Describe your path up until what you’re doing now?

I grew up in Milwaukee, WI. Contrary to popular belief, black people do live in Wisconsin. I grew up in the middle class. My parents were both college-educated. They, like most college-educated well-meaning parents, wanted me to be a good kid, get good grades, go to a nice college, get a good job, and be happy.

I had other things in mind. I constantly underachieved in school. I was asked not to return to my grade school because I was “disruptive.” I got kicked out of two different high schools. In short, I think I always had deep-seated issues with authority, but mostly I was a jackass and lived in an environment conducive to being a jackass. No matter how badly the people around me wanted me to succeed, I’d fall short. I was always told I was bright, had potential, was going to do great things, etc, but for the large majority of my life, I did the opposite. My first run-in with the law was at age 17, and it wouldn’t be the last. Even though

I grew up middle class and never wanted for anything, I found my way into the wrong crowds and started doing some seriously illegal stuff. Fortunately for me, the consequences didn’t match what I did.

I made it through high school and went to college, where I took underachieving to a new level. One semester in college I had a 0.00 GPA because I drank seven days a week and got high at the same rate. During that time, when I did stumble into class, I actually enjoyed it. I’d take part in discussions and had a genuine appetite to learn, but often I felt like the way school was set up didn’t make sense. Everyone would struggle to get these perfect grades that I didn’t think would matter in the long run. They’d take tests and then forget everything. I always had the nagging sense that perhaps we should be learning more about how to navigate the real world. So there was always this undertone of “maybe people in authority don’t have my best interests at heart,” coupled with me royally fucking up.

These two factors also led to where I am today. My bad choices in the past led to me reaching a point where I hit rock bottom. After that point, I decided I wanted to do something different with my life. My appetite for learning was still there and slowly but surely I started making changes. I read more, watched Ted Talks, and listened to interviews with successful people. Around that same time, I stumbled into writing. A friend noticed my positive attitude and thought I’d be a good fit to write for his website.

That was a few years ago. I’ve been writing incessantly since then. My past experiences and my inner worldviews can be reflected in what I write now. I’m actually glad I got in a lot of trouble and didn’t do well in school because if I had I might have ended up getting an M.B.A and being a management consultant, which is my definition of hell. That answer seems long.

I love it. Have you had any mentors or influential people in your life?

Absolutely. The first one that comes to mind is Lance Pauker. Lance was an editor at the online magazine Thought Catalog. He helped me improve my writing and gave me feedback on everything for a year straight. I worked with Lance and published something like 80 articles on the website. It was a crucial time in developing good writing habits. I owe him. As far as mentors go, I like to read books for mentorship.

Books are great because you get to experience someone else’s life or life’s work in a short period. Some of my favorite books are The Meditations by Marcus Aurelius, Total Recall by Arnold Schwarzenegger (this is one of the most surprisingly great books no one talks about), and Rich Dad Poor Dad by Robert Kiyosaki. I’ve also read 100+ other books that have acted as mentors for me.

As far as seeking out mentors, it just hasn’t been a priority for me. I think the mentor thing got really big recently, but I think you can find sources of inspiration from anywhere really.

Have you taken any big risks to move forward?

No. Tangible concrete risks? Nah. Here’s the thing about risk-taking. Most people think successful people are these big risk-takers and it’s just not true. You don’t have to “burn the boats” behind you to build something. You can always do it on the side. In fact, you should always start something new as a side project or an experiment.

This isn’t 1992. You don’t need a ton of capital and a physical place to start a business, nor do you need a publisher or T.V. Channel to get your message out there. You just need some courage. The only real risk I guess is disappointment and heartache. In that regard, I’ve risked something, but nothing more.

I learned a cool concept from the writer-philosopher Nassim Taleb, which is to look for things with high upside and a low downside. Take writing books. There’s very little downside to writing a book.

You can’t sell negative books, and you’ll likely recoup your investment at least. The upside? You could be the next Andy Weir (Andy Weir Self-published The Martian and it has sold bazillion copies.) Even business. With the internet, you can start a business with very little capital. Just create the least viable product and grow it from there. I kind of hate the idea of big risk-taking because it isn’t necessary.

You talk about books: have you written any?

I have written two books so far. Writing books has always been a dream of mine. With my first book, I actually took a course on writing and self-publishing, which helped a ton. I knew I had the content. I had written for a year at that time. But I didn’t know how to put it all together in a concise way for hundreds of pages. I have a pretty detailed process I use to write my books. I wrote a 4,000-word article about it actually – you can find that here.

I brainstorm ideas with a mind map. I do this over and over in 30-minute sessions. I’ll do a 30-minute session one day, sleep on it, and do another one the next day. Eventually, I’ll have everything dumped from my mind and I’ll create a detailed outline. After the outline is finished I write a minimum of 1,000 words per day until the first draft is finished. I don’t focus on anything else. After the rough draft is finished, I go through several rounds of self-editing, often chopping off entire sections or chapters in the process. I know I’m done with the book if I’m starting to get very nitpicky. At that time I send it off to an editor

Are your friends and family supportive of what you do?

They’re not supportive. Actually, I don’t spout off my dreams much to anyone. I prefer to do the work first then tell people about it once I’ve gotten some traction. If you let people, they’ll shit on your dreams. My fiancée was a bit skeptical about the writing/online biz thing. Not that she thought I was going to fail miserably, but she didn’t want me to be overly ambitious and disappointed. Most of the time with friends and family, they’re just concerned. They want you to be safe and happy.

I did have a friend who was outright negative about my writing. I cut him out of my life. When it comes to negativity, I’m ruthless about removing it from my life. Other than him though, I haven’t had any overt negativity directed my way.

(Laughing). I do the same. Are you creatively satisfied?

No. I’m the cliché writer who is never satisfied with their work. I will look back at something I’ve written and hated it. I always want to be better, more creative, more creative, more original, etc. I don’t have paralysis during the writing process itself, which is great, but I do look back and wish I would’ve done better. Each book I have out I want to rewrite entirely, but people have enjoyed them, which means I’m too critical of myself.

I’ll admit I get too caught up in views, sales, metrics, etc. I’m careful not to try and fit what I write into a package I think will do well, but I also try to join marketing into my work and engage with people. It’s tricky. I do love when people reach out to me and tell me they enjoy my work. I’m a narcissistic and arrogant person.

I love validation. I can’t help it. Anyway, back to the question at hand. I don’t think I’ll ever be creatively satisfied and I’m okay with that. I write because I don’t feel like I’d be better at anything else in the long run. I believe in the idea of being useful above being satisfied. I’ve thought about this before in-depth — wanting to be happy and fulfilled is kind of arrogant. Like, who says we are entitled to that? We just assume we are. The more I write the more I realize my work is for other people. It’s one of the few ways I’m able to be empathetic — it’s actually hard for me to show empathy in my life. So, I do my best now to focus on if I can satisfy other people.

That said, is there anything in the next five or ten years you’re interested in doing or exploring

I have a lot of books to write about. I plan on writing one every six months until I die. I read a blog post from James Altucher once where he talks about the fact that he wrote like 15 failed books and that his 16th outsold all of his earlier books combined times ten. That’s what I find solace it — placing enough bets until one of them hits. I’m trying to challenge myself more with each new book and come up with something interesting. I’m also into speaking. I’ve done it for about a year now, just practicing, and I just landed a TEDx talk, which I’m really excited about.

In the next five or ten years, I want to be wiser. I’m a big believer in erudition. I want to have read 500 books in that time. There’s so much to learn and not enough time.

More important than all the above stuff though is wanting to become a better father. My daughter is 14 months old. I look forward to her growing and teaching her about life. I plan, to be honest with her about how much life can suck. I don’t want her to be one of those sheltered kids. I also want to teach her how to still live well even though life inherently sucks.

I want to be as honest as possible and be a great example for her. I want her to see that I took my path regardless of what other people wanted for me. I hope she feels inspired to do the same. I will let her pursue anything she wants. I joke with my fiancée that if she wanted to be a clown, I’d let her. Like, if she was dead serious about it, had her whole clown kit put together, was practicing and watching YouTube videos of famous clowns learning their routines, I’d support her 100 percent. I think parents really fuck their kids up when they try to impose their wants and needs onto their kids.

What type of legacy do you want to leave?

I want to help as many people as possible live up to their own definition of success. Keywords being their own. I feel like we have been programmed to believe certain things from the minute we were born up until our early adulthood. I’ve also seen this realization hit people like a sucker punch when it’s almost too late. I don’t want people to follow my program, but rather reprogram themselves.

I want to feel like I stood for something. I want to have told the truth. That’s why I feel better about this second book than the first one. The first one I wrote was cobbled together from other people. It was the “you must follow your dreams!”. Now I realize there is no one size fits all dream. Some people aren’t meant to be millionaires. Some are meant to make $30,000 a year selling handmade jewelry, being the world’s best mechanic, or taking care of a family. What I do know is that many people seem to be not doing whatever that thing, or those things, are.

I love writing because my great-grandkids can get to know me after I’m gone. Who knows how long my words will live, but I hope they’ll be around for a long time.