Meet Kaylee Tolley

We’re excited to introduce you to the always interesting and insightful Kaylee Tolley. We hope you’ll enjoy our conversation with Kaylee below.

Kaylee , looking forward to learning from your journey. You’ve got an amazing story and before we dive into that, let’s start with an important building block. Where do you get your work ethic from?

My work ethic comes from the example my parents set for me—they have always taught me to work hard, do my best, and take pride in what I create. I love to be doing, creating, and finding ways to serve others, whether that’s designing a cool piece of apparel to help someone showcase their brand or simply lending a hand when someone needs support. Hard work isn’t just about staying busy; it’s about making an impact. I find fulfillment in using my skills to bring value to others, and that drive keeps me pushing forward, learning, and giving back.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

I am passionate about business education and creating opportunities for young entrepreneurs. As a former high school business teacher and now the Program Manager for the Oregon Business Academy, I’ve dedicated my career to empowering students with the skills, knowledge, and confidence to turn their ideas into reality. I love helping young people see the possibilities in business and providing them with hands-on experiences that prepare them for the future.

In addition to my work with OBA, I run GEN TEE, a custom apparel business that allows me to merge creativity with purpose. Through GEN TEE, I not only get to design unique, high-quality apparel, but I also use my business as a platform to uplift and support the next generation of entrepreneurs. Whether it’s collaborating with students, creating merchandise that tells a story, or giving back to the community, I see business as a tool for impact.

I’m excited to continue expanding both my work with OBA and GEN TEE, finding new ways to inspire and equip young entrepreneurs to chase their dreams.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Looking back, three of the most impactful qualities in my journey have been collaboration, networking, and the willingness to put myself out there—all while leading with kindness.

Collaboration has been key in every stage of my career. Whether in the classroom, running a business, or working with professionals, I’ve learned that great ideas grow stronger when people work together. My advice: seek out partnerships, ask questions, and surround yourself with people who challenge and inspire you.

Networking isn’t just about making connections—it’s about building relationships. The opportunities I’ve had came from genuine conversations and showing up for others. To improve in this area, start by engaging with people in your field, attending events, and following up with those who leave an impression on you.

Putting yourself out there is often the hardest but most rewarding step. Say yes to new experiences, take on challenges even if they scare you, and trust that growth comes from discomfort. The best way to develop this mindset is to start small—whether it’s introducing yourself to someone new or sharing your work publicly.

Above all, be kind—to yourself and others. The way you treat people will always matter more than titles or achievements.

What’s been one of your main areas of growth this year?

Over the past 12 months, my biggest area of growth has been learning that serving others starts with also taking care of myself. I’ve always been driven by a passion for helping and creating opportunities for others, but I’ve realized that I can’t pour from an empty cup. Prioritizing my own well-being, setting boundaries, and making choices that allow me to grow—both personally and professionally—has ultimately made me better for those I serve. This is still a work in progress, but it’s something I actively work on each day, knowing that by investing in myself, I can show up even stronger for others.

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