Jonathan Jimenez pulled in six figures a month at his peak — off a chatbot he constructed with no web site, workplace, or backup plan. He’d gone from broke and Googling easy methods to make a funnel to operating contests for WorldStarHipHop that gave unsigned rappers a shot at a verse with Jadakiss.
It began when a bot wouldn’t cease texting him again.
“I used to be broke, working like 300 jobs, simply trying to find one thing that might maintain my consideration and be enjoyable. I stumbled throughout Manychat. I most likely noticed it in an advert or on YouTube and thought, this is likely to be it. Earlier than that, I’d been constructing web sites since I used to be about 20, however I made a decision to take it significantly as soon as I discovered chatbots. I dove into tutorials, how-tos, YouTube, Fb teams, all the things.”
He sighed, excited about that point when McDonald’s was a luxurious, and continued, “I went on Amazon, acquired a pack of pencils and a few paper, and set to work.”
The Hustle By no means Stops
After determining easy methods to make a plan utilizing Manychat and a few commonsense automation, he discovered an in — by WorldStar. “I stumbled throughout this contest WorldStarHipHop was operating. That they had a bot, and after I opted in and tried to unsubscribe by texting ‘STOP,’ it simply stored messaging me. So I began clicking round, determining who constructed it, and hit the man like, ‘Yo, your chatbot’s damaged.’”
The 2 acquired to speaking, and shortly, Jimenez got here in to work with WorldStar. “A DJ was touring with artists like French Montana, Jadakiss, Funk Flex, DJ Envy, and Lil Durk. I noticed tons of unsigned rappers had been dying for a shot however had no actual approach to attain these massive names.”
Jimenez constructed a bot that allow folks submit their tracks straight by Messenger. He tied it to YouTube and Spotify APIs so artists may search their stuff, submit it, hit a paywall, after which it’d go to an trade panel.
The highest 20 tracks acquired despatched to featured artists like Jadakiss or French Montana, who would choose a winner. That concept blew up. “I began operating campaigns, contests, constructing automation — subsequent factor I do know, I’m making $10K, $20K, $30K, $50K month-to-month. I purchased a Rolex. Moved to Florida. My complete life flipped as a result of I took this bizarre chatbot hustle significantly. I wasn’t making music however constructing instruments for the music world. And nobody was actually doing that on the time, particularly not in hip-hop.”
And that’s the magnificence of creating it work: The soul of hip-hop comes from the streets. There was no laboratory second, however DJ Kool Herc made a joyous mistake in a basement. Since that second of invention, hip-hop has influenced the world in an incalculable method.
From the Avenue to the Boardroom
Within the phrases of Rakim in “Microphone Fiend“:
I melted microphones as a substitute of cones of ice cream
Music oriented so when hip-hop was originated
Fitted like items of puzzles, difficult
‘Trigger I grabbed the mic and attempt to say, “Sure, y’all”
The music calls for avenue smarts, realizing easy methods to capitalize on a second, to see cash and transfer on it. Speaking with Jonathan Jimenez, a self-made entrepreneur who knew he had the technical chops however no prospects, the world of hip-hop offered a chance — an opportunity to make his mark, turning a second of desperation right into a residing. He went from his mother’s home to constructing a profitable digital advertising and marketing and automation enterprise. However getting there took main hustle. There was no in a single day success. No rich benefactor. Simply staying targeted on the work.
Ultimately, Jimenez acquired employed by WorldStar. They gave him a branded card. “That meant one thing to me. I grew up on that website; I’m 37 now, however again after I was 17 or 18, I used to be on WorldStar day by day. And now I used to be working with them. All of it got here from taking one little concept significantly and operating with it.”
Inside a blink, life went from zero to fifty giant — in a month.
(In fact, I needed to ask who his favourite rappers had been: Jadakiss, Fabolous, Mobb Deep, and 50 Cent. He tipped the cap to Tupac and Biggie Smalls, as one does, however moved past the standard reply folks of a particular age give.)
C. R. E. A. M: Money Guidelines Every part Round Me
How did he know he was transferring in the suitable course? When all the things was on autopay.
“All of it hit me — this wasn’t only a hustle anymore. This was my life. I may construct one thing sustainable, take care of myself and my household, and stay how I wished. I lower off distractions, discovered Fb advertisements, studied each night time, and informed myself: I’m beginning my very own company. And I did. It took consistency, self-discipline, and numerous trial and error, however I lastly discovered a path that was mine.”
“Once I was actually on prime, I had 5 contests operating without delay,” he explains. “We had been doing over $100K a month, generally far more. Between Chat Automations, the paywalls, and all of the follow-ups, I imply, I can present you my accounts. One had over $800,000. One other had $300K. Then a pair with $100K, $40K, $50K. It was wild. And this was with no web site — only a instrument that facilitated a complete life for me.”
The hustle has modified, however the guidelines haven’t. In a world the place hip-hop constructed an empire from mixtapes and avenue groups, right this moment’s recreation runs on chatbots, AI workflows, and DMs that convert.
Mixing Tech and the Tradition
The creator financial system is value over $250 billion, with hip-hop heads, sneaker resellers, and digital entrepreneurs swimming in the identical pool. WorldStar nonetheless pulls in tens of millions of month-to-month guests. Like those Jimenez constructed, Messenger bots boast open charges thrice increased than e-mail, making them the new-age avenue nook for grabbing consideration.
Artists like Jadakiss and French Montana could have constructed careers off verses, however now they’re investing in tech too, as a result of even they know the way forward for hustle is automated. With 80% of buyer interactions anticipated to be AI-driven by 2026 and the worldwide chatbot market pushing previous $5 billion, it’s not about clout alone anymore; it’s about who can construct the neatest funnel.
For entrepreneurs coming from the tradition, that’s the brand new cipher.
“We had a bunch of cool stuff happening — occasions at SXSW, a ‘win a verse with Jadakiss’ contest I ran, and mixtape options. Individuals had been getting legit publicity; think about getting on a monitor with Jadakiss for $30. That was the entry price. You possibly can market that characteristic and actually do one thing with it. Individuals liked it.”
However then got here the issue with all promotions: gaming the system.
“People jumped in and scammed. As soon as that began, the entire scene acquired tainted. What we had been doing was an actual alternative, however the effectively ran dry quick. It acquired oversaturated with folks operating faux contests and simply printing cash with out delivering. I even constructed an app — a Tinder-style music platform with voting and leaderboards — as a approach to pivot out of that house, however by then the magic was form of gone. It was a kind of moments the place timing was all the things.”
Rock The Bells
Wanting again on his profession, Jimenez is candid in regards to the highs and the lows. I requested him if there was something he would do otherwise, contemplating he constructed his enterprise from the bottom up. “I ought to’ve gotten a mentor. Every part occurred quick. I didn’t have the knowledge or expertise I wanted on the time. There have been many issues I didn’t do this I ought to’ve finished. I went from making nothing to doing fairly effectively — and as a substitute of reinvesting or considering long-term, I spent an excessive amount of and stored all the things on my shoulders.”
He paused briefly and continued, “Wanting again, I ought to’ve used that cash to convey somebody on board. Even only one worker to assist scale issues. However I at all times had this mindset that I needed to do all the things myself. Any time I attempted to show somebody, it by no means felt like they actually acquired it or didn’t take it as significantly as I did.”
“Every part got here at me quick — cash, alternatives, folks — and I didn’t know easy methods to deal with the enterprise facet. I had companions, however I didn’t perceive taxes, revenue splits, or easy methods to shield myself. I used to be simply excited to lastly be getting cash and didn’t understand I used to be being taken benefit of. One of many largest regrets was a falling out with a detailed good friend — the identical man who acquired me into the sport.”
“He was a prime promoter within the Northeast, and we used to mix his music relationships with my tech background. However then it turned shady. He began forcing folks into my offers, saying I needed to lower them in as ‘companions’ to convey down his overhead. What ought to’ve been a $10,000 slot became a $60,000 expense simply to fulfill his facet hustles. And I wasn’t getting a lower of any of it. That’s after I realized he wasn’t transferring in the most effective curiosity of our firm, simply his personal. That betrayal broke the friendship and confirmed me how ugly issues can get when cash’s concerned.”
Wanting Again
Jimenez seems again on that point as an train to recollect the place he got here from. Sitting over Zoom, he’s not a refined marketer, attempting to stay to the script of polished gross sales routines. As a substitute, he’s sincere—he owns his errors and is open about what’s labored and what hasn’t, which in the end humanizes him greater than many others who’ve hit a lick within the on-line world.
As he constructed his firm Chat Automations, he stored pushing how AI can assist small companies do extra in a world the place all the things is a swipe and a click on. His company helps firms streamline operations utilizing instruments like Manychat, automated workflows, and customized GPTs.
The main focus is on making on a regular basis duties simpler — issues like managing leads, dealing with buyer messages, or smoothing out gross sales funnels — by constructing methods that match how a enterprise runs. The thought isn’t to interchange folks however to take the repetitive stuff off their plates to allow them to give attention to the larger image.
I’ll Take you to The Sweet Store
After stepping away from chatbots for some time, admitting they began to really feel stale, he discovered his spark once more in AI. “All of the stuff we wished chatbots may do again then? You feed AI your information, and it simply works. So I jumped again in, began working with gyms, constructing out superior automations with Manychat, and extra. It’s like a brand new wave, but it surely’s constructed on all the things I discovered the primary time round.”
Jimenez was forward of the curve. Earlier than artists like Russ, Tobe Nwigwe, or Ice Spice used automation to scale their viewers, he was already constructing the roads they now run on. That’s the legacy — even when it didn’t include a label deal or a Tremendous Bowl industrial.
Nowadays, the strikes are quieter. Extra targeted. Extra deliberate. The hustle’s nonetheless there — it simply wears totally different garments. He could not have a blueprint. However he’s acquired the scars. The receipts. And a stack of instruments constructed from pure hustle.
The remainder? He’s constructing it stay.