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From Gangster to Lawyer: The Josephus Tan Story (Part 2)
Imagine losing everything—could you fight your way back?
In Part 2 of this episode, I continue my raw and powerful conversation with Josephus Tan, the "Gangster Lawyer." He reveals how he faced rock bottom and still found the strength to rise.
Despite his career success, Josephus hit some brutal low points:
Low Points:
- Overcommitted to free legal work—almost bankrupt.
- Marriage collapsed.
- Suffered a mild stroke.
- Ended up living in a van.
But Josephus didn’t just survive—he came back stronger.
His Comeback:
- Started smoking at 12, quit at 45—his latest victory!
- Rebuilt his life from nothing, twice.
- Went from a 1-room flat to a penthouse.
- Now a top lawyer, fiercely fighting for justice.
In this episode, Josephus gets real about the hardest moments in life, the importance of second chances, and the advice he’d give his younger self.
You’ll also hear critical tips on what to do if you’re arrested or caught in a police chase, and how defense lawyers handle client confessions.
Josephus Tan’s story is your roadmap to resilience.
This episode will move you—and leave you believing that no setback is final.
Follow Josephus Tan:
https://www.linkedin.com/in/josephus-tan-303352307/
Connect with me on LinkedIn at https://www.linkedin.com/in/shulinlee/
More on the podcast - https://www.AfterTheBar.com.sg
What to listen for:
00:00 Start of Episode
00:48 Pro Bono Overcommitment Leading to Debt
03:42 Near Bankruptcy and Failure of First Marriage
07:16 Suffering from a Medical Emergency
10:41 Going on Medication for the Rest of His Life
11:44 Becoming Pest Buster for Vessels
13:49 Dangers of Working on Vessels
15:30 Life of Living in a Van
18:38 Moments When Josephus’s Pride Is Shattered
22:15 Josephus’ Support in Tough Times
23:26 Josephus’ Advice for Life Struggles
25:49 From Pest Buster to Penthouse Owner
30:58 Josephus's Take on Embracing Second Chances
34:25 Remarkable Journey to Quit Smoking
40:33 Action Steps for Arrest Situations
42:49 How to Respond to a Police Chase Situation
45:45 How Defense Lawyers Handle Client Confessions
50:02 What Would Josephus Say to His Younger Self?
50:51 Personal Questions for Josephus
55:06 Outro
View all episodes
By Shulin LeeImagine losing everything—could you fight your way back?
In Part 2 of this episode, I continue my raw and powerful conversation with Josephus Tan, the "Gangster Lawyer." He reveals how he faced rock bottom and still found the strength to rise.
Despite his career success, Josephus hit some brutal low points:
Low Points:
- Overcommitted to free legal work—almost bankrupt.
- Marriage collapsed.
- Suffered a mild stroke.
- Ended up living in a van.
But Josephus didn’t just survive—he came back stronger.
His Comeback:
- Started smoking at 12, quit at 45—his latest victory!
- Rebuilt his life from nothing, twice.
- Went from a 1-room flat to a penthouse.
- Now a top lawyer, fiercely fighting for justice.
In this episode, Josephus gets real about the hardest moments in life, the importance of second chances, and the advice he’d give his younger self.
You’ll also hear critical tips on what to do if you’re arrested or caught in a police chase, and how defense lawyers handle client confessions.
Josephus Tan’s story is your roadmap to resilience.
This episode will move you—and leave you believing that no setback is final.
Follow Josephus Tan:
https://www.linkedin.com/in/josephus-tan-303352307/
Connect with me on LinkedIn at https://www.linkedin.com/in/shulinlee/
More on the podcast - https://www.AfterTheBar.com.sg
What to listen for:
00:00 Start of Episode
00:48 Pro Bono Overcommitment Leading to Debt
03:42 Near Bankruptcy and Failure of First Marriage
07:16 Suffering from a Medical Emergency
10:41 Going on Medication for the Rest of His Life
11:44 Becoming Pest Buster for Vessels
13:49 Dangers of Working on Vessels
15:30 Life of Living in a Van
18:38 Moments When Josephus’s Pride Is Shattered
22:15 Josephus’ Support in Tough Times
23:26 Josephus’ Advice for Life Struggles
25:49 From Pest Buster to Penthouse Owner
30:58 Josephus's Take on Embracing Second Chances
34:25 Remarkable Journey to Quit Smoking
40:33 Action Steps for Arrest Situations
42:49 How to Respond to a Police Chase Situation
45:45 How Defense Lawyers Handle Client Confessions
50:02 What Would Josephus Say to His Younger Self?
50:51 Personal Questions for Josephus
55:06 Outro