“I try to be cynical, but it’s hard to keep up.”

For this episode of Conversations, we venture into the world of finance and speak with Jared Dillian.

Jared is truly a fascinating guy with incredible insights into the world. 

I first came across his insights after reading an expose about him in the NY Times back in 2011. 

Jared worked as a trader at Lehman Brothers starting back in 2001–just weeks before the terrorist attacks of 9/11. He started with Lehman as an index arbitrage trader and then as head of the ETF (or exchange traded fund) desk. During this time, he routinely traded over $1 billion a day in volume. 

His tenure lasted 7 years and ended with a front row seat into the financial industry’s collapse and Lehman Brothers shocking bankruptcy.

After the financial collapse, instead of seeking a new position with one of the big financial firms, Jared started his own financial publishing business, the Daily Dirtnap. 

And it is from the Daily Dirtnap that I’ve come to know Jared so well. 

The Daily Dirtnap is a 3-page newsletter that is delivered to me by email each morning and has helped shape my beliefs not just about finance, but life in general. Honestly, it is pure gold.

In fact, other than reading the NY Times every morning since 1996, there is nothing I’ve read more consistently or with more anticipation than Dillian’s The Daily Dirtnap. 

He’s been described as one of the industry’s most original, entertaining, and contrarian voices and referred to as “the Dr. House of trading.”

His readership is wide ranging from casual investors to professional traders and hedge fund managers.

But wait, there’s more. 

Dillian also publishes the publication the 10th Man—which has the motto “it is a duty of the 10th man to disagree”—which takes a very different spin on the financial markets. It is also one of my favorite publications and one that I encourage you to try out, especially because it is free. 

Other newsletter publications of Dillian’s include ETF 20/20 and Streak Freak.

Beyond newsletter publications, Dillian has also authored two books, 

His first, Streak Freak: Money and Madness at Lehman Brothers, was described by Bloomberg as a disturbingly candid memoir about a poor kid who quit the U.S. Coast Guard to chase his dream of becoming a trader. 

And Publisher Weekly said Dillian offers a candid look at the demise of a corporate behemoth.

Dillian’s second book, All the Evils in the World,” has been described as a riveting tale of a high...