Grace Bay | Hello Truck Lease
CEO of Hello Truck Lease
Grace Bay is the CEO Hello Truck Lease, an industry-first truck leasing company that provides creative lease solutions to logistics entrepreneurs. She’s also involved in property management, interior design, and owns several rental properties.
What businesses do you run?
I’m Grace Bay, CEO of HelloTrek Lease, a full-service truck leasing company that focuses on providing creative fleet solutions for logistics entrepreneurs. In addition to that, I also dabble in Nashville real estate. I own a few rental properties myself and manage properties for clients, offering some interior design services as well. It's a busy life, but I thrive on the variety and challenges of these different industries.
How did you get started as an entrepreneur?
My story as an entrepreneur goes way back to my childhood. I didn’t follow the typical career path because, frankly, I’ve never done anything other than entrepreneurship. It all began with something as simple as selling wrapping paper for my elementary school fundraiser. The day the prize catalog came out, I’d study it obsessively, setting my sights on a specific prize I had to have. I’d make my plan, targeting neighborhoods before the other kids could, and even baking cookies to sweeten my sales pitch. I wasn’t afraid to work harder, think creatively, or break a few "no soliciting" rules to reach my goal. That’s where my entrepreneurial spirit was born—finding a way to win, no matter the odds.
After college, I went straight to work for a startup—a company that made modded video game controllers, which is kind of funny because I wasn’t even a gamer. But the idea of contributing meaningfully to a growing company, rather than sitting at a front desk of some corporate giant, was irresistible. Every day in that startup brought me back to that wrapping paper feeling—scrappy, fast-paced, and just a little chaotic. I loved the energy, the creativity, and the sense of building something from nothing. That’s when I truly fell in love with entrepreneurship.
How do you think about growth in your current business? How do you plan for the future?
For me, growth has always been tied to solving problems and turning things around. Early in my career, I realized my true gift: fixing things. Whether it was an organization in distress or a process that needed improvement, I got a huge sense of fulfillment from finding strategic solutions and turning things into well-oiled machines. I’ve learned that I thrive in growth mode, always pushing for more, looking for new ways to scale and expand. That’s where my entrepreneurial spirit really shines.
However, one of the biggest lessons I’ve learned is that growth doesn’t happen alone. I made the mistake of thinking I could do it all, and that led to burnout and failure. I didn’t build an effective team early on, and as a result, I found myself spread too thin, and things started to slip through the cracks. That was a tough season, but it taught me that delegation is essential for long-term success. I had to learn how to identify the right people for the right roles, anticipate future needs, and develop a team that could grow with the business.
Now, my focus is on building and nurturing a team that can help take HelloTrek Lease to new heights. It’s not about having a corporate playbook; it’s about leading through the chaos of entrepreneurship. When you find the right people and invest in them, the sky’s the limit. My team is the reason we’re here today, and I couldn’t do it without them.
What advice do you have for aspiring entrepreneurs?
My advice to aspiring entrepreneurs is this: Embrace the chaos and don’t be afraid to learn by doing. Entrepreneurship is about finding a way to win, even when the path isn’t clear. It’s not easy, and it’s certainly not for everyone, but if you have that burning desire to work for yourself and create something meaningful, go for it.
One of the most important things you can do is surround yourself with the right people. Whether it’s a mentor or a strong team, you need support to grow. I can’t stress enough the value of delegation and trusting others to help you build something bigger than you could on your own. Learn how to identify the right roles and develop your people alongside your business.
And most importantly, be willing to fail. Failure isn’t the end—it’s part of the journey. You’ll make mistakes, but those mistakes are where you’ll learn the most about yourself, your business, and what it takes to succeed. Once you embrace that mindset, there’s no limit to what you can achieve.
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Grace Bay 0:00
My name is Grace Bay. I'm the CEO of Hello truck lease. We're a full service truck leasing company focused on providing creative fleet solutions for logistics entrepreneurs and on the side, I dabble in a little bit of Nashville real estate. I have a couple rental properties myself, and then property manage and do some interior design for some clients. My story is a little unique in that I never really did anything other than entrepreneurship. I think it really started when I was a kid selling wrapping paper for an annual elementary school fundraiser. My favorite day of the school year was the day that the prize catalog came out. I'd study it all night, and I'd choose the prize that I was determined to earn through selling a certain amount of wrapping paper. And then I'd make my plan. I would target certain neighborhoods first so that other kids couldn't get the opportunity to sell them before me. I'd bake cookies and take them along my sales route, and I was hoping to entice people to invite me into their kitchen and show them the wrapping paper selections over freshly baked cookies. I broke a lot of do not solicit rules, but I set weekly goals to make sure that I was on target to achieve my ultimate goal. I wasn't afraid to work harder than anybody else and think creatively and cut through some red tape and maybe even cause a little disruption to go after what I wanted. And that's the spirit of entrepreneurship. I loved that feeling of finding a way to win. Fast forward to college graduation, and I went straight to work for a startup. It was a modded video game controller company, which is kind of strange because I never was a gamer, but the idea of being able to contribute really meaningfully to a company so early in my career, rather than just putting in time at a front desk of some mega corporation was really intriguing to me. Once I started, I was hooked every day was just a little dose of kind of that wrapping paper feeling our scrappy team of entrepreneurs worked together to achieve our goal of growing something out of nothing. We had to work really hard think creatively and cut through red tape. We even caused a little disruption, and I fell in love with that energy pace and honestly, pure chaos that is in the entrepreneurial environment. Early on in my career, I was leading an organization that was growing at lightning speed. It was really exhilarating, and we were constantly given opportunities to turn operations around and grow them, turn them into something that we could absorb into our portfolio. And this is when it clicked for me that I loved fixing things. That's really my gifting. I got so much fulfillment from taking something distressed, maybe even a dumpster fire, and implementing strategic solutions to turn it around and really make it a well oiled machine. Now, maintaining is a different story. I learned that's just not my forte. But as we grew and we were in growth mode, I felt really unstoppable. I wanted more and more of that growth, and that was a season that felt like huge success. However, not building an effective team around me as the operation grew was really challenging. I had a false sense that I could do it all forever, but I was really wrong, and that led to a season of failure when you as a leader are not exercising effective delegation, which in large part requires putting a team in place that you can delegate to. You won't be an effective leader. You'll be spread way too thin, and as a result, things will fall through the cracks. Once I learned that I wasn't super woman and I actually needed people to support me, I really dug in to learning how to grow a team, how to identify the right people for the right roles. What roles are even needed? How to anticipate future sustainability for growth, and how to motivate and inspire a team in an environment that's always changing. It's not inside of this corporate box, and it's really different to lead a team through entrepreneurial adventure versus something that has a playbook. But once you find the right people and you really commit to developing them in tandem with the right delegation, the sky's really the limit, and I wouldn't be here today if it wasn't for my team and implementing that approach and really digging into them.
