We recently connected with Juan Montes and have shared our conversation below.

Juan, appreciate you joining us today. Can you share a story that illustrates an important or relevant lesson you learned in school

I like to think of myself as your “average student,” just with a little more common sense than most. I was never an overachiever—I did just the bare minimum to pass my classes, except for math. Math? That was easy for me. I always loved numbers, and remembering formulas was second nature.

Now, as an entrepreneur, I realize that business is just another formula. If it doesn’t make cents, it doesn’t make sense. Of course, business isn’t just about numbers—there’s customer service, marketing, inventory, and all the other moving parts—but at the end of the day, profitability is key. If you’re not making money, you’re not in business.

Growing up, school wasn’t really a choice in my house; it was just something my single mother expected my sister and I to do. There was an unspoken rule: you go to school, you get good grades, and you stay out of trouble. Bad grades? That meant consequences—no PlayStation, no going outside to play with friends until the streetlights came on. Simple.

From an early age, I understood that actions had consequences, and I’m grateful that school came easy for me. Looking back, my creativity—and maybe a little undiagnosed OCD—helped me stay on top of things. But if I’m being honest, I was also a huge procrastinator.

Ironically, procrastination helped shape who I am today. The pressure of last-minute deadlines forced me to think quickly, solve problems efficiently, and make things work with limited time. That sense of urgency—the ability to adapt and execute under pressure—is something I now use every day in business. As an entrepreneur, you don’t always get the luxury of perfect timing. You don’t always get to prepare for months in advance. Sometimes, opportunities come out of nowhere, and you either rise to the occasion or miss out. That’s where the “art” of procrastination comes in—not as an excuse for poor planning, but as a skill for working under pressure and delivering when it matters most.

Of all my years in school, junior year stands out the most. Everyone says it’s the most important year because of SATs and college applications, but for me, it was probably my worst. I was sleeping through classes, doing the bare minimum, and just coasting by. I was never in danger of failing, but I wasn’t exactly pushing myself either.

The lesson that stuck with me came from my junior year English class. We had a major assignment: write an essay about an inspirational person. We had two months to complete it. Every few weeks, the teacher would check in, and students would go up to get feedback on their drafts. Fast forward to one week before the deadline—I looked around and saw my classmates with their essays nearly finished, some already three pages in.

Me? I hadn’t even chosen a person to write about.

The day before the essay was due, as I was leaving class, I turned to my teacher and said, “I need help. I haven’t even started my paper yet.”

I thought maybe she’d feel bad for me, give me an extension, or at least some sympathy. What was a 16-year-old kid thinking? I’ll tell you—I was thinking, I’m so screwed.

Somehow, the teacher handed me a book about Arthur Ashe and told me to take it home. My first thought? Who the hell is Arthur Ashe? I had no clue. But if you were to ask me today, I could tell you exactly who he was, why he was an inspirational figure, and why his name will always remind me of that grey, gloomy December day in English class—and why I went to school the next morning with the biggest dark circles under my eyes.

That experience taught me that procrastination is a double-edged sword. Sometimes, it works in your favor, and sometimes, it doesn’t. Some might call it luck; others might call it a lack of preparation. But in business, procrastination—when used correctly—can actually be a tool.

See, in entrepreneurship, things don’t always go according to plan. Sometimes, you’re forced to figure things out last minute. Sometimes, an investor backs out, a shipment gets delayed, or a competitor drops a surprise move that forces you to pivot immediately. Being able to think on your feet, make decisions under pressure, and produce results quickly is a skill.

Procrastination has always been my biggest enemy and my biggest motivator. I take my time getting started, but when the deadline is staring me in the face, I find a way to deliver. I’ve always been the type to try a million things until something sticks. That’s what entrepreneurship is—trial and error, persistence, and the ability to pivot when needed.

Success isn’t an overnight thing. It’s about showing up, over and over again, until you get it right. Sometimes, that means grinding for months. Other times, that means pulling an all-nighter the day before.

Just like I’m doing with this interview.

Juan, 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?

The main problem I solve for my clients is ensuring they don’t have a terrible time on one of the biggest days of their lives—aka their wedding day. Weddings are meant to be joyful and stress-free, and my job is to make sure the entertainment aspect is seamless, exciting, and unforgettable.

I’m someone with a deep passion for music who gradually found my way into the wedding and mobile entertainment industry by learning hospitality, event planning, and the art of creating memorable experiences. Like anything in life, success doesn’t happen overnight—after all, Rome wasn’t built in a day. That saying, as cliché as it may be, is something I still remind myself of daily, along with one of my favorite quotes: “The expert was once a beginner.”

Trying new things and failing can be discouraging for most people, but for me? I embrace it. I thrive on the mindset of, “Hey, at least you gave it a shot,” and “We’ll get them next time.” That attitude has been the driving force behind my growth as a DJ, Master of Ceremonies, and entrepreneur.

Being trusted with someone’s wedding day is a responsibility I never take lightly. I perform at around 150 events a year, with about 50 of those being weddings. It’s not like people get married every day—but I do weddings just about almost every other weekend. That means my job is to bring energy and excitement to every event, even when the routine could become repetitive. However, I know my clients don’t care about how many events I’ve done before—they care about their special day. That’s why, no matter the circumstances, I show up at 100% every single time. In this business, even 99% isn’t good enough.

The Discipline Behind My Work

My approach to business is rooted in my background in wrestling. I could write an entire book on how wrestling is the foundation of my business mindset, but I’ll leave you with this:

Although wrestling is somewhat of a team sport, when you’re out on the mat, it’s just you and your opponent. No one else. You can’t hide behind teammates, you can’t make excuses, and you can’t blame anyone else for a bad performance. Your skills, your preparation, your endurance—it’s all on display for the world to see. I’ve lost heartbreaking matches by a single point. I’ve been humiliated, losing 15-0 or getting pinned in 30 seconds by a state qualifier. But the real question is: How do you respond? Do you come back to practice the next day and put in the work, or do you quit, take time off, and blame your coach?

This mindset directly translates to entrepreneurship:

Losing money? What are you going to do to fix it and become profitable?
A client left a bad review? How will you address the situation and improve?
You didn’t deliver the quality service you promised? What will you do to make it right?
Problems will always arise, but what separates a great entrepreneur from a mediocre one is the ability to take responsibility, find solutions, and continuously improve.

What Sets Me Apart
I don’t just play music—I create an experience. My goal is not just to get people dancing, but to ensure they leave the event feeling like it was the best celebration they’ve ever been to. My ability to read the crowd, adapt to any situation, and bring a unique energy to every event is what sets me apart.

At the end of the day, I want my clients to know that I am not just a DJ—I am someone who truly cares about their experience. Whether it’s a wedding, a corporate event, or a small baby shower, I treat every event like it’s the most important one I’ve ever done. Because for my clients, it is the most important event.

That’s the level of passion, commitment, and excellence I bring to the table every single time.

How about pivoting – can you share the story of a time you’ve had to pivot?

Absolutely! Two words: March 2020. Let me paint a picture.

2019 was, by far, my best year as a private event DJ. I had about three weddings of my own under my belt and was slowly building my reputation and social media brand. By the end of the year, I had already booked four weddings for 2020. Things were looking great! It was a big deal for me.

And then, of course, March 2020 happened.

After being stuck at home for two months with no certainty about when the world would reopen—and with events and gatherings at a complete standstill—I found myself going from getting home at 2–3 a.m. to being in bed by 10 p.m. I was losing my mind.

I already had a small 6×12 trailer that I used to haul my DJ equipment, so I decided to start posting on Facebook to see if anyone needed anything moved—specifically gym equipment. With gyms closed, people were in a frenzy buying equipment for their homes. That’s how my small side hustle started. It kept me above water and helped me stay afloat financially.

At first, I was skeptical. Maybe I was embarrassed? Maybe I didn’t want to seem desperate? But I asked myself: What do I have to lose?

What started as a side hustle quickly became something much bigger. I began hiring my friends (who were also DJs), and before I knew it, I had outgrown my little 6×12 trailer. If I had just sat around waiting for the world to open back up, I probably would have lost everything or go back to a warehouse 9-5. But this side hustle helped me weather the storm.

I used my hospitality skills and transparency to show potential clients that the guy they found on Facebook Marketplace was legit. I showed them proof of my work, shared text reviews from previous clients, and built trust.

Eventually, the world opened back up, and things slowly started returning to normal. Weddings and events picked up again, and I was able to get back to doing what I loved. But that experience showed me that pivoting or starting fresh isn’t so bad—especially when you have a system in place (aka the math formula). Now, I know that if life throws another curveball, I have the skills and mindset to adapt.

The hardest question in business isn’t just “When do you pivot?”—it’s “Are you willing to?” Because sometimes, the opportunity is right in front of you, but pride, fear, or doubt can keep you from taking that first step. I almost let that stop me, but I realized I had nothing to lose—and everything to gain.

Any insights you can share with us about how you built up your social media presence?

This also may sound cliché, but follow the trends—just make sure to add your own twist. I always look at what the big brands in my industry are doing and ask myself, “How can I make this better?” or “How can I do this in a way that’s uniquely ‘Montes Pro’ without copying?”

Building a brand isn’t easy, but you know what is easy? Being authentic and standing out. It’s 2025—by now, we can all tell when an account has 20K followers but only 11 likes per post. Many business owners try to take shortcuts or don’t put in the work when it comes to social media, and trust me, it really shows and your followers can see it from a mile away.

Everyone wants that viral video with a million views and 50K shares, but before that happens, you need to get that first post with 1K views, then 2K, and keep building from there. I haven’t hit a million views yet, but I know I have to hit 10K first, then 20K, and keep climbing.

What I’ve learned about social media is that it’s all about personal connection. How do you connect with your audience in a meaningful way? For me, I use emotion and realism—with a splash of marketing.

If you check out my Instagram, @MontesPro, you’ll see a lot of behind-the-scenes (BTS) reels of me talking to couples, running around, working with other vendors, and giving my followers—whether they’re potential couples, past clients, or other industry professionals—a real look at what I do on a wedding day.

Why does this work? Because not many people show the real behind-the-scenes moments—the nitty-gritty of what vendors go through on a couple’s big day. Giving people that raw, unfiltered perspective builds trust and engagement.

So if you’re just starting out, my advice is simple: be authentic, put in the work, and focus on real connections. The numbers will follow.

Contact Info:

• Website: https://montespro.com
• Instagram: @MontesPro
• Facebook: https://Facebook.com/montesproductions
• Soundcloud: https://soundcloud.com/djfiinest
• Other: Tik Tok – MontesProNJ

Image Credits

@jllenzphotography
@flowvisualss
@weddingsbydavidalex