For Jonathan Anastasia, leadership isn’t just about strategy or vision—it’s about service.
Growing up in a military family on Long Island, Anastasia’s life was shaped by a deep commitment to protecting others. His father, a Coast Guard veteran who moved frequently as a child, made it his mission to create stability and safety for his own family.
“My dad always emphasized the importance of keeping our family close and protecting what matters most. That’s a mindset that stuck with me.”
Anastasia’s early foundation of discipline and resilience set him on a career path that few could have predicted. From West Point to the U.S. Army, from a career in law to leading innovation at Mastercard, Anastasia’s career has been defined by a relentless drive to solve big problems and create meaningful solutions.
As the president of CUBE3.AI, a cutting-edge fintech platform combating fraud in the crypto world, he’s channeling his military discipline and entrepreneurial drive to bring stability and trust to one of finance’s most unpredictable arenas. By leveraging AI and machine learning, CUBE3.AI is redefining security in the crypto space, empowering users and the ecosystem alike to stay ahead of emerging threats.
A Foundation of Discipline and Service
As a child, Anastasia didn’t dream of running a tech company or innovating in fintech.
Instead, he was drawn to the values he saw in his father and grandfathers—discipline, loyalty, and service. Those principles eventually led him to West Point, where he endured four grueling years of military training.
“West Point was the hardest four years of my life,” he admits. “You wake up at 5 a.m., you’re constantly under pressure, and you learn to push yourself beyond what you think is possible. But it also teaches you teamwork, leadership, and how to thrive under high stakes.”
Graduating with a degree in systems engineering, Anastasia went on to serve five years as a U.S. Army captain. But even as he thrived in a military environment, he knew his path wouldn’t end there.
“I always had this entrepreneurial itch,” he admits. “I wanted to build something, to take all the lessons I’d learned about leadership and systems and apply them in a different way.”
A Misstep and a Realization: 'I Thrive on Collaboration'
After leaving the military, Jonathan Anastasia followed what he calls the “default path” to law school. But his time in big law proved underwhelming. “I hated it,” he admits. “I’m an extrovert who thrives on collaboration and building things. Law felt isolating—like I was fixing other people’s problems instead of creating something new.”
Looking for a change, Anastasia was approached by a recruiter for a role at Mastercard. His initial reaction was skeptical. “I asked, ‘Do you mean the credit card company?’” he recalls, laughing. “It sounded so corporate and unexciting.”
The recruiter explained Mastercard’s focus on technology and innovation, which piqued his interest, though learning the company was headquartered in a town called Purchase, New York, gave him pause. “I even asked my mom, ‘Did Mastercard buy a town and name it Purchase?’”
The chance to work with Mastercard redirected his entire life. “The people were passionate, smart, and genuinely excited about what they were building,” he says. “Their energy was infectious, and I knew I wanted to be part of that.”
From Legal Counsel to Business Builder
Anastasia began his career at Mastercard in the legal department, focusing on intellectual property and emerging technologies. But his interest in innovation quickly drew him to the company’s R&D labs, where he collaborated with teams developing groundbreaking products and frameworks for working with startups.
“We were doing things 10 years ago that felt futuristic—like retina verification technology and mobile ordering for stadiums.”
Anastasia recalls. “Now, those things are everywhere, but back then, people thought we were crazy.”
His ability to bridge the gap between legal expertise and business strategy didn’t go unnoticed. Recognized for his collaborative approach and forward-thinking mindset, Anastasia was soon leading the legal team for Mastercard’s cyber and intelligence solutions group, a $7 billion business unit.
It was during this time that Anastasia’s focus shifted. “I realized I wasn’t just advising on legal matters—I was deeply involved in the business side of innovation,” he explains. “It became clear to me that I wanted to play a more active role in building these solutions, not just supporting them.”
This realization pushed him to make the leap from legal to business leadership, where he could take on a more hands-on role in driving innovation and strategy. Anastasia spent over a decade at Mastercard, ultimately rising to the role of Executive Vice President.
Eventually, he decided to take on a new challenge—one that allowed him the freedom to build and lead something entirely new.
Leading the Charge at Cube3 AI
In June 2024, Anastasia was introduced as the president of CUBE3.AI, a platform dedicated to stopping scams and fraud in the crypto ecosystem. The transition felt natural. “At its core, CUBE3 is about trust—creating real-time safeguards for an industry that desperately needs them,” Anastasia explains.
CUBE3 goes beyond a decision-making engine for financial institutions like banks and fintech companies. Whether it’s a payment provider, behavioral biometrics, data intelligence modeling, the company can augment transaction monitoring data, so companies can best support their customers.
For Anastasia, this isn’t just a technical challenge; it’s a mission that aligns with his lifelong commitment to service.
“Crypto has massive potential, but it’s plagued by bad actors. We’re building the tools to detect and prevent fraud in real-time, giving people confidence to engage in this space.”
Building a Legacy of Trust
Anastasia’s career has always been about protecting and building. At CUBE3.AI, he’s now tackling one of the most complex and high-stakes challenges in finance, but his approach remains rooted in the values he learned on Long Island.
“At the end of the day, it’s about creating something that matters,” Anastasia says. “If I can build trust in an industry that desperately needs it, then I’ve done my job.”
He offers three pieces of advice for fellow entrepreneurs and visionaries:
1. Serve Something Bigger Than Yourself
“Leadership is about serving a larger mission,” Anastasia says. “Whether it’s your team, your customers, or your community, the focus has to be on creating impact beyond your own ambitions.”
He stresses the importance of surrounding yourself with people you can trust. “If you know the person you’re working with has your back—and you have theirs—you can make a real difference,” he says. Building a trust-based culture doesn’t happen overnight, but it’s critical.
2. Family Comes First
“From 7:30 to 8:30 in the morning, that’s my family time,” Anastasia shares. “I wake up, get dressed, help get the kids off to school, and talk with my wife about the day. It’s the same in the evening during dinner, bath time, and bedtime. Those hours are non-negotiable.”
He recognizes the constant pressure of running a business, particularly in the high-stakes world of fintech. “As an entrepreneur, you’re never really turning it off,” he admits. “You feel everything—the highs, the lows, and the existential dread of ‘What happens if this fails?’ But you have to carve out time to be present with the people you love. That time keeps you grounded.”
3. Embrace Change and Stay Flexible
For Anastasia, adaptability is a key to success. “When things don’t go as planned, it’s not the end—it’s a chance to pivot, reassess, and try something new,” he says. “That’s where real innovation happens.”
He believes the ability to adapt is what sets great leaders apart. “The only constant in this space is change,” he says. “If you can stay flexible while staying true to your mission, you’ll not only keep up—you’ll stand out.”
Interested in Partnering with Jonathan Anastasia and Cube3?
Connect with Jonathan on LinkedIn or visit CUBE3.AI’s website.
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