We recently connected with Matthew Romero and have shared our conversation below.

Matthew, appreciate you joining us today. Being a business owner can be really hard sometimes. It’s rewarding, but most business owners we’ve spoken sometimes think about what it would have been like to have had a regular job instead. Have you ever wondered that yourself? Maybe you can talk to us about a time when you felt this way?

For the most part, yes — I’m much happier as a business owner. I get to chase big ideas, solve problems with creative freedom, and build something that didn’t exist before. That’s exciting. But I’d be lying if I said I never thought about what it’d be like to clock in, clock out, and leave work at work.

The last time that thought hit me was about three months ago. We were in the thick of a product push at JamJuice, racing to fix a critical bug that affected our artist payout automation system. At the same time, I was fundraising, negotiating contracts, onboarding a new venue, and trying to prep for a family weekend. I remember sitting at my kitchen counter at midnight, eating cold takeout, staring at a blinking cursor in an investor email draft, and thinking, “Man… it would be kinda nice to just go to work, do the job, and be done.”

It wasn’t about quitting — it was about the mental weight that comes with ownership. When things break, when a customer’s upset, when an investor needs answers — it all lands on your shoulders. And in that moment, I felt it. But then, I thought about the freedom I have to create, the way we’re reshaping live music with JamJuice, and how many musicians and venues we’ve helped. I thought about our mission — not just building a business, but actually changing how entertainment works in the hospitality space.

That’s when it clicked for me again: I’d rather carry the weight of something I believe in than be off the clock for something I don’t. So, I shut the laptop, microwaved that takeout, and went right back at it the next morning.

Matthew, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Sure thing — I’m Matthew Romero, founder of JamJuice, a live entertainment operating system built to completely simplify how people book, manage, and pay for live music. I’ve been in the music and hospitality space for nearly a decade, and honestly, I got into this business the old-fashioned way: by being in the trenches.

I started out managing artists and handling bookings myself, grinding to get musicians into venues and keep both sides happy. Over time, I realized something was broken — venues and hospitality groups were wasting time juggling spreadsheets, texting artists at the last minute, chasing invoices, and hoping the music quality matched the vibe they wanted. On the flip side, musicians were gig-hopping without a clear system, often waiting days (or weeks) to get paid, and lacking a professional way to showcase themselves. It was chaos.

So I built JamJuice to fix it. We’re a platform that makes live music plug-and-play. For organizers, we’re the easiest way to discover, book, schedule, and pay top-rated, vetted talent — all in one place. For artists, we’re a professional profile, booking tool, and same-day payment solution all rolled into one. Our platform also includes AI tools and a team of JamJuice Pros who serve as dedicated account managers to ensure things run smoothly.

What sets us apart is how hands-on we are. We’re not just another marketplace — we’re a service-forward operating system built with the reality of this industry in mind. We manage over 700 bookings a month, support a community of 900+ musicians, and serve some of the most iconic hospitality brands in Nashville and beyond. I’m proud of how far we’ve come — not just in numbers, but in impact. We’ve helped artists get paid faster, get more work, and feel more secure in their careers. And we’ve helped businesses elevate their guest experience through better music without the usual headaches.

The main thing I want people to know is: we’re here to bring live music into the modern era. If you love music but hate the logistics, we’re your team. We believe artists deserve better, venues deserve ease, and guests deserve unforgettable experiences. That’s the heartbeat behind everything we do at JamJuice.

Can you open up about how you funded your business?

Funding JamJuice wasn’t a straight line — it was more like a scrappy, strategic sprint.

I didn’t come from money, and I wasn’t sitting on a massive savings account when I started. The initial capital came from a mix of reinvested revenue from my first business, Affinity Entertainment, and a healthy dose of sweat equity. Affinity was already managing hundreds of bookings a month, so I used that as both proof of concept and a financial engine to bootstrap the early stages of JamJuice.

We didn’t raise money right away. In fact, I was pretty intentional about staying lean in the beginning — testing the idea, building the first version of the platform with a shoestring dev team, and using real client feedback to shape what JamJuice would become. It wasn’t glamorous, but it gave us traction. Real customers. Real revenue.

Once we proved product-market fit — with venues signing on, musicians getting paid out instantly, and a model that was actually scalable — we started attracting attention from investors. I ended up raising a $1.1M seed round to fuel our next phase of growth. But honestly, that money didn’t build JamJuice — the groundwork did. Every late night, every call with a venue, every artist we helped book — that’s what got us here.

So, if you’re looking for a story about overnight funding and unicorn valuations — this isn’t that. But if you’re into building something real with hustle, resourcefulness, and relentless belief in solving a real problem — that’s the JamJuice story.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

I think my reputation was built the same way any real business relationship is built — by showing up consistently and delivering.

In this industry, it’s easy to overpromise and underdeliver. A lot of people talk a big game, but when showtime comes, they disappear. I made it a point from day one to do the opposite: underpromise, overdeliver, and never miss a call, a payment, or a commitment.

That reputation started during my time running Affinity Entertainment. I was boots-on-the-ground — answering late-night calls from venues, showing up to gigs in person, fixing things on the fly, and making sure the music matched the moment. Word travels fast in hospitality, and the people we served noticed that we weren’t just booking musicians — we were helping them build a better guest experience.

With JamJuice, that same energy carried over — but now it’s backed by a platform that scales that reliability. We don’t just throw tech at people and hope it sticks. We pair cutting-edge tools with real human support. Our JamJuice Pros are trained to go above and beyond, and that level of service builds trust.

So if you ask what built my reputation — it was consistency, responsiveness, and a deep respect for the relationships we’ve built. People know we’re not in this just to make a buck. We actually care. And in this industry, that matters.

Contact Info:

• Website: https://jamjuice.com
• Instagram: @mogulmatthew
• Linkedin: https://www.linkedin.com/in/mogulmatthew/