being the CEO after serving in more of a creative role for most of his career

[00:56:32] – Patrick asks about some other entrepreneurial ventures that Christian might have up his sleeves, possibly something to do with animal rights and fair treatment

[00:59:08] – Other entrepreneurial ventures that are exciting Christian