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Invest Like the Best

Patrick O'Shaughnessy

179
Followers
374
Plays
Invest Like the Best
Invest Like the Best

Invest Like the Best

Patrick O'Shaughnessy

179
Followers
374
Plays
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About Us

Exploring the ideas, methods, and stories of people that will help you better invest your time and money. Learn more and stay-up-to-date at InvestorFieldGuide.com

Latest Episodes

Daniel Ek – The Future of Audio

My guest this week is Daniel Ek, the founder and CEO of Spotify. In my conversations with Daniel, I’ve found him to be one of the most interesting and thoughtful business leaders in the world. You’ll see what I mean as you listen to our conversation. We talk about Spotify plenty, but what I so enjoy about Daniel is his way of thinking in systems and frameworks. He is committed to evolution, innovation, and growth for both himself and for Spotify and is on my shortlist of CEOs to emulate. This was one of my favorite conversations on the podcast, I hope you enjoy it. 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 1:21 – (first question) – Management lessons from a Dubai chocolate maker 4:54 – Trends shaping the business landscape today: globalization, automation, and digitation 7:51 – How he thinks about the vertical integration of his business and scale 10:37 – Are companies doing a good job adjusting to the changes in the global business landscape 14:44 – How does Spotify view scale moving forward 17:59 – What trends has he seen among creators as a result of the Spotify platform 20:32 – The community benefit that has been created by the platform 23:47 – Intimacy of audio 25:31 – Creating an environment that continues to spur innovation 29:12 – Star vs constellation business strategy 32:21 – Measuring network health 35:12 – Spotify Originals and what his competition in the video market is doing 39:36 – How podcasts play into the growth strategy 43:04 – How did he solve the problem of competing with free 47:21 – Is their strategy repeatable, going after fractured suppliers 49:02 – Role of the CEO in a startup 51:22 – Others who have taught him great business lessons 53:18 – Kindest thing anyone has done for Daniel 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

56 MIN5 d ago
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Daniel Ek – The Future of Audio

George Rzepecki – Investing in Africa

My guest this week is George Rzepecki, the found and managing partner Raba, an Africa focused investment firm. George is making investments across Africa in early-stage companies. Africa represents a fascinating opportunity: a huge and diverse population and enormous room for per capita GDP growth. We cover all aspects of investing in the continent, including unique potential rewards and risks. 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 1:18 – (first question) – Interest in emerging markets and the tech landscape in Africa 4:57 – Similarities across all of the different metro markets across Africa 8:05 – Why has the continent lagged behind the rest of the world 10:49 – What is the history and landscape of capital in the African continent 13:32 – The market opportunity given the demographics 15:44 – US investment/involvement in Africa 18:06 – Kinds of companies that he likes to invest in 23:26 – Initiatives and investments that could help lift the population out of poverty: finance 29:33 – The public marketplace landscape in Africa 31:49 – Capacity on the private side 34:24 – How the valuation of deals compares to other markets 36:13 – Unique risks in the investments they are making 38:28 – Most exciting trends or changes he is seeing 40:22 – The professional investor environment 43:25 – How to learn more and get involved 43:49 – China Africa Research Initiative 44:17 – China Africa Project 44:38 – Factfulness: Ten Reasons We're Wrong About the World--and Why Things Are Better Than You Think 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

46 MIN1 w ago
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George Rzepecki – Investing in Africa

Chad Cascarilla – The Future of Blockchain and Financial Services

My guest today is Chad Cascarilla, the CEO and co-founder of Paxos, which describes itself as a financial technology company “mobilizing assets at the speed of the internet.“ Thanks to more than 20 years of investing and financial services experience, Chad has a unique perspective on integrating blockchain technology with traditional systems. He also has one of my favorite bitcoin origin stories, which we explore. Before Paxos, Charles co-founded institutional asset management complex Cedar Hill Capital Partners in 2005 and its blockchain-focused venture capital subsidiary, Liberty City Ventures (LCV). Our conversation is less about cryptocurrencies and more about the history, current state, and potential future states of our financial system. 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 1:32 - (First Question) – His work in the finance world before crypto’s 5:12 – Experience navigating the subprime mortgage trend and what it taught him about blockchain 9:59 – The levers that matter in the financial services industry today vs when he first started 14:07 – Open vs closed money in financial services 19:16 – How slowdowns are different in the modern era 23:06 – What would lead to a major winding down of global debt 27:09 – What would be his focus as a traditional investor 29:21 – How he first got involved with bitcoin 29:47 – Elliott Wave Newsletter 31:53 – His measured view of Bitcoin and living through the volatility of it 32:03 – Bitcoin: A Peer-to-Peer Electronic Cash System 35:57 – Allocation of a portfolio which includes crypto 36:54 – His involvement and feelings on gold 37:56 – The formation of Paxos and the problem it exists to solve 41:34 – How Paxos is impacting the space 44:12 – Advantages of a private blockchain 43:59 – What is Pax Gold and how does it work 48:53 – Bad ways and situations to own gold 52:12 – Using a stable coin 56:00 – Biggest problem they are working on now 57:23 – What should people be paying attention to in the crypto currency space 59:23 – Coindesk Research Archive 59:39 – Has the influx of interest in crypto helped in other spaces 1:02:11 – Other lessons people should learn from his career 1:04:53 – Kindest thing anyone has done for Chad 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

66 MIN2 w ago
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Chad Cascarilla – The Future of Blockchain and Financial Services

Bill Gurley – Direct Listing vs. IPO

My guest this week is Bill Gurley, general partner at Benchmark Capital. Our conversation is about one specific issue that has popped up as a topic of interest in the investing community in recent months: the comparison between bringing a company public through a traditional IPO vs. what’s known as a direct listing. As a third party observer with no real dog in the hunt (as we don’t buy IPOs at O’Shaughnessy Asset Management), I thought this was a small and nuanced issue. I’ve therefore been surprised by the strength of opinions on both sides of this issue as I’ve explored it behind the scenes this past week. It feels almost like I’ve encountered a political third rail, where one side throws a lot of vitriol towards the other. To be clear, this episode is very much in favor of direct listings instead of traditional IPOs. For those that want a good discussion of the IPO process and its upsides, check out episode 173 of the Exponent podcast with Ben Thompson. Now please enjoy my very interesting conversation with Bill Gurley 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 1:22 - (First Question) – His view on the IPO process 5:42 – Will now be the turning point for IPO’s 6:40 – The engagement between a new company going public and their counterparty and the IPO process 13:38 – The math of capital costs 18:18 – Banks that underprice the IPO’s 20:45 – The psychology of IPO’s 23:14 – The pop in the IPO and the media 24:54 – The value that shareholders give vs VC’s 25:37 – The Green Shoots 28:17 – The lock-up 31:40 – Direct listings vs IPO’s 36:07 – Spotify’s CEO Reveals Why He’s Not Doing a Traditional IPO 38:23 – The capital raised in an IPO and diluting the company 40:18 – Privilege access and buy-side firms 43:33 – What will actually lead to changes in the IPO space 44:48 – Why he became so interested in the IPO space 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

47 MINSEP 24
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Bill Gurley – Direct Listing vs. IPO

[REPLAY] Albert Wenger - World After Capital - [Invest Like the Best, EP.80]

My guest this week is Albert Wenger, a managing partner at Union Square Ventures and the author of the book World After Capital. Albert studied economics at Harvard and earned a PhD in information from technology, but if you’d asked me to guess before looking those up, I’d have guessed that he studied philosophy because of how widely he has thought about the world and the impact of technology. Our conversation is about how technology is changing the world from an Industrial Age to a knowledge age. We explore how cryptocurrencies, low cost computing, and regulation will impact our future and why the transition may require delicate care. I loved this conversation because of my obsession with the concept of scarcity. We explore what has been scarce through time and what may be scarce in the future. Albert is one of the most interesting thinkers I’ve come across and was a pleasure to speak with. I hope you enjoy our conversation. Hash Power is presented by Fidelity Investments 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 Links Referenced World After Capital Show Notes 2:16 – (First Question) – Defining what it means to be human 2:58 – World After Capital 3:56 – Trans-humans vs neo-humans 4:37 – The concept of Qualia 5:25 – Albert’s investment philosophy= 8:27 – How Albert began his exploration into cryptocurrencies 12:59 – Most exciting things blockchains could enable 14:27 – How does Albert view blockchain technology from the view of an venture capital investor 17:00 - Why Albert thinks that the dominate cryptocurrency of our time may not exist just yet and what he is looking for in protocols that will become the leader in the space 20:16 – What are the central functions that will be important in cryptocurrencies 21:22 - The state of regulation in the cryptocurrency space 27:37 – What has Albert most excited for the future of blockchain 29:10 – The idea of universal basic income 32:26 – How do you solve the problem of giving money value in a world of universal basic income 35:00 – How scarcity has changed over time 39:01 – Role of financial capital in the last 200 years of civilization 42:39 – Are we as a society only capable of solving problems once they become an immediate threat 44:15 – Explaining the idea of attention as a scarce resource 47:56 – The two key drivers of change; zero marginal cost distribution and universality of computational power 53:13 - What should we as investors and inventors be focusing on as the new objective function 57:24 – Scariest aspect of this transition into the knowledge age 59:45 – Three basic freedoms we all seek; informational, economic, psychological 1:02:13 – Fermi’s paradox and the scarcity of attention 1:02:56 – How Albert thinks about his own day and wellbeing given all of this information 1:05:01 – Kindest thing anyone has done for Albert 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

66 MINSEP 17
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[REPLAY] Albert Wenger - World After Capital - [Invest Like the Best, EP.80]

[REPLAY] Deep Basin – Earning Alpha in Energy - [Invest Like the Best, EP.81]

My guest this week are Matt Smith and Ian singer of Deep Basin Capital, a hedge fund specializing in the energy sector. I first met Matt almost 10 years and, in that time, I’ve grown to respect him as much as any investor that I’ve ever met. Now having spent time with Ian, who specializes in oil and gas field exploration companies and the rest of the Deep Basin team, I have similar respect and admiration for all of them. Deep Basin does almost the exact opposite of what us quants do. In fact, their entire goal is to build a portfolio of mostly idiosyncratic or stock specific risk, the very thing us quants mostly remove from portfolios. Deep Basin positions the portfolio to make a series of carefully constructed bets, long and short, without taking market risk, style-factor risk, or even commodity risk. They use a hybrid fundamental and quantitative process which we explore in detail. This is definitely another good example of who we are all up against in public markets. What makes this story unique is that we are investors in Deep Basin’s management company and so have a clear interest in their ongoing success. Listeners know that I want to be as transparent as possible on this podcast so we event spend a little time telling the story about how it all came together a few years ago. I have learned a ton about investing from my countless hours with this team and hope that this conversation gives you a glimpse into what is happening at the cutting edge of investing in the world of hedge funds. Please enjoy my conversation with Deep Basin 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 Expectations Investing: Reading Stock Prices for Better Returns Show Notes 2:47 – (First Question) – Looking at the universe of the energy space that they are focusing on 7:48 – Breaking down the important components and their labels in this space 10:27 – What makes energy companies distinct from the broader market. 12:52 – How the isolate unique value creation 14:58 – Ian’s take on the upstream part of the business where he has spent a lot of time 18:35 – How does Deep Basin use data and what edge do they derive from it. 21:31 – What insight are they looking for from updated well data 23:59 – How do they use combine the business value that they measure with the market price that is being forecasted 24:40 – Expectations Investing: Reading Stock Prices for Better Returns 29:34 – How do they build an actual portfolio 31:51 – Their systematic approach to energy investing 37:53 – What are their thoughts about using leverage when making investments in the energy space 40:53 – A look at the changes to the hedge fund industry over the entirety of their careers 45:46 – Defining the culture of Deep Basin 49:15 – The story of how OSAM and the O’Shaughnessy’s came to be investors in the Deep Basin 54:13 – Kindest thing anyone has done for each of them 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

54 MINSEP 11
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[REPLAY] Deep Basin – Earning Alpha in Energy - [Invest Like the Best, EP.81]

[REPLAY] Pat Dorsey - Buying Companies With Economic Moats [Invest Like the Best, Episode 51]

My guest this week is Pat Dorsey, who was the longtime director of equity research at Morningstar, where he specialized in economic moats: sources of sustained competitive advantage that allow a few companies to deliver huge returns over time. Several years ago he left Morningstar to form his own asset management firm, Dorsey asset management, and build a portfolio of companies with wide moats like those he studied at Morningstar. And while moats are critical, equally important is how companies allocate the capital generated--or made possible--by the existence of the moat. A special thank you to Brian Bares who introduced me to Pat, and to Will Thorndike--an earlier guest on the show. In the vast majority of conversations you hear on this show, I'm meeting the guest for the first time. I mention this to encourage you to connect me with anyone whose story or way of looking at the world might resonate. Always feel free to contact me with ideas. Pat and I begin our discussion with the key differences between the sell side and the buy side, and then discuss all aspects of moats and capital allocation. For comprehensive show notes on this episode go tohttp://investorfieldguide.com/dorsey For more episodes go toInvestorFieldGuide.com/podcast. To get involved with Project Frontier, head toInvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month atInvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at@patrick_oshag Show Notes 2:23 – (First question) – Transition from the sell side to the buy side and the biggest surprise 3:40 – What is a moat 5:16 – What part of the stock market universe has a moat 6:57 – Pat’s framework for identifying moat, starting with intangibles 8:32 – The power of brands 9:44 – what chance does an upstart have to come in and usurp a well-established brand 12:24 – Switching costs as part of the framework for identifying a moat 14:55 – The third component of identifying a moat, network effects, and what businesses should do to effectively build one 17:29 – Last component, cost advantages/economies of scale 19:29 – How do you analyze these four components into an investing framework that can be built into an actual strategy 21:13 – How does Pat think about this from a mis-pricing standpoint 23:37 – How does Pat incorporate current price of a company in consideration for future returns when pricing a moat 25:39 – How should a company with a moat operate to protect that characteristic, especially when it comes to their capital allocation 26:51 – Which characteristic of a moat does Pat find most intriguing 30:35 – What makes for good and smart capital allocation 35:58 – What is Pat’s process for identifying the best investment opportunities 38:38 – What are good economics when looking at a company 41:03 – If Pat could take any business, but have to swap leadership, what would he choose. 44:13 – Back to his process of finding investment opportunities 46:05 – Kindest thing anyone has ever done for Pat Learn More For more episodes go toInvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month atInvestorFieldGuide.com/bookclub Follow Patrick on twitter at@patrick_oshag Read more at https://investlikethebest.libsyn.com/pat-dorsey-buying-companies-with-economic-moats-invest-like-the-best-ep51#oBGdOp1br4EMtORd.99

50 MINAUG 27
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[REPLAY] Pat Dorsey - Buying Companies With Economic Moats [Invest Like the Best, Episode 51]

Joe McLean – How to be a Pro’s Pro

My guest this week is Joe McLean, the founder of Intersect Capital, which provides financial advisory services to a variety of clients, including a number of NBA players and other professional athletes. What I loved about this conversation was the weaving of sport, coaching, and finance into a cohesive whole. There’s so much to take from this discussion—from the importance of service and low self-orientation to the impact of strict standards for who you work with, to common mistakes we all tend to make with money. Please enjoy my conversation with Joe McLean. 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 1:18 - (First Question) – His backstory and the combination of athleticism and finance 2:43 – His time in Ireland 3:29 – Moving away from basketball and into finance 6:08 – What the Intersect business is today and his early lessons 7:55 – Most important coach/mentor 8:59 – Where the name Intersect came from 10:22 – Setting high standards early on 12:35 – Biggest mistakes he saw in his early clients 14:04 – Developing his value proposition to clients 14:24 – Michael Kitces Podcast Episode 16:57 – Process when he’s working with a client signing a new athletic contract 19:53 – The concept of a Pro’s Pro and Top 50 Reasons Professional Athletes Remain Wealthy 22:40 – Managing clients’ interest in creating businesses off their brand 24:20 – The role media plays in athletes’ long-term strategies 25:40 – Getting early clients into compliance with his strategy 28:24 – Daily maintenance role he plays with clients 32:24 – What has impressed him most from his young clients 33:36 – What makes for a great coach 34:50 – The meaning of “all in” to Joe 35:54 – His assessment of the financial services industry today 37:32 – Where his value in service came from 39:05 – Longer term vision for his business 40:33 – Unique ways he finds himself helping his clients 43:49 – Watching his client’s mentor the next generation 45:10 – Historical players and teams he personally admires 46:22 – Athletes and venture capital investing 47:38 – Who makes up his trust network 49:09 – What he’s most excited about for the future of the business 49:46 – Kindest thing anyone has done for Joe 50:24 – Biggest impact a coach had on his life 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

52 MINAUG 20
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Joe McLean – How to be a Pro’s Pro

Zack Kanter – All Things Business

This week’s guest is, Zack Kanter, the founder and CEO of the Stedi. Zack and I decided not to talk much about his business on this podcast and opted instead to explore more generally, so a bit of an introduction to what they do may be helpful here for some extra context. Stedi is a platform for exchanging and automating 300+ types of business-to-business transactions - transactions like purchase orders, invoices, etc. It’s a modern take on an archaic protocol called EDI - electronic data interchange, something I’d never even heard of until several months ago. Learning about EDI is a bit like finding out about the Matrix - every physical object you come across, from the food you ate for breakfast to the clothes you’re wearing and consumer electronics you use - anything with a barcode on it - was likely touched by EDI, often dozens of times before making it into your hands. Stedi is the first update to this messaging later in decades. Our conversation in this podcast is about business in general, starting with Zack’s fascination with Walmart and Amazon. I should also not that my family is a recent investor in Stedi, and I’m thankful to have learned a great deal from him over the past few months. 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 1:52 - (First Question) – Interest in Walmart and Amazon 4:02 – Sam Walton: Made In America 4:49 – What from their success can be applied elsewhere 11:07– The idea of tempo with a business 17:17 – Ability for a business to expand laterally 24:33 - Magic of Amazon as a constitution 26:24 – The concept of the OODA loop 26:40 – Boyd: The Fighter Pilot Who Changed the Art of War 31:51 – Orientation within software businesses 32:24 – The Systems Bible: The Beginner's Guide to Systems Large and Small 38:03 – Lessons in building software 38:37– Certain to Win: The Strategy of John Boyd, Applied to Business 41:51 – Setting a common vision for a company 44:14 – Changing the dynamic of teams and how different size teams can accomplish different things 48:00 – How leaders should think about build vs buy 51:07 – The different types of value propositions 53:07 – Utility for companies 57:31 – Concept of network health and the best question from VCs 1:04:04 – Massive projects are less frequent in a world where we can do a lot quickly 1:04:08 – Wait but Why 1:09:37 – Just in time vs just in case learning framework 1:11:55 – His favorite question 1:13:39 – Why is most commonly heard advice wrong 1:18:06 – Kindest thing anyone has done for Zack 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

82 MINAUG 13
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Zack Kanter – All Things Business

Chris Bloomstran – What Makes a Quality Company

My guest this week is Chris Bloomstran, the president and chief investment officer of Semper Augustus Investments Group. He became famous in investing circles a few years back for his incredibly detailed investigations of Berkshire Hathaway. While we do cover Berkshire towards the end of the conversation, we spend most of our time talking about what makes for a quality business. I loved some of his angles on the current landscape, including our discussion of companies like Richemont and Disney which are actively taking distribution back in house. 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 1:18 - (First Question) – Largest investing error 4:52 – Defining quality investor and their investment strategy 11:48 – Incremental return on capital and...

77 MINAUG 6
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Chris Bloomstran – What Makes a Quality Company

Latest Episodes

Daniel Ek – The Future of Audio

My guest this week is Daniel Ek, the founder and CEO of Spotify. In my conversations with Daniel, I’ve found him to be one of the most interesting and thoughtful business leaders in the world. You’ll see what I mean as you listen to our conversation. We talk about Spotify plenty, but what I so enjoy about Daniel is his way of thinking in systems and frameworks. He is committed to evolution, innovation, and growth for both himself and for Spotify and is on my shortlist of CEOs to emulate. This was one of my favorite conversations on the podcast, I hope you enjoy it. 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 1:21 – (first question) – Management lessons from a Dubai chocolate maker 4:54 – Trends shaping the business landscape today: globalization, automation, and digitation 7:51 – How he thinks about the vertical integration of his business and scale 10:37 – Are companies doing a good job adjusting to the changes in the global business landscape 14:44 – How does Spotify view scale moving forward 17:59 – What trends has he seen among creators as a result of the Spotify platform 20:32 – The community benefit that has been created by the platform 23:47 – Intimacy of audio 25:31 – Creating an environment that continues to spur innovation 29:12 – Star vs constellation business strategy 32:21 – Measuring network health 35:12 – Spotify Originals and what his competition in the video market is doing 39:36 – How podcasts play into the growth strategy 43:04 – How did he solve the problem of competing with free 47:21 – Is their strategy repeatable, going after fractured suppliers 49:02 – Role of the CEO in a startup 51:22 – Others who have taught him great business lessons 53:18 – Kindest thing anyone has done for Daniel 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

56 MIN5 d ago
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Daniel Ek – The Future of Audio

George Rzepecki – Investing in Africa

My guest this week is George Rzepecki, the found and managing partner Raba, an Africa focused investment firm. George is making investments across Africa in early-stage companies. Africa represents a fascinating opportunity: a huge and diverse population and enormous room for per capita GDP growth. We cover all aspects of investing in the continent, including unique potential rewards and risks. 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 1:18 – (first question) – Interest in emerging markets and the tech landscape in Africa 4:57 – Similarities across all of the different metro markets across Africa 8:05 – Why has the continent lagged behind the rest of the world 10:49 – What is the history and landscape of capital in the African continent 13:32 – The market opportunity given the demographics 15:44 – US investment/involvement in Africa 18:06 – Kinds of companies that he likes to invest in 23:26 – Initiatives and investments that could help lift the population out of poverty: finance 29:33 – The public marketplace landscape in Africa 31:49 – Capacity on the private side 34:24 – How the valuation of deals compares to other markets 36:13 – Unique risks in the investments they are making 38:28 – Most exciting trends or changes he is seeing 40:22 – The professional investor environment 43:25 – How to learn more and get involved 43:49 – China Africa Research Initiative 44:17 – China Africa Project 44:38 – Factfulness: Ten Reasons We're Wrong About the World--and Why Things Are Better Than You Think 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

46 MIN1 w ago
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George Rzepecki – Investing in Africa

Chad Cascarilla – The Future of Blockchain and Financial Services

My guest today is Chad Cascarilla, the CEO and co-founder of Paxos, which describes itself as a financial technology company “mobilizing assets at the speed of the internet.“ Thanks to more than 20 years of investing and financial services experience, Chad has a unique perspective on integrating blockchain technology with traditional systems. He also has one of my favorite bitcoin origin stories, which we explore. Before Paxos, Charles co-founded institutional asset management complex Cedar Hill Capital Partners in 2005 and its blockchain-focused venture capital subsidiary, Liberty City Ventures (LCV). Our conversation is less about cryptocurrencies and more about the history, current state, and potential future states of our financial system. 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 1:32 - (First Question) – His work in the finance world before crypto’s 5:12 – Experience navigating the subprime mortgage trend and what it taught him about blockchain 9:59 – The levers that matter in the financial services industry today vs when he first started 14:07 – Open vs closed money in financial services 19:16 – How slowdowns are different in the modern era 23:06 – What would lead to a major winding down of global debt 27:09 – What would be his focus as a traditional investor 29:21 – How he first got involved with bitcoin 29:47 – Elliott Wave Newsletter 31:53 – His measured view of Bitcoin and living through the volatility of it 32:03 – Bitcoin: A Peer-to-Peer Electronic Cash System 35:57 – Allocation of a portfolio which includes crypto 36:54 – His involvement and feelings on gold 37:56 – The formation of Paxos and the problem it exists to solve 41:34 – How Paxos is impacting the space 44:12 – Advantages of a private blockchain 43:59 – What is Pax Gold and how does it work 48:53 – Bad ways and situations to own gold 52:12 – Using a stable coin 56:00 – Biggest problem they are working on now 57:23 – What should people be paying attention to in the crypto currency space 59:23 – Coindesk Research Archive 59:39 – Has the influx of interest in crypto helped in other spaces 1:02:11 – Other lessons people should learn from his career 1:04:53 – Kindest thing anyone has done for Chad 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

66 MIN2 w ago
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Chad Cascarilla – The Future of Blockchain and Financial Services

Bill Gurley – Direct Listing vs. IPO

My guest this week is Bill Gurley, general partner at Benchmark Capital. Our conversation is about one specific issue that has popped up as a topic of interest in the investing community in recent months: the comparison between bringing a company public through a traditional IPO vs. what’s known as a direct listing. As a third party observer with no real dog in the hunt (as we don’t buy IPOs at O’Shaughnessy Asset Management), I thought this was a small and nuanced issue. I’ve therefore been surprised by the strength of opinions on both sides of this issue as I’ve explored it behind the scenes this past week. It feels almost like I’ve encountered a political third rail, where one side throws a lot of vitriol towards the other. To be clear, this episode is very much in favor of direct listings instead of traditional IPOs. For those that want a good discussion of the IPO process and its upsides, check out episode 173 of the Exponent podcast with Ben Thompson. Now please enjoy my very interesting conversation with Bill Gurley 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 1:22 - (First Question) – His view on the IPO process 5:42 – Will now be the turning point for IPO’s 6:40 – The engagement between a new company going public and their counterparty and the IPO process 13:38 – The math of capital costs 18:18 – Banks that underprice the IPO’s 20:45 – The psychology of IPO’s 23:14 – The pop in the IPO and the media 24:54 – The value that shareholders give vs VC’s 25:37 – The Green Shoots 28:17 – The lock-up 31:40 – Direct listings vs IPO’s 36:07 – Spotify’s CEO Reveals Why He’s Not Doing a Traditional IPO 38:23 – The capital raised in an IPO and diluting the company 40:18 – Privilege access and buy-side firms 43:33 – What will actually lead to changes in the IPO space 44:48 – Why he became so interested in the IPO space 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

47 MINSEP 24
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Bill Gurley – Direct Listing vs. IPO

[REPLAY] Albert Wenger - World After Capital - [Invest Like the Best, EP.80]

My guest this week is Albert Wenger, a managing partner at Union Square Ventures and the author of the book World After Capital. Albert studied economics at Harvard and earned a PhD in information from technology, but if you’d asked me to guess before looking those up, I’d have guessed that he studied philosophy because of how widely he has thought about the world and the impact of technology. Our conversation is about how technology is changing the world from an Industrial Age to a knowledge age. We explore how cryptocurrencies, low cost computing, and regulation will impact our future and why the transition may require delicate care. I loved this conversation because of my obsession with the concept of scarcity. We explore what has been scarce through time and what may be scarce in the future. Albert is one of the most interesting thinkers I’ve come across and was a pleasure to speak with. I hope you enjoy our conversation. Hash Power is presented by Fidelity Investments 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 Links Referenced World After Capital Show Notes 2:16 – (First Question) – Defining what it means to be human 2:58 – World After Capital 3:56 – Trans-humans vs neo-humans 4:37 – The concept of Qualia 5:25 – Albert’s investment philosophy= 8:27 – How Albert began his exploration into cryptocurrencies 12:59 – Most exciting things blockchains could enable 14:27 – How does Albert view blockchain technology from the view of an venture capital investor 17:00 - Why Albert thinks that the dominate cryptocurrency of our time may not exist just yet and what he is looking for in protocols that will become the leader in the space 20:16 – What are the central functions that will be important in cryptocurrencies 21:22 - The state of regulation in the cryptocurrency space 27:37 – What has Albert most excited for the future of blockchain 29:10 – The idea of universal basic income 32:26 – How do you solve the problem of giving money value in a world of universal basic income 35:00 – How scarcity has changed over time 39:01 – Role of financial capital in the last 200 years of civilization 42:39 – Are we as a society only capable of solving problems once they become an immediate threat 44:15 – Explaining the idea of attention as a scarce resource 47:56 – The two key drivers of change; zero marginal cost distribution and universality of computational power 53:13 - What should we as investors and inventors be focusing on as the new objective function 57:24 – Scariest aspect of this transition into the knowledge age 59:45 – Three basic freedoms we all seek; informational, economic, psychological 1:02:13 – Fermi’s paradox and the scarcity of attention 1:02:56 – How Albert thinks about his own day and wellbeing given all of this information 1:05:01 – Kindest thing anyone has done for Albert 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

66 MINSEP 17
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[REPLAY] Albert Wenger - World After Capital - [Invest Like the Best, EP.80]

[REPLAY] Deep Basin – Earning Alpha in Energy - [Invest Like the Best, EP.81]

My guest this week are Matt Smith and Ian singer of Deep Basin Capital, a hedge fund specializing in the energy sector. I first met Matt almost 10 years and, in that time, I’ve grown to respect him as much as any investor that I’ve ever met. Now having spent time with Ian, who specializes in oil and gas field exploration companies and the rest of the Deep Basin team, I have similar respect and admiration for all of them. Deep Basin does almost the exact opposite of what us quants do. In fact, their entire goal is to build a portfolio of mostly idiosyncratic or stock specific risk, the very thing us quants mostly remove from portfolios. Deep Basin positions the portfolio to make a series of carefully constructed bets, long and short, without taking market risk, style-factor risk, or even commodity risk. They use a hybrid fundamental and quantitative process which we explore in detail. This is definitely another good example of who we are all up against in public markets. What makes this story unique is that we are investors in Deep Basin’s management company and so have a clear interest in their ongoing success. Listeners know that I want to be as transparent as possible on this podcast so we event spend a little time telling the story about how it all came together a few years ago. I have learned a ton about investing from my countless hours with this team and hope that this conversation gives you a glimpse into what is happening at the cutting edge of investing in the world of hedge funds. Please enjoy my conversation with Deep Basin 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 Expectations Investing: Reading Stock Prices for Better Returns Show Notes 2:47 – (First Question) – Looking at the universe of the energy space that they are focusing on 7:48 – Breaking down the important components and their labels in this space 10:27 – What makes energy companies distinct from the broader market. 12:52 – How the isolate unique value creation 14:58 – Ian’s take on the upstream part of the business where he has spent a lot of time 18:35 – How does Deep Basin use data and what edge do they derive from it. 21:31 – What insight are they looking for from updated well data 23:59 – How do they use combine the business value that they measure with the market price that is being forecasted 24:40 – Expectations Investing: Reading Stock Prices for Better Returns 29:34 – How do they build an actual portfolio 31:51 – Their systematic approach to energy investing 37:53 – What are their thoughts about using leverage when making investments in the energy space 40:53 – A look at the changes to the hedge fund industry over the entirety of their careers 45:46 – Defining the culture of Deep Basin 49:15 – The story of how OSAM and the O’Shaughnessy’s came to be investors in the Deep Basin 54:13 – Kindest thing anyone has done for each of them 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

54 MINSEP 11
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[REPLAY] Deep Basin – Earning Alpha in Energy - [Invest Like the Best, EP.81]

[REPLAY] Pat Dorsey - Buying Companies With Economic Moats [Invest Like the Best, Episode 51]

My guest this week is Pat Dorsey, who was the longtime director of equity research at Morningstar, where he specialized in economic moats: sources of sustained competitive advantage that allow a few companies to deliver huge returns over time. Several years ago he left Morningstar to form his own asset management firm, Dorsey asset management, and build a portfolio of companies with wide moats like those he studied at Morningstar. And while moats are critical, equally important is how companies allocate the capital generated--or made possible--by the existence of the moat. A special thank you to Brian Bares who introduced me to Pat, and to Will Thorndike--an earlier guest on the show. In the vast majority of conversations you hear on this show, I'm meeting the guest for the first time. I mention this to encourage you to connect me with anyone whose story or way of looking at the world might resonate. Always feel free to contact me with ideas. Pat and I begin our discussion with the key differences between the sell side and the buy side, and then discuss all aspects of moats and capital allocation. For comprehensive show notes on this episode go tohttp://investorfieldguide.com/dorsey For more episodes go toInvestorFieldGuide.com/podcast. To get involved with Project Frontier, head toInvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month atInvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at@patrick_oshag Show Notes 2:23 – (First question) – Transition from the sell side to the buy side and the biggest surprise 3:40 – What is a moat 5:16 – What part of the stock market universe has a moat 6:57 – Pat’s framework for identifying moat, starting with intangibles 8:32 – The power of brands 9:44 – what chance does an upstart have to come in and usurp a well-established brand 12:24 – Switching costs as part of the framework for identifying a moat 14:55 – The third component of identifying a moat, network effects, and what businesses should do to effectively build one 17:29 – Last component, cost advantages/economies of scale 19:29 – How do you analyze these four components into an investing framework that can be built into an actual strategy 21:13 – How does Pat think about this from a mis-pricing standpoint 23:37 – How does Pat incorporate current price of a company in consideration for future returns when pricing a moat 25:39 – How should a company with a moat operate to protect that characteristic, especially when it comes to their capital allocation 26:51 – Which characteristic of a moat does Pat find most intriguing 30:35 – What makes for good and smart capital allocation 35:58 – What is Pat’s process for identifying the best investment opportunities 38:38 – What are good economics when looking at a company 41:03 – If Pat could take any business, but have to swap leadership, what would he choose. 44:13 – Back to his process of finding investment opportunities 46:05 – Kindest thing anyone has ever done for Pat Learn More For more episodes go toInvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month atInvestorFieldGuide.com/bookclub Follow Patrick on twitter at@patrick_oshag Read more at https://investlikethebest.libsyn.com/pat-dorsey-buying-companies-with-economic-moats-invest-like-the-best-ep51#oBGdOp1br4EMtORd.99

50 MINAUG 27
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[REPLAY] Pat Dorsey - Buying Companies With Economic Moats [Invest Like the Best, Episode 51]

Joe McLean – How to be a Pro’s Pro

My guest this week is Joe McLean, the founder of Intersect Capital, which provides financial advisory services to a variety of clients, including a number of NBA players and other professional athletes. What I loved about this conversation was the weaving of sport, coaching, and finance into a cohesive whole. There’s so much to take from this discussion—from the importance of service and low self-orientation to the impact of strict standards for who you work with, to common mistakes we all tend to make with money. Please enjoy my conversation with Joe McLean. 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 1:18 - (First Question) – His backstory and the combination of athleticism and finance 2:43 – His time in Ireland 3:29 – Moving away from basketball and into finance 6:08 – What the Intersect business is today and his early lessons 7:55 – Most important coach/mentor 8:59 – Where the name Intersect came from 10:22 – Setting high standards early on 12:35 – Biggest mistakes he saw in his early clients 14:04 – Developing his value proposition to clients 14:24 – Michael Kitces Podcast Episode 16:57 – Process when he’s working with a client signing a new athletic contract 19:53 – The concept of a Pro’s Pro and Top 50 Reasons Professional Athletes Remain Wealthy 22:40 – Managing clients’ interest in creating businesses off their brand 24:20 – The role media plays in athletes’ long-term strategies 25:40 – Getting early clients into compliance with his strategy 28:24 – Daily maintenance role he plays with clients 32:24 – What has impressed him most from his young clients 33:36 – What makes for a great coach 34:50 – The meaning of “all in” to Joe 35:54 – His assessment of the financial services industry today 37:32 – Where his value in service came from 39:05 – Longer term vision for his business 40:33 – Unique ways he finds himself helping his clients 43:49 – Watching his client’s mentor the next generation 45:10 – Historical players and teams he personally admires 46:22 – Athletes and venture capital investing 47:38 – Who makes up his trust network 49:09 – What he’s most excited about for the future of the business 49:46 – Kindest thing anyone has done for Joe 50:24 – Biggest impact a coach had on his life 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

52 MINAUG 20
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Joe McLean – How to be a Pro’s Pro

Zack Kanter – All Things Business

This week’s guest is, Zack Kanter, the founder and CEO of the Stedi. Zack and I decided not to talk much about his business on this podcast and opted instead to explore more generally, so a bit of an introduction to what they do may be helpful here for some extra context. Stedi is a platform for exchanging and automating 300+ types of business-to-business transactions - transactions like purchase orders, invoices, etc. It’s a modern take on an archaic protocol called EDI - electronic data interchange, something I’d never even heard of until several months ago. Learning about EDI is a bit like finding out about the Matrix - every physical object you come across, from the food you ate for breakfast to the clothes you’re wearing and consumer electronics you use - anything with a barcode on it - was likely touched by EDI, often dozens of times before making it into your hands. Stedi is the first update to this messaging later in decades. Our conversation in this podcast is about business in general, starting with Zack’s fascination with Walmart and Amazon. I should also not that my family is a recent investor in Stedi, and I’m thankful to have learned a great deal from him over the past few months. 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 1:52 - (First Question) – Interest in Walmart and Amazon 4:02 – Sam Walton: Made In America 4:49 – What from their success can be applied elsewhere 11:07– The idea of tempo with a business 17:17 – Ability for a business to expand laterally 24:33 - Magic of Amazon as a constitution 26:24 – The concept of the OODA loop 26:40 – Boyd: The Fighter Pilot Who Changed the Art of War 31:51 – Orientation within software businesses 32:24 – The Systems Bible: The Beginner's Guide to Systems Large and Small 38:03 – Lessons in building software 38:37– Certain to Win: The Strategy of John Boyd, Applied to Business 41:51 – Setting a common vision for a company 44:14 – Changing the dynamic of teams and how different size teams can accomplish different things 48:00 – How leaders should think about build vs buy 51:07 – The different types of value propositions 53:07 – Utility for companies 57:31 – Concept of network health and the best question from VCs 1:04:04 – Massive projects are less frequent in a world where we can do a lot quickly 1:04:08 – Wait but Why 1:09:37 – Just in time vs just in case learning framework 1:11:55 – His favorite question 1:13:39 – Why is most commonly heard advice wrong 1:18:06 – Kindest thing anyone has done for Zack 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

82 MINAUG 13
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Zack Kanter – All Things Business

Chris Bloomstran – What Makes a Quality Company

My guest this week is Chris Bloomstran, the president and chief investment officer of Semper Augustus Investments Group. He became famous in investing circles a few years back for his incredibly detailed investigations of Berkshire Hathaway. While we do cover Berkshire towards the end of the conversation, we spend most of our time talking about what makes for a quality business. I loved some of his angles on the current landscape, including our discussion of companies like Richemont and Disney which are actively taking distribution back in house. 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 1:18 - (First Question) – Largest investing error 4:52 – Defining quality investor and their investment strategy 11:48 – Incremental return on capital and...

77 MINAUG 6
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Chris Bloomstran – What Makes a Quality Company

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