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    Business

    Invest Like the Best with Patrick O’Shaughnessy

    Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can’t find anywhere else. If you’re a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.colossus.com

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    Latest Episodes:
    Ira Judelson - Bail Street, with NYC's Leading Bail Bondsman - [Invest Like the Best, EP.40] Jun 06, 2017
    Show notes

    This week’s episode is very unique. It is the first episode devoted to bonds, just not the kind of bonds you are used to. My guest is Ira Judelson, who is the leading bail bondsman in New York City. I met Ira through my friend and former podcast guest Danny Moses, who is also a part of this conversation.

    I have always had a passion for understanding how different businesses work. In this case, this week we are exploring a different business, but also a different world. Ira’s story is larger than life. He is as authentic and hard working as they come. In both his book and this conversation, there is a lot about family, loyalty, and hard work—principles which really resonate with me.

    You’ll emerge from this hour with an appreciation of hustle and what it takes to get ahead. I can’t stop thinking about our discussion on how sources of power in any career morph through time, a framework that can help anyone think about their work and where to apply effort.

    The conversation goes all over the place, but suffice it to say we discuss bond collateral, Dominique Strauss-Kahn, and DMX—and that is but one small fraction.

    Please enjoy my conversation with Ira Judelson and Danny Moses.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/ira

    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

    The Fixer: The Notorious Life of a Front-Page Bail Bondsman

    Links Referenced

    Rao’s Restaurant

    Show Notes

    1:55 – (First question) – The role that Rao’s restaurant has meant to Ira’s business and career

    6:11 – A look at Ira’s bail bonds business and how that industry works

    6:22 – The Fixer: The Notorious Life of a Front-Page Bail Bondsman

    8:31 – The story of how a pizzeria was a bad piece of collateral

    11:10 – How often does Ira deal with bail jumpers

    12:10 – What is the size of the open liabilities

    13:14 – How long will the open liabilities last

    14:55 – Ira’s relationship with his clients and the importance of character in this business

    17:46 – the amazing story of how Ira got started in this business

    31:05 – His early years of being a bail bondsman and how important his wife was to his success

    29:52 – How Ira balances family with this kind of work

    32:22 – Ira’s ability to be amazingly efficient on the phone when in social settings and a work call comes in

    33:14 – Ira is the fixer

    36:40 – Exploring the “Sources of Power” and where the balance for Ira of who he knows vs who he has shifted in this line of work.

    38:29 – The importance of intense reliability, consistency and empathy, and why Ira can trust his clients may be considered bad people

    30:19 – Two cases where Ira got emotionally involved

    47:26 – Why Ira is not worried about people coming after him

    48:57 – When a bunch of detainees were wailing to wait an extra day in jail for Ira because his wife was pregnant with their first daughter

    54:06 – Ira’s relationships with Ja Rule and DMX

    58:32 – What does Ira enjoy most about the business still

    1:01:51 – Will Ira ever stop?

    1:04:02 – What advice would Ira give to someone early in their career just getting started

    1:08:42 – The importance in having a willingness to fail mixed with the passion for what you are doing

    1:10:11 – Ira’s health scare and what it taught him about appreciating life


    David Chilton - The Human Blitzkrieg - [Invest Like the Best, EP.39] May 30, 2017
    Show notes

    This week's conversation was especially fun. I have a long history with my guest, Dave Chilton, but this was the first time we'd met in person. I'd heard stories about him from people I work with for twenty years, so getting to finally spend time with him was a real treat. I'll let him reveal the connection.

    This episode will also be fun for listeners in the US, as Dave is one of the best-known people in Canada because of his famous book the wealthy barber and his more recent stint as a dragon on Dragon’s Den, which is Canada's version of shark tank.

    I called this episode the human blitzkrieg because of Dave's relentlessly positive style and curiosity. He has dabbled in many parts of the business and investing worlds. He is one of the most successful authors in history, has invested in dozens of interesting businesses, and is a Jedi master in the long-lost art of the phone conversation.

    We discuss business, investing, and writing. If you enjoy this conversation and have any aspirations as a writer, I highly recommend you check out the series of videos Dave and his son recently released called the Chilton method, which I will link in the show notes. I have no financial interest in this recommendation, and neither does Dave! He put it together in large part to stop people from calling him for advice. We discuss a few of the hundred plus lessons from his course in this conversation.

    As you'll be able to tell early and often, it is hard not to have a good time with Dave.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/chilton

    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


    David Salem - The Art of Asset Allocation - [Invest Like the Best, EP.38] May 23, 2017
    Show notes

    My guest this week is David Salem. David was the founding president and CIO for The Investment Fund for Foundations, which served 800 endowed charities under David’s 18-year tenure. He's now the CIO of the Windhorse Group, which focuses on long-term, value oriented investing.

    This conversation wanders into and explores many different areas of investing and life. The theme is how to think about asset allocation and investing holistically--from first principles--but we talk a lot about motivation, incentives, human behavior, and the fear of missing out as key variables in money management.

    We discuss the history of the Yale and Harvard endowment models and how their success has affected the asset management world for better or worse. I had never heard such an interesting take on two very important institutions.

    I also can't stop thinking about David’s "Mt. Everest" question, which we explore early in our conversation. I'd love to hear your answers to that question, so email me or message me with your thoughts.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/salem

    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


    Michael Mauboussin - Man + Machine, Moats, and Power of the Outside View - [Invest Like the Best, EP.37] May 16, 2017
    Show notes

    My guest today is Michael Mauboussin, who is the head of global financial strategies at Credit Suisse and is on my short list of must read writers on all things investing. If you read his entire catalogue, Howard Marks's memos, and Buffett's shareholder letters, you be sitting pretty. Michael was also a big reason for the early success of this show appearing as my second guest and now my 37th. He and his team have been prolific in the last six months, publishing several long research reports on the most interesting aspects of the investing landscape. In this conversation, we talk about business moats, industry analysis, and how to combine man and machine when building an investment strategy and portfolio. As I tell Michael at the end, you won't be able to listen to this episode at two times speed, because we go deep quickly.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/michael

    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


    Will Thorndike - How Skilled Capital Allocators Compound Capital - [Invest Like the Best, EP.36] May 09, 2017
    Show notes

    This week’s guest is Will Thorndike, an author and investor whose book The Outsiders is an all-time favorite of mine. Our conversation is in two parts. First, we dive deep into the lessons of his 8-year research project studying CEOs who were master capital allocators. These CEOs include Henry Singleton, John Malone, Tom Murphy, Katherine Graham, and Warren Buffett. We discuss how these CEOs tended to be contrarians on topics like dividends, buybacks, acquisitions, and the use of debt. As we go through each of the tools in the capital allocators toolkit, you’ll hear several useful lessons for running or evaluating a business.

    In the second part, we cover Will’s career in private equity. Will founded and continues to run Housatonic Partners, investing in buyouts, recaps, and search funds. Will has been one of the most active search fund investors for decades, and given how much time I’ve spent in past episodes on the searchers or operators in the micro-cap, permanent equity space, it was great to get the perspective of an experienced LP. As always, we also take time to survey the dangers and opportunities in today’s private equity market.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/thorndike

    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


    Ted Seides - The Bet with Buffett – Hedge Funds vs. The S&P 500 - [Invest Like the Best, EP.35] May 02, 2017
    Show notes

    This coming weekend is the annual Berkshire Hathaway shareholder meeting in Omaha. That means this week is the perfect opportunity to discuss a topic which will likely figure prominently at Berkshire this weekend: Ted Seides’s famous bet with Buffett. Ted and I discuss the origins of the bet, the nuances beneath the headlines, and whether he’d make the bet again for the next ten years. Along the way, we cover many hot topics like hedge funds, alternatives, fees, and indexing. Please enjoy!

    For comprehensive show notes on this episode go to http://investorfieldguide.com/bet

    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


    Danny Moses - The Big Short and Beyond - [Invest Like the Best, EP.34] Apr 25, 2017
    Show notes

    My guest this week is Danny Moses, who was directly in the middle of the biggest trades in market history, chronicled by Michael Lewis in his book the Big Short. Danny was the head trader on the Frontpoint team led by Steve Eisman, which was one of a small group of firms that figured out, in real time, the dire situation with mortgage-backed securities during the financial crisis, and how to build a portfolio to bet against the U.S. housing market. We cover his part in the Big Short story, but also lots of other interesting ground, including the state of sell-side research and financial markets. I love conversations with traders because they live and breathe market risk. You’ll be able to see why quickly in this great conversation with Danny Moses.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/danny

    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


    Royce Yudkoff and Rick Ruback – REALLY Private Equity - [Invest Like the Best, EP.33] Apr 18, 2017
    Show notes

    In this episode, I continue to pull on one of the most interesting threads that I have uncovered while producing this podcast: the world of permanent equity. My guests today are Royce Yudkoff and Rick Ruback, two Harvard Business School professors who have partnered to create a popular class that teaches students how to search for, acquire, and run a small business directly after graduation.

    I approach this conversation from an investors standpoint. LP investors usually partner with these searchers to form what is called a search fund. A search fund allows recent MBA grads to spend time looking for a business and ultimately acquire it. The result is a small scale but often high return proposition for investors. I loved our discussion of what to look for in a business and what to avoid. The principles we list are useful for investors of any kind, and will particularly appeal to those from the buy and hold, value investing, and quality investing camps.

    One point of note which wasn’t captured during the recording. One of the reasons this style of investing isn’t more well known that it is extremely costly upfront. It can take years to find a company, and once found, the transaction costs can be 20% of the total purchase price. Rick calls this category “REALLY private equity.

    If you enjoy this conversation, be sure to check our Royce and Rick’s book. HBR Guide to Buying a Small Business, which goes into many of the topics we cover in even greater detail.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/hbs

    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


    SPECIAL EPISODE: Introducing Capital Allocators Podcast with Host Ted Seides Apr 13, 2017
    Show notes

    SPECIAL EPISODE: Introducing Capital Allocators Podcast with Host Ted Seides This is a special episode to premiere a new podcast from my friend, Ted Seides. In this show, Capital Allocators, Ted will feature a broad range of people that control the flow of money through the capital markets. Ted is in a unique position to this; he knows this world as well as anyone having spent with both allocators and the money managers who invest on their behalf. Below is the information about this first episode including a link to the homepage of this show, where you can subscribe. Enjoy the first full episode of Capital Allocators. ———————————————————————— Steven Galbraith is best known as the former Chief Investment Strategist at Morgan Stanley. He also sat in every seat in the asset management industry – credit and equity analyst, portfolio manager, business executive, entrepreneur, and Board member at an endowment and a large family office. We discuss Steve's journey, incorporating his deep insights in the investing world alongside colorful anecdotes of market inefficiencies in European football, college sports gambling, local breweries, and Charter Schools. For more episodes, go to capitalallocatorspodcast.com/podcast Follow Ted on Twitter at @tseides


    Boyd Varty – The Art of Tracking - [Invest Like the Best, EP.32] Apr 11, 2017
    Show notes

    This week’s episode is the most unique to date. My guest is Boyd Varty, who grew up in the South African Bush, living among and tracking wild leopards. The main theme of our conversation is tracking, and how the same strategy for pursuing animals in the wild can be applied to all aspects of our lives. Boyd’s family has been tracking animals for four generations, and he is bringing what they have learned to a larger audience around the world.

    The episode includes the best answer I’ve ever heard (which comes when I ask Boyd to describe his most memorable experience). We also discuss the dangers of an achievement or goal oriented mindset, and what he learned from spending time with Nelson Mandela as a boy.

    This episode is one I hope you share with those you love, because I think Boyd’s ideas will have a profound impact on many who are thinking about what to do with their lives—whether they are young or old.

    Please enjoy.

    For comprehensive show notes on this episode go to http://investorfieldguide.com/boyd

    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


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