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The Distressed Investing Playbook: How the Smart Money Profits When Companies Fail and Markets Go Haywire
Want to break into distressed investing but aren’t sure how? The Distressed Investing Playbook by Joseph E. Sarachek, one of America's leading authorities on distressed debt and intangible asset trading, offers a definitive guide to succeeding in this highly volatile and highly lucrative area of investing. With the right strategy, proper timing, and a willingness to bet big when opportunity knocks, savvy distressed investors can transform even the most hopeless-seeming scenario into a remarkable financial opportunity earning two, three, or sometimes even one-hundred times their invested capital.
Inspired by Sarachek’s popular course on bankruptcy investing at New York University's Leonard N. Stern School of Business, The Distressed Investing Playbook blends foundational investing concepts with dozens of vivid, real-world examples drawn from his decades of experience. The result is a comprehensive, practical playbook that can teach anyone—from curious amateurs to seasoned investment professionals—how to navigate the complexities of corporate bankruptcy, trade claims, distressed equity, cryptocurrency insolvencies, real estate foreclosure sales, and other common distressed investing opportunities.
The book will show you how the many different types of distressed assets and determine which best fits your investment profilesource distressed opportunitiesaccurately value potential assets for purchasecreate a liquidation analysisbuy and sell trade claimsaccess and dissect bankruptcy filingsassess when to offer debtor-in-possession (DIP) financing to purchase assets on the cheapdevelop a personal distressed investing framework
This is just a small sample of the covered topics. So if you're ready to go long on your financial future, The Distressed Investing Playbook may be the strongest asset in your arsenal.
Inspired by Sarachek’s popular course on bankruptcy investing at New York University's Leonard N. Stern School of Business, The Distressed Investing Playbook blends foundational investing concepts with dozens of vivid, real-world examples drawn from his decades of experience. The result is a comprehensive, practical playbook that can teach anyone—from curious amateurs to seasoned investment professionals—how to navigate the complexities of corporate bankruptcy, trade claims, distressed equity, cryptocurrency insolvencies, real estate foreclosure sales, and other common distressed investing opportunities.
The book will show you how the many different types of distressed assets and determine which best fits your investment profilesource distressed opportunitiesaccurately value potential assets for purchasecreate a liquidation analysisbuy and sell trade claimsaccess and dissect bankruptcy filingsassess when to offer debtor-in-possession (DIP) financing to purchase assets on the cheapdevelop a personal distressed investing framework
This is just a small sample of the covered topics. So if you're ready to go long on your financial future, The Distressed Investing Playbook may be the strongest asset in your arsenal.
410 pages, Kindle Edition
Published June 9, 2025
22 people are currently reading
20 people want to read
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July 18, 2025
I’ve read a combination of Moyer, Caesars Coup, and Marvel’s Bankruptcy, along with the other main distressed books, and I believe this could have been improved by targeting it to a more experienced reader in the field. As it stands, it’s just a combination of anecdotes and points that an experienced reader is already familiar with.
This is not really a field for the day-to-day retail investor, especially when you consider legal fees and the deep due diligence required across accounting, legal, and financial restructuring. Beyond that, retail investors have no influence in the restructuring process, so at best, they play a passive role. This could have opened up the opportunity for a deeper discussion with proper mental models on how to approach passive investing in distressed debt.
At best, as a retail investor, you can trade vendor claims. So if the intention was to target a retail audience, then that angle should have been explored more thoroughly, with a deeper analysis of how to approach the legal aspects, return potential, risks, and structural limitations. I mean, how realistic is it for someone investing in a mutual fund for retirement to monitor a company’s SEC filings, read creditor documents, and run a liquidation analysis to estimate recovery in a debt restructuring?
That’s precisely why such discussions, as presented in this book, would have been more appropriate for an experienced investor, someone whose job actually involves monitoring these developments and positioning for such plays, not a retail investor, and as such, elevate this book to a higher level (I would have proposed that the target audience be lawyers or industry professionals, who would have benefited from a more detailed exploration of specific legal and strategic dimensions).
There’s also a lack of first-principles thinking, just recycled points like “an investor must pay attention not only to ABC but also to XYZ,” or “distressed is not only about 123, but also about 456,” and so on. And, frankly, the overuse of such phrasing has become a recognizable hallmark of AI-generated writing - often used to close paragraphs without offering substantive insight - which can feel off to the experienced reader. Albeit, even if this observation may be speculative and wrong, it’s a stylistic choice that could have been more thoughtfully reworked.
This is not really a field for the day-to-day retail investor, especially when you consider legal fees and the deep due diligence required across accounting, legal, and financial restructuring. Beyond that, retail investors have no influence in the restructuring process, so at best, they play a passive role. This could have opened up the opportunity for a deeper discussion with proper mental models on how to approach passive investing in distressed debt.
At best, as a retail investor, you can trade vendor claims. So if the intention was to target a retail audience, then that angle should have been explored more thoroughly, with a deeper analysis of how to approach the legal aspects, return potential, risks, and structural limitations. I mean, how realistic is it for someone investing in a mutual fund for retirement to monitor a company’s SEC filings, read creditor documents, and run a liquidation analysis to estimate recovery in a debt restructuring?
That’s precisely why such discussions, as presented in this book, would have been more appropriate for an experienced investor, someone whose job actually involves monitoring these developments and positioning for such plays, not a retail investor, and as such, elevate this book to a higher level (I would have proposed that the target audience be lawyers or industry professionals, who would have benefited from a more detailed exploration of specific legal and strategic dimensions).
There’s also a lack of first-principles thinking, just recycled points like “an investor must pay attention not only to ABC but also to XYZ,” or “distressed is not only about 123, but also about 456,” and so on. And, frankly, the overuse of such phrasing has become a recognizable hallmark of AI-generated writing - often used to close paragraphs without offering substantive insight - which can feel off to the experienced reader. Albeit, even if this observation may be speculative and wrong, it’s a stylistic choice that could have been more thoughtfully reworked.
Displaying 1 of 1 review