Chris Webby holding a psilocybin mushroom

Honest, sincere and unapologetic. Chilled out, yet energetic. Smart, yet unpretentious. Successful and prolific, yet humble. Thats Chris Webby for you.

Guess cannabis, a bit of whisky, and the occasional psilocybin microdose have made him this way.

But whats behind this self-managed rappers success, both in music and business?

What inspires a guy who can talk about getting high by the beach and owning gold toilets as eloquently as he can talk about political corruption, sexual abuse, or racial issues?

This is the story of a white Connecticut rapper, his cannabis-infused rise to stardom, his entry into the business world, and all the things that have helped make this atypical musician one of the most prominent lyricists of the last few years.

Webby catapulted to fame in 2008 with a weed-themed song, LaLaLa, which to date remains his most listened-to track on YouTube.

Ever since, hes managed to build one of the most loyal fan bases in rap, largely on a pro-cannabis, anti-mumble rap, anti-creeps, anti-corruption, pro-freedom platform. Hes also dropped a few infamous freestyles on radio shows down the way, and collaborated with some of the biggest names in the music industry, from Mac Miller and B-Real, to Tech N9ne and Justina Valentine.

LaLaLa was the song that got me going in the first place, and it was a total weed song. But I dont consider myself to be a weed rapper, he said during a recent conversation. But some of my weed songs have been my biggest songs; they are a very important staple of my catalogue... I drop a weed song every 4/20, so theres at least one completely weed-themed song every year And this without considering the countless songs that reference weed.

See also: More Potent Than CBD, THC: Dr. Raphael Mechoulam Explains His Latest Discovery

Music and weed have always been such a hand in experience for me But I feel like Im so much more than a weed rapper: I stand for stuff.

And indeed, he does. Over the years, hes come after almost every major politician in the U.S., a long list of high profile sexual predators, and countless mumble rappers in his songs.

Since I last spoke with Webby a couple years ago, the rapper launched a new label, EightyHD, and signed hip hop artist ANoyd.

Chris Webby

Its nice to have something thats bigger than myself, he said. Instead of just working on Chris Webby stuff, I'm really trying to build a brand and work with other artists.

Of course, the COVID-19 pandemic presented numerous challenges for a business that relies heavily on live shows, but Webby says hes managed to weather them relatively well.

As someone running a business, you need to adapt and adjust, he explained.

However, in spite of the popular belief about artists making a large majority of their money from live shows nowadays, one would be surprised to know that this is not the case for everyone.

Streaming is a pretty incredible revenue source when you own your masters, he voiced, adding that dropping new music consistently and understanding streaming services algorithms are key elements to success.

But playing the system wont get you anywhere on its own. For Webby, building a strong team around you is equally important.

In recent months, Webby also got into psychedelics, joining the many people advocating for the renaissance of psychedelics as a valid therapeutic option to treat certain mental ailments.

I haven't been smoking a ton of weed lately, but I've been taking mushrooms... I've really started to embrace psychedelics in a new way than I did as a kid. They can be used in a way that can be so productive, use them as an alternative to many other medicines The gate is really opening and people are seeing psilocybin really differently and I think thats a great thing because it can do a lot of good, he said.

See also: Mike Tyson Will Print (Yes, Print) Cannabis Beverages

Interestingly, Webby credits SNL comedian Pete Davidson for his newfound (or rediscovered) love of psychedelics. I visited him on a set and he was microdosing, and I did it with him. I felt great: it was not intense, I was around people and not freaking out, just feeling like it was really nice.

Ever since, the rapper has educated himself on the medical benefits of microdosing psilocybin, and doing it the right way by dosing it properly in a controlled environment.

It was, in fact, psychedelics that led Chris to one of the most important realizations of his life so far: love is the most powerful thing.

Chris Webby

This new-found appreciation for love as a whole, and as a tool, he says, has been a constant throughout his trips. The reckoning of the value of love.

I can be a pretty harsh critic. But sometimes you realize that the only way to combat this is with love, in a lot of cases. And that is a realization that Im always reminded of when I open that psychedelic door in my head.

I would also say that everything is connected. As an environmentalist, that's something that really rings true. You look at the tree in your yard and you think the tree has been around for a long time; a lot of animals have lived in this tree; this tree has provided food for the ecosystem of my lawn I've always looked at nature that way, but psychedelics really remind you we're just part of this whole thing, we're part of nature, and we're f*cking it up, obviously.

This year, before the COVID-19 pandemic broke out, Chris rented a cabin in upstate New York, near Woodstock, and got all of his team up there. After a few days of administrative work, it was time to get to creating.

There's nothing like the energy of a roomful of people with a common goal in mind, he said.

Once again, psychedelics would come play for the team, inspiring recording sessions and even an entire song.

The song Drugs in a Suitcase came out of we tried the approach of watching movies with the sound off, which was a Mac Miller album. I had never really done that in the studio before and someone suggested it I thought it was an incredible idea, because movies are art, and to play a movie without the sound while you're working on music, and letting one inspire the other

See also: Little Dragons Yukimi Nagano On Psychedelics, Isolation And Connection

As a little gift to his fans, Chris Webby shared his video for Drugs in a Suitcase ahead of its official release on Friday. Check it out:

At the end of the day, its all about overcoming the stigma. Webbys ultimate goal is for people to understand that, even though he consumes cannabis and mushrooms, he is a productive human being. And others can be too.

Until recently, Webby was not a big believer in the benefits of CBD. He thought of it, like many others do, like snake oil.

Chris Webby

But quality and dosing are everything. Find the right product and dose for you, and youll likely feel the propper effects.

I have a new respect and love for CBD and hemp; CBD joints specifically. I'm someone who deals with mild-but-chronic back pain and, you know, that really, really helps and anxiety and stress

I feel like some people see CBD like it's just kind of all smoke and mirrors, but I will speak to the medical benefits of it and it's real. It can really chill you out, ease the aches and pains, and I'm a big fan.And so, in becoming a fan, Webby, in his characteristic entrepreneurial fashion, got into the CBD business.

See also: UNM Study: Cannabis Is Effective In Treating Depression, Improving Mental Health

I actually recently aligned myself with a really great cannabis company up in Maine called Humble Family Farms. One of the things were doing together is developing a CBD line, he concluded. Were really focused on genetics, and putting the quality and the farmers before profits.

Stay tuned for more on all things Chris Webby and cannabis.

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Chris Webby Talks Cannabis, Psychedelics, Rap And Business: Everything Is Connected - Forbes