Every Tuesday at 10:30 a.m., the 10 employees of Rostrum Records, one of the biggest independent labels in the rap world, and a generational successor to labels like Def Jam, 4th & B’way, and Death Row, mingle in a large conference room in Hollywood, off of Vine. Leading the group is Benjy Grinberg, the founder and CEO of the label. He’s of average height with slicked-back hair and a formidable beard speckled with gray. On that Tuesday, the same as every day I met with him and his team at Rostrum, Grinberg had a casual, postgraduate look, in a hoodie, blue jeans, and a pair of glasses that added charm without betraying too heavy an air of intellectualism. He was focused on the here and now.That day, the label boss presided over a group of passionate employees as they debated items as small as when to schedule tweets, to bigger topics like when albums should be announced and when videos should air. Everything mattered to Grinberg. The battle of the everyday, the grind it takes to run an independent record label and have it succeed, is all about little moments turning into big ones. After 17 years in the rap game, starting in New York City, where he began Rostrum Records in 2003 before moving it to his hometown in Pittsburgh, and then, eventually, to LA, Grinberg knows better than anyone that every detail matters.“Every song is an album, you know what I mean?” he told me. “That’s how we think about it, and that’s what I’ve instilled in the company, too. Every song is really its own project. We do full campaigns around just the song and not just as a single leading up to a project but as an end to itself,” part of a continuous experience that Grinberg and his staff take great pride in.When I asked him about the first rap song he ever heard, he chuckled. “I was actually in Israel, of all places. I was on a trip with a bunch of other families from Pittsburgh,” he recalled. “I was 7 years old and it was 1985. There was a kid and he put his headphones on my ears. He said, ‘You got to check this out,’ and it was a Run DMC song. I immediately felt like it was something fresh and exciting. That was the beginning of my love affair with hip-hop.”Grinberg’s hometown couldn’t be less similar from the insanity he now navigates on a daily basis. He was born in the neighborhood of Squirrel Hill, Pittsburgh, the Jewish hub that sits south of Shadyside and east of downtown. The neighborhood hovers around the Jewish Community Center, a sprawling, beautifully redesigned building that serves as the center of Jewish life for the neighborhood. After the Tree of Life massacre in October of 2018, the JCC served as the central location for the reunification of families displaced during the chaos.“When it happened, I was in Los Angeles, but of course the first thing I thought of as news reports were starting to come out was that my dad was there, my uncle was there,” Grinberg recalled. My uncle had done a service the night before and decided not to go that morning and my dad went to Beth Shalom, a different synagogue that morning. So I’m very, very thankful that they weren’t there. But, for something like that to happen at a place where you have gone to so many times, to have something that horrifying happen to people that you know, is unimaginable.”The Squirrel Hill JCC is a celebration of culture as much as it is of religion, and the community center walks a delicate line in espousing Jewish beliefs without proselytizing non-Jews who use its programs and services. He runs the label he founded in a similar fashion, bringing proponents of his upbringing and his love of hip-hop into an environment that emphasizes collaboration and a ‘best idea wins’ philosophy.The connection between hip-hop and Judaism in Benjy’s life runs directly through his childhood in Pittsburgh and the Squirrel Hill JCC. “I went to EKC camp [Emma Kaufmann Overnight Camp], which was run by the JCC. There were some people I went with that were definitely as into rap as I was,” Grinberg recalled. “I had a counselor named Jimmy Wegnor who was really big into rap. I'm still in touch with him. He exposed me to Boogie Down Productions and he had some albums I didn’t have. In the Jewish community, rap was very prevalent.”On his 11th birthday, the young hip-hop-loving Benjy was given tickets to the DJ Jazzy Jeff & Fresh Prince concert in Pittsburgh. He went with his father, and the show solidified a lifelong love affair with the music. Grinberg’s parents supported his passion―or, at the very least, they turned a blind eye. “I never really played that sort of music for them,” Grinberg said, when I asked about some of the defining records of that decade. “I would listen to it on my Walkman. I had it on cassette. I remember those tapes so clearly. I had the Eazy-E album and the N.W.A. album. The Eazy-E album was given to me by a kid on my paper route.”Grinberg’s father served as chair of the Community Relations Council―the arm of Pittsburgh’s Jewish Federation in charge of building ties to other minority groups in the city. “As chair, my role was to develop relations with different black leaders throughout the city,” Skip Grinberg explained to Tablet over breakfast at Squirrel Hill’s world famous Pamela’s Diner. Between bites of California French toast, Grinberg added, “Sometimes, we had a specific goal in mind, and sometimes we just wanted to let them know that we were around in case of an emergency. The black middle class in Pittsburgh is small relative to the population, and we feel solidarity in fostering that community.”According to Grinberg’s father, Benjy’s love of rap had always blended the joy of artistry with the uniqueness of the industry’s business side. “He’s always had an entrepreneurial mind. He wanted a paper route when he was 9 or 10, which he kept for two or three years and actually used some of the money to start Rostrum. That, plus a little bit of his bar mitzvah money, of course,” he explained with a laugh. “At school, he was a disc jockey, and he always envisioned music as a viable career path.”Grinberg’s rise to the top of the independent rap world is a story about hard work and good fortune. He’s always stayed later, cared more, and consulted with more affiliates than anyone else. But he also has a knack for being in the right place at the right time. “I moved to New York after college at Penn without having a job. I lived with my brother, literally on his couch,” explained Grinberg. “I was hired to do artist relations for a company called Digital Club Network, which basically meant I had to get artists to sign contracts so we could webcast their shows.” The job was not particularly fulfilling, but only a few months later Grinberg would back his way into a job working for the legendary L.A. Reid at Arista Records.One night after a dinner date with a friend in New York City, Grinberg was headed downtown to meet another friend. He traversed the city, on foot, as so many New Yorker’s do when they need to head down and across town, and he ran into a friend who asked what he was doing: “Well I’m at this company, but I really want to be working for a record label,” Grinberg replied. His acquaintance happened to be with another friend, who said, “Oh, I’m temping at Arista Records.” Grinberg immediately asked to give her his resume and pass it to whoever her boss was. She agreed, and Benjy ended up interviewing five times for one of Reid’s confidants, Karen Kwak. After the fifth interview, Kwak said she was going to refer Grinberg to another position—working with L.A. Reid.“After about five minutes of interview time, Reid stands up and says, like, ‘Thanks, we’ll let you know,’” explained Grinberg. “In my mind, I’m like, fuck that. I’m in L.A. Reid’s office. I said to him, ‘Well, I’m here right now. Is there anything I can do for you while I’m here?’”Reid asked Benjy to write a letter to another label executive, which Reid ended up using. “That’s what got me in the door and I stayed with him for nearly three years,” Grinberg explained. “It was an incredible experience. I was thrown into the deep end of the music industry immediately. That’s where I got a really strong network of people. That’s where I learned a lot. It was an incredible experience for me.”After sharing this anecdote, Grinberg paused for a moment and looked out his window. He said, “When you’re trying to get to from the west side to the east side and down a couple of blocks and the light happens to change, you just do what you do. What if I hadn’t been walking down that street? What if I hadn’t made a left there, but made a left on the next block? So, part of this whole thing is luck. I don’t take that for granted.”After three years under L.A. Reid, Grinberg struck out on his own and founded Rostrum Records on the relatively simple principle of supporting good music and spreading it to whomever would listen. His first artist was a rapper named Nitty, and the first song they worked on was called “Nasty Girl.” Nitty got signed to Universal, and Grinberg pretty quickly understood he didn’t want to be dependent on a major label to realize the vision he had for his artists.Rostrum found huge success for the first time in 2011 with Wiz Khalifa’s Rolling Papers, although that album was co-released with Atlantic Records, which helped contribute to its peak at No. 2 on the Billboard charts. Later that year, though, Rostrum again struck gold with Mac Miller’s Blue Slide Park. With no major label co-signs, Rostrum and Miller reached No. 1. Said Grinberg, “This was the validation we needed, that we could compete on a major level if we were smart about it and if we found amazing artists we loved working with.”While the label had found stars in its two premiere artists, it took half a decade to hone that talent into monetizable success. Grinberg had met Wiz Khalifa during Thanksgiving of 2004 at E. Dan’s legendary ID Labs―a hub for Pittsburgh rap music that is as influential today as it was in 2004. Yet from 2004 until 2009, when Wiz’s Deal or No Deal made a small ripple in the landscape, Rostrum’s impact on the scene was negligible.“We toiled for a long time in the trenches with Wiz. I think it was a good five years or so before anybody really gave a shit at all about what we were doing,” said E. Dan, the studio’s in-house utility belt. “We were many, many mixtapes deep before things started to catch on.” In 2006, Grinberg had to leave New York City because he could no longer afford it. “I moved back to Pittsburgh because I felt like I had to make the Wiz Khalifa situation work out if I wanted the company to work out. I really put just about all of my eggs in that basket at that time,” said Grinberg.After Khalifa and Miller skyrocketed to superstardom, things seemed to be going well for Grinberg and his label. While the label put out albums from Wiz and Mac, Grinberg also managed them, a lucrative gig, but one that didn’t allow him to prioritize the label in a way he’s able to now. “While I was managing Mac and Wiz, most of my focus had to be with them, as it should have been. Yes, we had a small team at that time, three or four people, but I worked every day to make sure that both of their careers were heading in the right direction and that I was doing everything I possibly could for them. As a CEO,” he admitted, “I wasn’t so much focused on the company as I was focused on the individual artists that I needed to pay attention to.”His artists soon resolved that issue for him. Miller left the label amicably in 2013, after his initial deal expired. “It was a period where he was able to take a look and think about whether he wanted to try something different. He had only known our situation. So, that’s a decision that he made very methodically. We were in communication, talking about it, figuring out what the best way to move forward would be. It was very cordial,” said Grinberg.His relationship with Khalifa fizzled in a much more dramatic way, though. Khalifa split from the label in 2014, but in 2015 a surprise lawsuit filed on the artist’s behalf shocked Grinberg and rattled him in a way he only began to recover from a few years ago. Khalifa and Rostrum had spent their breakup trying to figure out the easiest way to split profits, and when an agreement wasn’t settled upon, Khalifa’s team took the label to court in a $1 million lawsuit alleging that Grinberg and the label had unfairly profited from a “360-deal” the rapper signed as a teenager. A 360-deal entails a piece of every dollar the artist makes off of their likeness, music, tours, and merchandise. Khalifa, unhappy with the way this contract played out, thought he was owed more than he was given.“The lawsuit was a huge surprise to me. It came out of nowhere and it was one of the hardest times in my professional life,” explained Grinberg. “I really felt like I needed to stand up for myself and stand up for my name and my reputation which I worked so hard to build up. Some things were being said that were not true. It was a painful situation, but we’ve gotten through it. On the other side, we’re cool. We still have business together and it’s one of those things you have to weather when you run your own company. Particularly, when you’re in an industry like this where there are changes all of the time. I’ve had to learn how to not take it so personally,” he added.There were still more shocks to follow. On June 18, 2018, Jimmy Wopo, Pittsburgh’s most promising rapper since Mac Miller and Wiz Khalifa, was assassinated in a drive-by shooting. Miller, the white rapper turned superstar and acclaimed collaborator, died of an accidental drug overdose just three months later, on Sept. 7. The pop critic of the Pittsburgh Post-Gazette, Scott Mervis, said, “The loss of Jimmy Wopo was still being felt when Mac Miller died in September. It sucked the life out of the hip-hop scene here in a certain way. It was pretty shocking.”When Mac died, Benjy lost a friend, a client, and a former label star. While Grinberg and Miller ceased working together in 2015, they still had a tight bond. “I’m back to normal life in one sense, but things are different. You know what I mean? Your life goes kind of 100% back to normal, but the world around you and the fact that Mac isn’t here, that doesn’t change just because I went back to my regular routine. Yes, I’m back doing what I would normally be doing, but I think about him every day,” Grinberg said.Grinberg’s office is decorated with various rap paraphernalia. There’s an MF DOOM poster, a beautiful painting on canvas of Mac Miller, and on the opposite wall, a Magic-Markered area with the names of every artist on the label and the relevant details for upcoming releases. The object in his office that matters the most to Grinberg is a plaque from the Boys & Girls Clubs of America, which memorializes an idea that the label head and his star had before releasing Miller’s breakthrough Blue Slide Park.“When we were coming up with our plan for Blue Slide Park, part of that involved presale goals,” Grinberg explained. “If we got a certain amount of preorders for the album, we decided to give $50,000 to the Make-A-Wish Foundation,” he said proudly. “We never reached that point, but we spoke to each other and realized that we still had to do it. There was no way we weren’t doing it, you know? He gave 25, I gave 25 and we gave $50,000 to Make-A-Wish.”The thank you from the Make-A-Wish Foundation seems to be important to Grinberg not only because it commemorates his good deed, but because of what it signifies about Miller. “His heart was always big. He always wanted to do things for other people. He was very, very giving and loving,” he said. “That’s why it’s special that his family has the Circles Fund, where they’re helping to support music for kids. It’s in honor of him, but it’s exactly what Mac would have done anyway.”Grinberg’s charitable conscience was instilled within him by parents who emphasized tzedakah as a foundation of everyday life. “There was, I don’t want to call it a tradition, but I was brought up learning that you’ve got to give back. I’ve tried to impart that to my kids, too,” Skip Grinberg told me, when we had breakfast. “Benjy’s gotten that too. He’s done a lot of charity, both within and outside the Rostrum work. When he told me, ‘I want to start giving back,’ I said, ‘Well, what had an impact on your life?’ He went to day school about a mile from here and summer camp at the JCC. So, he’s taken pride in supporting that community.”When the Pittsburgh Jewish community was attacked on Oct. 27, 2018, the JCC was immediately on Benjy’s mind. “Within a week of the shooting, Benjy was back in town. He couldn’t be apart, he felt like he needed to connect,” explained JCC CEO Brian Schreiber. Grinberg’s wife, Ellen, was also born and raised in Pittsburgh, and together, they made the decision to rush back home to offer any type of support those closest to the victims needed.“I just felt the need to be part of the community. It felt weird not to be there. Ellen felt the same way. We just needed to go back, if anything, just to be there with people and to be there with my dad and my uncle who were obviously going through very hard times. They knew these people even closer than I did,” Grinberg explained.The unfathomable tragedy never ceases to produce a pit of your stomach, but wounds begin to heal. Because of the incredible network Skip Grinberg helped organize, the Jewish community of Pittsburgh was supported by Muslim, black, and Christian neighbors both in the aftermath of the event and in its long-term recovery. “I think the most amazing thing is not that the Jewish community pulled together because that’s to be expected,” said Skip Grinberg at the end of our breakfast. “What inspired me was the impact of the other faith communities just jumping right on board. We had developed a very close relationship with the Islamic Center. We had a really good working relationship with them, and they helped almost immediately. They raised a lot of money for our community within 10 days.”It’s inspiring to see communities come together when so much of the world feels broken. “It will never be exactly the way it was before. I don’t think it can be. I would say that for a while we maintained normalcy only in the sense that normal activities resumed, but the community mindset wasn’t there,” explained Schreiber during our meeting at the JCC. “To some degree people adapt to that reality, though I think that to some degree people are still looking for places to try to figure out where that pain is coming from.”Professionally, Grinberg has emerged from a tumultuous few years with a healthy roster of reliable stars and up-and-coming artists. 24hrs has emerged as a fresh voice in Atlanta, earning collaborations with Ty Dolla $ign and Wiz Khalifa. Pittsburgh born-and-bred Boaz has found a wide audience with his new LP, Hope Dealer. The U.K.-born Taliwhoah has given the label a fresh female R&B voice in a male-dominated genre. Rostrum’s roster is diverse, but its essence is rooted in Grinberg’s love of hip-hop. The environment he has fostered among his employees and artists is one of loyalty, community, and family. The similarities to his upbringing in Squirrel Hill are striking. “There’s a lot of compassion in what Benjy does. That trickles down to how we are with our artists and treating them like partners, not just having them sign contracts, putting music out, and moving on,” explained the general manager of Rostrum, Jonathan Partch. “It’s a real family and I think that that’s superimportant to him.” As a result, Rostrum seems remarkably well adjusted to the unpredictable waves that regularly crash upon the shores of the music industry.“Being able to work with artists to make albums and help them reach their goals; professionally, that’s what I’m here to do,” Grinberg said at the end of our few days together. He took a moment to think to himself, before adding, “If I wasn’t doing this, I don’t know what I’d be doing.” In truth, it’s hard to imagine Benjy Grinberg anywhere else besides in his office, headphones on, looking for the next artist he can’t wait to show to the world.