From Asshole To Meaningful Entrepreneur: How Tucker Max Went Inward For Healing, Love & Happiness

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Tucker Max - Asshole to Meaningful Entrepreneur
Tucker Max - Asshole to Meaningful Entrepreneur

Tucker Max is no stranger to the typical “disclaimer” that most blogs, interviews, articles and podcasts give in their preamble. Tucker was one of the first outspoken bloggers on the internet. If you have not heard of him, you will probably google his name. What you will find is the writing of a very creative and entertaining young man in his early twenties depicting a certain phase in his life that included his sex and party life. What you probably won’t find is the Tucker Max that I met in his downtown Austin apartment.

Back in the early 2000s, I was in my prime college years. And although I have written about my ongoing depression and panic attacks, I did have plenty of fun. It was about that time that I stumbled upon Tucker Max. My roommate at the time had literally pulled me over to his CRT monitor in the computer lab to read this massively long article about drinking. What 21-year-old isn’t intrigued by that stuff? (There are certainly some, but I was a buffoon back then.)

By the time I left college, most of the internet was familiar with the musings and rendezvous of Tucker Max. He went on to write six books, became a New York Times bestseller, and turned his life into a Hollywood movie. An internet legend that was soon to be forgotten for me, as I embarked on a world of post-college career flipping. (keep reading below the podcast for more)

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It wasn’t until recently, in the past six months, that I once again stumbled upon Tucker Max. This time I was listening to him on the James Altucher podcast, talking about being a parent, eating a paleo diet, going through psychoanalysis, and meditation.

What?! How can this be? This did not sound like the guy who wrote I Hope They Serve Beer in Hell. This was actually someone who I could relate to. Again. As a father. As a healthy eating advocate. As an entrepreneur. As a writer. As a meditator.

I then started reading more of Tucker’s most recent work. They are well-documented pieces of his current life as a hard-working dad, dedicated to his children, and as an avid meditator.

However, one thing that rings abundantly loud and clear throughout his current writing (2015–2016) is a voice that is very honest about his brash and machismo early writing. He’s not apologizing for his actions, which would be super easy to do. Tucker Max actually takes a hard line with himself, and at times, seems to beat himself up a little too much.

This brings to light an all-too-common trait in most human beings. We are too hard on ourselves and a lot less forgiving. I’d be lying if I said that while listening to Tucker speak, I wasn’t reminded of my previous wrongdoings, and began to punish myself for them. It is also worth noting that although some would disagree with his very risqué previous lifestyle, everything he did was consensual and not harmful.

What I found in that Austin apartment, was a man who has had more success than most can dream of, who fell on his face after an unsuccessful movie, and found a more enlightened path through introspective work.

Although most of us may not have the same monetary success as Tucker, there are many similarities in our own Hero’s Journey, where we are on top of the world, and if we can just get that one last taste, that one more thing, we will call it a success. Then the world rears its ugly head and slaps us right in the face. It isn’t until we are left cleaning up the mess and stop feeling sorry for ourselves that our next, deeper, more fulfilling journey begins.

Tucker’s recent project, Book in a Box is what he describes as him finally “doing meaningful work” in this world. Not as a remorse project, but a new journey to solve an age-old problem of book writing.

As you will hear in our conversation, and probably relate to and find very endearing, even though we might be on a more fulfilling path, and as we try to suppress our old voices and habits, a flavor of them occasionally comes through. But it is just enough flavor to be perfectly appealing to the senses.

Don’t think that Tucker Max is now contemplating his navel all day, or has given up that remarkable story-telling of his past. No, he has a very colorful counterargument to the ongoing legal battles of Gawker Media. Often a target of the controversial media outlet, Tucker shares that Peter Thiel’s backing of Hulk Hogan is not anything new in legal practice, and in addition, is a beautiful reflection of the working man’s journey to take on a conglomerate much bigger than himself.

Tucker is also a vocal critic of the Donald Trump vs. Hillary Clinton presidential race. While both are “monsters” in his opinion, Bernie Sanders is the most honest, but he will literally destroy our economy if elected.

What I learned from my visit with one of the first and most controversial voices on the internet is that there is always another story behind the story. There is a depth to each of us that we so often don’t ask about or share, and when we do, we connect, on a very deep and meaningful level, even if it is just for an hour.

I was able to meet and converse with one of the original bloggers on the internet. Love him or hate him, if you are a proponent of free speech, Tucker Max is on your side. And in an age where being more vocal may actually decide the new leader of the free world, it would be smart to pay attention to voices on a more enlightened path.

Please enjoy my conversation with Tucker Max.

Be nicer to yourselves, everyone, including you Tucker.

—Jake Carney

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