Ira Judelson - Bail Street, with NYC's Leading Bail Bondsman - [Invest Like the Best, EP.40]

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