Nicholas Ruggieri's journey to entrepreneurial success is a testament to the power of resilience and self-belief.

Purpose, Passion,
and Perseverance:
Nicholas Ruggieri’s
Rise to the Top

With a growing family and a newborn to support, Nicholas was presented with the choice of a lifetime: seek the safety of a career elsewhere or gamble on himself. The offer came with no salary, no guarantees—just a vision and a dream. But Nicholas believed in the vision. He chose to take the leap. He bet on himself.

Pinpoint Payments would go on to evolve into a full-fledged merchant services provider. Nicholas's unique approach to business helps set Pinpoint apart in the industry. He emphasizes building genuine partnerships with people, getting to know clients intimately and crafting customized solutions designed to help small businesses thrive, not just survive.

Nicholas’s understanding of business didn’t come from a textbook—it came from the real, raw lessons he learned as a child. Watching his father run a donut shop, he saw the grit and grind that went into making a business work. He witnessed firsthand the sacrifices, the stress, and the moments of doubt. He saw the triumphs—the sense of pride in building something from nothing along with the tragedies, after his father lost the business. It was that mix of struggle and success that shaped his perspective on business.

Alongside that, it was boxing that taught him the discipline, resilience, and the unshakable belief in himself. In the ring, he learned how to keep pushing even when every part of him wanted to quit, a lesson he would carry with him into his entrepreneurial journey. Nicholas learned that success isn’t just about talent—it’s about perseverance, about betting on yourself, and about rising every time you’re knocked down.

These core values, forged in both the family business and the boxing ring, became the foundation of his own journey.

Under Nicholas's leadership, Pinpoint Payments has grown into an eight-figure business, recognized by Inc. 5000 as one of the fastest-growing companies in America for five consecutive years. His story serves as an inspiration to aspiring entrepreneurs, demonstrating that with hard work, perseverance, and a willingness to bet on oneself, it's possible to overcome any obstacle and achieve remarkable success.

In this far-reaching Swagger interview, Nicholas Ruggieri brings his entrepreneurial insight as well as his passion in imparting his wisdom to others.


Tell me what was the tipping point to get clean and sober?

For me, sobriety was the last house on the block. I had nowhere else to turn. Mentally, physically, and emotionally, I was broken. I lived in the darkness for so long that I had grown to embrace the pain and the struggle. It became part of me and who I was. But I was tired of fighting every day. I was tired of going to bed every night wishing I wouldn't wake up, only to be disappointed every morning when I woke up still alive.

As my son grew closer to his first birthday, deep down inside me, I knew I wasn’t the man I wanted to be. What would my son think? How would I be remembered? Most of my friends were dead or in jail, and those who weren't, were on the fast track, myself included.

Then came the day before my son's first birthday. I tossed and turned. I was ready to be done with it all. I wanted to turn the lights out and just fade into eternity. But something inside me couldn’t bring myself to do it. I wasn’t ready to give up on myself, and more importantly, on my son.

It was that small seed of hope, found deep within the darkest parts of my soul, that turned everything around. I was forced to make a decision: stay in the dark or fight for the light.

In that moment, I chose to rise. I chose to turn my back on the pain that had defined me, and step into the light, even when it felt like the hardest thing I’d ever done.

Sobriety didn’t just give me a second chance—it gave me the strength to reclaim my life, rebuild my purpose, and become the man I always knew I could be. It wasn’t a perfect journey, but every step forward was a victory. Now, I’m not just living—I’m thriving, and every day, I get to show my son the man I was meant to be.



What do the words "self made man" mean to you?

Accountability! To me, a self-made man is someone who’s relentless in their pursuit of success. Someone who stares down the barrel of defeat, yet still finds a way to make it happen. An absolute savage who doesn’t use challenges or obstacles as excuses, but instead faces life with grit, takes full responsibility for their path, and turns adversity into opportunity.

It’s about owning your story—the messy parts included—and building something from the ground up. Being self-made means refusing to let people, places, or circumstances hold you back. It’s about turning every setback into fuel for your fire and proving that nothing—not fear, not failure, not even the odds—can stand in the way of what you’re destined to build.


What’s something about being an entrepreneur that most people need to know?

Entrepreneurship today is often portrayed as this glamorous, effortless path to success. People see the headlines, the fast cars, the big homes, and they think that’s the reality. But what they don’t see is the grind behind the scenes. They don’t see the sleepless nights, the sacrifices, the failures, or the moments when you wonder if it’s all worth it. It's easy to get caught up in the idea that anyone can start a business and just make a million bucks—but the truth is, it’s far from that simple.

What many people, especially younger aspiring entrepreneurs, don’t realize is how much grit it takes to succeed. The struggle is part of the process, and it’s where the real lessons are learned. No one talks about the blood, sweat, and tears—how hard it is to face failure head-on, how you have to put everything you have on the line, and how much sacrifice is involved.

For me, failure is an essential part of success. I don't look at success as the wins—I look at the losses, the things that didn’t work, and how we pivoted, adapted, and grew from them. The truth is, the first step you take is what matters most. It’s not about having the perfect plan—it’s about taking action. You can plan all you want, but if you don’t have the courage to start, none of it matters.

Entrepreneurship is about showing up, learning from your mistakes, and being willing to bet on yourself, even when it seems impossible.


How did Pinpoint Payments get launched?

Pinpoint Payments began as an idea sparked by necessity and purely a leap of faith. Before its launch, I worked at a startup e-commerce company owned by my now partners. I landed the role after proving myself as a top sales producer in phone rooms across South Florida, where I developed a reputation for not just closing deals but building lasting relationships and retaining customers with ease.

The company brought me on in a customer service role, but it didn’t take long for me to rise through the ranks. I was quickly promoted to team lead and then to a senior position overseeing multiple agents. I thrived on connecting with people and finding solutions, and it showed. Recognizing my ability to drive results, the leadership entrusted me with an entirely new challenge: building a fraud prevention program from the ground up.

I had no prior experience in fraud prevention, but I’m not one to back down from a challenge. I dove in headfirst and I absorbed everything I could. My determination paid off—we quickly saved the company over a million dollars. It was a proud moment for me, I finally found a sense of purpose. But it also set the stage for something even bigger.

In 2013, the company was sold, and my world shifted again. I received a phone call that would change everything: I was being let go. But instead of a simple goodbye, the owners extended a lifeline—a bold proposal.

They saw in me what I had not seen in myself for a very long time: potential.

They wanted to take what we had created for their business and offer it to others. It was a leap of faith—no salary, no safety net—no guarantee, just a dream and an idea.

With a growing family and everything on the line, I had a massive choice to make: take the easy route with a steady paycheck, or go all in on myself. I didn’t just take the gamble—I owned it. With nothing but a laptop, a cell phone, and the relentless fire in my soul, I went to war—making call after call fueled by the unrelenting drive to create something extraordinary out of nothing.

Within months, Pinpoint Payments wasn’t just an idea—it was now a business.

What started as a fraud prevention and chargeback management company has evolved into a full-service merchant services provider, but its foundation remains the same—a relentless commitment to the grit, grind, resilience, and the unwavering belief in what’s possible. Every challenge, every setback, every risk, and all the moments of doubt all became stepping stones to a vision far greater than I could have ever imagined.

Choosing to bet on myself wasn’t just a decision—it became a way of life. I’m reminded daily that with enough determination and belief, you can turn obstacles into opportunities and dreams into reality.



What is the wow factor behind the business?

About seven years ago, we took a bold step and pivoted fully into merchant services, and it completely transformed our business. This wasn’t just a shift in what we did—it was a shift in how we viewed our role. We didn’t want to just be another service provider. We wanted to be a true partner, working side by side with business owners to protect and grow their businesses.

What sets us apart is the way we approach payments. Whether it’s a terminal at a convenience store or the checkout page on an e-commerce site, we’re not just facilitating transactions—we’re actively contributing to the success of our clients. By implementing cost-reduction programs, fraud prevention, chargeback management, and optimizing payment solutions, we directly impact their bottom line.

We’re not just processing payments—we’re creating a partnership that helps them thrive.

Our "wow factor" comes from doing things differently than the industry norm. Too many payment providers sign businesses up and disappear, leaving them high and dry. If I asked 100 businesses when they last heard from their payment provider, 99% would say, "The day I signed up." There’s no relationship, no follow-up, no real partnership.

We’ve changed that by focusing on the long-term. We believe that when our clients succeed, we succeed. That’s why we invest in their growth, offering open communication, strategic advice, and real support to help them optimize and maximize their potential. For us, payments are just the beginning—helping businesses grow, innovate, and thrive is where the true value lies.


What do you like best about your work?

What drives me every day is the chance to be a game-changer for businesses. We’re not just processing payments—we’re transforming the way our clients do business. I thrive on optimizing their payment systems, cutting unnecessary costs, and offering the kind of hands-on, tailored support that truly propels them forward.

There’s nothing more fulfilling than watching a business owner’s face light up when we help them solve a problem they’ve been grappling with. It’s that sense of relief, that moment of clarity, that fuels my passion. Seeing them shift from overwhelm to excitement—that’s the win.

But the real magic happens when we become more than just a service; we become a true extension of their team. We’re not here for the quick win—we’re here for the long haul, for growth, for real partnerships. Because when our clients succeed, we succeed. That’s the heart of what we do—and that’s what keeps me fired up to keep making an impact, one business at a time.


2025 SWAGGER MAGAZINE

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