Invest Like the Best with Patrick O'Shaughnessy

Annie Duke, a world champion poker player and decision-making authority, shares her insights on improving decision-making in high-stakes scenarios. She breaks down decision components like values and beliefs, emphasizing the importance of evaluating the decision process over outcomes. Duke discusses the power of identity and group dynamics, revealing how group influence can shape individual choices. With practical strategies for self-reflection and cognitive bias reduction, listeners gain tools to enhance their decision quality and foster personal growth.

Michael Mayer, entrepreneur and founder of Bottomless, shares insights on the intersection of pseudonymity and social capital. He discusses how his online identities have helped him grow personally and professionally. Mayer's innovative coffee subscription model features a smart scale that optimizes coffee orders based on consumption, revolutionizing the coffee experience. He also delves into the challenges of co-founding a business with a spouse and critiques traditional social media, proposing a new model for meaningful engagement.

Peter is a geopolitical strategist who combines expertise in demography, economics, energy, politics, technology, and security to assess an uncertain future. Before founding his own strategy firm, Peter helped develop the analytical models for Stratfor, one of the world’s premier private intelligence companies.   I came across Peter via his books the Accidental Superpower and the Absent Superpower. We discuss America’s changing place in the world and four additional countries poised to do well in the future. Spoiler alert: he believes the U.S. is particularly well positioned.  While we don’t discuss equity markets per se, all of what we talk about will obviously impact companies across the world for the remainder of our careers. Please enjoy our conversation. 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   Show Notes 1:32 - (First Question) – His model of the world 4:05 – What makes for a strategically advantaged country 5:35 – History of the Bretton Woods agreement and the order that it created 8:47 – The security apparatus that has made globalization of manufacturing possible 12:04 – The US’s pullback from being the naval police of global trade             12:08 – The Absent Superpower: The Shale Revolution and a World Without America 14:57 – How energy has played into America’s disinterest abroad 21:52 – Moving towards global disorder 24:55 – Characterizing factors that will impact countries in any collapse 27:38 – How this manifest in physical conflict 32:44 – How the new world order will end the ease of innovation we are accustomed to today 34:13 – What gets the US to reengage before this new world order 38:08 – Demographics that make a country prepared for this, Japan as an example 40:57 – A look at China 43:59 – What the story is about Argentina 45:52 – How North America fares based on their geography and relationships 49:50 – The trader wars that are currently ongoing 52:17 – US political system 56:15 – Most important policy issues moving forward 58:27 – His view on American infrastructure 1:00:33 – Technologies that interest him the most 1:02:55 – What he is watching most closely in his research, starting with media 1:05:59 – What are and should be the countries of the future 1:06:55 – Kindest thing anyone has done for Peter 1:07:32 – Favorite places he’s been   Learn More 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 Michael Kitces, who is one of our industries go-to experts on all things financial advise and financial planning. We discuss the past, present, and future of financial advise, financial technology, and investing. If you are a financial advisor or use one, this conversation is full of great history and perspective. Please enjoy. 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   Show Notes 1:08 - (First Question) – History of financial planning/advice model 5:26 – Fee changes in the 1970’s 10:01 – The start of the AUM model 10:44 – Value proposition for financial advisors beyond trading vs robo-advsiors             11:49 – Why Robo-Advisors Will Be No Threat To Real Advisors 18:20 – Why are humans still dominating the space 23:58 – Future of advisor fees 32:50 – Viability of the human driven flat fee model 37:50 – The dominance of flat fee models 43:13 – What services are financial advisors offering to justify their fees 47:17 – Dimensions to divide potential customers 52:20 – Exciting updates on the investment side that will help differentiate managers 55:37 – Any investment function beyond the basics that is intriguing to him 58:45 – Most interesting problems to be solved on the investing and non-investing sides 1:04:52 – Advice for young advisors 1:09:24 – How does he invest his own money 1:11:31 – Kindest thing anyone has done for Michael   Learn More 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 Alex Danco. Alex is a member of the Discover Team at Social Capital, has a background in biology, and has written about all things tech and business. While Alex is only 30, it seems like he has spent decades thinking about all the topics that we discuss, from changing business models, to railroads, to the shift from products to functions, and the rise and fall of asset bubbles. I hope you enjoy this wide ranging conversation.  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   Show Notes 1:15 - (First Question) – A look at his day job on the discover team             2:20 – 40 problems doc 4:27 – How companies get on the list and the turnover 5:21 – Hardest problem they are looking at…housing 11:37 – The investment component that fixes housing 15:35 – Where we are in the technology cycle in the view of abundance vs scarcity 20:54 – Change in distribution and the business vs utility business idea. 28:40 – Bifurcation of small and larger businesses 32:48 – New forms of scarcity today 38:31 – The trend of massive company incumbency 41:07 – The utility of bubbles 49:08 – His favorite bubble 51:18 – Challenges and nuances of bubbles             53:35 – Zero to One Notes on Start-Ups, or How to Build the Future 1:02:22 – Future for VC funding in Silicon Valley 1:04:07 – Advice for business builders             1:08:23 – The Three True Outcomes 1:13:04 – His background in biology and innovation in that space that is coming 1:19:46 – Company examples that are of interest to him and that encapsulate his way of investing 1:24:56 – Kindest thing anyone has done for Alex   Learn More 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 Keith Wasserman, co-founder of the real estate investment firm Gelt. This was my first fully dedicated conversation on direct real estate investing, so we cover many different topics, including the pros and cons of different types of real estate, current valuations, risk vs. reward, tax protection, and the most interesting emergent areas.   You can tell Keith is an entrepreneur at heart so I enjoyed his energy and all that he has learned. Please enjoy.   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   Show Notes 1:15 - (First Question) – Their interest in apartments and mobile homes as investments 2:32 – The returns spectrum for different classes of real estate 4:03 – His early entrepreneurial ventures and the start of Gelt 7:45 – Don’t be afraid of negotiating 8:34 – Going through early deals in real estate 11:57 – How he determines when it’s time to sell a property 14:13 – How do they think about taxes in their investment offerings 16:57 – Depreciation strategies in real estate investing 18:27 – The evolution of the types of real estate properties they’ve invested in 21:41 – Most important factors when evaluating a building to invest in 23:50 – Barriers to entry 25:41 – Changes in his cost of capital 28:51 – Cost of debt and deciding how much to put into a building 30:33 – A look at the competition 34:51 – Effective marketing strategies 37:07 – How demographics impact their strategies 39:11 – The co-living space 40:34 – Cloud kitchens and how he would invest in these 46:11 – How autonomous vehicles will impact real estate 47:52 – Pros and cons of developing new properties vs buying existing ones 49:59 – Early stage investing interest 53:48 – Favorite business/entrepreneur story 55:10 – Advice for younger entrepreneurs 57:09 – Kindest thing anyone has done for Keith   Learn More 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

My guest this week is Alex Mittal, co-founder of Funders Club. Following past guest Jeremiah Lowin, Alex is my second elementary school friend to appear on the podcast—a trend I hope continues. Funders club is a unique venture firm, because it is build around a network of investors and entrepreneurs who submit deals for consideration and invest together. But as you’ll hear, Alex and his co-founder Boris aren’t just building an open platform for early stage investing: they also then take a very traditional venture approach, making investing decisions themselves when it comes to building a centralized portfolio. Our conversation is about what Alex has learned investing in almost 300 early stage companies over the past 7 years. Please enjoy.   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   Show Notes 1:30 - (First Question) – Inception of the Founder’s Club             1:36 – Jeremiah Lowin Podcast Episode 3:59 – How the process of their platform works 5:40 – Role of the network in Founders Club setup and success 8:26 – What he has learned from all of the data he has access to 16:00 – Early stage investing and finding the sweet spot 22:17 – What makes a really intriguing bad idea 25:23 – Why he remains so excited about Ethereum 31:18 – More bad ideas             31:55 – Apoorva Mehta on How I Built This Podcast 37:15 – Thoughts on retail and logistics and how they fit his Venn diagram of boring and crazy 43:13 – Chip and electronic design 45:47 – Companies that are not just increasing efficiencies but actually making foundational changes             45:54 – Energy and Civilization: A History 52:34 – What does he look for in founders             55:26 – Pivot or Fail 57:05 – Kindest thing anyone has done for Alex   Learn More 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, Eugene Wei, has one of the most interesting backgrounds of anyone I’ve had on the podcast. He worked at Amazon early in its life, was the head of product at Hulu and Flipboard, and head of video and Oculus. Our conversation is about the intersection of technology, media, culture. We discuss Eugene’s concept of invisible asymptotes: why growth slows down (for both companies and people) and how some can burst through. I’d list more of the topics, but we covered so much that you should just listen. Finally, I’ll say that after spending a day with Eugene (including a wildly interesting dinner with Eugene, past podcast guest Sam Hinkie, and future podcast guest Kevin Kwok) that he is the type of uniquely interesting and kind person I am always searching for and one that I wish I could bet on somehow. If you know more people like this, reach out and suggest them for this podcast. Now, enjoy our conversation. 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 Show Notes1:38 - (First Question) – Idea of cuisine and empire             1:52 – Cuisine and Empire: Cooking in World History4:20 – Key takeaways from the Defiant Ones Documentary8;25 – Being convinced to buy a sports coat11:10 – The concept of invisible asymptote17:43 – How the medium shapes the messaging and the impact of cameras everywhere on society             17:48– Invisible asymptotes             17:56 –  Selfies as a second language22:57 – Proof of work in building a social network32:51 – Magnification of inequalities in digital networks             34:01 – The Lessons of History36:47 – His thoughts on the media industry’s impact on society as a whole39:42 – His time at Hulu44:48 – Places where video could replace text47:30 – The need for media for any business looking to grow             49:35 – Amusing Ourselves to Death: Public Discourse in the Age of Show Business53:08 – Personal asymptotes57:19 -  Habit building and goal setting1:00:29 – Travel recommendations1:03:24 – Movie recommendations1:08:16 – Product recommendations and what makes them indispensable             1:10:44 – Creation: Life and How to Make It1:13:23 – Thoughts on the art of conversation             1:14:59 – The Most Human Human: What Artificial Intelligence Teaches Us About Being Alive1:18:30 – Kindest thing anyone has done for Eugene Learn 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

My guest this week is Michael Duda, and the topic of our conversation is the role that brand plays in business and investing.  Michael has worked on and invested in a wide-range of brands including Birchbox, Casper, Harry's, Citibank, DirecTV, Google, TripAdvisor, Under Armour and vineyard vines. His background in advertising made this a unique and interesting conversation. please enjoy. 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   Show Notes 1:11 - (First Question) – Mission of Bullish 2:15 – Typical relationship they have with companies 3:01 – Defining brand             4:35 – Ryan Caldbeck Podcast Episode 5:51 – A dive into how brands make people feel 7:54 – Does the emphasis on brand still matter to consumers and if so, where 10:01 – Process of building up a brand 14:53 – What has changed most in the planning of a brand strategy 18:35 – How does his thinking impact his investing strategy 21:48 – Where does he differ from the rest of the market 23:34 – Advice he would give to companies in general 26:18 – How advertising has changed in the current landscape 28:35 – The screening process for picking potential investments 35:16 – How they analyze valuation 37:31 – Unusual traits he likes in founders 40:12 – Categories most ripe for young companies to disrupt 44:03 – Most interesting marketing channel for direct to consumer businesses 46:45 – Marketing piece he is most proud of 49:23 – Companies that embody the best of what has been discussed 52:31 – His love for people in business 53:41 – Kindest thing done for Michael   Learn More 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

Over the summer. I spent time with Abby Johnson, who is the chairman and CEO of Fidelity Investments and several other business leads at Fidelity to understand how a very large firm like theirs is navigating change in our industry. What follows is a condensed version of my various conversations with Abby and her team. We discuss the big buzzwords like blockchain and machine learning, but also thoughts on leadership, client centricity and measures of success. I hope you enjoyed this exploration 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   Show Notes 1:16 - (First Question) – [Abby] A look at the early part of Abby’s career 2:45 – Analyzing the skill of capital allocators 3:27 – A look at the asset management world of today and what to focus on today 7:23 – A set of decision-making principles that guide Abby 12:55 – Their strategy around the digitization of the world 16:07 – Balance between robo-advisors and humans and the markers of a good relationship 18:24 – What is the future of the role of the human in these relationships 20:15 – Their interest in emerging technologies like Blockchain 24:50 – Will crypto be its own asset class in the future 25:58 – [TOM] State of the business and the most interesting points of change 28:14 – Who is winning the battle for the next generation of investors 29:24 – How much of the change in financial business is cyclical 30:17 – What are businesses doing right to bridge that generational gap 31:01 – What does the future of the asset management industry look like 32:13 – What technologies could impact the asset management business the most 33:44 – The difference between machine learning and AI in this format 35:26 – In what way will AI impact these processes and replace humans 36:41 – What has him most excited about the future 37:54 – Advice for people thinking about pursuing a career in financial services 39:20 – Markers of a business that would be attractive for the next generation to consider working for 40:33 – The importance of brand when thinking about their business and those they work with 41:57 – Ways of engendering trust from a branding prospective 43:20 – Kindest thing anyone has done for Tom 44:28 – [VIPIN] Building a team around AI 45:21 – Markers for a good data strategy 47:25 – Kindest thing anyone has done for Vipin 48:58 - [ABBY] – How Fidelity thinks about data as an investing initiative 50:24 – Differentiating attributes of good analysts and if they’ve changed 51:34 – Investor she has always enjoyed learning from 52:37 – Favorite Peter Lynch story 53:17 – Business lessons that people could take away from Abby 54:59 – The role of women in financial services and what can be done to improve the situation there 57:35 – Trends that Abby is most excited to explore 1:00:22 – Positives and negatives of being part of a family business 1:01:46 – Kindest thing anyone has done for Abby   Learn More 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