Jonathan Jimenez pulled in six figures a month at his peak — off a chatbot he built with no website, office, or backup plan. He’d gone from broke and Googling how to make a funnel to running contests for WorldStarHipHop that gave unsigned rappers a shot at a verse with Jadakiss.
It all started when a bot wouldn’t stop texting him back.
“I was broke, working like 300 jobs, just searching for something that could hold my attention and be fun. I stumbled across Manychat. I probably saw it in an ad or on YouTube and thought, this might be it. Before that, I’d been building websites since I was about 20, but I decided to take it seriously once I found chatbots. I dove into tutorials, how-tos, YouTube, Facebook groups, everything.”
He sighed, thinking about that time when McDonald’s was a luxury, and continued, “I went on Amazon, got a pack of pencils and some paper, and got to work.”
The Hustle Never Stops
After figuring out how to make a plan using Manychat and some common-sense automation, he found an in — through WorldStar. “I stumbled across this contest WorldStarHipHop was running. They had a bot, and when I opted in and tried to unsubscribe by texting ‘STOP,’ it just kept messaging me. So I started clicking around, figuring out who built it, and hit the guy like, ‘Yo, your chatbot’s broken.'”
The two got to talking, and soon, Jimenez came in to work with WorldStar. “A DJ was touring with artists like French Montana, Jadakiss, Funk Flex, DJ Envy, and Lil Durk. I realized tons of unsigned rappers were dying for a shot but had no real way to reach those big names.”
Jimenez built a bot that let people submit their tracks directly through Messenger. He tied it to YouTube and Spotify APIs so artists could search their stuff, submit it, hit a paywall, and then it’d go to an industry panel.
The top 20 tracks got sent to featured artists like Jadakiss or French Montana, who would pick a winner. That idea blew up. “I started running campaigns, contests, building automation — next thing I know, I’m making $10K, $20K, $30K, $50K monthly. I bought a Rolex. Moved to Florida. My whole life flipped because I took this weird chatbot hustle seriously. I wasn’t making music but building tools for the music world. And no one was really doing that at the time, especially not in hip-hop.”
And that is the beauty of making it work: The soul of hip-hop comes from the streets. There was no laboratory moment, but DJ Kool Herc made a joyous mistake in a basement. Since that moment of invention, hip-hop has influenced the world in an incalculable way.
From the Street to the Boardroom
In the words of Rakim in “Microphone Fiend“:
I melted microphones instead of cones of ice cream
Music orientated so when hip-hop was originated
Fitted like pieces of puzzles, complicated
‘Cause I grabbed the mic and try to say, “Yes, y’all”
The music demands street smarts, knowing how to capitalize on a moment, to see money and move on it. Talking with Jonathan Jimenez, a self-made entrepreneur who knew he had the technical chops but no prospects, the world of hip-hop presented an opportunity — a chance to make his mark, turning a moment of desperation into a living. He went from his mom’s house to building a successful digital marketing and automation business. But getting there took major hustle. There was no overnight success. No wealthy benefactor. Just staying focused on the work.
Eventually, Jimenez got hired by WorldStar. They gave him a branded card. “That meant something to me. I grew up on that site; I’m 37 now, but back when I was 17 or 18, I was on WorldStar every day. And now I was working with them. It all came from taking one little idea seriously and running with it.”
Within a blink, life went from zero to fifty large — in a month.
(Of course, I had to ask who his favorite rappers were: Jadakiss, Fabolous, Mobb Deep, and 50 Cent. He tipped the cap to Tupac and Biggie Smalls, as one does, but moved beyond the typical answer people of a specific age give.)
C. R. E. A. M: Cash Rules Everything Around Me
How did he know he was moving in the right direction? When everything was on autopay.
“It all hit me — this wasn’t just a hustle anymore. This was my life. I could build something sustainable, care for myself and my family, and live how I wanted. I cut off distractions, learned Facebook ads, studied every night, and told myself: I’m starting my own agency. And I did. It took consistency, discipline, and a lot of trial and error, but I finally found a path that was mine.”
“When I was really on top, I had five contests running at once,” he explains. “We were doing over $100K a month, sometimes way more. Between Chat Automations, the paywalls, and all the follow-ups, I mean, I can show you my accounts. One had over $800,000. Another had $300K. Then a couple with $100K, $40K, $50K. It was wild. And this was with no website — just a tool that facilitated a whole life for me.”
The hustle has changed, but the rules haven’t. In a world where hip-hop built an empire from mixtapes and street teams, today’s game runs on chatbots, AI workflows, and DMs that convert.
Blending Tech and the Culture
The creator economy is worth over $250 billion, with hip-hop heads, sneaker resellers, and digital marketers swimming in the same pool. WorldStar still pulls in millions of monthly visitors. Like the ones Jimenez built, Messenger bots boast open rates three times higher than email, making them the new-age street corner for grabbing attention.
Artists like Jadakiss and French Montana may have built careers off verses, but now they’re investing in tech too, because even they know the future of hustle is automated. With 80% of customer interactions expected to be AI-driven by 2026 and the global chatbot market pushing past $5 billion, it’s not about clout alone anymore; it’s about who can build the smartest funnel.
For entrepreneurs coming from the culture, that’s the new cipher.
“We had a bunch of cool stuff going on — events at SXSW, a ‘win a verse with Jadakiss’ contest I ran, and mixtape features. People were getting legit exposure; imagine getting on a track with Jadakiss for $30. That was the entry fee. You could market that feature and really do something with it. People loved it.”
But then came the problem with all promotions: gaming the system.
“Other folks jumped in and scammed. Once that started, the whole scene got tainted. What we were doing was a real opportunity, but the well ran dry fast. It got oversaturated with people running fake contests and just printing money without delivering. I even built an app — a Tinder-style music platform with voting and leaderboards — as a way to pivot out of that space, but by then the magic was kind of gone. It was one of those moments where timing was everything.”
Rock The Bells
Looking back on his career, Jimenez is candid about the highs and the lows. I asked him if there was anything he would do differently, considering he built his business from the ground up. “I should’ve gotten a mentor. Everything happened fast. I didn’t have the wisdom or experience I needed at the time. There were many things I didn’t do that I should’ve done. I went from making nothing to doing pretty well — and instead of reinvesting or thinking long-term, I spent too much and kept everything on my shoulders.”
He paused briefly and continued, “Looking back, I should’ve used that money to bring someone on board. Even just one employee to help scale things. But I always had this mindset that I had to do everything myself. Any time I tried to teach someone, it never felt like they really got it or didn’t take it as seriously as I did.”
“Everything came at me fast — money, opportunities, people — and I didn’t know how to handle the business side. I had partners, but I didn’t understand taxes, profit splits, or how to protect myself. I was just excited to finally be making money and didn’t realize I was being taken advantage of. One of the biggest regrets was a falling out with a close friend — the same guy who got me into the game.”
“He was a top promoter in the Northeast, and we used to blend his music relationships with my tech background. But then it turned shady. He started forcing people into my deals, saying I had to cut them in as ‘partners’ to bring down his overhead. What should’ve been a $10,000 slot turned into a $60,000 expense just to satisfy his side hustles. And I wasn’t getting a cut of any of it. That’s when I realized he wasn’t moving in the best interest of our company, just his own. That betrayal broke the friendship and showed me how ugly things can get when money’s involved.”
Looking Back
Jimenez looks back on that time as an exercise to remember where he came from. Sitting over Zoom, he’s not a refined marketer, trying to stick to the script of polished sales routines. Instead, he’s honest—he owns his mistakes and is open about what’s worked and what hasn’t, which ultimately humanizes him more than many others who’ve hit a lick in the online world.
As he built his company Chat Automations, he kept pushing how AI can help small businesses do more in a world where everything is a swipe and a click. His agency helps companies streamline operations using tools like Manychat, automated workflows, and custom GPTs.
The focus is on making everyday tasks easier — things like managing leads, handling customer messages, or smoothing out sales funnels — by building systems that fit how a business runs. The idea isn’t to replace people but to take the repetitive stuff off their plates so they can focus on the bigger picture.
I’ll Take you to The Candy Shop
After stepping away from chatbots for a while, admitting they started to feel stale, he found his spark again in AI. “All the stuff we wished chatbots could do back then? You feed AI your info, and it just works. So I jumped back in, started working with gyms, building out advanced automations with Manychat, and more. It’s like a new wave, but it’s built on everything I learned the first time around.”
Jimenez was ahead of the curve. Before artists like Russ, Tobe Nwigwe, or Ice Spice used automation to scale their audience, he was already building the roads they now run on. That’s the legacy — even if it didn’t come with a label deal or a Super Bowl commercial.
These days, the moves are quieter. More focused. More deliberate. The hustle’s still there — it just wears different clothes. He may not have a blueprint. But he’s got the scars. The receipts. And a stack of tools built from pure hustle.
The rest? He’s building it live.
