The Plight of “Tipper X”: How Tom Hardin Became The Most Notorious FBI Informant in the Biggest Insider Trading Case in Decades — And The Long Run To Redemption

{{ currentTime / duration }}
{{ currentTime | prettyTime }} {{ duration | prettyTime }}

“I am my own undoing. But there have been many positives to come out of it.”

Tom Hardin


This week we explore some very new terrain.

Let’s kick it off with the Greek myth of Icarus.

As the story goes, Daedalus — a master craftsman best known for building King Minos’ labyrinth to trap the Minotaur — plied his talent to construct a pair of wax and feather wings to help him and his son Icarus escape from Minos’ vendetta (it’s a long story) and Crete altogether.

Being the good father he was, Daedalus pled with his son not to fly too close to the sun for fear that the heat would melt the wings. But as sons are wont to do, Icarus ignored his father’s advice.

The rest is history. The heat indeed melted Icarus’ wings, sending him into a deathly free fall collision with the sea which today bears his name, the Ikarian Sea near Ikaria — ironically one of the Blue Zones as described in my recent podcast conversation with Dan Buettner.

As most know, this is an age-old remonstration about ambition. A tragic allegory about the perils of hubris, particularly when fueled by a sense of entitlement, and perhaps sprinkled with a light dusting of denial.

These are all very human traits of course. And if today’s guest is anything, he is quite human indeed.

Tom Hardin was a highly motivated young guy with a big bright future and Wall Street aspirations. After graduating from the prestigious Wharton School of Business, he was on track to achieve his dream when he landed in the fast paced hedge fund world and quickly rose through the ranks.

But it wasn’t long before Tom felt he was falling behind – lacking that mysterious competitive ‘edge’ so many others seemed to freely enjoy (without repercussion) to their reward in untold millions.

What was that edge? If you ask Tom, he will tell you the not so secret to success within the insular hedge fund world meant having a network of inside sources willing to share reliable confidential information about companies they worked for or with.

Everybody’s doing it. Nobody’s getting caught. I’m falling behind.

Then one day Tom got a call from an investor colleague named Roomy Khan – a woman with some pretty juicy insider tips.

The timing was right. Tom was primed. And that fateful moment arose. That moment when you make a decision to take a very small step over a very important line. A decision you simply cannot undo. Not now, not ever.

For Tom, it started with taking a few small crumbs off the table. An imperceptible insider trade here, another one there. Until one day, the previously unthinkable became easy. Almost too easy.

Capitalizing on a handful of secrets fed by Khan and others about companies like Google, 3Com and Hilton Hotels, Tom’s flight towards the sun escalated to the tune of $1.7 million in gains for his fund and $46K in personal profits.

Then in July 2008, while dropping of his dry cleaning one morning, Tom felt a tap on the shoulder. A tap that would alter the trajectory of his life forever.

Like a scene out of a movie, Tom turned to face two FBI agents boxing him in with with a Hobson’s choice – either get in the back of the black sedan for a trip downtown, or start providing actionable information on those higher up the food chain.

Panicked and heart pounding, he immediately opted for the latter.

Ultimately, Tom became one of the most prolific informants in securities fraud history. Soon infamous as the mysterious, unnamed Tipper X, Tom spent the next several years wiretapping and documenting the illegal misdeeds of friends and colleagues as an instrumental, key figure in what the FBI deemed “Operation Perfect Hedge” — a Wall Street house-cleaning campaign that matured into the biggest insider trading case of this generation.


When the dust settled, Tom’s cooperation led to over two dozen convictions, most notably the toppling of billionaire and Galleon Group hedge fund founder Raj Rajaratnam, who was accused of making $75 million personally and is now serving an 11-year prison term.

Due to his extraordinary cooperation, Tom avoided jail time, but did not escape the scarlet 5-letter word: felon.

Although his wife and family stood steadfast, Tom lost his job, his friends, his standing in the community, his dream, his sense of self and what his life was supposed to be. His relationship with sanity started to slip. With right and wrong confused, heavy bouts with depression ensued. His spirit sank in proportion to his expanding waistline.

Today he finds himself unemployable. Racked by guilt. Afraid. And, it can be fairly said, quite alone.

I am my own undoing.

Our culture thrives on schadenfreude. But it’s easy to judge when we’re watching comfortably from the sidelines. Whether it’s a professional cyclist’s decision to dope or a trader’s choice to barter on insider information, we all think we would make a different decision. I know I do.

But I also know that unless I have walked a mile in someone else’s shoes, it’s not my place to say with any degree of certainty what I would have done under similar circumstances.

But that’s not really the question I am interested in. From my perspective, it’s far more interesting to explore:

  • the factors that lead a person towards their own dismantling;
  • the emotional landscape that accompanies such a scenario;
  • what can be learned from Tom’s experience; and
  • the inherent power of moments like these to become reborn

Tragedy can be recast as divine. Not just as an opportunity for a second chance, but as a true gift — a brief moment in which the door cracks open, the light shines in and the stars align to provide a rare opportunity to harness the painful past; learn something crucial about yourself; set a new trajectory; and ultimately transform everything about who you are to become an entirely different and better person altogether.

I won’t say Tom is there yet. He remains unclear on where his life might lead. But his journey has begun — a soulful exploration and search for answers he is slowly beginning to discover through community service; a newly discovered love of ultrarunning; and his simple willingness to entrust me with his story.

I am honored that Tom agreed to sit down with me in March (just weeks after his sentencing hearing) to share — for the very first time on record — the details behind the choices he has made, the wreckage it has caused and what he has learned about himself in the process.

Snitch? Hero?

Maybe both. Maybe neither. Maybe more complicated than that. Probably.

Whatever your take, I applaud the courage it took to engage me in this conversation. Candor, vulnerability and raw honesty are hard to come by, and Tom demonstrates it today in spades. I’m proud to share this exchange and my hope is that you find something compelling about the human condition that will better inform your own path.

I genuinely hope you enjoy the conversation and look forward to your thoughts in the comments section below.

Peace + Plants,

RR-SIGNATURE-FOR-WEB 110

Listen & Subscribe on iTunes | Soundcloud | Stitcher | TuneIn

Production, music & sound design by Tyler Piatt. Additional production by Chris Swan. Graphic art by Shawn Patterson. Thanks boys!

This week’s show was sponsored by Audible.com® offering more than 180,000 audiobooks and spoken-word audio products. Get a free audiobook of your choice at audiblepodcast.com/richroll

SHOW NOTES

Follow Tom’s Journey Online: TipperX.com | @iamtipperx

Books and other online resources mentioned in the podcast:

*Disclosure:Books and products denoted with an asterisk are hyperlinked to an affiliate program. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.

The Plantpower Way is now available at these fine retailers!

Amazon  |  Barnes & Noble  |  IndieBound  |  Penguin

Are you a company interested in sponsoring the podcast? Click here to learn more & take our sponsor survey.

HOW CAN I SUPPORT THE PODCAST?

Tell Your Friends & Share Online!

Subscribe & Review:  iTunes | Stitcher | Soundcloud | TuneIn

Donate: Check out the DONATE button on the podcast homepage or click HERE to learn more.

Download Our Free App! Now you can access, stream, download and share the entire RRP catalog in the palm of your hand on any iOS mobile device (iPhone, iPad and iPod Touch) with our new mobile app. Never miss an episode, plus special announcements, discounts, giveaways. Already downloaded? Awesome. When you have a minute, and it feels right to you, do us a solid and give the app a review in the iTunes Store.