What happens when the worst thing you’ve ever done becomes the foundation for your life’s work?

Episode Summary
My guest on this episode is Tom Hardin, otherwise known as Tipper X. He's been on the show before, but this time we're tackling a different angle.

If you don’t already know his story, Tom was a rising star in the hedge fund world in his twenties when he became involved in insider trading. Caught by the FBI, he made the decision to cooperate — ultimately becoming one of the most prolific informants in the largest investigation of its kind in U.S. history. His work with the FBI helped secure dozens of convictions, and while his own case remained under seal for years, he eventually chose to speak publicly about what happened — not to excuse it, but to help others understand how good people can make bad decisions.

If you haven’t heard Tom’s first appearance on the show, where he tells that extraordinary story in full, I highly recommend listening to it here before diving into this episode.

Because this time, we’re not talking about what he did back then; we’re talking about what he’s done since. Tom has built a powerful second act, using his experience to educate organisations about ethics, decision-making and behavioural risk. He’s now delivered over 600 talks, and what fascinates me is how he’s turned that into something both impactful and sustainable.

His forthcoming book Wired on Wall Street is due out next year, and he’ll be back on the show to talk about that. But for now, I wanted to explore what it means to build a career from a cautionary tale. In this conversation, we explore:

How Tom built a speaking business around his past without glamourising it
The frameworks he’s developed to help companies recognise ethical pressure points
How he navigates scepticism, manages reputation, and avoids turning his story into a performance
The impact he hopes to have, and how he measures it

This is a conversation about vulnerability, professionalism, and doing good with what you’ve learned the hard way. Whether you're in compliance, leadership, education, or just curious about how we turn failure into purpose, this one’s for you.

Guest Profile
Tom is a former hedge fund analyst turned FBI informant, now a globally recognised speaker and ethics educator. Known as Tipper X, Tom shares his story to help others understand the behavioural drivers of misconduct and the power of accountability.

AI Generated Timestamped Summary
00:00 – Introduction
Christian shares the origin of this episode, his relationship with Tom, and the context behind the conversation.

06:30 – The label “Tipper X” and living with it
Tom reflects on how it feels to be known by his code name and why he uses it professionally.

09:00 – What it’s like to talk about the worst thing you’ve done, repeatedly
The emotional and psychological toll of speaking publicly about past wrongdoing.

13:00 – Keeping it fresh: updating the story and the message
How Tom avoids becoming performative and ensures audiences always get something valuable.

16:40 – Why it’s not entertainment
Tom draws the line between education and storytelling-as-performance, and how he avoids glamorising his past.

20:50 – The business model behind Tipper X
The practicalities of how Tom has built and sustained a speaking career rooted in his past.

26:30 – Frameworks and tools Tom uses in his talks
He discusses behavioural insights and models he shares with audiences to make the message stick.

31:00 – The “AI homework” story
A compelling example Tom uses to explain rationalisation and ethical grey areas.

36:00 – Over 630 talks: managing the workload and the mission
How Tom tracks his talks and why he keeps going despite the repetition.

39:10 – Audience reactions and confessions
What people tell Tom after his talks — and what that reveals about corporate culture.

42:30 – “Why should we pay someone who committed a crime?”
Christian and Tom unpack this ethical tension and why context, intent and delivery matter.

48:00 – Building trust with clients and collaborators
The importance of transparency, humility and boundaries in how Tom presents himself.

53:20 – What success really looks like
Tom reflects on purpose, legacy and the long-term impact he hopes to have.

57:00 – Looking ahead: the forthcoming book and continuing the conversation. Christian mentions Tom’s upcoming book Wired on Wall Street, and plans for a future episode.

Links
Podcast: Tom’s previous appearance on the show

Tom's website: TipperX.com

Pre-order Tom's book Wired On Wall Street; https://www.amazon.com/Wired-Wall-Street-Prolific-Informants/dp/1394348878

His LinkedIn profile: https://www.linkedin.com/in/tipperx/

Tom's Substack Newsletter: https://tipperx.substack.com/

Frustrated by a relationship? Questions to ask yourself to move forward

Life Kit

Staying with boundaries and self-care strategies

The AI-powered Podcast Player