Back in 2010, I deliberately decided to kill off my old record label/crew and start something from the ground up. Totally dolo. Castro was on board as the only defector from the previous camp.

I chose the name “Three Dollar Pistol” in 2011 as a play on Tom Waits’ line from “Jockey Full of Bourbon” and the Black Keys song “Ten Cent Pistol”.

It was ONLY going to be what I wanted to do and not a group situation of constant bickering, different passions, and outright tastes that were evolving away from each other in this thing called rap. I went from a crew of 10+ people who met on a monthly basis (rappers, producers, web guys, camera man, singers, etc), including 2 other decision makers, to me sitting in a new apartment on South Street in Philly making things up on the fly.

I discovered Bandcamp as the best means to host music via Justin Boland. He used to write a great indie rap blog (the name escapes me) and I eventually reached out to him about linking with his crew at World Around Records (RIP).

At that point, “Three Dollar Pistol” was just a landing page to host a new EP I made called “Bad Weather Classic.” It’s got some joints with Small Pro, Castro, and MaLLy that I’m still proud of 15 years later. But at the time, I still thought a “real” record label was the look, indie or major.

Castro and I got approached by a drum-n-bass label to be their first hip-hop act. We did quite a few jams for them, including “Philly Crime” with a young ELUCID that ended up on the first GRIFT COMPANY project. Did some shows, remixes, etc in Philly as well but it sputtered out.

I did some work with World Around Records in a handshake partnership to host my album “Nights & Weekends”. This girl I was dating at the time was quite impressed that they dropped an S.Maharba record, so I was pumped to be on that roster. However, it felt like I was giving them more visibility than they could return in kind. I didn’t see the point of being a workhorse for a loose unit of hyper creatives that weren’t truly focused on being a tried and true label.



There were brushes with Mello Music Group about dropping a 7inch for my song “Young Blood” featuring a very early post-”Marcberg” feature from Roc Marciano. They stopped responding to emails about the paperwork on the single. I did more work for hire with MMG, notably mixing Castle’s “Return of the Gas Face” record, but no deal as a soloist emerged.



It’s crazy how much of a quest for validation getting signed really was to me and rappers in general, even as the “industry” was in a hugely transitional period of “pay what you want”, illegal downloads, and little to no physicals.

Castro took his first deal with Man Bites Dog Records around that time to drop “FIDEL”, and Small Pro linked up with Coalmine Records to put out “Gigantic Vol. 1”. I felt like the eternal bridesmaid. Being featured on both records was dope as hell, and hearing the machinations of those labels from my discussions with the fellas gave me tons of insight as to what real promotions, budgets, and reach looked like.

My main man Fresh from the old blog 33jones.com (where I first heard of Alex Ludovico in 2007) had a potential label deal with Bad Boy and Universal that fell apart during the 2008 financial crisis. That will be its own post someday.

Anyway, we linked up to drop my album “No Vacation For Murder” as a joint deal between 33 Records and Three Dollar Pistol Music around 2015. I still wasn’t thrilled about being my own label boss because to get to that point, I was turned down by Anticon, Mello Music Group, and Man Bites Dog to release that album.

Artwork by Dewey Saunders (my man!)

I kept thinking a label would solve all my problems. They would blow me up quick, get me more fans, crank up my sales, book me on a tour, etc.

My first deal via PremRock and FreshKils with URBnet in Canada for the Career Crooks debut album “Good Luck With That”. I’ll never forget reviewing, signing, and faxing the contract over to the good folks at URBnet. I did it - got a real record contract!

Stay tuned for part 2 next week!

-ZR

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