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Inspiring Conversations with Whitney Osborne of Stem & Proper

Today we’d like to introduce you to Whitney Osborne.

Hi Whitney, so excited to have you with us today. What can you tell us about your story?
My maiden name is Rose—how could I not be a flower enthusiast?

I have always loved flowers. Some of my earliest memories of receiving them go back to my dance recital days when my parents would present me with a beautiful bouquet for a job well done. The flowers always made me feel special, allowing me to relive that moment of celebration every time I passed them on the kitchen counter. Over the years, I would buy flowers from the grocery store to brighten my home and insist that my now-husband gift me flowers. But it never occurred to me that I could arrange them myself—until 2022, when my best friends gifted me a virtual flower-arranging class for my 31st birthday. They knew I loved flowers and that COVID had sparked a wave of DIY projects, inspiring people to discover new hobbies and passions. I was excited to take the class, mostly as a fun activity to do with friends and an excuse to have more flowers around the house. I never imagined it would ignite a deep passion for floral design.

After taking the class, all I wanted to do was arrange flowers. Every week during my grocery store runs, I would buy fresh blooms to practice with. I became a dedicated student of “YouTube University,” watching hours of tutorials and learning new techniques to implement in my weekly arrangements. Eventually, I told my husband that I wanted to take a formal course and had found a local flower school. He had been watching me work and encouraged me to go for it, with one caveat—if I was going to invest in the class, I should seriously consider turning it into something more. I shrugged off the idea. I had a full-time job, one child at the time, and had never seen myself as the entrepreneurial type. I simply wanted to learn more about design for the joy of it. So, I called my aunt, and we signed up for the class together.

At the same time, my friend—the one who had gifted me the virtual class—was hosting a birthday party at her home and asked me to create some floral arrangements. It was my first real assignment and the first time I considered the possibility of turning this hobby into a business.

Fast forward to 2024—I’m still making my weekly arrangements, but now friends and family are reaching out for small projects, gifts, and events. In the meantime, I had my second child, which gave me time to focus on my craft and seriously consider starting a business during my maternity leave. Then, I got a call from a family friend—who also happened to be my wedding planner—saying she had a friend looking for a florist for her son’s wedding. Nervously, I accepted the challenge. Immediately, I called my god-sister, an incredible event designer, and told her, “I have to do a whole wedding, and I have no idea where to start!” She guided me through everything, let me use her space to design, and supported me through the entire process.
The morning of the wedding, I was running on just five hours of sleep in a 48-hour window. In my head, I was thinking, I am never doing this again. It was the hardest thing I had ever done—and I am saying that as someone who is a former collegiate athlete, graduate school alum, mom, and works a corporate job. I was utterly exhausted. But when I saw the space transformed by my work, I knew there was no way this could be the last time.

And that was the moment Stem & Proper was born. I was all in—ready to bring my designs into people’s homes and special moments.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
The biggest challenge has been time management. As I mentioned, I work a full-time job and have two young children, so finding the time to dedicate to building my business is not always easy. And if you know me, you know I value my downtime—I put a premium on relaxation.

When I first started, I was on maternity leave, which gave me more flexibility to take orders, think through my business, and create arrangements for myself. That time was invaluable because it allowed me to practice and build my initial content for social media. But as life picked back up, balancing it all became more difficult.

Thankfully, I have an amazing support system. My husband and family step in to help create time for me because they believe in my work and see my passion. Without them, I wouldn’t be able to juggle it all. Their support has been essential in allowing me to keep growing Stem & Proper while managing everything else in my life.

Thanks – so what else should our readers know about Stem & Proper?
Stem & Proper is a floral design company that delivers flowers to fit your life. We provide everyday florals for gifting, gatherings, and those “just because” moments. Flowers have a unique ability to bring beauty, warmth, and elegance to any space, and that’s what inspired me to start arranging them in the first place. I loved how a simple bouquet on my kitchen table or island could instantly make my house feel like home.

While we design florals for every occasion, our true passion lies in creating arrangements for intimate home gatherings. We specialize in crafting designs that become part of a beautiful tablescape, setting the stage for people to come together—to eat, drink, celebrate, and create lasting memories. There’s something incredibly special about enhancing a home with fresh flowers, and that feeling is deeply rooted in our company’s DNA. Stem & Proper started with a love for floral design that grew from my own home, from always having fresh flowers around to designing arrangements for my friend’s birthday party.

What sets us apart is our approach—our florals are intentional, and designed to complement your space rather than overpower it. We believe flowers should feel natural and inviting, not just reserved for grand events. Whether it’s an elegant dinner party, a cozy brunch with friends, or a simple arrangement to brighten your day, we create designs that feel personal and thoughtfully curated.

What I’m most proud of, brand-wise, is how Stem & Proper has grown from a personal passion into a brand that brings joy into people’s homes and special moments. Every arrangement we create carries the same heart and purpose that started it all—making spaces feel more beautiful, inviting, and full of life.

I want readers to know that Stem & Proper is more than just a floral design company—it’s about celebrating life’s little moments with flowers. Whether you’re hosting a gathering or simply want to bring fresh beauty into your home, we’re here to provide florals that feel like you.

What has been the most important lesson you’ve learned along your journey?
The most important lesson I’ve learned so far is not to take things personally. I get so excited when people reach out with inquiries, but when they don’t ultimately place an order, it can feel discouraging. I’ve sometimes taken it as a reflection of my work’s quality or questioned my pricing, becoming overly critical of myself.

But what I’ve come to realize is that I’ve been that same consumer—someone who explores options but ultimately goes in a different direction for reasons that have nothing to do with the quality of the work. Understanding this has helped me shift my mindset.

Now, I focus on staying positive and continuing to put myself out there. I’m always open to constructive feedback and eager to learn how to convert more inquiries into sales, but I also know that every “no” is just part of the process. Instead of dwelling on what didn’t happen, I channel my energy into perfecting my craft, creating beautiful designs, and letting my work speak for itself.

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Image Credits
Kelly Monique

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