Alright – so today we’ve got the honor of introducing you to Greg Kapitan. We think you’ll enjoy our conversation, we’ve shared it below.
Greg, we’re thrilled to have you on our platform and we think there is so much folks can learn from you and your story. Something that matters deeply to us is living a life and leading a career filled with purpose and so let’s start by chatting about how you found your purpose.
To be honest, it often feels like purpose finds me. Life has a way of placing the right opportunities and experiences in front of us—almost as if the universe is guiding us, one step at a time. As I’ve grown older, I’ve come to recognize these moments more clearly. They arrive like quiet signals or gentle waves, and when you’re open and willing, you naturally move with them. Then something shifts—you commit, you engage, and suddenly you’re being carried by a powerful, positive momentum that moves you forward with clarity and intention.
Thanks, so before we move on maybe you can share a bit more about yourself?
I’m a strong believer in the power of visuals—especially when it comes to explaining payment solutions for small businesses. Whenever we offer a new solution, I focus on creating clear, visual content on our websites to help business owners quickly understand how each system works. Visual storytelling has proven to be one of the most effective ways to communicate complex payment processes.
Our main site, iSmart Payments, serves as the central hub with over 50 pages dedicated to a wide range of payment solutions. Drawing from my own experience as a contractor, I launched Contractor SmartPay, which focuses on tools like dual pricing and mobile payments—ideal for getting paid directly on the job site with zero credit card processing fees. It also features Text-to-Pay, a simple and effective option perfectly suited for Contractors or any other type of business that wants to offer text-to-pay to customers.
I also founded Automotive SmartPay, a specialized solution for auto shops. It offers a dual pricing point-of-sale system with a customer-facing PIN pad. After the transaction amount is entered by the merchant, the device displays both card and cash pricing options, giving the customer the ability to choose. It also features Text-to-Pay, a simple and effective option perfectly suited for Auto Shop businesses.
In my home state of New York, I created NY EZ Pay—a cutting-edge, fully compliant Triple Pricing payment solution built to align with the state’s updated 2024 surcharge regulations. This innovative system wasn’t just a project; it was a mission to make compliance simple and profitable for business owners. Our advanced Dejavoo credit card terminals automatically display three clear, customer-facing prices for every transaction—credit card, debit card, and cash—empowering customers to choose while keeping your business fully within the law.
In New York and other northeastern states, the Durbin Amendment prohibits adding any fee to debit or EBT card transactions, whether PIN or PIN-less. That’s exactly why we developed Triple Pricing—so you can transparently pass on processing costs for credit cards while protecting your margins, staying compliant, and delivering a smoother checkout experience.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
1. Falling down is a good time to learn
Failure isn’t the end—it’s feedback. Some of the most valuable lessons come during the moments we stumble. When things don’t go as planned, we’re given a rare opportunity to examine what went wrong, why it happened, and how we can improve. These experiences build resilience, refine our instincts, and shape us into stronger leaders. In business and in life, falling down isn’t failure—it’s part of the process of growth.
2. Learn from others—and even more so from your competitors
You don’t have to reinvent the wheel. Some of the best insights come from observing others—especially your competitors. Rather than seeing them purely as threats, view them as a source of market-tested strategies and lessons. What are they doing well? Where are they falling short? Stay curious, stay observant, and you’ll often discover better ways to serve your customers, avoid common pitfalls, and elevate your own business by building on what already works.
3. When you think you know it all, that’s when real learning begins
Confidence is important, but humility is essential. The moment we believe we’ve mastered everything is often when we stop growing. The world is constantly changing—new technologies, new challenges, new opportunities. True professionals stay open, curious, and adaptable. They ask questions, seek feedback, and embrace every chance to evolve. In reality, the more we learn, the more we realize how much there is left to discover.
How can folks who want to work with you connect?
I’m always looking to connect with others—whether it’s business owners searching for the right payment solution, or individuals simply interested in having a meaningful conversation. Every connection is an opportunity to learn, grow, and share knowledge. Some of the most valuable insights I’ve gained have come through unexpected conversations and relationships. Whether we end up working together or simply exchanging ideas, I believe that staying open and engaged with others is one of the best ways to continue evolving—both personally and professionally.
Contact Info:
- Website: https://ismartpayments.com/
- Youtube: https://www.youtube.com/@iSmartPaymentsLLC
- Other: https://contractorsmartpay.com
https://automotivesmartpay.com
https://nyezpay.com
so if you or someone you know deserves recognition please let us know here.
