105. The Grand Delusions of Fame & Success w/ Adrian Grenier

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. 

EPISODE HIGHLIGHTS 
(00:00) Intro
(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,