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Paul Glover spent 30 years as “Mad Dog” — a Chicago trial attorney who would do whatever it took to win. That instinct carried him into 33 white-collar felonies and five and a half years in federal prison. He got out in his 50s with no law license and no network. Today his largest coaching client is a billion-dollar distribution company.
“I’m also a recovering lawyer,” Paul says, maybe thirty seconds into the call.
He lists it the way you’d mention a hobby. “I practiced labor law in the city of Chicago for 30 years. I’m also an ex-felon. I went to prison for five and a half years for committing white-collar crimes.” Then he keeps moving, smooth, like the prison sentence was one bullet on a résumé he’s read aloud a hundred times. “Got out in 2001 and decided, since I could no longer practice law, to start a coaching business.”
“Wow,” I say. And then again, because the first one didn’t cover it. “Wow.”
I’d come in with the question I usually save for people who’ve made a hard pivot — the one about limiting beliefs, about what they had to unlearn. I start to ask it. Paul cuts the frame out from under me before I finish.
“When you talk about limiting beliefs, I have a different term for it,” he says. “I call it blind spots.”
The distinction matters more than it sounds. A limiting belief is something you hold. A blind spot is something that holds you, and you can’t see it doing the holding.
“Everybody has blind spots,” Paul says. “They’re called blind spots because we don’t see them, but everybody else does. And every blind spot has a trigger attached to it, and if you don’t know what your trigger is and you don’t know what your blind spots are, you are primed to be manipulated by the world. You will not be able to choose your own course because somebody else will choose it for you.”
His own blind spot was the size of a courtroom. “I had an extraordinarily large ego. I truly believed I was the smartest guy in every room.” He’s not bragging when he says it — he’s diagnosing. The ego came from winning, and the winning came easy, and that was the trap. “Once you become successful, you start to live in your own echo chamber, and people will surround you in that echo chamber doing exactly that, continuing to tell you how good you are. At some point, you’ll believe it. Once you believe it, then you start to fail.”
At trial, they called him Mad Dog. “I would do whatever was necessary to win,” he says. “Unethical behavior was fine with me. I just looked at it differently.” He was good. He was also bored. A trial lawyer, he tells me, is an adrenaline junkie — a performer in a room with a referee and an opponent, and he loved the performance. The problem was everything between performances. “When you’re not at trial, when you’re doing preparation, that’s not adrenaline, that’s drudge, and I hated it. So I started to seek adrenaline, and I got it from my clients, who were not nice people, to be kind.”
They were criminals. Good ones. “Good grifters, they find your blind spots and your triggers immediately, and they pressed mine right away.” What they found was a man from a broken home who wanted to belong. They gave him a group. “But the initiation fee,” Paul says, “was committing crimes.”
He paid it 33 times.
There’s a scene he tells next that I keep turning over after the call ends.
Two trials. The first ended in a hung jury. The second convicted him. He’s standing in front of the sentencing judge, looking at seven years, and the judge offers him a deal — a way to cut the sentence by twenty percent. A year and a half, maybe two years, back. All he has to do is two things. Admit he committed the crimes. And help the prosecutor go after the men who committed them with him.
“And my answer to both of those was no,” Paul says.
He’s already convicted. He’s already going to prison. The math is not subtle — two years of his life, free for the taking. He turns it down anyway, and he tells me exactly why, and the why is the whole man in two sentences. “First, I could not admit I was wrong and got caught. Second, I could not give up the people who were in my group.”
The ego that made him a felon followed him all the way to the chair in front of the judge. The blind spot doesn’t care that you’ve already lost. It just wants to keep you from saying the words.
What broke it wasn’t the sentence. It was the traffic.
For the first two and a half years inside, Paul ran revenge fantasies. He was going to get even with everyone who put him there. He’d accepted no responsibility for any of it. And then he started noticing the men who’d already served their time and walked out — coming back. Returning. To prison.
“That shocked me,” he says, “because why would anybody wanna come back to prison? It’s a terrible place.” He’d watched freedom get taken from him without understanding what it weighed until he saw other men volunteer to lose it again. “When they started coming back, I realized that if I did not change, I was going to become a career criminal, because I would return to exactly the same situation I had left.”
He has a theory about this now, built from the inside. “If you have blind spots and triggers, something has to break the pattern, because otherwise there’s no reason for you to change.” For most people the something never arrives, and they stay the same until they die. For Paul it arrived as a turnstile of returning men, and it was enough.
Here is the part that should not work and somehow does.
A 50-year-old ex-felon walks out of federal prison with his law license revoked — thirteen years before he can even apply to get it back. He has, by his own accounting, narrow options and a personality that has never played well with others. So he reaches for the only tools he kept: he can tell a story, and he has failed at the highest possible level and survived it.
He decides to coach. But coaching, as it’s usually sold, makes him wince. “The concept of coaching, to me, always felt too soft,” he says. “And that’s not who I am, and therefore, that’s not how I could coach.”
What he reached for instead, he found in a book he read in prison. In medieval courts, the king was anointed by divine power, which meant challenging the king was heresy, which meant death. “The one exception to that was the fool,” Paul says. The jester in the gaudy outfit, jumping and dancing at the foot of the throne — we remember him as entertainment. He was something else. “Because they were seen as being crazy, they had an exception to the rule of being able to tell the king the truth. So that psychological safety allowed them to tell the king when they were behaving badly or making a bad decision.”
That, Paul decided, was the job. “I’m going to present myself as that person that cares enough about you to give you the gift of truth.” The branding wrote itself. The No BS Executive Coach isn’t a slogan about being blunt. It’s a man who spent 30 years living inside an echo chamber appointing himself the one voice in the room allowed to puncture someone else’s.
His first proof that it might work came as a reference, or rather two of them. Within two years of getting out, Paul asked a client to vouch for him. The client offered a choice. “He said, ‘The first one is, Paul’s an acquired taste, like cyanide.’” Paul laughs telling me this. “I said, ‘I don’t think I’m gonna use that one. Give me the second one.’”
The second one became his entire philosophy. “Paul is a Sherpa. He will get you to the mountaintop, but he will not carry your pack.”
He means it structurally, not just spiritually. Paul puts half his fee on the outcome. A one-year contract, goals set together, and if the year ends without those goals met, he collects only half his compensation. “I believe I have to have skin in the game,” he says. “If I don’t have skin in the game, then I’ll let you off the hook. If my money’s at stake, I’m gonna put my boot up your tail if you’re not doing what you’ve agreed to do.”
I tell him this is, whatever else it is, excellent positioning — clear about who he’s for and unbothered by everyone else. He agrees without flinching. “If you don’t like the taste, I’m okay with that. It’s not gonna work, I don’t wanna take your money, and I don’t wanna waste my time.”
He is not a life coach. He says this twice, in case I miss it. “I’m a performance coach. I get hired to improve performance, and I will push you to the edge. I will not accept mediocrity.” His clients are already successful — that’s the point, he says, that’s how they can afford him. The work isn’t getting them from struggling to fine. “Everybody can be high-performing,” he says. “That’s no longer the goal. The goal is you wanna be world-class. World-class requires a much different set of requirements and effort.” Most people stop short, comfortable, well-paid, respected. He calls that the comfort zone and tells them, gently, that they’ll never get better inside it.
I ask him what he actually sees when a new executive walks in the door. The answer comes fast, like he’s been waiting for the question.
“They are trying to do too much too soon to make that impression that they believe is necessary to convince the person who put them in the position it was the right choice,” he says. They don’t breathe. They don’t listen. They invent problems so they can solve them. Paul has a 90-day program he runs new executives through, and the first instruction is always the same: slow down.
“Start to talk to the people,” he says. Mine what’s already there before you decide what to build on top of it. Most new leaders got promoted for being doers, and now they’re suddenly supposed to lead — a different skill set entirely. The instinct to do more, faster, is the very instinct that will bury them.
Then he gets to the part I don’t expect. He talks about sleep. About exercise. About family time. “If you’re not gonna take care of yourself physically and mentally, I don’t want you in my program,” he says. He runs a monthly audit — a full 24-hour walkthrough of how his clients spend their time and energy. He wants to know where the hours go. Travel, he tells me, is the worst productivity suck in corporate life. And family gets sacrificed first, always. “People who are promoted sacrifice family first, and that is a short-term — just a — it’s an ignorant way to look at it,” he says. “Your family is your support base outside of work. They are the ones that you should care about more than the job, so don’t shortcut them.”
He advocates for two phones — work and personal — and for turning the work phone off. “That freaks people out,” he says, and something in his voice suggests he enjoys the freaking out. “There’s this thing called voicemail. You’d be shocked how it works.”
The mechanism underneath all of it is the same one that saved him in prison. Something has to matter more than your ego. Something has to break the pattern. “If you’re still self-centered, there’s no reason to change,” he tells me. “It’s when you suddenly realize the impact you’re having on others that gives you the necessary strength to break the pattern.” For his clients, that something is usually their family. For Paul, it was the men coming back through the gates.
I ask him why the people at the very top — the ones who answer to no one but a board — are the ones who hire coaches. He gives me the line that reframes the whole conversation.
“The more successful you are, the more you need a coach.”
Then he reaches back across two thousand years for the picture. A conquering general gets his parade through Rome, the loot and the prisoners marched in front of him, the general himself in a gold chariot behind six white stallions. And riding in the chariot with him, the entire length of the procession, a slave. The slave has one job. “To continually whisper in the general’s ear,” Paul says, “’You are but a man.’ Because that type of success will overwhelm you and start to convince you that you are more than a man, and that means you think you’re infallible.”
That’s the chariot Paul rode for 30 years with no one whispering anything. The echo chamber had no slave in it. Everyone in there told him he was the smartest man in the room, and eventually he believed them, and then he committed 33 crimes and told a judge he’d done nothing wrong.
So he built the thing he never had and rents it out by the year. The man who could not say I was wrong to save two years of his own freedom now makes his living saying it for other people, before the parade, while there’s still time to climb down from the chariot.
It’s an acquired taste. He’s the first to tell you. He’s also, somehow, the only one in the room allowed to.
Guest Bio: Paul Glover
Paul Glover is the No BS Executive Workplace Coach at Paul Glover Coaching, where he works with C-suite leaders and high-performing executives across the United States on performance, accountability, and organizational resilience. Rising to prominence over more than two decades of coaching work following a complete professional reinvention, he became known for a performance coaching model built around blind spots, outcome-contingent fees, and a refusal to allow clients the comfort of self-deception. His largest active client is a billion-dollar distribution organization.
Previously, Glover spent 30 years as a labor employment trial attorney in Chicago, earning a reputation as an aggressive courtroom litigator. His legal career ended in 1995 when he was indicted on 33 counts of white-collar crimes — including kickbacks, bribery, and tampering with government witnesses — and subsequently sentenced to federal prison. He refused to cooperate with prosecutors to reduce his sentence, and served approximately five years before beginning what would become a second career launched from scratch in his fifties.
Released in 2001 with his law license revoked and ineligible for reinstatement for 13 years, Glover rebuilt entirely as a coach, eventually building a national practice. He structures his engagements as one-year contracts with 50 percent of his fee contingent on clients achieving mutually defined goals — a model designed to give him skin in the game and eliminate the incentive to let clients off the hook. His coaching approach draws directly from his own reckoning with ego, echo chambers, and the moment accountability finally broke through.
Glover is the author of WorkQuake™, a book on surviving and thriving in the Knowledge Economy, praised by executive coach Marshall Goldsmith as agitating “the business status quo.”
Hey,
Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.
I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.
So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.
I make this for myself first. If you read the way I do, you’ll want it too.
PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.
