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.
Early Hustle, Big Vision
Grace Bay didn’t grow into entrepreneurship—she was built for it. From the moment she laid eyes on a school fundraiser prize catalog, her competitive streak kicked in. Selling wrapping paper with baked cookies in hand, she learned to out-hustle, out-plan, and out-perform—long before she had a business card. That same drive led her straight out of college into a fast-moving startup, where the chaos of creation felt like home. Grace never wanted the front desk of a corporate giant. She wanted the seat at the table where real ideas got built—and she never looked back.
Hitting the Wall, Rebuilding Right
Grace’s gift for solving messy problems gave her early momentum. Whether in truck leasing or property management, she thrived in growth mode, always chasing better. But in her drive to do it all, she hit a wall: burnout, overextension, and the realization that solo success can’t scale. It was a humbling moment. She had to stop, reassess, and start building what she hadn’t prioritized—an actual team. Learning to delegate, anticipate, and develop people wasn’t just a business decision. It was survival.
A Company That Carries People
Today, Hello Truck Lease is more than just a full-service fleet solution—it’s a team-powered business built on trust, grit, and clarity. Grace leads with creativity and resilience, knowing firsthand that failure isn't a sign to quit—it’s part of the blueprint. Whether it’s helping entrepreneurs scale logistics or designing smart spaces in Nashville real estate, she’s found purpose in building systems that work and teams that last. Her story is proof: when you embrace the chaos, empower the right people, and stay committed to growth, your business can carry more than cargo—it can carry legacy.
“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. ”
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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 of 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 to 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 mod 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 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 and 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 superwoman and I actually needed people to support me, I really dug into 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 an 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.
Why We Share These Stories
We believe that celebrating Tennessee’s entrepreneurs will inspire the next generation of bold thinkers, risk-takers, and community builders. Entrepreneurs don’t forget where they come from—and they carry the power to transform not just their businesses, but entire neighborhoods, towns, and local economies. See more entrepreneur stories from the Patton Foundation.
