This week we explore a rare and underappreciated skill through the lens of an incredible story. My guest is Eric Maddox, whose name you probably don’t know but won’t soon forget. Just trust me that you need to listen to this entire episode, and listen carefully—because that is what the episode is ultimately all about: how to listen to others, with care and empathy, in the age of distraction. Sometimes it’s fun not to know what’s coming and be surprised, so I won’t say anymore. After the episode, you can learn more about Eric at Ericmaddox.com. On his wall, Eric has a framed Cuban cigar, he starts his story by explaining the significance of that cigar. Enjoy this episode, and try Eric’s method. It has worked wonders for me. Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/maddox/ 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_oshag

My guest this week is one of the reasons that this podcast exists.  Josh Brown is a financial advisor and the CEO of Ritholtz Wealth Management. He is also the creator of TheReformedBroker.com, a blog about markets, politics, economics, media, culture, and finance that has become one of the most widely-read sites on the financial web.  He is the author of Backstage Wall Street and Clash of the Financial Pundits. Josh was instrumental in finding me an audience years ago when he shared one of my research pieces with his rapid base of fans.  This conversation includes a look at his journey, what he’s learned along the way, and most importantly, his top five, dead or alive.   Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/brown/ 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_oshag

My guest this week is Christopher Cole, founder and managing partner at Artemis Capital Management. Chris’s specialty is in long volatility strategies, setting up portfolios that will benefit from significant change and volatility in markets.  We discuss how a series of small bets can lead to disproportionally large nonlinear payoffs, in both life and in markets.  We also discuss the kind of watch Chris wears, Dennis Rodman, and movies, all as metaphors for his life philosophy.    Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/cole/ 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_oshag

Today’s episode features one of my favorite thinkers and writers: Kevin Simler.  Kevin has a background in technology and was one of the earliest employees at Palantir Technologies.  Palantir specializes in big data and has worked closely with clients ranging from the Department of Defense to the world’s largest hedge funds.  In this conversation, Patrick and Kevin explore startup culture, how to spark creativity, how social status functions like money, and how to think about the universe.  This will be one of the most unique conversations you will hear on this podcast.  Please Enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/simler/ 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_oshag

This week Patrick takes a deep dive in the world of Venture Capital with Craig Shapiro, founder and CEO of the New York based Collaborative Fund, which was an early investor in companies like Lyft, Kickstarter, and Reddit.  We cover Craig’s investing roots, his process for sourcing and evaluating investment opportunities, and the very useful “villain test.”  Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/shapiro/ 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_oshag

This week’s guest is Brent Beshore, Founder and CEO of adventur.es, a family of companies that invests in family-owned companies. Brent has a very specific mission with this company, to cultivate a disaster resistant, compound interest machine. At just 33 years of age he has already built a portfolio of private companies that has produced impressive results.  He’s done all this out of the limelight and with no outside investors.  Brent discusses his rewarding but difficult journey and what he has learned, including sourcing and evaluating businesses, how he and his team have improved profitability at his portfolio companies after acquisition and so much more.   For comprehensive show notes on this episode go to investorfieldguide.com/beshore/ 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_oshag

Would you be comfortable with a robo-advisor running your entire investment portfolio?  That’s the hope of our guest this week, Jon Stein, founder and CEO of Betterment.  Betterment manages $5 billion dollars for over 175,000 clients.  Patrick and Jon explore the challenge of getting young people to invest, Betterment’s recent foray into areas like the 401(k) market, and how Betterment works with financial advisors.  If you’re unsure about robo-advisors, this conversation will make you better understand what they can do for you. Please Enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/stein/ 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_oshag

This episode is a major departure from the norm.  My guest, Kiley Adams, is only 21 years old. She has crammed more learning and adventure into two decades than most people could hope to in a lifetime.  She’s track-and-field star, valedictorian, varsity soccer player, Tae Kwon Do fourth degree master black belt, and philanthropic researcher.  She has traveled all over the country and the globe, recently spending two months by herself in India.  I had the pleasure to meet here while teaching an investing class at Notre Dame and am thrilled to share her incredible story and her attitude that makes all of this possible.   For comprehensive show notes on this episode go to investorfieldguide.com/adams/ 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_oshag

This week’s guest has forgotten more about hedge funds than most people will ever know. This episode will appeal to managers, allocators and any investor interested in the world of hedge funds.  Ted Seides worked under David Swensen at Yale’s endowment and was a co-founder, President and Co-chief investment officer at Protégé Partners, a multibillion dollar alternative investment firm. I met Ted after reading his book, “So You Want to Start a Hedge Fund: Lessons for Managers and Allocators.” He has taught me a lot ever since. Hedge funds have taken a beating, so this very nuanced investigation into the industry comes at the right time.  Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/seides/ 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_oshag

There is a good chance that this week’s guests manage your money. This episode is a rare and fascinating look into the world’s largest asset manager. My first guest is Gerry O’Reilly, who is the portfolio manager for the largest mutual fund in the world, and oversees more than $800 billion for Vanguard. My second guest is Jim Rowley, a Senior Investments Analyst with deep knowledge of indexing and ETF’s.  The two provide incredible insight into some of the particulars that make Vanguard and its funds tick.  Please enjoy!   For comprehensive show notes on this episode go to investorfieldguide.com/vanguard/ 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_oshag