Meet Kaylee Haire

We were lucky to catch up with Kaylee Haire recently and have shared our conversation below.

Hi Kaylee, thanks for sharing your insights with our community today. Part of your success, no doubt, is due to your work ethic and so we’d love if you could open up about where you got your work ethic from?

People ask me all the time, “Where do you get your work ethic from?”

Honestly it’s just something that’s always been a part of me. But if I had to trace it back to one thing, it would be this: I genuinely love people. I love their stories, their energy, their quirks, even the awkward small talk. I love creating things that make someone’s day better. And I think that love is what drives me to work hard.

I started my first business when I was seven. It was just lemonade, but to me, it was my whole world. Kaylee’s Lemonade wasn’t just about selling drinks it was about putting a smile on someone’s face on a hot Tennessee Saturday. I’d squeeze lemons with sticky hands and wave at every customer. That experience taught me that work isn’t always perfect, but when you care about what you’re doing and who you’re doing it for, it becomes meaningful.

Since then, I’ve had more jobs than I can count on both hands. I’ve been a podcast producer, farmers market event coordinator, snack store employee, intern, business founder, and t-shirt designer. I’ve sold comfort clips and cringey dad jokes. I’ve led my DECA chapter, created schedules, trained new hires, and even graded student presentations. Each of these jobs was different, but they all had one thing in common, people. I love connecting with others—whether I’m telling a joke into a tiny mic at the market or helping a classmate prep for their first business competition.

My work ethic doesn’t come from pressure or fear. It comes from a place of purpose. I work hard because I want to—because I see the impact it makes and the relationships it builds.

I wouldn’t trade it for anything. Every task, every job, every responsibility—it all teaches me something new. And every time I show up for others, I grow into the kind of person I want to be.

So if you’re wondering where I get my work ethic from, the answer is simple:

I get it from love.
Love for people.
Love for purpose

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

Right now, I’m focused on two things that I absolutely love: my podcast and my work at the farmers markets.

I recently graduated high school, but my entrepreneurial journey started long before that. I’ve been involved with the Nolensville Farmers Market since I was seven, and over the years I’ve gone from selling lemonade to becoming an assistant manager at both the Nolensville and Westhaven Farmers Markets.

That love for real conversations and community inspired me to start The Hustle Generation Podcast. It’s a show for young people, especially student entrepreneurs, who are chasing big dreams and trying to figure it all out. On Fridays, I drop a new episode that features real stories from real kids doing real things. It’s honest, it’s inspiring, and it’s meant to be that push someone might need to take the next step in their own hustle. What makes it special is that it’s not polished or sugar-coated it’s relatable, and it’s all about helping young entrepreneurs feel seen.

I’m currently working on expanding the podcast, growing the audience, and launching official Hustle Generation merch soon. I’m also continuing to serve the farmers market community and find new ways to support local vendors and shoppers.

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. Communication

Everything I’ve done whether it’s hosting a podcast or working the farmers market comes down to how well I can connect with people. Knowing how to hold a conversation, send a professional email, or even just smile and say hello can open so many doors. Advice: Practice talking to people. Seriously. Ask questions, listen well, and don’t be afraid to speak up even if your voice shakes a little at first. The more you do it, the easier it gets.

2. Consistency

Success doesn’t come from doing something once it comes from showing up over and over, even when it’s hard. I show up at the farmers market every week, rain or shine. That kind of commitment builds trust and momentum.
Advice: Start small and stay steady. Even if only five people are watching or buying, treat them like five hundred. Keep showing up it pays off.

3. Confidence (even when you have to fake it)

When I started out, I had no idea what I was doing half the time. But I acted like I belonged in the room anyway. Confidence isn’t about knowing everything it’s about believing you can figure it out.
Advice: Don’t wait until you “feel ready.” Start messy, learn as you go, and trust that your effort matters. You don’t need all the answers to start you just need to start.

Alright so to wrap up, who deserves credit for helping you overcome challenges or build some of the essential skills you’ve needed?

Hands down, the people who have been most helpful in helping me grow are my parents. They’ve been my biggest supporters and my real-life business coaches

My parents never forced me into anything but they always encouraged me to chase what I loved. From my first lemonade stand at seven to running a podcast and managing farmers markets, they’ve been there every step of the way. They taught me how to work hard, stay grounded, and keep my word.

My dad is the one who taught me how to show up on time, give a firm handshake, and take pride in what I do. My mom showed me how to lead with heart, stay organized, and treat people with kindness whether it’s a customer, a vendor, or someone I’m interviewing for my podcast.

They’ve helped me through tough decisions, supported me when I was overwhelmed, and reminded me why I started when I felt like giving up. Honestly, I owe so much of my work ethic and mindset to the example they’ve set.