OwlTail

Cover image of Five Good Questions Podcast

Five Good Questions Podcast

Welcome to Five Good Questions. I’m your host, Jake Taylor.Fact: the average American watches 5 hours of television per day. What would the world be like if we dedicated one of those hours to reading books instead?I don’t know, but I’d like to find out.So to inspire others to read more, I ask five good questions of interesting authors and share the results with you every Friday. Let’s see if together, we can’t rescue some of those lost hours.

Weekly hand curated podcast episodes for learning

Popular episodes

All episodes

The best episodes ranked using user listens.

Podcast cover

5GQ Aswath Damodaran - Narrative and Numbers

Aswath Damodaran holds the Kerschner Family Chair in Finance Education and is Professor of Finance at New York University Stern School of Business. Before coming to Stern, he also lectured in Finance at the University of California, Berkeley. He has been voted "Professor of the Year" by the graduating M.B.A. class five times during his career at NYU and was profiled in Business Week as one of the top 12 U.S. business school professors.  Professor Damodaran currently teaches Corporate Finance and Equity Instruments & Markets. His research interests include Information and Prices, Real Estate, and Valuation. 1.  Why has access to increased data and computing power ironically made us more dependent on and susceptible to storytelling? 2.  What makes numbers so powerful? How do we guard against being fooled by numbers, especially when we’re fooling ourselves? 3.  There seems to be competition amongst many firms on who has the most “unbiased” process and is the most quantitatively-driven. What are some potential shortcomings of being so quant focused? 4.  Your book is chock full of great insights on some of the biggest business and investing stories over the last few years including, Amazon, Uber, Valeant, Ferrari, GoPro, Yahoo and Vale. To take one interesting example, can you walk us through how both numbers and narrative impacted your valuation of Uber? 5.  What’s the one narrative today that’s likely to eventually cause the most financial pain over the next 3-5 years?

16mins

7 Apr 2017

Rank #1

Podcast cover

5GQ Christopher Mayer - 100 Baggers

Chris Mayer is the Investment Director of Bonner & Partners, a financial research firm.  He is the author of Invest Like A Dealmaker: Secrets from a former banking insider, World Right Side Up: Investing Across Six Continents and, most recently, 100 Baggers: Stocks that Return 100-to-1 and How to Find Them. Five Good Questions: What are some of the key ingredients that might point to a 100x investment return?  Do we just have to depend on luck and strike oil or benefit from a big pharmaceutical drug approval, or is there any skill involved? When I was teaching at UC Davis’s MBA program, we did a study where we examined the performance of investing gurus vs. various value investing studies (Tweedy Browne, Magic Formula, What Works on Wall Street etc.).  It was amazing how the studies trounced even the pros.  One reason is likely liquidity, the bigger pros couldn’t get into smaller investments that the study did, which could constrain returns.  But another hypothesis I had was that because the studies are so mechanically driven and only sell after certain time periods, perhaps the studies participated in some of the market irrationality to the upside for a given stock.  A guru would have taken advantage of the downside irrationality of a low P/E, but then sold out before it ever got to an extreme high P/E.  How does this fit into your “coffee can” approach. Your book is full of off-the-beaten path stories, including a tontine.  What the hell is a tontine? ;) We all know about Graham and Buffett, but what made Keynes such a great investor? Buffett has a great article from way back in the day called “How Inflation Swindles the Equity Investor.”  It’s early Buffett, so it’s a little technical, but I thought you did a great job of simplifying it in your book and explaining how light-asset businesses are a better bet in inflationary environments.  Can you walk us through your reasoning?  

27mins

12 Feb 2016

Rank #2

Similar Podcasts

Podcast cover

5GQ Jereon Bos - Deep Value Investing

Author Background: Jeroen Bos, a Dutch investor, has worked his entire career in the financial services industry in England.  He worked for many years at stock broker Panmue Gordon, in the City of London.  It was here that his interest in value investing  developed.  This process accelerated after the October 1987 market crash, during which time he took inspiration from the Intelligent Investor by Benjamin Graham.

14mins

23 Aug 2015

Rank #3

Podcast cover

5GQ Mebane Faber - Invest with the House

Meb Faber is a co-founder and the Chief Investment Officer of Cambria Investment Management.  Faber is the manager of Cambria’s ETFs, separate accounts and private investment funds.  Mr. Faber has authored numerous white papers and several books: Global Asset Allocation, Shareholder Yield, The Ivy Portfolio, Global Value, and Invest with the House.   He is a frequent speaker and writer on investment strategies and has been featured in Barron’s, The New York Times, and The New Yorker. Mr. Faber graduated from the University of Virginia with a double major in Engineering Science and Biology.  It seems like a basket composed of each gurus’ highest conviction pick would be a smart strategy.  Yet you found their top pick was the worst performer of their top 10!  How is that possible?  And what can we do to benefit from that information? If I believed in following a copycat 13F strategy, how would I go about doing that in an intelligent, systematic manner? Only 25% of stocks are responsible for all of the market’s gains.  What implication does this have for stock picking vs. indexing? As ETFs proliferate and various strategies become available, do you think people will still pay 2% and 20% for these kind of strategies when you could have all of them for a fraction of the expense? I know this doesn’t fit your investing style, but if you had to pick one of these managers to invest 100% of your net worth, who would it be and why?  You have to factor in age and length of potential service to you.  

27mins

11 Mar 2016

Rank #4

Most Popular Podcasts

Podcast cover

The Hikecast 6

The Hikecast is a show where interesting people take me on their favorite hikes or walks and we talk about big ideas in an unconstrained format. No planned agendas, just deep conversations, recorded out in nature. The idea is for you to put on The Hikecast and get outside to simulate taking a hike with us. I want you to feel like you're there with us out in nature. Care to join us on a hike? :) My guest for this episode is Tobias Carlisle.  Toby is principal at Acquirers Funds, LLC, and serves as chief investment officer.  He is best known as the author of Acquirer's Multiple, Deep Value, Quantitative Value, and Concentrated Investing.  He has extensive experience in investment management, business valuation, public company corporate governance, and corporate law. We went on a blustery morning hike in Southern California. Please enjoy this hikecast with Toby Carlisle. *** Also, pick up a copy of my first literary effort: The Rebel Allocator. It’s a coming-of-age story of a young man who learns about business and life from an unlikely teacher. Imagine The Karate Kid meets Thorndike’s The Outsiders. You’re right, it’s probably not what you were expecting, but I have my fingers crossed that you’ll really enjoy it. It's available on amazon now in both print and digital formats. With gratitude, Jake

1hr 26mins

1 Mar 2019

Rank #5

Podcast cover

5GQ Pabrai & Spier - The Education of a Value Investor

Author Backgrounds: Mohnish Pabrai is the Managing Partner of the Pabrai Investment Funds and Dhandho Holdings.  Since inception in 1999 with $1 million in assets under management, Pabrai Investment Funds has grown to over $690 million in AUM with an annualized gain of 17.7% (versus 5.2 % for the Dow).  He is the author of two books, including The Dhandho Investor.  Mohnish is also is the Founder and Chairman of the Dakshana Foundation, which is focused on providing world-class educational opportunities to economically and socially disadvantaged gifted children worldwide. Guy Spier is the manager of Aquamarine Fund, an investment partnership inspired by the original 1950’s Buffett partnerships.  In 2007 he made headlines by bidding $650k with Mohnish Pabrai for a charity lunch with Warren Buffett.  Guy recently published his first book, The Education of a Value Investor.  In 2009, Spier and his family moved from New York to Zurich, Switzerland to escape the noise of Wall Street.  He attained his MBA from Harvard Business School and has a First Class degree in Economics from Oxford University.  He spoke at TED India and co-hosted TEDx Zurich.

37mins

22 Aug 2015

Rank #6

Podcast cover

5GQ Pabrai & Spier - The Dhandho Investor

Author Backgrounds: Mohnish Pabrai is the Managing Partner of the Pabrai Investment Funds and Dhandho Holdings.  Since inception in 1999 with $1 million in assets under management, Pabrai Investment Funds has grown to over $690 million in AUM with an annualized gain of 17.7% (versus 5.2 % for the Dow).  He is the author of two books, including The Dhandho Investor.  Mohnish is also is the Founder and Chairman of the Dakshana Foundation, which is focused on providing world-class educational opportunities to economically and socially disadvantaged gifted children worldwide. Guy Spier is the manager of Aquamarine Fund, an investment partnership inspired by the original 1950’s Buffett partnerships.  In 2007 he made headlines by bidding $650k with Mohnish Pabrai for a charity lunch with Warren Buffett.  Guy recently published his first book, The Education of a Value Investor.  In 2009, Spier and his family moved from New York to Zurich, Switzerland to escape the noise of Wall Street.  He attained his MBA from Harvard Business School and has a First Class degree in Economics from Oxford University.  He spoke at TED India and co-hosted TEDx Zurich.

18mins

22 Aug 2015

Rank #7

Podcast cover

5GQ Alan Klement - When Coffee and Kale Compete

Alan Klement helps individuals, teams, and companies become great at making and selling products that people will buy.  His own experience as an entrepreneur helps make him effective at helping others.  He is the author of When Coffee and Kale Compete. Five Good Questions Perhaps you could explain what Job to Be Done (JTBD) and Customer Jobs mean through the example of buying a Snickers vs. Milky Way? What is the problem with Chasing Visible Figures and how it relates to creative destruction? What are the forces of progress and how do they fit with JTBD? What do systems have to do with innovation? What does Clayton Christensen have wrong?

40mins

15 Nov 2019

Rank #8

Podcast cover

5GQ Paul Allen - Choose Stocks Wisely

Author Background: Paul Allen is a Professor Emeritus at Mississippi State University.  He holds a CPA, DBA (Doctor of Business Administration), MBA, BPA (Bachelors of Professional Accountancy) and previously worked as a senior accountant for 5 years with Exxon Co. USA .  He has been widely published in accounting, finance and marketing journals.

19mins

23 Aug 2015

Rank #9

Podcast cover

5GQ Sean Iddings - Intelligent Fanatics Project

Sean Iddings is co-founder of the Intelligent Fanatics Project which helps investors and entrepreneurs see further by standing on the shoulders of organizational and leadership giants. The book series, of the same name co-authored by Ian Cassel, is the introduction into the overall project. Sean is also a member of MicroCapClub and runs Unconventional Capital Wisdom, a registered investment advisor in New York State. http://amzn.to/2nQlEu2 1. What is an “intelligent fanatic,” and why do we want to recognize them as investors? What are some qualities you didn’t like in some of the leaders or their organizations you highlighted in the book? Why? 2. Who was John Patterson and how did he embody an intelligent fanatic? 3. Finding a Jeff Bezos or Warren Buffett after they’re big and famous seems easy. How do we find an intelligent fanatic early enough to invest in them to really see the benefits? Are there markers we can look for a priori to success? 4. A large addressable market with a big runway for growth was a common theme among everyone profiled. The timing also happened to coincide with an epoch of unprecedented economic growth in the US. If you consider that the tide might not be coming in as quickly in the developed world as it once was, are the spectacular results of an intelligent fanatic still replicable? 5.Many of the intelligent fanatics chose a lowest-cost-provider business model to succeed. Is that the most likely way to succeed for them? Or are there others who were able to create differentiated products instead?

27mins

31 Mar 2017

Rank #10

Podcast cover

5GQ Alex Soojung-Kim Pang - Rest

Alex Soojung-Kim Pang is the founder of The Restful Company and a visiting scholar at Stanford.   He spent more than a decade as a science and technology forecaster, most recently as a senior consultant at Strategic Business Insights. Alex received a Ph.D. in History and Sociology of Science from the University of Pennsylvania. http://amzn.to/2jmwHcM Five Good Questions:   1. What’s Wallas’s four-stage model of creativity? 2.What’s the Default Mode Network? 3. Our society idolizes the 80-100 hour work week as a requirement for success.  How do you explain the paradox of the most productive and creative people working much less than that?  Also, what is this notion of “deep play” that a lot of creative people practice? 4. What was a Bill Gates’s “Think Week” and what can we learn from it? 5. How has your daily, weekly, monthly, and yearly schedule changed based on what you learned writing a book about rest?  How has it impacted how you think about work and creativity?

42mins

27 Jan 2017

Rank #11

Podcast cover

5GQ: Gautam Baid - The Joys of Compounding

In this week's Five Good Questions, we're interviewing Gautam Baid about his book The Joys of Compounding. Gautam Baid is Portfolio Manager at Summit Global Investments, an SEC-registered investment advisor based out of Salt Lake City, Utah. Previously, he served at the Mumbai, London, and Hong Kong offices of Citigroup and Deutsche Bank as Senior Analyst in their investment banking teams. Gautam’s views and opinions have been published on various forums in print, digital, and social media. In 2018, He was profiled in Morningstar’s Learn From The Masters series. Five Good Questions: 1. In your book, you state that “I am a better investor because I am a lifelong learner, and I am a better lifelong learner because I am an investor.” Why is continuous learning so important in investing? 2. What does the equation [Ego = 1 / Knowledge] mean? 3. How has minimalism improved your investment process? 4. Given the increase in the rate of change of business, is there cause for concern about the durability of moats? 5. How do you balance high conviction with maintaining mental flexibility? Disclaimer: The views and opinions expressed by Gautam Baid are solely his own and do not reflect the views of Summit Global Investments. Any recommendations, examples, or other mentions of specific investments or investment opportunities of any kind are strictly provided for informational and educational purposes and do NOT constitute an offering or solicitation, nor should any material herein be construed as investment advice.

22mins

28 Jun 2019

Rank #12

Podcast cover

5GQ Mark Simpson - Excellent Investing

In this week's Five Good Questions, we're interviewing Mark Simpson about his book Excellent Investing. Mark is a UK-based deep value investor and author with over 15 years of experience investing in individual securities. He writes about finding sources of edge in the market, investor psychology, avoiding investment mistakes and building better portfolios. Five Good Questions 1. Why do you think the microcap space is inefficient, and how much less efficient is it? 2. Wes Gray has this concept called the “God Portfolio.” What is it and what does it mean to knowing yourself as an investor? 3. What are your thoughts on averaging down when a stock you own drops in price? What are assassins, hunters, and rabbits in this context? 4. A percentage of the Kelly Criterion (½ Kelly or ⅓ Kelly) are popular upper limits for position sizing. What are lower limits and why are they important? 5. What do oxytocin and empathy have to do with story stocks?

50mins

6 Sep 2019

Rank #13

Podcast cover

5GQ Michael Shermer - Skeptic

Dr. Michael Shermer is the Founding Publisher of Skeptic magazine, a monthly columnist for Scientific American, a regular contributor to Time.com, and Presidential Fellow at Chapman University. His new book is "Skeptic: Viewing the World with a Rational Eye." He is also the author of “The Moral Arc: How Science and Reason Lead Humanity Toward Truth, Justice, and Freedom”, “The Believing Brain: From Ghosts and Gods to Politics and Conspiracies”, “The Mind of the Market”, “Why Darwin Matters: Evolution and the Case Against Intelligent Design”, and “The Science of Good and Evil”. He has been a college professor since 1979, also teaching at Occidental College, Glendale College, and Claremont Graduate University, where he taught a transdisciplinary course for Ph.D. students on Evolution, Economics, and the Brain. As a public intellectual he regularly contributes Opinion Editorials, book reviews, and essays to the Wall Street Journal, the Los Angeles Times, Science, Nature, and other publications. Dr. Shermer received his B.A. in psychology from Pepperdine University, M.A. in experimental psychology from California State University, Fullerton, and his Ph.D. in the history of science from Claremont Graduate University. He appeared on such shows as The Colbert Report, 20/20, Dateline, Charlie Rose, and Larry King Live. His two TED talks, seen by millions, were voted in the top 100 of the more than 1000 TED talks. 1.  How has reasoning and scientific thinking changed the way we view morality and created a more just world? 2.  Why do people think that things are bad and getting worse when, in fact, they are good and getting better? That is, why all the doom and gloom pessimism when optimism and gratitude should be the response to all the progress we have realized in our time? 3.  There are many reasonable and smart people on both sides of the climate change issue. What are your thoughts these days? 4.  There are many products that seem to fall into the “can’t hurt, might help” category. Is there anything wrong with taking advantage of the placebo effect? 5.  Are there any investment takeaways from your research and insights?

26mins

24 Mar 2017

Rank #14

Podcast cover

5GQ John Browne - Make, Think, Imagine

In this week's Five Good Questions, we're interviewing Lord John Browne about his book Make, Think, Imagine. John Browne trained as an engineer, was CEO of BP from 1995 to 2007 and remains an influential leader in the energy business. He is Chairman of the Crick Institute, a Fellow of the Royal Society, past President of the Royal Academy of Engineering and former Chairman of Tate. He is a collector of antique books and art and the author of four previous books, including The Glass Closet: Why Coming Out is Good Business. Five Good Questions: 1. Do you have a sense that much of cutting edge technology relies on intervention into complex, nonlinear systems and fattens the probability tails of undesirable outcomes? Said more simply, does technology invite more black swans? 2. What’s the one new tech on the horizon that you’re most excited for? 3. How was the stirrup such a powerful invention and what does it tell us about the future of technology? 4. How did gunpowder ironically lead to greater peace in the world? 5. Investors like Warren Buffett have borrowed the engineering principle of margin of safety for their investment processes. What’s another concept from engineering that might also be useful for us?

27mins

27 Sep 2019

Rank #15

Podcast cover

The Hikecast 7

The Hikecast is a show where interesting people take me on their favorite hikes or walks and we talk about big ideas in an unconstrained format. No planned agendas, just deep conversations, recorded out in nature. The idea is for you to put on The Hikecast and get outside to simulate taking a hike with us. I want you to feel like you're there with us out in nature. Care to join us on a hike? :) My guest for this episode is Dan Sheehan.  Dan is the general partner of Sheehan Associates Limited Partnership, an investment partnership created in 1999. Dan has a degree in economics from McMaster and an MBA from York. We went on a chilly hike in Toronto. Please enjoy this hikecast with Dan Sheehan. *** Also, please check out my first literary effort: The Rebel Allocator It’s a coming-of-age story of a young man who learns about business and life from an unlikely teacher. Imagine The Karate Kid meets Thorndike’s The Outsiders. You’re right, it’s probably not what you were expecting, but I have my fingers crossed that you’ll really enjoy it. It's available on amazon now in print, digital, and audiobook formats. With gratitude, Jake

1hr 28mins

26 Apr 2019

Rank #16

Podcast cover

The Hikecast 9

The Hikecast is a show where interesting people take me on their favorite hikes or walks and we talk about big ideas in an unconstrained format. No planned agendas, just deep conversations, recorded out in nature. The idea is for you to put on The Hikecast and get outside to simulate taking a hike with us. I want you to feel like you're there with us out in nature. Care to join us on a hike? :) My guest for this episode is Nyle Bayer.  Nyle is the Chief Marketing Officer at Helios Quantitative Research (HQR), an investment research company which assists financial advisors in creating, implementing, and monitoring quantitative investment strategies for their clients and boasts over $20 billion in assets under influence.  Previous to his work at Helios, Nyle served as the President of Up Capital Management, a Registered Investment Advisor and he is the founder of Financial Time Traveler, a financial media company.  Nyle is a father of three children, and lives in Roseville, CA with his wife Nicole. We went for an awesome hike in the Sierra Nevadas. Please enjoy this hikecast with Nyle Bayer.   *** Also, please check out my first literary effort: The Rebel Allocator It’s a coming-of-age story of a young man who learns about business and life from an unlikely teacher. Imagine The Karate Kid meets Thorndike’s The Outsiders. You’re right, it’s probably not what you were expecting, but I have my fingers crossed that you’ll really enjoy it. It's available on amazon now in print, digital, and audiobook formats. With gratitude, Jake

49mins

25 Oct 2019

Rank #17

Podcast cover

5GQ Brent Beshore - The Messy Marketplace

In this week's Five Good Questions, we're interviewing Brent Beshore about his new book, The Messy Marketplace. Brent is the founder and CEO of adventur.es, a family of companies that acquires family-owned companies. He recently published “The Messy Marketplace: Selling Your Business in a World of Imperfect Buyers” and lives in Columbia, MO with his wife and three daughters. Five Good Questions: 1. There’s a tremendous amount of information that needs to be sorted through before a buyer can get comfortable purchasing an entire business. What percentage of information do you shoot for before making that final decision? 2. Like any investment, you often have to pay up for quality. What’s your thought process as you balance the quality of the business versus your purchase price? 3. How do you assess capital allocation skills in a small business? 4. What’s the most preventable deal breaker you see sellers making on a regular basis? What about buyers? 5. After analyzing more than 10,000 deals, what’s been the craziest clause you’ve ever seen in a contract? And make sure you pick up your copy of the Rebel Allocator, available now on Amazon in both digital and physical formats!

13mins

25 Jan 2019

Rank #18

Podcast cover

5GQ James Clear - Atomic Habits

In this week's Five Good Questions, we're interviewing James Clear about his book Atomic Habits. James is an author, entrepreneur, and photographer. He writes about habits and human potential on his website JamesClear.com. His focus is self-improvement that is supported by scientific research. James’s work ends up being one-part storytelling, one-part academic research, one-part personal experimentation. Five Good Questions:  1. What makes being thoughtful about our habits so important? 2. What are a few best practices for good habit hygiene? 3. What habit would you guess is a commonality among great investors? Or maybe, we should invert and ask what are the bad habits of investing? I’m imagining checking stock prices too often has to be up there? 4. Is there a dark side to habits? Is it possible that too much structure can sap away spontaneity, joie de vivre, and being present? 5. What’s the one bad habit that’s been hardest for you to personally break?

34mins

18 Jan 2019

Rank #19

Podcast cover

5GQ David Hassell - The Great eBook of Employee Questions

David Hassell is the founder and CEO of 15Five, the leading web-based employee feedback and alignment solution that is transforming the way employees and managers communicate. Named "The Most Connected Man You Don't Know in Silicon Valley" by Forbes Magazine, David has also been featured in The New York Times, The Wall Street Journal, Inc., Entrepreneur, Wired, Fast Company, and the Financial Post. You can learn more about 15Five and David Hassell at www.15five.com. 1.  Children ask upwards of 300 questions per day. As adults we only ask a handful. Why do we change, and are we missing something as adults by asking fewer and less thoughtful questions? 2.  You have two “must ask” questions every boss should be asking. What are they, and why are they so effective? 3.  What are some tips for managing introverts? 4.  What are the best questions to ask to help a remote team succeed? 5.  How have you personally used asking better questions to influence the evolution and success of your company, 15 Five?

21mins

3 Mar 2017

Rank #20