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

My guest this week is Keith Rabois. Keith is currently an investment partner at Khosla Ventures, but has a storied and diverse background as an investor, entrepreneur, and executive. He has worked in senior positions at Paypal, LinkedIn, and Square; has led investments in companies like Stripe, YouTube, Palantir, and AirBnB; and started the company OpenDoor, which aims to transform the process of selling a home through technology. One fun fact about Keith is that he may have the most impressive list of bosses I’ve ever seen, which we discuss during the episode. We cover a lot, but one thing we kept returning to was business strategy. Keith’s frameworks for gaining and building strategic power helped me clarify my thinking on the topic, and his examples of contrarian thinking will hopefully make you question some commonly held beliefs. 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 1:35  (First Question) – A look at his investing philosophy 3:16  – Favorite examples of his own investment history             4:40 – 7 Powers: The Foundations of Business Strategy 5:07 – Understanding what is anomalous in a given investment 7:07 – How much a secret needs to be protected within a business 11:51 – Why accumulating advantage with data is of interest to Keith 15:12 – Digital health companies and ideas that he finds compelling 16:17 – Nuance around financial services that investors should be mindful of 17:56 – How do they evaluate managers ability to recruit talent 19:36 – How similar are the roles of entrepreneur, board member, investor, etc that Keith has had in his career 24:02 – Ways that Keith is a contrarian, including his feelings on “lean startup.” 27:04 – Is problem identification a specific skill set 28:29 – Objection with experimentation/iteration 30:02 – Bad ideas in venture 31:36 – What he likes about Apple             31:51 – Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs 32:26 - Interview questions for identifying great talent 35:41 – Elements of good design 37:14 – Impact of platforms on opening new opportunities 38:42 – His take on valuation in the early stage environment 40:33 – Advice he would give people early in their careers 43:58 – Do high growth companies get beat by established larger businesses 45:25 – Popular narratives that he thinks are just wrong 48:22 – His thoughts on how people should learn, balancing experience vs information gathering 50:00 – Other investors that are taking a unique approach to investing 51:57 – Reflecting on the entrepreneur as a client model of private equity 55:04 – Books that he recommends that is least known             55:18 – The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It 56:30 – 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 Follow Patrick on twitter at @patrick_oshag

My guest today is Bryan Krug, who manages the Artisan Partners Credit Team and overseas more than $3B in high yield credit investments for the firm. This was my first conversation on high yield, so I took it as an opportunity to get an overview on the investment universe and home in on the tools used for analysis and security selection. As an equity investor, I think one of the most fruitful areas of research is into ways that companies fail or go wrong, and credit investors focus almost entirely on this potential for impairment. My guess is that all equity investors will learn something useful from this 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 2:11 – Overview of the high yield debt markets 5:05 – Why should investors consider this investment class 7:11 – How analyzing a company’s debt is different from what equity analysts look for 8:42 – Primary factors when exploring a company’s ability to de-lever 9:43 – What is their alpha vs others in the space 12:02 – Deep dive into the quantitative factors for them to look into a deal 14:25 – Benchmarks he uses 16:08 – Portfolio construction 17:15 – Their preference for broadband providers over cable tv networks 20:01 – What piques his interest about spreads 21:50 – The ratings of debt 25:40 – A recent example of an opportunity and how the mispricing was identified 29:17 – Most valuable data sets in this world 31:51 – Favorite part of this process 32:26 – Most surprising new learning 33:01 Maintaining your advantage 34:49 – The biggest pools of error in this industry 48:00 – What industries interest Bryan 40:50 – Dedication to this market 41:45 – Evolution of his healthy skepticism 42:38 – Can things in the debt market help to project what will happen in the equity markets 44:56 – Current view of the world based on what is happening in the credit markets 45:51 – Categories of convenience that he cares about 49:15 – Anything that has him worried in high yield markets 50:38 – Kindest thing anyone has done for Bryan   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 Maureen Chiquet, the former longtime CEO of Chanel. Maureen also spent much of her career at the Gap, growing Old Navy from scratch, and serving as the president of Banana Republic. The topic of discussion is her experience running large businesses and of finding one’s way in a career and as a leader of others. I hope you enjoy this unique conversation and that it encourages you to, among other things, travel somewhere new and interesting in the coming year. 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) – The importance of being able to put yourself in other people’s shoes             3:05 – Scott Norton Podcast Episode 4:36 – Most memorable sale from her early career 5:03 – The intersection of facts and emotions in sales 6:40 – Most important emotions in business 7:30 – The importance of identity as part of the selling/marketing of sales and products 9:10 – Difference in strategy for luxury brands vs others             9:21 – The Luxury Strategy: Break the Rules of Marketing to Build Luxury Brands 10:55 – Striking a balance between tradition and innovation 13:46 – Advice for new brand company related to rarity 14:59 – Importance of being organic with your brand purpose             15:01 – Wild Company: The Untold Story of Banana Republic 16:26 – Maureen’s purpose over the years 18:44 – How to harness your purpose for your job 20:53 – Her process for writing and desire to do TV 24:01 – Her time with Micky Drexler 27:40 – As a leader, guiding people to succeed. 32:33 – Strategy for shifting culture at a company 37:54 – The importance of courageous conversations we should all be having 43:45 – Markers of courageous conversations 46:43 – How she thinks about introspection 50:12 – What draws here to certain locations 55:15 – Advice for younger people starting out their career 57:11 – Kindest thing anyone has done for Maureen   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 Hunter Walk, the co-founder of Homebrew, a unique venture capital firm. Hunter is a tool builder, having spent his career before venture at companies like Google and YouTube. The topic of our conversation is the intersection of creative expression, technology, human behavior, and problem solving.  We discuss his time at the company behind the video game Second Life, building tools for creators at YouTube, and why a very hands-on style of early stage venture investing represents an interesting use of his skillset at this stage of his career.  Please enjoy my conversation with Hunter Walk. 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 1:24 - (First Question) – Background on Second Life and what role Hunter had there 6:10 – The virtual currency system at use in Second Life 9:51 – Measuring how people behaved in this virtual world 12:21 – How closely is the Second Life world mimicking real life 15:13 – The market for platforms that lets people take on creative ventures 17:58 – Investments that interest Homebrew 20:21 – Lessons learned while working at YouTube 28:34 – The idea behind Homebrew 33:44 – How to best describe good problems to solve for 36:10 – The Shadow economy and investing in companies operating there 42:17 – Monetization of attention 47:22 – His interest in fintech companies 54:03 – Major trends of change he’s observed over his first three funds 1:04:13 – What is there take on the state of returns for VC’s 1:09:52 – What is the most common way that founders need help and what advice is more helpful 1:14:35 – Kindest thing anyone has done for Hunter   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

[REPLAY] Modern Monopolies: What It Takes to Dominate the 21st Century Economy, which explores the platform business model (Uber, Airbnb, Github).  Alex is also the founder and CEO of Applico, a company that he started in his dorm room that is since grown into a huge enterprise that helps startups and Fortune 500 innovate with platforms.  Alex and I talk about history and future of businesses and different types of business models.  There’s a lot in here for investors, entrepreneurs, and historians.  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 Books Referenced Modern Monopolies: What It Takes to Dominate the 21st Century Economy The Systems Bible: The Beginner's Guide to Systems Large and Small The Master Switch: The Rise and Fall of Information Empires Zero to One: Notes on Startups, or How to Build the Future   Links Referenced Failed Color App Applico   Show Notes 2:39  – (first question) – Exploring the history of business models from linear to platform. 5:46 – A look at the share of overall business platform companies have taken over             7:06 - Modern Monopolies: What It Takes to Dominate the 21st Century Economy 7:48 – The potential for platform businesses over the next 20 years 9:18 – Detailing the difference between a linear and a platform business 12:08 – Exploring transaction costs and core transactions across different business models 19:49 – Is the platform business model good for investors and VC’s since so many can get crushed when there’s a sole victor, or is it just for the founders and entrepreneurs.  24:35 – How the self-driving car is going to deliver more opportunity for consumer consumption 27:15 – Untapped supplies as the opportunity for new platforms and where we could see new openings 30:24 – How consolidated will things become across all platforms 33:16 – How do platform companies create a moat to keep others from replicating their business strategy 37:03 – Are there platform strategies that specifically don’t work             37:40 - Failed Color App 38:45 – Why complex systems typically don’t scale up and you should think small and easy to get started             38:47 – The Systems Bible: The Beginner's Guide to Systems Large and Small 40:02 – How the origin of so many larger companies started out small and localized, and why it makes investors more comfortable 41:37 – How Alibaba had to tweak their business model to accommodate the Chinese market 44:07 – Why are the modern monopolies better for consumers 47:52 – Exploring platforms that are asset heavy 49:00 – What do you look for as a VC to determine 52:05 – Alex’s take on whether a platform based company like Uber should be more asset heavy 54:31 – Exploring some lesser known platform businesses that Alex finds interesting 56:18 – If there is a demand in the secondary markets for a product, why don’t the primary suppliers simply raise their prices 57:03 – What Alex’s portfolio of platform-based businesses would look like 58:48 – A couple of most influential books Alex has read             59:12 – The Master Switch: The Rise and Fall of Information Empires             59:38 – Zero to One: Notes on Startups, or How to Build the Future and other Peter Thiel books 59:53 – Looking at Applico, how it started and how it become so focused on the platform business model 1:03:56 - Most memorable day for Alex  1:05:13 – Kindest person to Alex in his life 1:06:10 – What platform opportunities could exist in the financial world 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