Read the Introduction & Chapter One

Introduction

June 15, 2024—The Best/Worst Day Ever

The sun was dipping low in the Los Angeles sky, casting an amber glow across the city as I cruised toward Dodger Stadium in my bright yellow 2022 Ford Bronco. Life, in that moment, felt good. I was headed to accept my newly appointed role as president of the Los Angeles chapter of the Entrepreneurs’ Organization, and a swell of pride carried me forward.

Then my phone rang. It was the call. The kind of call you never want to receive from your CFO.

As soon as I heard his words, I felt the blood drain from my head. My grip on the steering wheel tightened as I tried to navigate the chaotic traffic funneling into the stadium parking lot. By the time I parked in the uppermost section near the Dugout Club, my legs were weak. When I stepped out of the truck, I nearly collapsed. My stomach churned violently, threatening to reject everything I’d eaten that day.

I forced a deep breath and tried to gather myself. Just then, the outgoing EO president spotted me and rushed over with the energy of a man who had just been set free. His grin was so wide, he nearly knocked me over.

“Are you ready, Mr. President?” He beamed.

I couldn’t tell if he was genuinely excited for me or just thrilled to be handing off the responsibility. I grimaced, and he mistook it for nerves.

“Don’t worry. You’ll be great,” he assured me.

“I don’t know about that,” I muttered.

“Oh, come on, you’ve got this. You’re about to be president… and I’m finally free!” He cracked himself up, then noticed how pale I was. His smile softened. “What’s wrong? It’s not going to be that hard,” he said.

All I could manage was: “This is the best worst day ever.”

He looked confused for a beat, then surprised me with an unexpected hug.

Inside, the reception was warm… too warm. Nearly two hundred of LA’s most successful entrepreneurs filled the room, buzzing with excitement. They smiled at me, clasped my hand, and congratulated me. And all the while, fear spread through my body like wildfire.

It wasn’t the presidency that scared me. It was something darker. Impostor syndrome.

How could I, of all people, lead this group of wildly ambitious, fearless, wickedly smart leaders? What if they discovered what I really was… a fraud? That after seventeen years running my agency, I didn’t know how we were going to survive?

Then it was time for my speech.

Normally, a microphone in my hand felt like home. I’d been on stage since I was fourteen, plays, musicals, bands, public speaking, you name it. I loved performing. But this time, my hands trembled. My voice threatened to crack.

I had prepared a rousing, motivational speech, full of inspiration and uplift, the kind of thing that was supposed to ignite the room for the year ahead. But standing there, looking out at all those faces, I knew I couldn’t do it.

EO is built on vulnerability. On sharing the 5 percent of your life you don’t tell anyone else. And so, in that moment, I abandoned the script and told the truth.

“I just got off the phone with my CFO,” I began, “and it looks like we’re going to lose almost half a million dollars this month. Tomorrow, I’ll have to make a lot of hard decisions. I’ll probably need to fire people, cut salaries, and forfeit my own pay until we recover. And this comes right on the heels of owing nearly six figures for my son’s elaborate, yet unforgettable, bar mitzvah last month. I’m drowning.”

“But here’s the thing. In this room of inspiring entrepreneurs, I’ve been reminded of what EO really means. When I’ve shared pieces of this privately, no one judged me. Instead, you asked how you could help. Who you could connect me with. What I needed. You embraced my challenge as your own. That is what this organization is all about. And it’s why I’m honored to be your president for the coming year.”

The room erupted in applause. The rest of the evening was spent connecting, brainstorming, and problem-solving with people who genuinely wanted to help. For a few hours, I felt buoyed, supported, and loved. Part of something bigger.

But when I got home, reality sank its claws back in. I dreaded falling asleep, because I knew what awaited me in the morning: The music. The reckoning.

As I lay in bed, staring at the ceiling, my phone buzzed with a text. It was from a life coach I had hired for a workshop the previous year. I don’t know if she reached out because she’d heard about my new role, or if the universe simply nudged her toward me at the exact moment I needed it most.

“For some reason,” her message read, “I was just thinking of you and wanted to reach out. How is everything?”

“Terrible,” I typed back. “This is the best/worst day of my life.”

“Would you like to talk?”

“I would… but I don’t have any money to pay you.”

“Call me tomorrow at 9 a.m. I want to help. Don’t worry about the money.”

“Ok. Thank you so much.”

“My pleasure,” she wrote. “You’re going to be just fine.”

“We’ll see.”

The next morning, I called her. I poured it all out: how we’d just come off the strikes, how business had been improving, but now we were hemorrhaging money. I told her I was facing impossible decisions, layoffs, pay cuts, and for the first time in a long time, I was afraid. Not just for the company, but for my own livelihood.

She listened and then asked, “How are your partners handling this?”

I told her I had spoken to one of them. He was sympathetic. He’d said, “Wow, that’s awful. What are you going to do?”

In that moment, it hit me, and her, that he hadn’t said “What are we going to do?” but “What are you going to do?”

And that single word shift cracked something inside me.

I realized that while I loved my partners, and still do; we remain best friends, but I had reached a fork in the road. I had to consider whether we were truly adding to each other’s businesses anymore. The truth was, I felt I needed to go in a direction they wouldn’t support.

That’s when Dr. Nemeth said, “I’d really love to coach you through this.”

“As much as I’d love that,” I told her, “I can’t afford it right now.”

She said, “Don’t worry about the money. We’ll settle that later. You’re a good person, Brett. You’re kind. You’re smart. You’re capable. And I believe in you. I want to help you navigate this.”

At that, I broke down in tears. Because in that moment, she gave me an outside perspective on my inner truth: that I am kind. I am a good leader. I amsmart. And I didn’t need the crutch of partners to keep moving forward.

That realization became a mental and emotional breakthrough.

And what followed was one of the most profound Epic Shifts of my professional career: a new way forward, one that would redefine everything. RAVE Collective.

The First Fault Line

I was born Brett Cary Gordon on April 8, 1973, in St. Louis, Missouri, a brand-new baby in a brand-new marriage that was already starting to crack. My father, Stephen, was a traveling salesman for the world-renowned clothing line Christian Dior. He was living his best life, gone a total of four weeks throughout the year, traversing the Midwest, city to city, wining, dining, and placing orders. Back at home, he relaxed, golfed, partied, worked on the house, rode his motorcycle… oh yeah… and spent time with my mom. My mother, Marlene, was a young woman with a degree in social work and a heart built for helping others, but she suddenly found herself confined to the house. She was a strong feminist, a product of the late sixties, and this was not the life she had signed up for.

They were young. They were hopeful. Maybe they were in love, or maybe it was something that only lookedlike love from the outside. They’d both grown up in northeast Philadelphia, and legend has it they met at an Oldsmobile dealership, which might explain my lifelong obsession with cars. (For the record, my first word was “car.” I’m not sure my parents were thrilled about that, but I think it tracks.)

After the whirlwind courtship came the inevitable: engagement, marriage, relocation. St. Louis. A new home. A baby on the way. My mother was twenty-three, pregnant, and far from the friends and family who grounded her. She wanted to work. She wanted independence. But this was the early seventies, and my father’s Cuban American family believed a woman’s place was at home. She was supposed to cook, clean, and care for the child. That vision of marriage wasn’t hers.

Still, she tried.

When I arrived, my father celebrated in the only way men were allowed back then: from the waiting room. While my mother endured hours of labor, he puffed cigars and enjoyed a lobster dinner. That was fatherhood in the seventies, all ceremony, no substance.

Once we were home, the tension deepened. My father’s family came first. Every holiday, every decision, every need of my mother’s seemed to orbit around them. She was lonely. Stranded. Her world shrinking.

I’ve pieced this all together through fragments of conversation, half-remembered stories, and the kind of emotional archaeology every child of divorce eventually undertakes. My father still doesn’t quite understand why she left. From his perspective, he was a good provider. They had a new home, they both had cars, and they had extra income to play with. My mother always said he gave her no choice. Somewhere between their versions lies the truth, probably hidden in the gray space between love and exhaustion.

But one day, she was done.

She packed up her life, packed me in the car, and drove east… back to Philadelphia, back to her parents, back to herself.

In Philly, my mother rebuilt everything from the ground up. She got a job in social work, rented a small apartment on Parlon Street, and began raising me as a single mom. My father would fly in from St. Louis on weekends, renting an apartment of his own to be near me. I remember fragments: the smell of his cologne, the sound of his laughter echoing in small rooms, the cold taste of iced tea (which I hated but drank anyway because he handed it to me), and the sweet, crispy goodness of Frosted Flakes cereal, which I’m still fond of today.

I remember the red motorcycle most of all. He’d sit me in front of him, practically on the gas tank, between the handlebars, no helmet, the wind whipping through my hair as we cruised the streets. At three years old, I didn’t know about fear. I only knew that this… this feeling was freedom.

Until one day, that freedom ended in the driveway.

As we rounded a corner, I saw my mother’s car parked by my father’s garage. She was waiting. Arms crossed. Eyes sharp enough to cut steel. What happened next was a full-scale emotional explosion, a fight that could have registered on the Richter scale. I was too young to understand the words, but I understood the tone: betrayal, fury, finality. That was the night I learned how loud love can break.

A few years later, the visits slowed. Then they stopped.

My mother met Jeff, a kind, grounded man introduced by her father over lunch. He wasn’t flashy like my dad; he was steady, present, and patient. My father came from northeast Philly, where men were “men.” Jeff, on the other hand, came from upstate New York—Rochester, to be exact—and went the whole “hippie route.” When my mom got sick one day, Jeff offered to play with me so she could rest. We built entire Lincoln Log cities together, tiny wooden worlds that felt safe, sturdy, unshakable.

He loved cars too. That helped.

Before long, he was “Daddy Jeff,” and not long after that, he was my legal father. I remember standing in a courthouse as a judge signed the papers. My last name changed that day from Gordon to Winn. I was told it was for the best. That it would make things easier. That Steve, now referred to as my biological father, wouldn’t have to pay the child support he’d fallen behind on. Whether that was the truth or not, it hardly seemed like a good enough reason to stop being my dad.

I was told he could see me anytime he wanted.

He never did.

At first, I thought maybe he was angry at me, maybe he didn’t want a son who now called another man “Dad.” Maybe I’d done something wrong. Maybe I wasn’t worth coming back for.

It’s strange how early abandonment plants its seeds, quiet little roots of self-doubt that burrow deep and show up years later in ways you don’t expect: in workaholism, in perfectionism, in the need to be liked, in the panic that people will leave once they really see you.

Even as a child, though, I never fully gave up on him. I carried this stubborn belief that one day, somehow, we’d find our way back to each other. That the universe wouldn’t end the story there.

And eventually… decades later… it did. But that’s a story for another chapter.