Image via Chris Engelsma

Image via Chris Engelsma

By Daniel Isenberg

It’s crazy to think that 2006 was ten years ago. In the past decade, I got married, had three kids (all boys), bought a house, and transitioned careers from youth leadership to journalism to advertising. I’m a family man who drives a Honda Odyssey and changes shitty diapers on the reg. But in 2006, I was a bachelor, living on my own, trying to make it as a rapper. My stage name was Stan Ipcus.

I had gotten the biggest look of my rap life in 2005, when I landed a verse on my buddy Matisyahu’s Grammy-nominated Youth, on the song “WP.” But I also caught a tough break that year when the record label that had signed me to a production deal—InYerFace Records—crumbled before I could release anything.

I had spent all of 2005 in Sony Studios on 54th Street laying down tracks, and had begun performing regularly around NYC, but the label dissolved for reasons I’m still a bit unsure of. I was forced to start back at square one.


In January of 2006, the hype for Matisyahu’s Youth album was in full swing. He was all over MTV, and being that he was a Hasidic Jew that sang reggae music and beatboxed, he quickly became one of the most talked-about new acts in music. I was the only guest vocalist on the album, and since we were old friends who grew up in the same New York neighborhood, he would regularly invite me to come sit in with him at shows to perform our duet. And my first big guest spot of 2006 was at none other than Madison Square Garden during his concert with well-known jam band OAR.

This was a big deal for me, and for everyone we grew up with in White Plains. Our buddy Matt Miller was doing a show at Madison Square Garden! And I was part of it! Everyone I knew was there—my parents, all my friends, and even some kids I was teaching at White Plains High School. I still remember hanging out backstage, in the same hallway that led to the Knicks locker room, waiting for my moment to come out and spit my “WP” sixteen. From the audio of me yelling my verse, you can tell I was super-amped.


That was me, rapping in front of a sold-out MSG crowd, on the same stage where I had seen living legends like Jay Z, Billy Joel, and Janet Jackson. It was nuts.

But when the lights went up, reality set in. My production deal was null and void, so I had to figure out a way to record songs at my crib, by myself. I had no mic or booth or anything, just a laptop.

So I used what I had. I would lay beats into GarageBand and spit into the keyboard to record vocals through the internal microphone. It was decent enough to get the job done, though there was definitely a lot of unnecessary background noise and fuzz at times. But it was all I had, so I started laying down songs every night.

At InYerFace, there were producers who would feed me professional beats. I had the chance to collaborate with dudes who had worked with MCs like Kool G Rap and DMX, so I was getting quality tracks that I loved.

But now, I was forced to find my own beats. So I taught myself how to loop records in GarageBand, and I started to craft my own production sound. I would jack old and new instrumentals too. My goal was to compile enough recordings to release my own mixtape in the spring, in the hopes of piggybacking off Matisyahu’s release and showing people what I had to offer as a solo artist.

But when the lights went up, reality set in. My production deal was null and void, so I had to figure out a way to record songs at my crib by myself.

In March, Matisyahu celebrated the Youth album release with back-to-back shows at Hammerstein Ballroom, and I performed at both. The album was now officially out, and I had a decent buzz brewing as more and more people heard it.

There were little things that could’ve made it easier for me (they spelled my rap name wrong in the credits), but it was all good. The right people were starting to take notice, and in the Rolling Stone review, they called “WP” the album’s “most lyrically attractive track.” And the second night at Hammerstein, there was an Epic Records executive who approached me before one of the shows and said, “I was just telling my wife I wanted to sign you.” Wait, Epic Records wants to sign me? Off one verse? It was like Matisyahu was Nas, and I was AZ.

Image via Daniel Isenberg

Image via Daniel Isenberg


A week later, I was in the Epic Records offices on Madison Avenue, meeting with that same executive. I rolled by myself, and really had no clue what to expect. I had a demo of sorts with a few songs on it that I considered to be my best stuff, but when he put it on, it seemed like he didn’t get it at all.

Truth is, he wasn’t a hip-hop guy. He had a huge Ben Folds Five poster on the wall, and he even admitted during our conversation that he wasn’t that knowledgeable of the genre. So his assistant gave me a Matisyahu poster and a couple of copies of the album, and I was on my way, never to hear from him again.

It’s important to remember that this was still 2006, and aside from the aging Beastie Boys and a few one-hit wonders, Eminem was really the only mainstream white rapper that existed to most people on a national level.

So me, a Jewish kid from Westchester County, made no sense to him, or really anyone. Dudes like Mac Miller and Asher Roth had yet to hit the scene, so the thought of a streetwise kid from the suburbs getting a major label deal was still foreign to people in the record industry. It was one of the reasons I never quit my day job—the whole idea of me actually making it as a rapper on some full-time career shit always felt like a long shot.

So I was still working—directing after school programs in New Rochelle and Port Chester and substitute teaching at White Plains High School and Mamaroneck High School to earn extra bread. My life was totally weird—I was literally signing autographs at WPHS while I was subbing.

Everyone knew me as “the rapping sub.” It was a little silly, and honestly, I didn’t dig it—it made me feel more like a loser than a celebrity. I needed to get out of the 9-5 trap and just go full force with the music. But I couldn’t, because I had my own apartment and bills to pay, and even though I was getting loot to do shows a couple times a month (at dope NYC venues like Joe’s Pub and CBGB), it wasn’t nearly enough to support myself.


But then, about a month after Youth dropped, I got my first royalty check in the mail. “Oh shit, I’m getting paid to rap for real now,” I thought. And it was double the money I was making every month working two jobs, so I was gassed. I thought these were gonna keep coming every quarter for the rest of my life! I was so naïve.

Before long, the publishing splits on the song got renegotiated, and I never saw another check that big again. But hey, it was all good. I would’ve done that song for free, because Matisyahu is one of my best friends, and he was the reason I got a check in the first place. He was always looking out for me, but some of this business stuff was new to him too, and was also out of his control. In the end, I was just happy to be on the album, and I was still getting incredible looks because of it.

By the end of May, right around my 28th birthday, DJ ROZ from White Plains and I released a new Stan Ipcus mixtape, Real Breezy. It was 26 tracks of straight Ipcus spittage over original production and industry beats, all meticulously mixed by ROZ. It had crazy Ipcus drops from The Mask in it (that’s where my rap name comes from), dope scratches, blends, samples, and an overload of bars.

I was incredibly proud of it, and everyone in White Plains was pumping it. Even the dudes in the hood who knew me through school and playing basketball were giving me props, running up on me quoting shit like, “Young Ippy dumb sticky in the whip!” It was awesome to have my hometown fully behind me.

That summer, Matisyahu invited me out to do a couple shows with him in California. So I pressed up 100 Real Breezy mixtapes, and a group of friends and I flew out to L.A. We rocked the Santa Barbara Bowl and the Greek Theatre, and had one of the best weeks of our lives. But beyond passing out a bunch of CDs and making some new fans, I was still in the same spot I was at the beginning of the year.

To be completely honest, I was going about it all wrong. I had no strategy, I was just working and making music and doing shows when I could, hoping someone would come along to help me make something happen, rather than making something happen myself. Matisyahu was my boy and was always supportive, but I was in a different lane. He was religious at the time and making a much less explicit form of music than the Stan Ipcus shit I was making, which was all about weed and sex and New York street MC braggadocio. Of course, my appearance on his album was far from that, but when it came to my solo music, I was too grimy to stand next to him and ride his wave. I had to make my own.

I was going about it all wrong. I had no strategy, […] hoping someone would come along to help me make something happen, rather than making something happen myself.


Luckily, I had other friends with industry connections. One in particular, Mike G from White Plains, made it a point to help me. He was in the private jet business, and knew dudes like Jay Z and Diddy personally. He tried to get me my big break.

First, he brought me up to Atlantic Records, and walked me right into Mike Kyser’s office, one of the most well-known record executives in hip-hop. It was kind of hilarious how easily we just walked in there with no appointment, but it happened. Kaiser was on the phone when we came in, but he did pause his conversation to meet me and take a copy of my CD. But that was it.

Mike G also brought me up to Universal Motown to see Eric Nicks, a Senior VP of A&R there who had a deep history in the music industry working with guys like Busta Rhymes and LL Cool J. This time, dude actually took the time to listen to my joints, and seemed genuinely struck by me. He felt the bars, the songs, and the style. He knew all about Matisyahu and was a big fan of his. And he gave me one of the best compliments I ever got, saying, “You are hip-hop.” He got it.

But he also struggled with what to do with me. He wondered if I made sense existing in a more Warped Tour type space rather than in a pure hip-hop environment. He was thinking about my show, and if I should be backed by a band rather than a DJ, which is something I had been experimenting with myself a bit on recordings and at recent solo gigs. And it also seemed like at the time he was thinking about his own next move, and starting his own label, which he eventually did. Still, he took interest in me to the point where he made a trip up to White Plains just to see one of my shows.

To this day, that White Plains show is my favorite ever performance. It went down the Friday before Thanksgiving in 2006. I brought Matisyahu out for his first hometown appearance since his album was out, as well as a whole cast of local characters, and it was an incredible 90 minute set. But the craziest thing about that night—as I explained in the song—is that it was the first night I kissed my wife.


As much as Eric Nicks liked my music and performance, he just wasn’t in a position to take a real chance on me. He was getting ready to transition out of Universal, and I probably wasn’t the right fit for that label anyway. I thought I was ready for rap stardom, but I really wasn’t. Outside of White Plains and Matisyahu fans and pockets of New York City and California, I still hadn’t generated a real buzz.

One thing that I do admit to myself looking back at this time in my life—and also having dealt with so many rap artists since then as a journalist—is that I never really had that intangible star quality a lot of famous rappers do.

I’m just a regular guy. I don’t have that “thing” someone like Mac Miller has that makes kids idolize him. And I’ve humbly accepted that. I also hate traveling, and can’t imagine a lifestyle that lends itself to being in and out of airports all the time. So in many ways, I’m glad I didn’t blow in 2006. I got something way better out of that year—a beautiful wife, and ultimately, three beautiful boys.

But still, it sucked to face the reality of my rap career head on. As much as I wanted to make music professionally full-time, my anti-climatic major label meetings and tour performances made me think this would never amount to anything more than a few clips for the highlight reel and some extra stacks a year in show money. So as 2006 came and went, I decided to focus on starting a family and furthering my career outside of rap. I had to put the bars on the back burner.

Ten years later, I still daydream of being in the studio, recording songs with my favorite producers and doing live shows in front of huge hip-hop crowds. I never lost my passion for the music, and I still try to find time to write, record, and release when I can. And once in awhile, my boy Matisyahu or other friends will pull me on stage or ask me to perform as part of their gig, and the moment I grab that mic, I’ll get that familiar feeling back. It feels good.

But I’ve come a long way since then. As much as I still love to rap, I wasn’t built to be a rap star. I was built to be a father, a writer, and to live a quieter, more relaxed life. This is a much better reality. But I still think back to 2006 sometimes and wonder, “What if?”


Catch Matisyahu and Stan Ipcus live at The Capitol Theatre in Port Chester, New York on Friday, March 11th as they celebrate the 10th anniversary of ‘Youth.’ Tickets are available here.