For most artists, their career changing moments, good or bad, happen very publicly. These moments can be anything from breakout song, to a legendary performance, to a collaboration with a prominent act. For Homeboy Sandman, however, one of his career changing moments happened on a street corner, with just one other person present.

On the heels of the release of his latest album, All That I Hold Dear, Homeboy Sandman told us about that moment, as well as his new music.

Adam Bernard: Let’s start by talking about the new album, All That I Hold Dear. What was going on in your life that inspired this EP?

Homeboy Sandman: There were a lot of different things going on. On a song by song breakdown, “Musician” came from a lot of frustration at the clowning that hip-hop is the recipient of all around the world, how it’s kind of a joke to the universe, and how hip-hop, and everybody affiliated with it, is looked at as the same person. There was this TED Talk the other day, not that I’m huge into TED Talks, but there was this one with this dude talking about the dangers of one story, of when you try to give a whole people one story. That’s really what’s happening to hip-hop.

With “Relapse” I had just broken up with this girl, and had relapsed in the physical manner.

My niece and nephew, I spend a lot of time watching them grow up, that’s what “Runts” is about.

“Sure Shots,” as I get more and more opportunities to spread my music around there are more and more opportunities to fall flat, there are more and more big shows where I can fall flat, there are more and more people asking me to rhyme at a radio station, which I think is kind of bizarre. I think it was Three Stacks (Andre 3000) who said, “I don’t kick rhymes at radio stations.” Earlier in my career I was like what’s up with that? Now, looking at it, it’s kind of like, you’re playing my record, everybody here knows I can rap. You don’t hear Stevie Wonder on radio and they’re like “yo, Stevie can you sing for us a little bit?” “Sure Shots” is about maintaining that mental, handling anything that comes my way.

AB: You mentioned there are more opportunities to fall. Has there ever been a point when you were, maybe not worried, but saw that opportunity was present?

HS: There have been times when I realized that if things had gone a different way it would have been an opportunity to fall, it would have been a very bad look, but it’s never occurred and I don’t believe it will ever occur as long as I keep doing the best that I can.

I don’t know if I’ve ever told you this very true story. At the Brooklyn Hip-Hop Festival, I believe it was the year 2009, I had a little mini-set. I had hosted earlier in the day, and I had a little mini-set where I was doing some joints produced by Shawn J. Period (Mos Def, Universal Magnetic, Rawkus). I was a big Shawn J. Period fan, and had actually linked up with him and done two joints with him. He had been tight with Wes Jackson, who runs the BHHF, and so had I. They were like “listen, they’re going to give you a prime time slot at the BHHF, you’re gonna come out and do a couple of Shawn J. joints,” and I said absolutely.

The BHHF was packed that year, Pharoahe Monch was headlining. I had such a busy week because I was about to leave on my first sustained road time in my career. I was leaving the day after the BHHF, so I spent all that week getting ready. I was busy doing a lot different things, so much so to the point where I hadn’t even gotten a chance to memorize my verses for these Shawn J. Period songs. I was very shaky on my verses. Normally if that happens I can always just switch to another song, but in this case I couldn’t switch, because it was just these Shawn J. joints, so my nerves were a bit wracked.

I was walking around for an hour before (the show). Normally before I go on stage I’m very relaxed, I’m very cool, but I was very nervous going over my rhymes again and again and again. I actually wound up about two blocks away from the hip-hop festival, just going over bars, and the thought occurs to me, why don’t you just read em off a piece of paper? Why don’t you just read em off a pad? You’re Homeboy Sandman, you can do whatever you want, why don’t you just read em off a pad? But I felt a little, ehh, I’m not ashamed to read off a pad, but I’ve never read off a pad at a show. I was an unestablished guy at that time and I was like, “Is this the right look, to be reading off a piece of paper,” so of course I thought to myself what would Black Thought do? That’s still pretty much my standard for what I’m supposed to do, and I pictured Black Thought doing it, and I pictured him pulling it off, so I said hey, I’m gonna do it.

At that point I was comfortable, I had a picture of Black Thought doing it in my head, so I was confident. I’m practicing opening my book, switching pages while I’m rapping while I walk back to the thing, and I turn the corner, and I swear to God, 30 seconds after I decided to do it because (I thought) Black Thought would do it, I turn the corner and Black Thought is right there on the corner. I had met him before, but I hadn’t spoken to him a lot. It was crazy, it was serendipity, destiny, fate, and nobody knew he was going to be there. He was a special guest, because J.Period was doing the live mixtape, which was a special part of the BHHF. J.Period I already knew pretty well by that time, so I just stepped up on Thought and said, “Yo this is crazy, 30 seconds ago I decided to do something because of you, and now here you are, right here, and I can ask you in person if you would do it.” He said what’s the science? I told him the science, and he told me you know what, I don’t feel like I’d do it. I said really? He said yeah, I don’t feel like this is the right atmosphere. You’re kinda new to these cats. He said he’d read off a book before, but he doesn’t feel like this is a right atmosphere.

I went up, I did the set without my book, and my bars were shaky. I take a lot of pride in the fact that I always get up on stage and I’m never shaky. This was one of the rare times when I was shaky, and I know the people who were there that day that had heard about me, or had heard about this kid Homeboy Sandman, let me see about him, they were thinking, “What’s up with this kid? I don’t get it. I don’t really see it,” but if I had brought the book out there and been shaky it would have been career death. It would have been “not only is this cat not coming correct, he’s sitting there reading out of a book.” It would have looked immature, amateurish, it would have looked terrible, but the fact of the matter is, the only person in the whole world that could have told me at that point not to do that was Black Thought, who was standing on the corner. So I run into situations like that where I’m on the brink of destruction, but God always looks out.

AB: So Black Thought was literally your guardian angel on that day.

HS: Black Thought was literally my guardian angel. I try not to talk about Black Thought so much because it actually makes Black Thought uncomfortable, and me, but I just gotta keep it real.

AB: Another person you can talk about a lot is your sister, because she did your album’s cover art.

HS: Yeah, my sister, Natalie del Villar, did the cover art and I’m really excited about that. Jeff Jank, the art director at Stones Throw, is very gifted, and he takes everything into account, he takes his job very seriously, and with every project I’ve released on Stones Throw there’s been a lot of back and forth about the art, and I’ve loved all the art that we’ve done. I’ve been looking to involve my sister in a release as the cover art for a little while, but there just hasn’t been right aesthetic yet for anything that she’s done until this particular time. This time we were all on the same page, Jeff, my sister, and I, and we all loved this artwork, so we were finally able to get it done. In this case it was a three headed monster, but it always needs to be at least a two headed monster, so me and Jeff always have to find something that he loves and I love. Big shouts to him. He has great ideas and I really appreciate how he takes into consideration whatever ideas I have. In this particular case it’s been awesome to be able to get my sister involved. She’s my favorite visual artist of all-time. Perhaps I’m biased, but I think she definitely has the talent. She’s another artist whose monetary intake is not an indicator of skill, but what does money have to do with anything important anyway?

AB: Certainly not in the arts. Going back to the piece, was it specially made for the album, or is it one that spoke to you, and you felt represented what you’re talking about?

HS: It was a piece that spoke to me. It’s part of her Strangers on the Train series. It’s on exhibit on 110th Street at the Aguilar Public Library. She has the whole exhibit. She would take snap shots of people she didn’t know on the train, without them noticing, and paint pictures of them. That piece, that picture, it’s two young gentleman, and it reminded me of taking the train home one day after school, being kind of tired, sitting there kind of lethargic. There was a vibe, and an energy about the painting that I found real reminiscent of youth. I thought of it as New York City youth. Their expressions are kind of like, it’s not a happy look, but it’s not a sad look, it’s not content, but it’s not really melancholy. I was feeling it.

AB: It’s a look of existence, almost. It’s sort like “we’re here.”

HS: That’s a great way to put it. I’m gonna bite that if you don’t mind.

AB: No problem. You are currently on tour with Random, and Open Mike Eagle. I may have misheard you, but at the end of the New Haven, CT, show did you say people should buy merch because you have a one year old at home? This is something I don’t recall you revealing so publicly before.

HS: The truth about it is this is my girlfriend’s one year old son. We recently have gotten to the level of closeness, over the last couple of months or so, that her son, I’ve come to look at as my son. We’re living together, and I’m absorbing him into my family. That’s how I had a one year old out of nowhere.

AB: OK, that clears A LOT up! Switching topics, and countries, you’ve traveled quite a bit. What’s the most lost, or out of your element, you’ve felt in a foreign country?

HS: I don’t have too many examples of that, but I do remember the first time we were going to Munich, the German language is so abrasive that this woman was actually trying to help me and (DJ) Sosa, and tell us we were getting off at the wrong stop, but the way she said that, with the language being so abrasive, I thought she was being like, “Get off the train!” That was a culture shock when it comes to the German language.

AB: Finally, doing a complete 180, what’s the most at home you’ve felt away from home?

HS: I’ve spent a good amount of time in London, and they speak English there, and I have family in Walden, and London kinda reminds me of New York. There’s a lot of multiculturalism, there’s a far reaching transit system. There’s shuts down at 12:01am, so it’s not the exact same thing, but London feels a bit like home. I don’t feel like I gotta get back to civilization right away.