Invest Like The Best
Episode 40 Bail Street, with NYC’s Leading Bail Bondsman
Invest Like The Best

Episode 40: Bail Street, with NYC’s Leading Bail Bondsman

Bail Street, with NYC’s Leading Bail Bondsman

Ira Judelson is the leading bail bondsman in New York City. We cover the business of being a bail bondsman, some of his most memorable clients including Dominique Strauss-Kahn and DMX, and his advice for younger people just starting out in their careers.

[00:01:55] – (First question) – The role that Rao’s restaurant has meant to Ira’s business and career

[00:06:11] – A look at Ira’s bail bonds business and how that industry works

[00:06:22] – The Fixer: The Notorious Life of a Front-Page Bail Bondsman

[00:08:31] – The story of how a pizzeria was a bad piece of collateral

[00:11:10] – How often does Ira deal with bail jumpers

[00:12:10] – What is the size of the open liabilities

[00:13:14] – How long will the open liabilities last

[00:14:55] – Ira’s relationship with his clients and the importance of character in this business

[00:17:46] – the amazing story of how Ira got started in this business

[00:31:05] – His early years of being a bail bondsman and how important his wife was to his success

[00:29:52] – How Ira balances family with this kind of work

[00:32:22] – Ira’s ability to be amazingly efficient on the phone when in social settings and a work call comes in

[00:33:14] – Ira is the fixer

[00:36:40] – 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.

[00:38:29] – The importance of intense reliability, consistency and empathy, and why Ira can trust his clients may be considered bad people

[00:30:19] – Two cases where Ira got emotionally involved

[00:47:26] – Why Ira is not worried about people coming after him

[00:48:57] – 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

[00:54:06] – Ira’s relationships with Ja Rule and DMX

[00:58:32] – What does Ira enjoy most about the business still

[01:01:51] – Will Ira ever stop?

[01:04:02] – What advice would Ira give to someone early in their career just getting started

[01:08:42] – The importance in having a willingness to fail mixed with the passion for what you are doing

[01:10:11] – Ira’s health scare and what it taught him about appreciating life

Bail Street, with NYC’s Leading Bail Bondsman

Introduction

Patrick
This week's episode is very unique. It is the first episode devoted to bonds, just not the kind of bonds you might be expecting. 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 part of this conversation. I've always had a passion for understanding how different businesses work. In this case, this week we're exploring a different business, but also a different world. Ira's story is larger than life. He is as authentic and hardworking 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 discussed bond collateral, Dominique Strauss-Kahn and DMX. And that is but one small fraction. Please enjoy my conversation with Ira Judelson and Danny Moses.

Rao's

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