Locked In with Ian Bick - Robbing A Drug Dealer & SURVIVING Jail | Chris Webby

Episode Date: September 21, 2023

Born & raised in Connecticut, Chris Webby showed drive and passion for music at a young age, beginning to write rap songs at age 11. The only child of a middle school teacher and guitarist, Chris enjoyed his alone time and began experimenting with drugs. In 2009, he was arrested for an attempted robbery on a drug dealer at his college. Though he only spent a week in jail, he was expelled from the college. This was the catalyst for him. In two years, he released six mixtapes, went on to found his own label, toured all over the country & worked with some of the biggest names in the industry. Thank you to Factor for sponsoring this episode: Go to FACTORMEALS.com/lockedin50 and use code lockedin50 to get 50% off your first box. Connect with Chris Webby: https://www.chriswebby.com https://www.youtube.com/@chriswebby Buy Merch: https://lockedinbrand.com Use code lockedin at checkout to get 10% off your order Connect with Ian Bick: https://www.ianbick.com 00:00 Intro 00:50 Factor AD. 03:35 How he got the name Chris Webby 04:09 Childhood 06:11 Being lonely as an only child 07:50 Turning pain into humor 08:15 The start of selling & using 10:00 Diagnosed with ADHD 12:25 Knowing he wanted to be a rapper 13:49 Jobs before becoming a successful rapper 15:31 Social media & overnight success 16:58 The truth about wanting to be famous 18:06 The truth about getting signed to a label 20:20 Selling in high school 21:40 Stigma Around substances 22:40 The Slim Shady influence 24:04 Parent’s finding out he’s using 25:00 Using Edibles 25:44 Dangers of using and having rules 26:55 Factor AD 28:45 Rethinking Substance use 29:58 Being a party kid 30:26 Why does alcohol get a pass 32:10 Promoting drinking as an artist 33:24 Going to a concert as an artist 34:00 Graduating High school 36:00 What it’s like to go on tour 36:33 not letting your passion become something you hate 37:39 Committing a robbery & getting arrested 46:49 Booked into jail and Bail 49:20 Snitching 51:30 Experience in jail 1:00:00 Conclusion of the case 1:01:55 thinking about the legal system 1:04:00 The power of second chances 1:05:50 Kicked out of college 1:08:00 Creating a music career 1:10:00 Funny urine test story 1:12:30 Biggest misconceptions of the music Industry 1:15:04 How his criminal experience prepared him for his career 1:18:00 A world of being able to go viral 1:18:50 Tuxedo Junction 1:21:55 Promoters who lose money on shows 1:23:42 Talking about getting arrested 1:26:30 Message Produced by: https://www.instagram.com/shanedanahy https://www.shanedanahy.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Welcome back to the Lockton with Ian Bick podcast. I'm here sitting in our brand new studio that's designed just for the locked-in set. And I'm so, so excited that our first guest in our new studio is Chris Webby. He's a rapper from Connecticut, who I actually booked when I used to own a nightclub as a teenager. He's a great guy. We had an amazing conversation about how he actually got caught up in a failed robbery attempt while he was in college, spent a week in a Connecticut state prison and then ended up having to turn his entire life around

which led to a successful rap career. This episode, we dive into his childhood, his upbringing, and the actions that led him to go down a bad path and how he was able to turn it all around. I also wanted to give a huge, huge thanks to Factor, our delicious sponsor. With Factor, you could choose from 34-plus weekly flavored pact

dietitian-approved meals ready to eat in two minutes. Head to Factor Meals.com slash Lockton 50 and use code Lockton 50 to get 50% off. Thank you again to Factor who has sponsored multiple episodes of the Lockton with the NBIC podcast. And thank you guys, the listeners, the viewers who have continuously made us a top 200 podcast for society and culture in the world. I hope you guys sit back, relax, and enjoy. my episode with Chris Webby. Chris, thank you so much for coming on Locked in.

Absolutely. Good to be here. It's insane. Like, I never thought 10 years ago when I was booking you on concerts at Tuxedo Junction, which we'll get into, that we'd be sitting across from each other on a podcast that I'm the host of. Yeah, there wasn't even such thing as podcast back then. It's a crazy, a lot of time. A lot of time has gone by since those old days.

I miss Tuxedo Junction. That was a fun venue. Yeah. I haven't seen you since the Kid Ink show, I think, when I book Kid Ink and you came out as a cameo. And we used to do the Christmas charity drives together, too. Yes, we did. Yeah. I think I was dealing with Chris Fury and Justina Valentine.

Right? Yeah, she came out to a couple. But I did Tuxedo. I mean, a good handful of times. That was actually my first show. There was one where this guy booked me. I want to say this is like 2009. and I was not ready to have a show at all, you know,

and he never paid me. We didn't bring out that many people. And that was like the first official show, but I'll tell you what, there were some fans who drove from Wisconsin to come to that show, and I still see them when I go out to Milwaukee. They still come out.

That's so cool. And that was like in the era of like Asher Roth and Sammy Adams and that whole group. That was, yeah, that particular show, that was literally 2009. Fresh Mango Productions. You remember them? That might have been the show.

Yeah. They were doing the Thursday college nights. Yeah, no, those came a little bit later, but wow, I totally forgot. Fresh mango. I actually have a picture of you in my office from the show. You're shirtless, and I think it has, what, 203 tatted on you or something like that? Yeah, yeah. On the side.

That's on the banner because our photographer put together a whole thing. But, yeah, thanks again, man. Let's jump into it. Is your name actually Chris Webby? I was always curious about it. Christian Webster. Christian Webster. How did you turn that into Chris Webby?

Well, when I got to middle school, my mom was a sixth grade teacher at West Rocks. Middle School in Norwalk. I later got a scholarship to private school for being smart. But when I was at public school in Norwalk, everybody called her Miss Webby. So when I got there, I was Little Webby. and then I got big and became just Chris Webby.

That's awesome. What was your childhood like growing up? What area did you grow up in? What's your family like? I grew up in Norwalk, Connecticut. I'm an only child. I have very loving parents, you know, very supportive. At first, they didn't really understand the hip-hop thing at all because they're a little bit older.

They're like, my dad's like about to be 75. My mom's in her early 70s. So, you know, they were more like the Woodstock generation. So they raised me on great music, really good music. But they definitely did not understand. But throughout life, being an only child is weird. It's a very weird experience. I've talked to other only children.

And we all seem to be, I would say, precocious. You know what I mean? We're around adults a lot when we're kids. So we pick up on certain social things and we're good in conversation, but also it's very weird being an only child. you know. I had friends who were like siblings, for sure, a couple in particular, but I'm still an only child at the end of the day. So I spent a lot of time reading, playing with action figures, making like these crazy storylines, you know, with all my X-Men and Ninja Turtles and all that. Had a lot of free time on my hands. You got to figure out what to do with it. But it was good, you know, very middle class. My mom was a public school teacher, like I said. My dad was, he was a guitar player, still is a guitar player. So at the time, he was doing a lot of weddings. It was that era. But he was playing around doing, you know, guitar lessons, stuff like that.

He taught me a lot about music. But, you know, just standard middle-class American family. Grew up in a condo in Norwalk over by the batting cages, not too far from here. And, you know, kind of like the type of situation, you're going to see less and less of that in today's America. You know, it's really hard to the middle classes. getting all the way edged out, you know, the wealth gap is insane. But this was the 90s, you know, late 80s, 90s, it was a different time. Things were good, you know, or seemed to be, you know.

Were you ever lonely, like, as an only child? Oh, yeah. Oh, yeah, definitely. But I also, I think all only children, even though it's kind of a lonely experience, we very much value alone time. We can't be around people all the time. It's important to have that detox period where we can sit with our thought. and do some alone shit, some only child shit. Not that other people don't need that too,

but I've noticed, at least in my experience, a lot of people with siblings like to be around people all the time. You know, they kind of like that. I have like a social limit, you know. And that's where, like, touring can be a lot. Because you're just around, you're around your own crew, then you're around, you know, venues where the people meet and greets. It's a lot.

It's very taxing, but it's all about this. you get back to the hotel room at the end, silence. Yeah, something I've seen a lot in, like, music and growing, a following myself is there'll be some followers or fans that, you know, whether they're bullied and they look up to individuals like yourself in music. Do you feel like you relate to them because you've experienced that alone time as an only child? For sure. And I wasn't like, I wasn't a cool kid per se. I found my way because I think I had the social intelligence to be able to maneuver, but I wasn't, like, good at sports. I was a scrawny little thing. You know, it took me a while to grow into, you know, being an adult, getting a little

beard and some tattoos, you know, did me wonders. I was kind of like a little scrawny, ugly duckling. So it was weird trying to figure out where I fit in. So I developed a sense of humor. And that helped a lot because, you know, when you're getting fucked with, it's better to be in on the joke. You know what I mean? And so I think I developed a real sense of humor about just life as a whole,

as kind of probably that like as a coping mechanism, you know, therapist-wise, if you really like think about it. But yeah, I, you know, and then I started doing and selling drugs. So that kind of like. In high school. Yeah, that was like my lane. That's where I kind of added value to the social. Do you think that came from being like kind of secluded and bullied and picked on?

that that developed? You know, I wonder, a little mix of that, listening to Eminem, you know, it just, drugs have always been a large part of my life, especially as a rapper, you know, once I discovered, you know, weed initially. But I've been on Adderall since, like,

I was in seventh grade. So I was accustomed, you know, biologically to drugs and at a pretty early age. And, you know, drugs are not for everyone. I try not to endorse them too much, but I have found a way to kind of like be Hunter S. Thompson-esque in terms of figuring out a little bit of this, a little bit of that. And then, you know, that'll put me in the right headspace to do this.

So that's kind of how I've operated through a unbelievable portion of my life. Like, you know. Was that Adderall prescribed to you? Yes. Oh, yeah. So do you think you would have the same view on drugs or same taste for drugs if you were never prescribed that as a child? That's a very good question. That's a very good question.

You almost wonder if, like, Big Pharma was just conditioning an entire generation of kids to, you know. Well, even that aside, like, imagine if your parents never brought you the doctor that day to get that prescription. And I don't ever want to put any blame on them because this was a different era. And, you know, I was definitely like acting out, I suppose. Uh, class clown, you know, it just, and. What it comes down to is I do have ADD, ADHD, what they say, you know. I've also heard some people say that that's made up, you know, in more recent times. But as far as what they say, the diagnosis is, I fall very much under that.

I was tested in a facility. And, you know, the thing about it, though, is, like, you can learn to work with it. I just can't focus on things that don't interest me. So when it came to math and, you know, chemistry and things like that, no wonder, of course, I couldn't focus. I have no interest in that shit whatsoever. So I borderline couldn't do it. My math skills are atrocious, which is sad because my mom's a math teacher. She was a math teacher.

So it was even more of a joke at home. But, you know, when it came to English and history and things that I was interested in, I actually, like, over-excelled in it. And what I've noticed is like a lot of people with ADHD, their ability to hyper focus on things that they're interested in is almost like abnormally efficient. So obviously fell in love with hip hop, making music. And when I dial in on that, it's almost like I tap into something, you know, divine almost.

You know, it's crazy where I can, my brain just totally flips how it's operating. And I just, I lock in. But at the same time, you know, some days I'm just wandering around my house, vacuuming corners and, you know, taking one pile of clothes, putting it over there. And that's what my Adderall got me that day. You know what I mean? I just move some shit around and end up doing a whole bunch of nothing. But I do think, I do think there's beauty to probably the majority of what people would call disabilities.

You know what I mean? It's like, for everything that you saccharacter. Like, yeah, okay, I can't focus on all these things that I'm not interested in, but then I have this gift to be able to hyper focus on things that I am. So it's like you've got to just find the good with the bad and anything in life. You know, some people are dealt awful hands, you know, and you can't really give that advice to them. You know, life is a bitch. Sometimes it's not fair, you know, but you work with what you got as best you can.

You have to roll with the punches. You got to just roll with the punches. And if anything, moving through my career like I have, man, there's been a lot of of punches. A whole lot of punches. Did you know what you wanted to be when you grew up at that freshman sophomore year of high school? Maybe right before. I knew what I wanted to be in fifth grade when I first really discovered hip hop. From that moment, it was like, I'm going to be a rapper, period. That's it. Were people trying to talk you out of it during that time period? Definitely, like I said, my parents didn't understand it. And a lot of other people thought it was

absurd, but I could not be swayed in any direction other than the mission. And like it's just, you know, that's why sometimes when I see some of these guys where it clearly is like a hobby or a hustle to them that just kind of turned into a fruitful endeavor, that can be, I don't want to say like frustrating, but it's just like this is all that I've been put on this planet to do in terms of a job, you know. And when you end up in a cool position, you're able to do things, other things add value to society in other ways. but, I mean, as far as what I've wanted to do with my life, hip hop, from the moment I discovered it, that was it, battling in the lunch line, freestyling at parties. It just was everything to me. You know, and I try to stay in love with it like I did then, you know. Sometimes you've got to find ways to, like, re-fall in love with it. I'm about to be 35.

I've been a professional rapper for like 15 years. It's been my actual job since I was able to quit where the little kid party place that I worked at, pump it up. That's where you work. I worked at a few places. Leslie's pool supplies, border grill, worked with my grandpa fixing bathtubs, my cousin doing boat electronics, and the final job I had was pump it up,

which was a literally, it was like Discovery Zone, like a little kid party place, except everything was inflatable. So I would just walk around with a whistle on my neck and tell kids not to run. And it got to the point where some of these little kids would be there for birthday parties and be like, oh my older brother loves your music.

I'm like, dude, this is weird. You know, but yeah, that was the last job. So I consider once I quit an actual job and started rapping full time, that's kind of like in my head as long as I've been a professional rapper. You know that period of time is the most humbling, though,

because I remember before I could take the podcast full time, I was Uber driving, but I was still pushing out content on social media so people would pop in the Uber and they'd be like, hey, I saw you on TikTok. And it's such like a weird limbo because like you're doing your passion, but your passion's not paying for your life. But it's definitely humbling to think about as you get to where you want to be. It is.

And, you know, there's no shame in it. I think that social networks have warped people's perception so much where they think that that's like embarrassing. But there's no shame in working a job until you don't have to anymore. It's like people just want to be a rapper overnight, be a podcaster overnight. night. It should take time to get where you want to get. If it doesn't, then that's going to come back around. These people who skip all the steps and find success immediately, I feel like a lot of times that backfires down the line. Well, and you know, social media contributes negatively to that. You look at like that girl Bobby who blew up on the podcast, who's doing all these big

interviews and like the Alex Earls of the world. Young people are looking at that and thinking that that was just an overnight success. And I don't know like the backdoors of what those went through, but that's just how it's portrayed in that world. And it does happen. You know, some things do blow up overnight, but the best things don't. And I'm very thankful, even though it's like my career is a very interesting beast to look at because it's like I've had all these triumphant moments, but then they were followed by kind of just like either a plateau or a humbling and, you know, then build back up.

So it's like my journey made me very tough, very thick-skinned because it's, It's like just when you thought you were, you know, really on the path, you know, you end up on your face and you got to get back up and figure out what to do next. And I'm very thankful that that happened. I think if I had blown up when I was, you know, back in the tuxedo days, when I'm putting out mixtapes, A, my music was not there. I wasn't ready to be just on the full world stage. My head definitely wasn't there. I was very childish. I was doing a lot of drugs.

and I think that could have gone horribly awry if that it all just panned out and everything that I thought I wanted had happened. Yeah. You know, because I look back, you know, when you're young, you think you want to be famous, you know, you think that that's a big part of it, but then when you get older, you realize that's actually the worst part of it.

You know, you want the financial security of it. You want the respect. You want, you know, obviously to be admired in a certain sense, but you don't want this massive fame. I would never want to be as famous as Eminem. Listen to a lot of his songs. You know, it sounds like a tough life. I like to be able to go out, you know, do things on a whim,

not need a ton of security, you know. Yeah. And just be able to go get a bite to eat with my girlfriend or something like that. You know, it's like when you're super famous, you can't do shit like that. This is such an interesting perspective in conversation, too, because we're both on opposite ends. I was the concert promoter that wanted to be famous,

that fails miserably. and now here we are and, you know, life humbled me and I went through my stuff and figured out kind of what my purpose was. Right. And it's not chasing the fame. That comes with what you do naturally. Then here we have you from the artist's perspective. And so many kids relate to you because everyone wants to be that artist.

And you actually got to live that dream and get there. And if you think about it too, it's like, you know, a big thing when I was young, it was like, oh, I got to get signed. You know, for rappers especially, that was like the big. thing. I used to always, I was like, oh, when I get signed, you know, it's like, fuck that. Like, that's the last thing. I, you know, I do not want to be on a record label in retrospect. You know, at the time, it was a different time. Being independent, it was kind of a newer thing. Social networks were new. I got an Instagram right when Instagram came out. I made a Facebook

fan page right when they came out. So it's like, I've been around since the dawn of a lot of these platforms. And, you know, I came up in the mixtape era, so all that music was free. So it was kind of a tough business model. He spent all this time making a project just to give it away. But now with the streaming and everything, it's like I kind of wrote a blueprint, you know, for the independent artists. And I'm so glad I wouldn't be able to say half the shit I say if I was on a label. I say crazy shit because I have no master. I have nobody to slap my hand and say, no, you can't say that. I probably wouldn't be here today. They'd tell you no. Yeah, I mean, I literally, I answer to no one, you know, and that's like kind of the ultimate only child trajectory.

It's like I never did answer to anyone, you know, even my parents, because I figured out pretty early on, it's like I'm the only kid they got. What are they going to do? Send me away. Yeah, and I feel like I'm at that spot too because for so long I wanted an agent for first starting out and stuff. And now I'm at that level where people are interested, but it's like I got here on my own. I don't need someone's help to, like, go to that next level or change things and lose control. It's so much more rewarding and so much less complicated. I mean, when money does start coming in, then it's like you've got all these different layers. It's got to go through all these percentages.

It's like it ends up. I landed in a pretty nice spot, you know? So it's like I could have never predicted that. You know, my ride was so bumpy. It's a really, it's been a long, winded career. It's taken a chunk out of me. Don't get me wrong. It's been exhausting. But I'm happy and I wouldn't change a thing. And wiser. Much, much wiser. So let's talk about the bumpy parts. High school, you start getting into selling

drugs. Are you like a high level drug dealer, low level? What are you doing exactly? I mean, high school, it was really just selling, you know, buying an ounce, selling enough to smoke for free. You know, that was pretty much, that was pretty much the goal. I used to smoke. a lot of weed. I do not smoke anywhere near as much weed as I once did. I was out of control, waking up smoking weed, smoking weed throughout school, you know, like leaving, coming back. I don't know how I functioned, but I did somehow.

Sold a little bit of blow, you know, in high school. I did my share of blow back then, no doubt about it. Shitty drug, shitty drug, always pokes its head back up here and there. You know, it's a hard one to avoid in life. but definitely not a drug that I would suggest or give like a high Yelp review to as far as drugs go. There's some great ones out there. That one kind of sucks, but it's just, it's always around when you're drunk. But anyways, yeah, I mean, it really, that was pretty much that.

And it was just kind of like selling weed to kids at my school and, you know, the other school in my town. but it really wasn't, I was no kingpin. What was the stigma around drugs during this time period? Because this is about 10 years before I was even born, give or take. Well, it was like, you know, we're talking, how old are you? This was like 06, 07. I'm 28. So you were selling drugs.

You were born in the 90s, though. I was born 88. 88, okay, seven years. Yeah. So, I mean, I wasn't selling drugs before you were born. No, no, no. Of course not. But, like, different childhood, you know, growing up.

To me, there was no, like, and no one was doing coke in high school when I was in high school. I feel like it was a little different. Yeah. Or at least none of my friend group. They were doing weed. Doing weed. I used to call it.

I was a kid that would pretend to take a hit and then blow it out thinking I was like one of the cool skateboarding kids and whatnot. Oh, I was inhaling that shit. It's funny too because like when I discovered weed, it was kind of like when I discovered hip-hop I smoked weed for the first time and was like, oh yeah, I'm going to do this all the way. I love this. I'm now like immediately a stoner.

So, and that was the case. Was it just a known thing that drugs were associated with hip hop back then? There was, really, I mean, when you listen to old Eminem, he was one of the first guys, at least in my experience, who talked about doing them. You know, a lot of these guys had always talked about selling them. But, you know, I was the perfect age for like the slim, shady influence. You know, when he was coming out, I was in like fifth grade. So it's like, I got the best of Eminem and the influence of him and his lyrical abilities, you know. But also, you know, I can't say he was the greatest role model on the one hand.

But, you know, at the end of the day, it's entertainment. So it's, you know, what you do as a person from the things you're exposed to, it's like Grand Theft Auto. You know, just if you play Grand Theft Auto and then you go steal a car and run six people over, you can't blame the game, you know. But a lot of people do, especially when there's violence and in the world. I would never, I would never blame Slim Shady for me tinkering with drugs in my early days. But I can't say that it didn't make me curious. And I think that's really what I always had a curiosity with drugs. I thought it was interested.

There's so many of them, you know. So I, yeah, I tinkered quite a bit. What did your parents think about your drug use during that time? Did they know? They didn't know a lot, obviously. But, I mean, they caught me smoking weed in eighth grade and they were pissed. They caught me again when I was a freshman in high school and I kind of was like, I smoke weed, you know? And they smoke weed, you know?

Like, it's just kind of like weed is not a big deal. At the time, the laws made it seem like that. But here we are now in 2023. It's not a big deal. It never really was. You go down the road, there's a dispensary now in Danbury. Yeah. That's insane.

Yeah. I mean, it isn't. It isn't. Like, weed is not crazy like that. It helps people. It can be very medical to, you know, a lot of people dealing with a lot of things. There's also several types of weed that have different, you know, medicinal benefits. But back then it was like whatever your dealer had, you know, and we were just looking for the strongest it could possibly be.

I was so anti, like any type of drug for a while. and then my girlfriend recently got me into doing edibles, and I sleep great. See, edibles, those things, man, they get me, like, I get, like, panicky. So, like, edibles don't agree with my genetic disposition. I feel safe for taking some mushrooms, honestly. Really? My cousin loves mushrooms.

Mushrooms are great. Mushrooms are a drug that I would give a fantastic guilt review to. I think psychedelics in general, if you go into them, with intention and you respect them, you can walk away with a lot. And I have. I've realized a lot of very important things throughout the course of my life from taking psychedelics. Now, is there a danger to any of these drugs that you do and that you're open about talking about? There's a danger to anything, you know?

And what it comes down to is, like I said, I don't endorse doing certain things. I've seen a lot of people, you know, do try a drug that I, you know, would do here and there and then develop a really bad problem with it. And I think you have to be very aware of your disposition because addiction is a crazy thing. And I've seen a lot of friends go down a very rocky path with that. And I think what's really, I'm really glad that I avoided the, Opiate epidemic. I just never really got into like the perks and a lot of that shit when it was going around the roxies.

Because that's that's like devil's potion. You know what I mean? And a lot of, it's the gateway to heroin. You know, I had rules for myself. It was crack, meth, heroin, never, you know. So you got to have rules. My entire life of doing drugs is following rules. Have you tried Factor Meals?

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slash Locked In50 and use code Locked In50 to get 50% off. That's code Locked In50 at Factor Meals.com slash Locked In50 to get 50% off. Big thanks again to Factor for sponsoring today's episode. When you see individuals go down that path of addiction, does that make you rethink your use of drugs at all? I mean, I'm very understanding.

and and I think we all got problems and I don't judge I don't judge people going through that especially you know the friends that I've seen going through it it's it's sad to see you know and I've seen people get on the other side of it I've seen people battle it and are still battling it and it's it's really again that's why you don't want to certain ones you've got to just stay away from and at the end of the day the music that I make is going to be kind of, it's going to be what I live and what's real to me. And drugs have played a role in my life,

therefore, you know, they found their way into my subject matter many times. But I also am not like, you know, drugs are awesome, go do them. I'm just telling my life experience. Exactly. Now you start selling drugs in high school. Is that the first entrance way to going down kind of a bad path to what you, were used to growing up with? Yeah, for sure.

I was a big party kid. So, I mean, that all kind of came, that all kind of came to a single head. So it's like, yeah, you start smoking weed, whatever. And then, you know, you get sophomore, junior, senior year. Now you're going to parties. You're drinking. Partying was a big part of my life for a long time.

Still is, to an extent, when I tour. But drinking, you know, drinking became a big part. of life in high school. And I hate drinking. I think drinking is the most overrated substance on the planet. And I think people are very hard on talking

about drugs and for some reason alcohol always gets a pass and I think, you know, I'm not saying I don't drink, I'm shaking a hangover still because I had people over last night for a Labor Day party. But at the same time, I view it as a social lubricant. I use it as such.

So when I have shows and I got to be around a lot of people, I'll drink because it makes me a little more cheerful and in a good mood. But it's really, it's not a good thing. And you see people who drink all the time, I think that's as bad, if not worse, in some instances, than people who have a drug problem of sorts, depending on the drug. And it kills more people than I think weed would in essence. The DUIs. Definitely more than weed. Yeah, 100%. Definitely more than weed.

I mean, if you drink all the time, like, you will die eventually. Your liver will shut down. It does a number on your body. So when I do drink, especially now, I drink, when I'm on stage, straight Jameson. So I'm not getting the mixers and all this extra shit. You know, it's just straight liquor. It agrees with my disposition. I've been known to kill quite a bit of a bottle on stage.

And it is what it is. It's just kind of part of the show. I walk out holding my Jameson bottle, and it's been like that for years. Will there come a time where, you know, I tour, and I decide I really don't want to drink anymore, and I don't want this to be part of what I need to perform? You know, yeah, maybe, but.

What's it like from an artist's perspective to be, in a way, I know you're not personally doing it, but in a way you're promoting like that drinking by the performing, in clubs that do serve liquor and there could be kids there underage that are drinking and whatnot. What's it like from an artist's perspective? Well, when you're at a show, it's a party. That is a time where drinking can enhance the atmosphere. You know what I mean?

I'm not saying people shouldn't ever drink unless you have a problem with it and, you know, you've had a stop. I do think that, like, you know, those are the type of occasions where drinking is a fun thing to do. You know, it's a vibe. Everybody's in there, you know, the energy, this big collective energy transferring from artists to crowd and back and forth. It's like a beautiful thing. You don't need to drink to enjoy it, but it can enhance it.

Like when I go see a concert every now and then, which sometimes I will pop out and just try to see one and not have anything to do and just enjoy a show, that's one of the times where I will drink for sure when I'm not on the clock. But I really try to not bring this. drinking home with me. You know, a lot of my touring habits, you got to leave that shit on tour. When you go to those concerts, are you like nitpicking in your mind like, oh, this production's off or this doesn't sound good?

I mean, yeah, it's kind of like a director watching a movie. You know what I mean? It's like you notice certain things because you understand. You can kind of see some of the band guys talking to each other. You could tell if there's a little technical issue they're having that most people probably wouldn't notice. And definitely, yeah, you see things through a different lens. Yeah, I do that too when I go on like other podcasts or just watch and kind of listen and see

what's going on. Yeah. And I felt that way as a club owner when I would go to like Toad's Place, the famous Toad's Place, and see shows, which is interesting. Do you end up graduating high school, get a diploma? Yeah, yeah, graduated high school, Greens Farms Academy. Like I said, I got the scholarship there. So I went there from seventh grade to senior year. And yeah, I mean, I did, I did good enough. I think I got honor senior year. Funny, funny story.

My math teacher definitely hooked me up on my finals, though, because I got a 16 out of 100 on my final for math. And he gave me a C-minus. So shout out to Mr. Lippman for that, because, man, that would have, like, completely plummeted my entire GPA. Like, 16 out of 100 is horrible. Yeah.

And I like tried. So that goes to show, you know, like, I'm very intelligently efficient in certain categories and very not in others. Do you think your life would be different now if you went to a public school instead of private? I think it was nice that I went to both. I think it gave me a better worldview, you know, and a better understanding of just people, you know. And that's part of what I like about touring, just meeting so many different. kinds of people who do various things, different socioeconomic classes, different jobs, you know, you meet a mechanic and a doctor in the same meet and greet. It's very interesting

getting that kind of perspective. Because at the same time now, you know, I'm not out and about all the time. I stay home as much as possible, honestly. I got a house in the woods. I try to be there as much as possible. But it's really nice to go out and connect, and that's one thing that still is very nice about touring. Because touring gets exhausting, man. At the same time, it's like, been doing this shit for a long time.

It really, like, you know, when a tour is coming up, sometimes I'm like, fuck, you know. I can burn you out. Yeah, and I know, I know it will. You know, so when I see him coming down the line, I'm like, all right, all right. Got to just mentally prepare for, because when you're on tour,

everything else that you have going, on in life, like it all gets put on pause. The only thing that matters every day of tour is the show that night. That's it. You know, it's really hard to stay on top of phone calls and personal relationships, anything. It's just your borderline unreachable for as long as you're out there. And I think it's just a matter of being careful, too, of making sure that your passion, what you love, doesn't become something you hate doing.

And that's something like I've been so focused lately on cutting out everything in my life that I don't see in the future friends, family relationships, work stuff. I love what I'm doing now and I don't want to like overwhelm myself with doing nine million things. Yeah. And it's taking a lot of like growth and maturity to get to that. Time management is really, you only got so much of it, you know, and you want a little bit of free time to be able to sit, do what you like to do.

I try to read every morning, you know, play the occasional video game. You want to leave a little bit of time for yourself to actually enjoy life. then you end up looking around. It's like all I've been doing is working. And, you know, and I love what I do, but you got to also just take some time to sit back and appreciate it. Appreciate the fruits of your labor. Life's too short to be doing anything else.

Yeah. And staying present's hard, man, because we're trained not to. We got the phone in front of us all the time. Ding, ding, text message. Oh, yeah, I got to do this. You know, it's like we live in this world that where the pace of it, you know, it makes it very difficult to sit back and, you know, be present. like people used to be, you know?

Absolutely. Now, college, you don't end up finishing college, do you? No, I do not end up finishing college. What happens? So, real interesting story happened there. You know, freshman year, did my thing, whatever, had a good time. Sophomore year, that's where the life-defining moment comes into play. And where we have, you know, a shared experience in terms of going through the legal system and walking away learning something,

which I think is very important. And I do think that people do deserve a second chance because some people fuck up. And some people don't learn. And those people become career criminals. Some people realize, man, I got to stop putting myself in situations like this or stop doing whatever I'm doing

and like change my life path to what, you know, I want to be doing. because this is going to hinder everything. So the way that all went down, and where I was in life, I feel like is important too. It's like broke college student, right? Recently had broken my laptop and had my car broken into by a crackhead

who stole my GPS and my iPod. So I couldn't even find my way home unless I printed out some MapQuest, which was like a thing back then. You print out the directions. And I was trying to get back from long, Island, man, that was not easy. So on top of that, my laptop and my iPod,

I now no longer have beats. Beats were kind of everything. So it's like, I have nothing, I have no music, my entire library's been gone. I was just in like a bad spot. So, was hanging out at a house of friends of mine, you know, and in the story, we'll call them,

we'll call them like a video game, player one, player two, player three, player four. Player one, was a, you know, what I thought, a good homie while I was there. We would go out, have a good time, get bitches, you know, do all this stuff that you think is important when you're in your early 20s. Player 2 lived there as well at this house, along with Player 3. And Player 4 was a girl. So one day we're just sitting over there.

And the girl, Player 4 comes in, she's talking about how much of a scumbagged is drug dealer on campuses, right? we'll just call him the dealer. I didn't really know him anyways. I didn't know who he was. Player one has the bright idea to rob him. Right? So they're concocting this whole plan. Someone's supposed to drive them.

Cool. I'm just sitting there getting high. Like, I think he was smoking weed, maybe doing a little coke. And then the kid who was supposed to drive ditches, you know? It gets cold feet. I'm sitting there. I got a car. Fuck it.

So player three drives player four, the girl, right? Who knows the guy. and I drive player one and player two in my 95 Nissan Ultima, which was in rough shape. She leaves the door open, and they ran in, the two guys I drove, they ran in and they robbed the dealer on campus with BB guns. And hop back in the car, drive back to the house. Everything seems, you know, this is not a situation I would put myself in normally.

I'm not a robber. You know, I'm a good, good vibe, usually. Robbing is a bad vibe. So, you know, we dump everything out at the house, right? So we now committed a robbery. I drove the car. You know what I mean? We don't really think of the ramifications of this, you know.

Omar from the wire, he robbed drug dealers. I'm like, dude, that great character, you know. So no one viewed my involvement as this as much. I just driven the car. So they just threw me like a couple hundred. and the ecstasy pills because I sold ecstasy in college that was kind of my niche because I had discovered ecstasy fun drug not a drug to do a ton of or your brain will end up mashed potatoes permanently I've seen it happen now this is where it gets crazy you know we're sitting there

cool whatever then everybody's Facebook starts ding ding ding ding ding huffstra's on lockdown Hofstra's on lockdown, all this shit. This was all Player One's idea. So, you know, he starts getting a little panicky. He tells me, he's like, Webb, take this back to your house. Because I didn't live with them, right? So I do. I take it back to the frat house that I lived in, right?

Threw it in a shed in the back. Next thing you know, Player 4, the girl, obviously. So important detail. The dealer called the cops. The dealer calls the cops. The dealer called the cops. Wow. So he goes in, right?

And the cops go in. He's like, yeah, they broke into the safe and took all the money. And the cops are like, okay, so you're a drug dealer, clearly. Not, it really is just the biggest, the amount of idiocy on all fronts by everyone involved. Like it was just stupid stupidity across the board. So he's very stupid for doing that. obviously they go pick up player four the girl because she was the one who was there you know what i mean so let's see what's going on with her they find her pick her up she had coke in her pocket boom

she tells them where player one and player two are player one mind you told me to take everything to my house just in case anything went wrong they go there now at the time i was trying to get some sleep if i recall and i took ambien right ambient back then used to get you all waxed out, like tripping, you know? Player three called me. He was all bugging out. He comes by. He had dropped the girl off. We were, I guess, the two drivers, right? So I'm like, yeah, man, no, it's crazy. It's crazy. Let's go take a walk, you know? So we go walk over by the fried chicken spot. We're out in Long Island, right? Just a little stroll,

try to cool off. Then I got a phone call from one of the kids who lived with Player 1 and player two and they said they just arrested them they're coming to your house right now and i was like what i fucking tell player four three excuse me i tell player three this is confusing the video game shit uh i tell him to just get the hell out of there he never got arrested for it god bless he was gone he's out of the story now i run back as i'm running back to my frat house full speed. I see a line of cop cars coming down the fucking street. And I'm just like, oh my God, I had time to run into my

house, throw out whatever personal drugs down the toilet, go answer the door. We're looking for Webby. Mind you, I'm on Ambien. I'm tripping. And hardened detectives have now showed up at my door. They're basically just like, yeah, we're

looking for this, this, this, and this. Like, the exact list of everything that I had been given in a backpack and told to take to my house. I'm just like, oh, Jesus Christ. So they had told them everything, told him where I lived. So they came in, started interrogating me, which is illegal, and that came into play down the line. And I basically was like, I don't know nothing. I don't know nothing. They're like, everything is here. Tell us where it is, or we're going to rip this entire house apart. This house

is a bunch of innocent bystanders. They may have had their own drugs or whatever, but no one was involved in this and I'm like damn I don't want to get everybody in trouble over here just like look in the shed you know maybe you'll find what you're looking for so cool now they have evidence but fuck you know real rock in a hard place so then uh you know get thrown in the back of the car i don't even think I'm in trouble at this point you know take us down to the station and uh sit me down I'm sitting in the in the police station for a long time just sitting there like yeah you know when can i leave etc etc and uh they're like why don't you just sit tight they come in about an hour later with a stack of papers just tap them on the table

and they said so you were the driver i was like oh no they had written statements from every single person involved and i just was like damn they all threw you under the bus they all threw everything under the bus, you know? I mean, again, it was like, I try not to hold anything against anybody. You find out down the line when you're actually, like, in court and you hear the cops say it out loud, be like, player one, then told us the location of Christian Webster

where everything was. It's like, damn, bro, like, fuck. But again, we were just idiots, you know? So then it's like, boom, we're chained to a wall in a police station for an entire day overnight. They offered to allow me to make a call, and at the time I didn't realize how serious it was, so I was like, can I just call in the morning

because my mom, you know, I don't want to bother. They absolutely did not allow me to make that call at any point. Days went by before I was able to make a call, mind you. So we go down there. Then they put you in the cell where it's like before, So now this is like day two. I'm in a, I'm in like a holding cell with a guy who's detoxing off heroin,

um, puking everywhere, you know, and I'm just like, Jesus Christ, haven't slept now in two days, Ambien, you know,

man, weird mind state. Mind you, they also put me in with the drug dealer at one point. I've never met this dude until then. And he just goes like, why, why did you? I'm like,

bro, I have no idea. I have no idea, bro. I don't even know you. My bad. You know what I mean? got, fuck man. He was like crying and shit.

I'm like, oh, no. This is, this has gone horribly awry. This is just snowballed out of control. So then, uh, we go to the arraignment, right? This is the whole, the whole step by step. Now, I found it very interesting because player one and player two literally had done the same thing. They both went in, you know?

So in my mind, you'd think that. that they should get the same punishment or the same bail, but Player 1 was white and Player 2 was black. And one of them, Player 1 got a $75,000 bail, player 2 got $150,000 bail. And I was like, wow, that's,

that is systematic racism right there. That's truly insane. Then it was my turn, and I had the additional charge of tampering with evidence. So then they said my number, and it was $200,000. Wow.

My parents still didn't know. Still didn't talk to my parents. Where did they think you are? They were panicking. They eventually found out my ex-girlfriend told him. But at this point, you know, on my own out here. So then I was just like, I honestly like chuckled. I was like $200,000.

Wow. Okay, this is a whole thing. This is literally like a whole thing. Take you to the back. You know, that's where you get your little orange jumpsuit. They check up your butt hole, you know. and I'm just like, man, this is, this is like, this is the real deal. Okay.

You probably never thought that would have ever happened to you before then. No, no, I did not. But that's what you learn, you know, hanging out with idiots. And, you know, it really taught me a lot about who your friends are, you know, to have been thrown under the bus. You know, the word snitch gets thrown out a lot, rat, whatever. And, you know, I feel like if you're a civilian and you witness a crime, that's not snitching.

You know, if you see someone get murdered and you're just a bystander and you're just trying to do the right thing, that's not snitching. But if you are involved in the same crime and you tell them about someone else involved in it, I feel like that's kind of snitching. I feel like I really kind of got snitched on, you know? Like, actually. So, wow. That's going to be a great clip for this show.

Yeah, like it hurt my feelings, man. You know what I'm just like, damn. But hey, it is what it is. And it's funny how convoluted information gets. And honestly, some people were trying to say that I was a rat because I had a vindictive ex-manager who started that little rumor. Back then at that time? It was like, it was a little bit later.

Okay. And like a year or so later, this is a bad guy. And, you know, I stopped working with him. How was your music career at that point? Are you on your own? It was like in the baby stages. La La La La had been recorded and was on MySpace. you know, so I was like, I was still on my space.

Do you think if this event happened at your peak, it would have derailed your entire career, just going through the legal process? Yeah, I definitely think it happened at the best time it could have. And I'm glad that it happened. It taught me so much. And I changed my entire life path. It really made me take stock of what was important.

And made me just realize, like, yo, I have this dream and I have to chase it. And mind you, a lot of the first part of my life, career, I'm still going to court. I still thought I was going to do at least a year. You know, I had six felonies. Wow. You know, nobody walks away from six felonies. You don't think.

Well, let's take it back. Now we're in jail. So you spend 72 hours. You get the little shot. I don't know. TB. Yeah, of course. And you get the bump on your arm.

If the bump goes away, you go to Genpop. So, you know, bided my time in there. hung out, made some friends. I actually, like, I was freestyling all over the place. There was one very important freestyle that happened, but that didn't happen until Jen Pop. I'll get there in a second. And I was only in for eight days.

I'm throwing out terms like I'm this hardened criminal. I am not. You know what I mean? I'm embarrassed, honestly, that this happened. That's why I don't talk about this that much because I don't want to glorify it. I don't think it's cool that, like, I got in trouble. Yeah, we never see you really talking about it. I think this will be interesting for your fans.

Yeah, yeah, I mean, it's, it's... There's a lesson behind it. There is a lesson behind it. And I think, you know, it's so long ago, the case is sealed at this point. You know, I still don't want to throw out any names of people involved just because I feel like that's tasteless. It's crazy how you remember, though, like the T.B. I bring on people who have done significant time and they don't remember. Well, maybe because the rest of their time was, you know, so eventful.

They kind of forgot, you know, I was in there for eight days. So I remember it all eight pretty well. But yeah, you know, there was a lot of, you know, you're going in the bus, you're going to court. I remember one time I was chained to a MS-13 member at the, I believe the wrist and ankle, maybe just the ankle. But he was very scary, did not speak English. He was one of the guys who made me quite uncomfortable. But it was interesting, while I'm chained next to this guy, you know, this guy up in the front, they're like, yo, you're the rapper kid.

And I'm like, yeah, they're like, yo, spit some. I'm like, all right, you know, like, okay. This guy next to me is terrifying me, but sure. And, you know, spit something and everybody, I almost like, I had a decent time when I was in there, all things considered. You know, my personality and charisma kind of carried me. I don't think that would have carried me in prison, but I think, you know, in just county lockup, I was enough of a little party trick that people kind of enjoyed my company. for the time I was in there.

But, you know, so you go, you do that. And by this point, my parents had found out. So they came down one day. You know, I come out in the orange jumpsuit. They're horrified, understandably. And, you know, they let me know, okay, we've talked to a lawyer. He's connecting us with another lawyer, and we got it under control. Luckily, my great-aunt had a medical settlement check,

and she helped loan money to my parents for, for the lawyer and for the eventual bail, thank God, you know, because it was a lot of money. And a good lawyer does not come cheap. Worth every penny. Now, at that point, then, you know, it was basically like, stick it out because they will lower your bail. You know, $200,000 is absurd.

So I was like, yeah, for sure. Let's wait until they lower it. So we go, now I'm, get to general population. All right, that's a whole different vibe. I got my little thing over my shoulder. I walk in and I'm like, yo, does anyone rap here? Everybody looked at me like I was speaking Chinese. Whatever.

That comes back to play into the story. But I ended up being next to a guy named Jojo. He was facing his second murder charge. And I believe it was self-defense. His story was, you know. It checked out. It checked out. It checked out to me.

And he loaned me a sandals so I could take a shower. And I thought that was very nice of him. One sandal or two? Both sandals. Both sandals, because you don't want to be bare for it. But I didn't have nothing. You know, I didn't really have much in the way of supplies here. So that was a really nice act of mercy in a time where I needed, you know, anything.

Now, that night, my first night in Gen Pop, that's where you have like the glass doors, at least in Nassau County. And Jojo is in the cell next to me. He said, yo, Webby, right? I'm like, yeah. He's like, you really rap? And I said, yeah. He's like, all right, spit something.

This is at night, all right? I walk up to the door. I see everybody walk up to the door. And I was just like, oh, my God. Okay, this is the most important rap I will have ever spit in my entire life. And I did. And I spit fire, apparently, because the next day, I was greeted with a lot of daps and pats on the back.

And it was a very surreal moment where I realized, wow, you know, I could do the, I could be rapping at house parties, but I can also wrap in jail and, you know, get pats on the back, you know, that's maybe I got something here. And I remember a much older gentleman came up and he was on the other side of the cell block the next day and he says, I couldn't, I didn't hear you last night. I'm all the way over there. Spit something for me right now. I was like, oh damn. All right. I did. He interrupted me maybe like, you, 24 bars in. He's like, I like you. I'm going to make you a sandwich. And he did. And it was the best just straight, cold cut sandwich I've ever had in my entire life. I think it was baloney.

The baloney prison sandwiches aren't bad. Underrated. What the hell is of the bologna, but. underrated. You think it's bad because you get them at first, and then you don't get them anymore when you get to Gen Pop unless you have commissary. So it's like, I remember they did like a turkey dinner one night and that shit was so gross, bro. It was like rubber. I will say the first time I ever had chicken salad, though, was in jail and that opened me up to realizing that I like chicken salad. Were you a picky eater at all? I was a picky eater. So going into prison must have been very hard for it. Yeah, I mean, but that's where, you know, you can't be picky. You got to, yeah. You got to eat every single calorie you're handed. Well, you could probably say you're a vegetarian or something, or some people in the federal prison system say they're Jewish,

and they need the kosher meals. Yeah, I got to cross on my arm, and I would prefer gross meat probably over, like, whatever half-ass vegetarian option. I don't think they, they don't really care about your wants and needs in there. That's something you realize real quick. You don't have rights. I remember one time one of the CEOs pulled me aside and got all in my face. He was like, you know, if you were my fucking son, blah, blah, blah, bah, talking about all the physical harm he would do me.

And, you know, I just was like, sir, good thing I'm not your son, you know. Like, get out of my face, bro. My life is in shambles right now. You're going to give me some sort of pep talk, scared stupid shit? Like, I'm already like, you know, I'm already pretty fucked up in the head right now. I'm holding it together, though. the other the rest of them they all got bailed out pretty quick um i was the last last man standing in there you know and and i think i handled it the best uh and uh you know it just was what it was like

when it comes to life you got to just like we said roll with the punches man you know it's like i'm in here right now you know let's make the best of it we can and uh you know so we did and then maybe like two or three days into being in Gen Pop whatever day eight was you know it was like

my bail had got lowered my parents finally got the money together and I got out said peace to everybody they wished me well I remember one guy pulling me aside and said I better not ever see you in here again

man you got something special and I remember that really really rang true to me this guy named twin nice guy and that I carried down that with me. You know, it was like,

these are some of these guys, you know, they already blew it, you know. They were in county lockup at the time, but they probably were facing charges, you know, they might not have gotten out for a long time. And their hopes and dreams were pretty fucked up, you know, they might not have a chance, a second chance, you know. And I took that seriously. And when I did get out, then, you know, it's like,

you got the whole court process and everything. but this is where getting a good lawyer comes into play. The best. Kevin. He was the best, man. Bald guy, very tall, wore a bow tie in these spectacles. And he was, he saved my life. I credit him to really having saved my life. I remember we got in with him.

When he found out who the judge was, he was just like, I went out vacation with him and his wife, who went whitewater rafting a year ago. And hearing that, I was just like, man, that's what it's all about. That's why you pay for a good lawyer if you're able to. And, you know, it was a long process and it all shook out. Really at first, the way this case was viewed by the DA,

the DA wanted to like make an example out of all of us, right? Then the assistant DA came into play and had a much more nurturing touch and realized like, Are we going to ruin all of these kids' lives forever? Or are we going to give them another chance and see what they do with it? And that's what they ended up doing. My lawyer did a great job. When the detective who was at the house initially came onto the stand, having him, you know, calling him out for interrogating me,

that made him look real stupid. Yeah. Because you're not allowed to interrogate someone until you've made the arrest. So that was good to just see him sweating up there because I fucking hated that guy. I hadn't seen him since, you know, it all initially happened, but fuck that guy, dude. And yeah, you know, I was able to walk away from it. One drug misdemeanor. That's it.

One drug misdemeanor. Unbelievable. Now, Chris, does it make you think about all the people, now that you're older, all the people that were in similar positions that didn't have the luxury of getting a paid lawyer and that have sat in prison and gone through that and faced that amount of time. Absolutely. I think the legal system is a really fucked up place to be. Just even seeing like there would be days we would have to drive all the way to Long Island

for a court date. And then we'd get there and be like, oh, no, it's rescheduled. It's just like, bro, what? It's a mess. It's a fucking mess. And they don't, nobody cares. You know what I mean? It's just very rigid.

But at the same time, sloppy system, so much unfairness is dealt. You know, it really, you just want to stay as far away from the legal system as humanly possible. And that's what I learned by it. And it is, it's unbelievable how someone could fuck up and not get a second chance because they weren't able to afford proper representation or because the judge just didn't like their face. You know, it's really like that's what it comes down to. Or their lawyer didn't have a relationship with them. There's a lot of things like, I don't know if you watch, like, the show suits or anything like that, but there's, those scenarios are very real of a judge not liking a lawyer.

You can say it's, it's not biased all you want in the world, but it is. Human beings are human beings. Former prosecutors that become lawyers, you're telling me they don't have favoritism with certain judges. They went to the Christmas party. Absolutely. No, it is, it's, it's a crazy thing. it's a crazy thing and you just want to like I said man just stay away from it

just stay out of trouble you know and I'm not the thing is like I'm not really a criminal I'm not a criminal like I sure drugs but you know I even dealt a drug ever since that happened you know that's for sure that's not a part of my life that I felt the need to continue

you made one bad decision it was really one bad decision and everybody made it and we all got shook the fuck up and we were all able to walk away from it. I think it's good to see that aspect on the show because we have a lot of people. I talk to a lot of people that make that one bad decision and they lose 20 years of your life. It's horrible how that can happen. In your scenario, you make that one bad decision and this is what society can see the good

of getting a second chance and the power of that. I wouldn't be here talking to you if it had gone a different way. Now, when you think about why you made that decision to get into that car and be the driver that day, do you think that goes back to like your early self trying to be fit in and getting bullied or being that alone person? What do you think caused that? I think just being a knucklehead, man, just not really thinking, you know, and maybe, maybe that. You know, wanting to be a good friend because I'm an only child and trying to overcompensate somehow. Because that's not my type of thing being involved.

Yeah, I sold drugs and I did drugs and I was, you know, a party kid. wasn't out here doing like criminal activity like that that wasn't very out of character for me um and uh yeah you know one of the really crazy things that happened too when i got in my car with everything to take it back to my house my car didn't start when i turned the key that had never happened to me up until that point never happened again it was almost like some sort of attempted intervention from some other realm, man. You know, I don't know. I don't know how much I believe in all that stuff.

And just the way it all panned out, you know, it's like there was some force of good watching over all of us really involved in this situation. Because it could have gone a totally different way. And, I mean, the whole first little chapter of my career, I am like out on bail assuming, like I said, that I'm going to go away for at least a year. I was mentally prepared for that. And you're kicked out of college, correct? Oh, my God, yeah. They changed the security measures at Hofster after this. You know what I mean?

This was like a big deal there. Yeah, super kicked out, not allowed on the property. So this has to be one of the lowest points in your life then at this point? Yeah, I mean, I got out and, you know, was back of my parents and just, you know, had this impending doom hanging over my head. It was a very low point. There were a few low points that I've had through life. but this one

the way I feel about low points is because I've had some really rough ones this one definitely being one of the most defining but also like you know 2015 when I'm out in California living out there run out of money have to move back into my parents like

that much further into my career another very low point getting back home to Connecticut wondering if like man that's when I became my own manager and everything. But at that point, you know, I had fans, but I didn't know if this was going to really pan out.

And that was the first time where I second-guessed a little bit and was like, man, do I need to start thinking about potentially getting a job? You know, not that there's anything wrong with that or embarrassing about that. But once you've been in the game for a certain amount of time, you don't really want to go back, you know. Contrary to what I said, you know, when you're coming up and having a job, there's no shame in that. no shame in having to go back and get a job after you've been in the game either.

But no one really wants that, you know. So that was another very low time in my life. But the lowest points that you will experience in life will teach you the most. And if you are able to pick yourself up from them, they will just bring so much more strength and power to what you're trying to do if you can get back up and keep moving. It'll make you that much tougher. everything, all these experiences made me a tougher person capable of withstanding more pressure, you know? Yeah.

How are you able to turn that negative experience into a successful music career after that? Well, I wouldn't call it successful for some time, you know, after that. It was the road to it. It led to the road, yeah. That was, I mean, well, that also took me out of college. So now that whole thing that was going on, now it's nothing but free time. You know, and I'm thankful that I went down that way. I really, I wouldn't change a thing because I was wasting my time at college.

I wasn't going to walk out of there with anything beyond what I already had. You know, it was, I had learned what I was going to learn. And at that point, I was just fucking around and doing drugs and partying and wasting money, you know, with, you know. tuition and I had a scholarship but still tuition and uh I think it's it's for the best honestly interestingly enough too after all this happened is kind of when the opiate epidemic swept through Hofstra so I kind of like was out of there and removed from that situation before that because that became commonplace everybody was doing painkillers then a lot of a lot of bad stuff yeah from there a lot of hairwear

and a lot of, you know, so it's, I like avoided that. When I was there, like, 2007, 2008, 2009, it was more ecstasy and drinking and, you know, a little bit of coke, but it wasn't, the painkillers hadn't taken over. And I remember going back and visiting some friends and it was like Zombie Land. Everybody was doing roxies and perks and all that shit. So I'm very glad that I wasn't around for that because. You probably would have ended up trying it. I mean, and I'm not going to say I've never tried it, but I wasn't around it, and I didn't like it when I tried it.

It made me sick. And I think if I was just continuously around it, yeah, maybe it would have gone differently, you know? So I'm thankful everything went the way it went. Yeah. But you learn so much from being at your lowest. You really do. What's your craziest tour story? I'm curious.

Craziest tour story. Well. Or show story. any type of story related the music industry. Well, I got a couple. I mean, there was a really sketchy time after all this happened where it's like, if I get in trouble, like, I'm fucked. You know, even after court was done, now I'm on probation.

Now, again, talk about lucking out. The case was in New York. My drug counseling was in Connecticut. I happened to go to a drug counseling center that didn't believe in drug testing. Never heard of it. But then when it was time for me to finally get off probation, they were like, all right, can you show us all your drug tests?

And then I was like, they don't believe in drug testing here. They were like, what? You got to go get one. I was like, all right. So I talked to the drug counselors. They sent me up with a guy, right? Craziest fucking thing. I drank one of those shakes to, like, scramble up your piss

because I was smoking weed, you know, whatever. I met this guy in the parking lot of a diner. This is to get my final drug test to get off a probation. The only drug test, but the final. He gives me a cup, says, go in the bathroom of the diner, come back, sit in the car, and we'll test it. I was like, what? Okay, I thought I was going to be like watched. You know, so I go in there, take a piss, come back in his car.

He tests it. He was like, yeah, it's inconclusive, but it didn't show positive for anything. So, yeah, you're good. I was like, oh, my God. That is, there's definitely a lot of luck, you know, and luck, you know, it just happens. Yeah. Like if I had popped for weed that day, that would have been a bad look. It would have complicated my life.

But God bless that guy. I've never seen drug testing done like that in my life. Yeah, I've never seen that ever. I don't know how that was a thing. When I was on probation, they're always hovering over you. They're making sure everything's good. They're riding you. But that goes to show like,

the kind of sloppiness of the legal system too because this whole time I wasn't even getting drug test. I was going to drug counseling and I just had a woman who taught me how to meditate, you know, which was cool and we would just talk about life, but that was pretty much it.

And obviously that's not what the court had in mind, but that's how it panned out and they didn't keep tabs on it. Yeah. What are the biggest misconceptions about the music industry? Well, I like to think, that I'm not in the music industry. I'm in the Chris Webby industry.

I live outside of this entire realm. And honestly, you think the music industry is cool, but it's really not, man. It's really not. It's a savage place, Hollywood in general, just all of this. It's a bad vibe a lot of it. And I try to stay as far away from it as possible

and live in my own world where we keep a good vibe and we do good things and we do right by people. And it's a small team. And I'm in charge of it. So, you know, I can make sure I take care of everybody. Everybody's happy. And we just keep the train moving. And that's how it's been for a while.

Once I really took the reins after, you know, like I said, coming back from Cali and, you know, having that whole meltdown where I realized, you know, I need to run this. If I want this to function, if I want everyone to get paid and for things not to slip through the cracks and leave people feeling a certain type of way because that was going on, you know, and I had nothing to do with the money for the longest time. Come to find out, you know, my taxes hadn't been paid in six years and, you know, everything was a mess.

This video guy still was owed money. You know, this, I had a maxed-out Amex. I was like 60 grand in debt to the government and like another 60 and just accumulated debts. And, like, I had no money, you know. I was still generating a little bit, but this was the beginning of the streaming. era. We're talking 2015, 2016.

And most of my music was mixtapes, so it wasn't generating any money. So I spent all of 2016 trying to, like, cure my financial karma, get everybody paid back, get my, you know, taxes paid, obviously. Don't ever play games with that. You know, that was

a lesson. And I didn't get in trouble, but if that had persisted, and I hadn't realized that, you know, a lot of musicians and athletes get caught up with that shit, and they don't even know. would have paid their taxes if they had known, but they didn't. So, you know, I was able to kind of get back to zero and then 2017 is when I started the Wednesday album series and I'd

been rocking with that. This is the last year of it. I'd been doing that for seven years. It's the seventh and final of that particular series. Yeah. That's awesome. Do you think that the criminal process you went through helped set you up as an artist in the, in the, in the concept of being able to keep a close circle and not entrusting so many people because you went through that experience of your close friends or whoever hanging around you. Now, I want to say yes, but I made so many more mistakes after that. Different types, you know, we're not talking about like legal ramifications so much, but I mean, yeah, I put my trust in a lot of the wrong people.

I think that's one of my serious character flaws that I've had to learn how to, do better at is you can't just trust people man you know it's like you want to because I'm a trustworthy person so I expect that from others but you got to really you know that's why it's important to just yeah keep a close circle but no I made that mistake so many times from that point forward in different ways you know sometimes it takes a while like if I added up all my failures just to get to where I'm at this is the last place I would have expected to be at yeah but I got here yeah man I mean it's about persistence is about getting back up. Like I said, you know, you got to just keep getting back up when you hit those low points because, I mean, that's how it's supposed to be, though. You know,

I see rappers coming out now and they have to, like, create their own origin stories because they're so fucking boring and they haven't been through anything. Like, the game was different back then. The internet has taken over since then. The internet was around. It was always a tool for my career, but now you have guys who blow up on the internet. They don't do any of these. They're They're not in the ciphers, freestyle in on their come up. They're not moving around, self-promoting, selling mixtapes out of their trunk. They're not doing all the things that I did that make you just tougher, more authentic. I don't know.

I feel like all the rappers I grew up listening to did it more the way I did, where, you know, you really, you sacrifice everything for it. You're not just sitting behind a screen and something goes viral and now you're just a thing. And I think, you know, there's an element of that. I can't be mad at it. It's the times. It just makes me sound old and grumpy when I get mad at this shit, you know? But it's like at the same time, I want the rappers that I listen to to have been through some shit. I want to hear that grit and gravel in their voice of like, you know, a life that wasn't always easy.

And their successes were hard earned. You know, I think that that's what I look for, especially in a musician. You want to hear the pain, you know. It's fucked up. And I think that's why, you know, a lot of musicians do have drug problems and things like that. You go through a crazy path. But I don't know, man. I see a lot of artists now.

It's just like I wonder who they are in real life, you know, how much of this is just a facade for TikTok. And you know what I mean? It's like, I don't know. Yeah. I mean, we're in a world now where it's so easy to go viral. It's hard, but it's not. Yeah, I mean. Anyone can go on there and do it if, you know, they watch some videos,

they kind of follow the steps and whatnot, and it just changes things. 100%. It could be argued that, you know, there's that many more people doing it now, so it's that much harder. But at the end of the day, it's like, I don't know, it's just a completely different blueprint than I used on my come up. But now, of course, I've adapted and adjusted, and you've got to learn, be with the times.

Like, streaming at first, I remember meeting someone, before Spotify existed, and they were like a little startup called Spotify, and they were pitching to me this idea. And I laughed in their face. I was like, that's absurd. People won't even own it. They'll just stream it. What does that even mean?

You know? Here we are all these years later. You know, bought a house off that shit. Now, I want to touch on Tuxedo Junction, because I feel like this is the perfect opportunity for my followers and fans to understand a little bit about me. What exactly was Tuxedo Junction? and what did it mean to you at that time period?

It was a special place. It was a venue, but it was like a lawless venue. You know what I mean? It was like a venue that had almost been, it kind of felt like it got like hijacked by pirates and anything could go. You know, it was just like, don't get me wrong. It was a functioning venue. It was great.

The shows we had there were awesome. But there was a certain lawlessness to it all. in that green room. Oh, legendary. Bro, that green room, the amount of oxygen in that green room would be so small between the weed smoke and the cigarettes. Like, there was no window,

and you're just in this little cubicle next to the stage. You can't even see through the smoke the person next to you. And then you go on stage, you know, it's crazy. Yeah. A lot of parties in that room, that little cube. What was your impression, like, you found out that a young, because I was 18 at the time, that a young kid took it over, because you were my second show I ever booked as the owner.

It was Chris Webby. We did GTA and Congo Rock, and then we did Chris Webby. You were the solo headliner. What year was that? 2014, June, 2014. I think I remember that show. Mike Squire's got an interview with you just asking about tuxitos because we were putting together this montage.

Was that the show where I came out to the Pokemon theme song? It might have been. I remember one time at Tuxedo. I just was like, I want to come out to the Pokemon theme song tonight. And I did. I thought it was awesome. I think it confused a lot of people, but whatever. Yeah, so what did you think about, like, a kid taking over, like, your spot that you had performed so much at?

I mean, I'm always down for the next generation to get their hands on it. And, you know, the show still went well. Yeah. I wasn't involved in the booking, so it's like I had nothing to do with that. Are you still with ICM? Or is that even a thing? No, no. I'm with this guy Eric at Adler Adler agency.

Oh, I remember the Adler agency. Yeah, yeah. So, yeah, it's more like a boutique thing. I've been with a lot of the big booking agencies. It's like at the end of the day, honestly, as of recently, the touring numbers are phenomenal. It's pretty cool to be going into your 15th year and everything's at an all-time high. Like, you don't see that much.

So I think that's pretty exciting. I mean, we just sold out, like, all of Canada. The numbers, numbers everywhere, as of recently, we're hitting highs, like, pretty much everywhere, except for New York City, which I feel like is just a market on the decline. I feel like some of the big cities, you know, post-COVID are weird. Yeah. How do you feel about, like, those young entrepreneurial, like, event bookers that book you for shows and maybe the show doesn't do as well? and you could just see it in their face that they lost on that show as an artist's perspective. I think that all plays into everything we've talked about where it's like you have to learn through your losses.

And especially being someone who books artists, like you're going to take losses. Unavoidable. And that's how you learn. That's how you learn to market differently or, you know, pick a better day. I mean, there's sometimes we've had shows in the past where we'll be in a city, but there's a massive event going on that no one took into account, you know, and it's like, damn, bro. It's like everybody's prom.

I remember that was one year. It was like prom season. And back when, you know, there would be a lot of high school kids at shows and college kids. It's interesting, though. My crowd has gotten older. Just, you know. They grow with you. It's cool.

Like the people that we were talking earlier about the day ones that ride with you all the way. As long as you stay true, stay authentic to yourself. I mean, it's not expected for me to be the same person I was, but you grow over time and evolve. And yeah, your fans grow with you and mine have. And I just, I always found it very important to stay authentic and stay real, even at a cost, you know, sometimes you see two paths. And one path you got to sacrifice a little bit of your integrity,

but it's a shorter path or this long-ass path where you, you know, hold on to every single shred of integrity. And I choose that one time and time again. It's definitely taken a very long time. But here we are at this stage in the game. And, you know, things are good. There's a lot of people that are successful in their careers that have a past like yours and have a past like mine

that aren't open about talking about it, maybe because they're afraid of the ramifications or they're not open to talking about it. What made you decide to be open about it? I mean, listen, man, you can't change things that happened. It's kind of embarrassing that we did that and got in trouble and it was stupid. But like, I was a kid. I learned from it.

And I've never allowed myself to end up in a situation like that again. And I've watched the people around me after being ratted on and just kind of, you know, taking stock in the people that you trust. And, uh, I mean, listen, man, I'm an old. open book. I'm an open book. My life has been incredibly eventful. There's been all sorts of things that have happened and I'm happy to talk about any of it. Especially now, that's

when I was first coming out, I didn't want to talk about it as much because it was like still very current, you know? And it's like I didn't want that to be, I didn't want to make it seem like I was trying to be hard. Like, yeah, I went to, you know, got arrested at eight days. Like, nah, it's not, it's not about that. It was like a mistake. And I learned from it and that's always been especially looking back on it

this far I mean this was like over 10 15 years or 16 years ago and back then people don't talk about prison as often I mean now there's a whole prison TikTok and prison YouTube is there I don't go on TikTok much really I'm surprised you don't watch like those types of clips

and stuff because you relate to that yeah interest in that I mean on the one hand I can relate to it but on the other like I did my little stint and stayed the fuck out of there ever since and I've done everything I can to just not

get in trouble. I'm very, it's good to be cautious man. You know what I mean? Especially if you're going to like ride the line a little bit like don't drink and drive. Know what you got on you. Don't be stupid. You know what I mean? If you're going to do drugs, don't travel with them in a just just be smart.

You know? And because you can get caught up for some little shit that you do all the time. and this time you got caught, and now your life's complicated. And that's really, like, at best, getting involved in the legal system will complicate the fuck out of your life for a while. Absolutely.

You know, and that's, like, the main thing. Whether you end up getting in a ton of trouble or being able to kind of step away from it in one piece, like we all were, in this case, it's still complicated everything for everyone. And I'm glad it happened when it did, but, you know. What do you say to the kid that maybe in middle school or high school, that's like that

loner, maybe he's getting picked on, bullied, but he has a dream and everyone's kind of laughing at that dream, but he's dedicated to it. Maybe, you know, you see a younger self in that kid. What do you say to him if you could sit down with him right now? A, develop a sense of humor because life's too short, you know, people are laughing at you, learn how to make fun of yourself, you know? It just is what it is. like I make fun of myself all the time.

It makes it a lot easier. And second of all, middle school, high school, all this shit, you think it's everything. When you're in it, you can't imagine a life outside of it. And then it ends and none of that shit matters ever again for the rest of your life. So just ride it out, you know? Life is a long, long road. They haven't even experienced the post, you know?

Like that whole like the 20s is crazy. Honestly, like I've been enjoying the 30s the most. 30s is like when I finally feel like I am in control. I'm at the wheel and the car is not spinning, you know, down the highway at 80 miles an hour. I finally got this thing, you know, and we're just, you got to stay paying attention,

but I feel like occasionally, occasionally I can look out the window and, you know, look at the view and be like, oh, it's nice. You know, can get back to drive. And, you know, enjoy life as much as you can, man, Because the way this world's headed, who the fuck knows where we're going, man? You know, and enjoy society as we know it right now. Because we didn't even get into conspiracies. But, man, probably for the best.

I'll get you kicked off all your platforms. Chris, thank you so much for coming here and being the first guest in the new studio. Absolutely. I wouldn't want any other way. You know, you're from Connecticut. I'm from Connecticut. I think this is great. Hell yeah.

And something different. And really appreciate you, my friendship with Mike. and reconnecting after all these years. It's been awesome, hopefully we stay in touch. Definitely. We'll link your website and music to the YouTube page and descriptions. And what's like the next few years look like for you?

Well, I'm going to ride out this final Wednesday album. So in the immediate, until that rollout's done, that's the main thing, that touring, et cetera, kind of what I've been doing for this past stretch. And then after that, I don't really know. I might take a vacation. I might finally go down to Peru and take ayahuasca or something. You know what I mean?

Like go go somewhere, get lost in a jungle or a mountain somewhere, come back with a crazy beard and, you know, some wisdom. I really don't know. I mean, I can't imagine a world where I'm not making music. But at the same time, I do feel like I've just had the pedal to the metal for really like the end. entirety of my career that's been in the driver's seat maybe after this album i actually take a little me time and go explore this incredible world for a second and then do something just for me you know that's awesome man well again chris thank you so much for you're the best excited to see you bring it to that next level oh yeah oh yeah