real Are: ****

Orion: We love the myth of the "crazy genius," don't we? The visionary founder, like a Steve Jobs or a Walt Disney, whose brilliance seems inseparable from their intensity. But what if that intensity isn't just a personality quirk? What if it's the symptom of a serious illness? And what happens when the "vision" spirals into a full-blown psychotic break, landing a celebrated CEO in handcuffs?

real Are: It’s a terrifying thought. We put these figures on a pedestal, but we rarely look at the foundation they're standing on.

Orion: Exactly. And that's the raw, unflinching territory of Andrew Dunn's memoir, "Am I Ok?". He built the iconic brand Bonobos, but he did it while secretly battling bipolar disorder—an illness he called his "Ghost." Today, we have real Are, a product manager in the education space with a keen interest in creativity and mindset, to help us unpack this.

real Are: Thanks for having me, Orion. This book is… a lot. It’s incredibly vulnerable and hits on so many themes relevant to anyone trying to build something new.

Orion: It really is. And that's why today we'll dive deep into this from two powerful perspectives. First, we'll explore the 'Hypomanic Edge'—the seductive and dangerous link between creative energy and mental illness. Then, we'll discuss 'The Ghost in the Machine,' looking at how vulnerability and disclosure can become a leader's greatest strength. real Are, as someone who works in the creative and innovative space of product management, this story of a founder's mind feels particularly potent.

real Are: Absolutely. The pressure to innovate is constant, and understanding the source of that drive—and its potential pitfalls—is crucial.

Orion: So let's start with this idea of the 'Hypomanic Edge.' Dunn makes a critical distinction in the book, and I think it’s the key to the whole story. He says, "Hypomania is a vibrant experience of reality. Mania is inventing your own reality." real Are, that feels like the difference between a productive 'flow state' and something far more dangerous.

real Are: That’s a perfect way to put it. In product development, we chase that 'flow state'—that period of intense focus and creativity where ideas just connect. But the idea that it could tip over into inventing your own reality, detached from user needs or business constraints… that’s the nightmare scenario for any product leader.

Orion: And for Dunn, it was both his superpower and his kryptonite. In the early days of Bonobos, this hypomanic energy was everything. He was on a mission. He describes relentlessly pursuing angel investors, raising nearly four million dollars in small checks of $25,000 to $100,000. He was inspiring his team, he had this incredible, unshakeable vision for an e-commerce-first menswear brand at a time when most people thought it was a crazy idea. He was, by all accounts, on fire, and the company was growing at a breakneck pace.

real Are: That’s the part of the story we all romanticize, right? The hustle, the unshakeable belief. It sounds like the perfect founder story.

Orion: It does. But then you fast forward to 2016. That same source of energy, left unchecked for years, metastasized. He describes a full-blown manic episode. He's in his New York apartment with his girlfriend, Manuela, and her mother. He starts howling at the moon, believing he's a messiah on a mission to save the world. The episode escalates into violence. He ends up striking both Manuela and her mother.

real Are: Oh, my gosh.

Orion: The police are called. He's taken to Bellevue Hospital's psychiatric ward. And upon his discharge a week later, he's met not by his family, but by NYPD officers who arrest him. He went from being the celebrated CEO of a hundred-million-dollar company to being in a holding cell, charged with felony assault. It's the same source of energy that built the company, but with a terrifyingly different outcome.

real Are: Wow, the contrast is just chilling. It completely shatters the 'genius' myth. It makes me think about the very real-world consequences for the people around him. How did his team even function with that level of unpredictability from their leader? As a product manager, you rely on a certain level of stability to execute a roadmap, to build trust with your engineers and designers. If your leader is operating in a different reality, the entire machine grinds to a halt.

Orion: That's the core of it. He’s brutally honest about this. He admits his team was often walking on eggshells. During other, less severe hypomanic periods, he'd have these grand, impulsive ideas—like deciding Bonobos should launch multiple new, distinct brands all at once. It was a huge drain on resources, burning millions of dollars. His CFO at the time, Bryan Wolff, was constantly trying to ground him in financial reality, and it created immense friction between them.

real Are: So the 'hypomanic edge' that was so crucial for the initial vision and fundraising was also threatening to destroy the company from within. It’s not a sustainable source of creativity. It really highlights the need for systems and, more importantly, a team that can act as a guardrail. It's not just about the visionary; it's about the entire ecosystem you build around them to keep the vision tethered to reality.

Orion: A perfect transition, because that ecosystem, that support system, becomes absolutely critical when we talk about our second topic: 'The Ghost in the Machine.'

Orion: For sixteen years, from his first breakdown in college until that arrest in 2016, Andrew Dunn's bipolar disorder was a secret. He calls it his "Ghost," an invisible presence known only to a handful of loved ones. He was terrified of what would happen if the business world, a world that values stability above all, ever found out.

real Are: And that fear is so understandable. As an INFP, I can deeply relate to the fear of being misunderstood or rejected for your deepest vulnerabilities. In a professional setting, that fear is amplified a thousand times. You're supposed to be competent, reliable.

Orion: Exactly. And he tells this heartbreaking story that shows why he was so afraid. Years before, after his first hospitalization in college, he was at a bar in Chicago called Ghost Bar—the irony is not lost on him. He tried to talk about the experience with a close friend who had visited him in the hospital. He just wanted to understand what had happened. But his friend got uncomfortable and shut him down, saying, "I don't want to talk about this ever again."

real Are: Ugh, that’s devastating. That kind of reaction just validates the shame. It tells you: 'This part of you is unacceptable. Hide it.' It makes the ghost bigger and scarier.

Orion: It made the ghost more powerful. But after his arrest in 2016, the secret was out of his control. He had to tell his board of directors. He describes preparing for this conference call, thinking his career was over. He gets on the phone, his sister Monica by his side for support, and he just lays it all out: "I have bipolar disorder. I was hospitalized. I was arrested for assaulting my girlfriend and her mother." He's just waiting for the axe to fall.

real Are: I can’t even imagine the terror of that moment. Everything he’d built was on the line.

Orion: And the reaction, real Are, was not what he expected. There was a pause, and then one of his earliest investors and board members, Joel Peterson, spoke up. He simply said, "Andy, we love you. We’re with you." They didn't fire him. They didn't ostracize him. They supported him.

real Are: That gives me chills. Seriously. What the board did there… they created psychological safety in the most high-stakes moment imaginable. They didn't see the diagnosis; they saw the person they had backed for years. It makes me think, as a product manager trying to build a team, that's the culture you dream of creating—a place where someone can bring their whole self, even the broken parts, and not be cast out. It's the difference between a team and a family.

Orion: And it proves that this approach isn't just 'nice,' it's good business. It goes further. A year later, when Walmart was in the process of acquiring Bonobos for $310 million, he had to disclose it all over again to their C-suite and HR department. He handed over his entire medical file.

real Are: The ultimate due diligence.

Orion: The ultimate. And again, they responded with process and professionalism, not stigma. They had their own corporate psychiatrist review his case, who confirmed he was fit for duty with his treatment plan. They moved forward with the acquisition. The ghost, once it was dragged into the light of the boardroom, lost its power.

real Are: It proves that vulnerability isn't a weakness in leadership; it's the ultimate strength. It builds trust and loyalty in a way that feigned invincibility never can. By facing his ghost, he gave his board, his team, and even his acquirers permission to be human. It ultimately saved him and the company. It's a powerful lesson in empathy.

Orion: So we have these two powerful, intertwined ideas from Andrew Dunn's journey. The 'Hypomanic Edge' is a seductive but ultimately destructive fuel for creativity if left unmanaged. And the 'Ghost in the Machine'—our hidden vulnerabilities—only has power over us when it stays in the dark.

real Are: I think that’s the perfect summary. His journey shows that true, sustainable success, whether in building a company or just building a life, comes from managing our minds with honesty and seeking support. It’s not about being flawless; it’s about being whole.

Orion: And that honesty, that wholeness, is what makes this book so important. It’s a call for a more human-centered approach to innovation and leadership.

real Are: Exactly. It’s not about glorifying the illness, but about destigmatizing the struggle. The story leaves me with a question for myself, and for our listeners: What is one 'ghost' in your own professional or personal life—a fear of failure, an insecurity, a past mistake—that you're hiding? And what's one small step you could take this week to bring it into the light, maybe with a trusted colleague or friend, and see if it loses some of its power?

Orion: A powerful question to end on. real Are, thank you so much for bringing your thoughtful perspective to this.

real Are: Thanks for having me, Orion. It was a privilege to discuss it.

real Are: ****