This week I have a very special guest years in the making. Like another favorite episode, with anonymous guest Modest Proposal, this conversation is with one of the stars of the financial twitter universe who writes anonymously and goes by the pseudonym Jesse Livermore. I met Jesse 6 years ago after reading his unbelievably unique investing research, which tackled all the big and interesting issues in markets. He now also works with me as a research partner at OSAM, where’s he’s used our data to continue to his search for truth in markets. Despite being one of the brightest minds I’ve encountered he is also as humble and unassuming as they come. I’m at least a slightly better person because of trying to emulate how he conducts himself. I get to have many conversations with him that go from 0-100 fast, and I’m thrilled to be able to share one of those with you.For more episodes go to InvestorFieldGuide.com/podcast.Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub.Follow Patrick on Twitter at @patrick_oshagShow Notes1:33 - (First Question) – Jesse’s origin story for investing4:37 – Exploring his ways of problem solving starting with intuitive7:53 – David Epstein Podcast Episode11:46 – Looking at the analytical way of problem solving15:42 – Statistical inference24:45 – Should we opt for simplicity in the investment process25:26 – Does his own investing include all three, intuition, analysis, and statistics26:09 – The evolution of his research, process, and thinking on various investment factors.31:38 – Thoughts on inflation and its impact on market valuation40:05 – The Earnings Mirage46:25 – Free Cash flow and valuations50:51 – What should investors take away from this research53:01 – Thoughts on trend as an interesting market signal59:00 – The problems with trend1:00:34 – Post on “The Single Greatest Predictor of Future Stock Market Returns”1:11:15 – His work into understanding factors1:15:36 – Looking at momentum1:18:16 – His curiosity into the current market cycle1:20:04 – Lessons learned from his time in the military, an effective way to create an environment where people can safely disagree with their co-workers1:30:10 – The concept of progress in meaningful work1:33:08 – Kindest thing anyone has done for himLearn MoreFor more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclubFollow Patrick on twitter at @patrick_oshag