Men, This Way
The Grand Delusions of Fame & Success w/ Adrian Grenier (105)
Today, I have the pleasure of hosting actor and activist Adrian Grenier as my guest. You may recognize Adrian from his roles in the popular HBO series “Entourage” or his appearances in films like “The Devil Wears Prada” alongside Meryl Streep, Anne Hathaway, and Emily Blunt. More recently, he has been featured in the Netflix hit series “Clickbait.” But, more importantly (at least for me) is that Adrian is my dear friend.
Adrian is part of my close-knit circle of friends, a group of remarkable individuals that I’ve featured in recent episodes. This circle includes the multi-talented artist Aryeh-Or, as well as my profound brothers Arjuna O’Neal, Stefanos Stefandos, and the brilliant Kelly Gardner.
Indeed, my circle of friends, known as “Man Cave Elite,” consists of extraordinary men. Today, I’m excited to introduce you to another thoughtful, introspective, and talented brother, Adrian Grenier. I’ve had the privilege of witnessing Adrian’s remarkable transformation journey. He has evolved from a wildly hedonistic and indulgent Hollywood actor—a lifestyle he openly admits to—to a grounded family man, a devoted husband, a new father, and a humble steward of 46 acres of land in deep Central Texas. On his new show, “Earthspeed,” which you can find on Instagram and YouTube, he shares his experiences and learnings from tending to and partnering with the land.
In this episode, Adrian shares the driving forces behind his transformation. What compelled him to change, and why? I believe every man, whether he openly expresses his ambitions or harbors them deep within, needs to hear the stories of men who have achieved cultural success, only to realize that the summit of fame and fortune isn’t all it’s cracked up to be. Adrian has achieved success at the highest level as an actor, and his journey is a testament to this.
Adrian and I also delve into our adventures and the challenges we’ve faced as brothers, both individually and together. We open up about some tender moments in our conversation—Adrian has just become a new father, while I’m in the midst of grieving the loss of my own. This conversation is a heartfelt exchange between brothers who sometimes have differing views on important matters but remain committed to supporting, loving, and respecting each other.
My new book Choose Her Every Day (Or Leave Her), written for men and women, is now also available for AUDIOBOOK as well.
(08:46) Adrian’s first video
In his first video, Adrian takes a nostalgic trip down memory lane as he reflects on the pictures and videos from that time. During that period, he was exceptionally sober and approached life with a profound seriousness. His beard was notably long and robust, and he paid meticulous attention to his hair and grooming. This was a time marked by deep retreat, meditation, self-examination, and a rejection of the material possessions he had amassed.
Adrian was constantly on the move, seeking to avoid materialism and distractions that might hinder his personal growth journey. As a result, he made the bold decision to move into a camper, which offered minimal amenities—a tiny refrigerator, a scant selection of cutlery, and a toilet. It was an incredibly challenging and uncomfortable experience.
Adrian expresses his gratitude to Bryan for being a supportive presence during his lowest moments, when he found himself at the rock bottom of his transformative journey.
(14:33) What stopped working for you?
Adrian took a moment to reflect. “Maybe everything was working out a bit too perfectly for me,” he began, acknowledging that he had surrendered his autonomy and authority to the unstoppable momentum and inertia that wasn’t truly his own. He described it as a thrilling ride, but it dawned on him that he was being drained. He had unwittingly become complicit in his own exploitation, allowing himself to be used for the sake of money, fame, and the illusion of power.
Over the years, even when he had all the trappings of success—money, fame, industry recognition, and access to all he desired—Adrian sensed that something crucial was missing. Despite life seemingly handing him everything on a silver platter, there was an underlying sense of hollowness. He had climbed the ladder of success, basked in the spotlight, and enjoyed the attention of admirers, but there remained an unshakable feeling that life couldn’t be this perfect.
Then, Adrian hit rock bottom, experiencing a profound breakdown. It was during this dark period that he confronted a deeply buried dread within himself, a part of him that had long been dormant and lifeless.
(25:12) What role did men play in helping you make that transition?
Adrian reflected on his journey and shared, “I began to realize that my perception of masculinity, as it’s often defined by society or portrayed in shows like ‘Entourage,’ tends to focus on power, good fortune, or sexual conquest. These cliches of masculinity can often lead to unhealthy expressions, which have been conditioned by the media for us to emulate or aspire to.”
He emphasized that it wasn’t the movies or media alone that influenced his behavior; it was the combination of these media portrayals with the masculine role models he had encountered while growing up. Adrian had men in his life who were physically present, but their teachings often veered towards destructive forms of masculinity. They taught him behaviors like indulgence, womanizing, deceit, evading accountability, and even absenteeism. Being an only child without a father figure to guide him, Adrian had to navigate these influences and figure things out on his own.
(31:56)How is your definition of brotherhood shifting as a result of your experience in this group of men?
Adrian shared his evolving perspective, saying, “I’ve often criticized ‘Entourage’ and that entire phenomenon because my awareness has expanded. However, I’m also careful to give ‘Entourage’ its due credit. It’s a fantastic show on a creative level, with exceptional writing, acting, and a captivating vibe. It served as a mirror to an era, being honest in its own way. It also provided an escape and a fantasy, allowing people to momentarily step out of the mundane reality and imagine a life with everything and no consequences.”
He continued, “Ultimately, ‘Entourage’ was about brotherhood and the unwavering loyalty of those four guys who could navigate the treacherous waters of Hollywood because they knew they had each other. If everything else fell apart, they could return home and find grounding in their origins. Loyalty is undoubtedly valuable, but it’s not enough for a mature brotherhood. You have to question what you’re loyal to. When you witness your buddies engaging in destructive, unhealthy, or misogynistic behavior, you should feel compelled to call them out. It’s about protecting them from making those mistakes and also shielding others from the negative aspects of masculinity.”
(37:31) How do you navigate these ideological differences between us in ways that don’t spoil our relationship?
Adrian explained his approach, saying, “What I’ve learned to do is to carefully dissect my own concepts and ideas of what’s right and wrong, what constitutes truth, and what loyalty means. I genuinely believe that these concepts aren’t fixed or static; rather, they exist on a spectrum. While the words themselves may seem absolute, they are more like vectors, pointing in various directions.”
(48:27) What do you think men are missing out on,who don’t have a solid trustable brotherhood?
Adrian pondered the question and responded, “Men who don’t have a dependable brotherhood miss out on a profound sense of place and belonging. We’ve also discussed the idea of a ‘dojo,’ a place to cultivate skills and become capable individuals who can achieve meaningful goals. A solid brotherhood consists of men who will not only call you out when needed but also call you forward, encouraging you to strive for more.”
He continued, “It’s about tapping into something more fundamental—the awareness that we are alive and sacred, yet we often feel alone. A brotherhood provides companionship and a sense of being held and supported. It allows men to be open, share their experiences, and find solace in knowing that they are not alone on their journey.”
(58:12)What is shifting for you now that you are stepping into fatherhood and particularly for a boy?
Adrian spoke from the heart, “I am profoundly grateful that I’ve managed to get my life together in time to become a father. There were moments when I wasn’t sure if this would happen for me, so I feel incredibly fortunate to now experience and witness life unfolding through the eyes of another being who shares a genetic connection with me. It’s a realization that clicks in your mind, like realizing that we are all part of this ever-evolving, growing, and timeless experience we call life.”
He continued, reflecting on his younger self, “In my youth, I had mortal fears, and I was genuinely afraid of the idea of dying. I wanted to cling to life indefinitely through my ego. However, I’ve come to understand that my existence is part of an infinite conversation—one that extends through our children. And it’s not limited to just biological children; it encompasses all the children we have the privilege of caring for and serving as role models.”
Adrian’s voice carried a deep humility as he spoke about his current life chapter. “The most humbling experience in my life right now is being a father and the challenge it presents to become the best possible version of myself for my son,” he concluded.
CONNECT WITH ADRIAN GRENIER
Instagram – @adriangrenier
Facebook – Adrian Grenier
CONNECT WITH BRYAN REEVES
Instagram – @bryanreevesinsight
Youtube – @bryanreevesofficial
Facebook – @Bryanreevesofficial
Tiktok – @bryanreevesinsight
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