Welcome to Lead Without Limits, where we explore what it really takes to lead with integrity, impact, and authenticity. I’m Kathy Wu Brady—executive coach, former CEO/COO, and your guide to leadership lessons that matter.
This piece captures my recent Substack Live conversation with Tom Hardin, the former FBI informant known as Tipper X. You can watch the full video above, read the article below, or jump to the timestamp summary at the end to find the moments that matter most to you.
The $46,000 Decision That Changed Everything
What’s the price of a career built over years of hard work and education? For Tom Hardin, it was $46,000.
Not millions. Not even hundreds of thousands. Forty-six thousand dollars in personal gain from four small insider trades that added just 1% to his hedge fund’s performance.
When I first met Tom two years ago at a local networking event, and he introduced himself as “a former FBI informant,” I’ll be honest, I had no idea what that even meant.
What I’ve learned since has fundamentally changed how I think about ethical decision-making in leadership.
Tom’s story isn’t about a bad person doing bad things. It’s about a good person, Wharton-educated, hardworking, from a middle-class Atlanta family, who made four decisions in isolation that derailed his entire career at age 29. He then became the FBI’s top informant (codenamed Tipper X) in the largest insider trading investigation in history, spending two years wearing a wire to help take down corruption on Wall Street.
His upcoming book (Wired on Wall Street), launching February 25th, chronicles this journey. But our recent Substack Live conversation revealed something more important than the dramatic tale of espionage and courtroom drama: the anatomy of how ethical lines get crossed, and what leaders can do to prevent it.
Because here’s what struck me most: Tom’s experience is a cautionary tale for every leader navigating ambiguous situations under pressure. The kind of pressure we’re all facing right now: to grow faster, cut costs, hit quarterly numbers, stay ahead of AI disruption, do more with less.
Here’s what I learned.
Theme 1: The Slippery Slope Starts Long Before the Line is Crossed
Tom didn’t wake up one day and decide to commit securities fraud. The groundwork was laid years earlier.
Insider trading was “an open secret.” Everyone knew. Hedge funds would have value-added investors who worked at public companies call them with inside information. Or they’d hire analysts from tech companies specifically to call back for tips from their former colleagues.
Tom knew this was happening. And like many of us when we see problematic behavior around us, he told himself: “That’s happening, but it’s not my world. I don’t have those kinds of contacts. It wouldn’t be me.”
The critical mistake? He never asked himself: “If I were in that position one day, what would I do?”
There was no pre-mortem. No mental rehearsal. No conversation with a mentor about the ethical dilemmas he was witnessing. He simply put it out of his mind and went back to the intellectual work he loved—analyzing market trends, debating stock positions, building investment theses.
Then his boss came to him after a bad quarter and said: “We need to make money every month, Tom, or we aren’t going to survive. We have to start looking for shorter-term opportunities.”
Ambiguous. Pressurizing. Open to interpretation.
Tom didn’t ask clarifying questions. Are we talking about doing what everybody else is doing? Are we staying within legal and ethical guardrails?
Within months, a tip landed in his lap. Then another. And because he’d never mentally prepared for that moment, he rationalized: These other guys are going to make millions. I’ll just buy a small amount. Who am I hurting? It’s just one trade. I’m still a good person.
Action for Leaders:
Don’t wait for the ethical dilemma to arrive.
Create space now—in team meetings, in one-on-ones, in your own reflection time—to discuss the gray areas you’re witnessing in your industry. Ask yourself and your team: “If we were in that situation, what would we do?” Make the discussion discussable before the pressure is on.
Theme 2: Ambiguity Is the Enemy of Ethics
When I asked Tom what could have prevented those initial trades, his answer was immediate: clarity and conversation.
His boss’s directive—”we need to make money every month”—was the textbook definition of ambiguous leadership communication. And as Tom now tells companies around the world:
“Ambiguity is the enemy of ethics and integrity.”
Here’s how the dangerous pattern unfolds:
Leaders send ambiguous messages (”We have to hit this number” / “Do whatever it takes” / “I don’t want to know the details”)
Teams pretend the message wasn’t ambiguous (nobody asks clarifying questions for fear of looking difficult)
The ambiguity becomes undiscussable (”Are you questioning my communication? You know what I mean, just get it done”)
The undiscussability becomes undiscussable (culture of silence is established)
This is how you end up with values on the wall that don’t match the behavior in the halls.
Tom described visiting companies for compliance training where young employees pull him aside afterward and say:
“Yeah, what they say on the wall about speaking up? We would never do that here. If we raise our hand, we’ll never hear back and then we’re worried about our jobs.”
The fraud triangle that explains why employees cross ethical lines requires three elements:
Perceived need (pressure to perform)
Opportunity (lack of controls—in Tom’s case, he could buy stocks under 1% of assets without approval)
Rationalization (self-exception by reasoning—”I’m a good person, this is just once, it’s a small amount”)
But here’s what struck me: All three of these elements are amplified by ambiguous leadership communication.
Action for Leaders:
Audit your recent communications to your team. Where have you been ambiguous—perhaps intentionally—about how to achieve goals? Where might your team be interpreting “do whatever it takes” as permission to bend rules? Schedule a conversation specifically to clarify: What are we willing to do? What are we absolutely not willing to do? Make it safe to ask these questions.
Theme 3: Isolation Accelerates Poor Decisions
One of the most haunting moments in our conversation was when Tom said:
“If I had been talking to somebody outside my firm, outside my industry, maybe a mentor, and said, ‘Hey, you won’t believe what’s happening. These guys are making millions. I just got this tip. I’m thinking about taking a small trade just to play along...’ Certainly anybody on this call, if you’re my mentor, you would have slapped young Tom around.”
But he didn’t have that conversation.
He made the decision in isolation. And in isolation, it was very easy to do his own mental gymnastics: I’m a good guy. I’m a faithful husband. I go to church. I make thousands of trades a year. I can make four bad ones. They’re small. Who cares?
Tom told me:
“It would have been very hard to do that if I just jumped outside my head.”
This resonated deeply with me.
How many of us, when facing a difficult decision, keep it entirely in our own heads? We tell ourselves we’re being thoughtful, strategic, protecting confidentiality. But sometimes we’re just protecting ourselves from accountability.
After the FBI approached him, Tom could only tell his wife. For two years, he wore a wire, building cases against other traders, while maintaining his day job and his cover. He was juggling multiple, challenging identities: former trader, FBI informant, stay-at-home dad after he left his firm, ultramarathon runner.
But even after his name came out as Tipper X, even after sentencing, Tom said:
“I was so focused on myself. I hate to say it, I wasn’t really considering what my wife was going through.”
It wasn’t until he started volunteering at his church, getting outside his own head by helping others, that he began to heal. And it wasn’t until he was interviewed for his book that he finally asked his wife: “What was it like for you?”
Her response: “Thanks for asking, Tom, because you never did.”
Action for Leaders:
Build your “personal board of directors.” The 2-3 people outside your immediate team or company who you can call when you’re facing ambiguous decisions. Make it a practice to voice your dilemmas out loud, even (especially) when you think you have it figured out. The act of explaining your reasoning to someone else often reveals the flaws in your logic.
Note: Worried about confidentiality? Engage an attorney, have your confidants sign NDAs. Even when you get help, do it all above board.
Theme 4: Redemption Requires Radical Honesty and Service
When the FBI approached Tom on a Manhattan sidewalk at 6:30 AM on July 8, 2008, his first thought wasn’t about prison. It was: “Oh my gosh, my dad’s going to kill me.”
His father had worked for 40 years, commuting daily from their middle-class Atlanta suburb, so that Tom could have better opportunities. His mother had run a childcare business from their home. They had instilled in him a work ethic and drive to succeed that led him to read the entire World Book Encyclopedia when he was 8 (taking two years to get from “Akin to Zygote”) and eventually to Wharton.
And here he was, having thrown it all away.
His second thought:
“My wife’s going to leave. We just got married. She had no idea about the trades. She has every right to leave.”
But when he finally told her that Friday (after days of bed sweats and panic attacks), she said something remarkable: “You didn’t do anything to hurt me. And if they’re giving you a chance to clean up the industry, you should do it.”
Tom shared that 85% of marriages end in situations like this. His survived because of radical honesty and her extraordinary grace.
For two years, Tom worked as an FBI informant, meeting targets at Starbucks (he mentions it 15 times in his book, he laughed), trying to get them to admit to federal crimes. He was terrible at it initially—too eager to get to the punchline. The FBI would listen to recordings and say, “Tom, you’re doing a bad job. You have to be silent.”
There was no training at the FBI Academy for this. It was swim by being dumped in the deep end.
After his sentencing in 2015 (no prison time thanks to an FBI letter detailing his cooperation), he still had a felony conviction. He couldn’t get a job. His wife continued working while he became a stay-at-home dad.
He tried real estate deals (investors Googled him), drop-shipping on eBay (suppliers hijacked his listings). He volunteered at church, shipping clothes to Haiti. He ran ultra marathons to get fit and mentally heal, but it sometimes turned into a way to avoid difficult conversations with his wife about their financial reality.
Then he went on a podcast to tell his story. An FBI agent happened to be listening and called him: “Come talk to the FBI. What you discussed: the pressures, the dynamics, the rationalization. You could do a better job of compliance training for this industry.”
For a year, Tom emailed every business school in the New York area: “I’m Tipper X. I won’t charge for this. I’m just trying to get my reps.” A few schools let him in. Then a company asked: “How much do you charge?”
“$3,000?” he ventured.
He got paid. He told his wife: “You can quit your job.”
She replied: “Are you crazy? You just made $3,000. That’s it.”
But Tom said:
“When my family was at stake, when my wife had been so amazing, I knew I had to step up. I had to make this work. Whatever it was going to take.”
Ten years later, he speaks to Fortune 500 companies around the world. His first book launches February 25th. And his definition of success has completely transformed.
“It’s not about chasing status anymore,” he told me. “Success for me is more about special moments than outcomes. If somebody can pick up this book who knows nothing about finance or Wall Street, and maybe they’re going through a terrible, maybe self-inflicted situation in their own lives and can pull a few nuggets from this experience to help them—that’s what matters.”
Action for Leaders:
When things go wrong, whether through your own mistakes or your team’s, resist the instinct to minimize, rationalize, or hide. Radical honesty, even when it’s painful, is the only path to genuine redemption and rebuilt trust. And consider: How can you transform your hardest experiences into service to others?
One Question That Changes Everything
Near the end of our conversation, Tom shared something that crystallized all of these themes.
He’s read countless corporate codes of conduct, those documents we all sign (but very few actually read) annually with 10 philosophical questions to ask ourselves before making a decision.
At one European company, he asked if he could rip up their 10-question checklist on stage.
“Could you just ask yourself one question?” he proposed. “If I make this decision, am I willing to be held accountable for this decision at the end of the day?“
That’s it. Not five philosophical questions from your college ethics class. Just that one.
“If you can answer that,” Tom said, “you’re pretty much on the right path.”
Why This Matters Now
Tom’s story happened during the 2008 financial crisis, a time when the entire financial world was collapsing, when institutions that were never supposed to be wobbly were literally crumbling.
Sound familiar?
We’re living through our own period of unprecedented disruption. AI is transforming how we work. Economic uncertainty is putting pressure on every leader to deliver results. The temptation to take shortcuts, to be ambiguous about how we achieve goals, to look the other way when we see problematic behavior, to make decisions in isolation, has never been stronger.
Tom’s journey from rising hedge fund trader to FBI informant to keynote speaker and author isn’t just a dramatic story. It’s a mirror showing us what happens when good people face pressure without preparation, when ambiguity fills the space where clarity should be, when isolation replaces conversation.
The good news? Every single one of the risk factors Tom faced is preventable. Not easy to prevent, but possible.
It starts with having the conversations before the pressure arrives. With making ambiguity discussable. With building your board of directors. With asking yourself that one critical question.
Tom made four bad choices at 29. But he made one very good choice: he married his wife Sue. And through radical honesty, service to others, and a complete redefinition of success, he’s built a second career helping leaders avoid the mistakes he made.
His story reminds us that redemption is possible. But prevention is better.
Get the Book
Tom’s book launches February 25th. Companies ordering 10 or more copies will receive supplemental discussion materials around ethics decision-making.
Visit tipperx.com/book to pre-order (pre-orders in the next six weeks help move the algorithms during publication week).
You can also find Tom on Substack at tipperx.substack.com and on LinkedIn under Tipper X.
Conversation Timestamps
Want to dive deeper into specific parts of our conversation? Here’s your guide:
[00:00 - 04:04] Introduction and Tom’s background growing up in Atlanta
[04:05 - 08:05] The Wharton experience and dealing with imposter syndrome
[08:06 - 12:16] Landing the coveted hedge fund job and the tech bubble
[12:17 - 17:09] Becoming aware of insider trading as an “open secret”
[17:10 - 23:38] The moment of crossing the line: receiving the tip and placing the first trade
[23:39 - 28:02] The FBI approach on a Manhattan sidewalk
[28:03 - 33:03] Telling his wife and becoming an informant
[33:04 - 37:57] Two years wearing a wire and the Tipper X reveal
[37:58 - 45:00] The dark years: stay-at-home dad, ultra marathons, and finding purpose through service
[45:01 - 50:02] Sentencing, starting the speaking business, and writing the book
[50:03 - 55:10] What could have prevented it: lessons for leaders on ambiguity and organizational culture
[55:11 - 57:55] Closing thoughts on success, accountability, and the one question that changes everything
Thanks for reading Lead Without Limits. If you found value in this conversation, please share it with a leader who needs to hear Tom’s story. And if you’re facing an ambiguous situation right now, I’d love to hear about it. Sometimes we all need someone to help us jump outside our own heads.
May you lead without limits,
