We’re excited to introduce you to the always interesting and insightful Dawn Pilpel. We hope you’ll enjoy our conversation with Dawn below.
Hi Dawn , thanks for joining us today. Can you talk to us about a risk you’ve taken – walk us through the story?
The biggest risk I’ve ever taken was starting my own business. It was a decision that completely altered the trajectory of my life, and one that I wouldn’t trade for anything. Let me take you back to the beginning so you can understand the why, the how, and the lessons that came from it.
From a young age, I knew I didn’t want to work for anybody else. I grew up watching my dad build his own companies, and his entrepreneurial spirit had a profound impact on me. He taught me that success wasn’t just about following the rules or taking a well-trodden path—it was about taking ownership of your dreams and being bold enough to make them real. That lesson stuck with me, and as I grew older, it became clear that I wanted to do something unique, something that hadn’t been done before.
I’ve always had a deep love for art. Growing up in one of the best cities in the world, Toronto, I was constantly surrounded by a rich, multicultural environment that shaped my perspective and fueled my creativity. My time at the Ontario College of Art & Design in Toronto only deepened that passion and gave me the tools to take my artistic vision to the next level. But I didn’t just want to make art for the sake of making it—I wanted to build something with it, to transform my art into a business.
Starting my own business was terrifying. It wasn’t just about creating art; it was about building a brand, navigating the unknowns of entrepreneurship, and staking my future on something that didn’t come with a blueprint. I didn’t have all the answers, but I had the determination to figure things out. Everywhere I went, I soaked up lessons—from the way people marketed their ideas to how they handled setbacks—and I applied those lessons to my own journey.
One of the biggest challenges was convincing myself that it was okay to fail. The fear of failure can be paralyzing, but I reminded myself that every great success story begins with a leap of faith. I poured everything I had into my vision, drawing inspiration from the world around me and the experiences that had shaped me. My multicultural upbringing, my education, and my love for innovation became the foundation of my business.
The risk paid off in ways I couldn’t have imagined. Not only have I been able to turn my passion into a thriving career, but I’ve also had the privilege of creating something that reflects who I am and what I stand for. It hasn’t always been easy, and there have been moments of doubt and struggle, but those moments have taught me resilience and adaptability.
Taking that leap was the scariest thing I’ve ever done, but it’s also the most rewarding. It’s a reminder that sometimes the biggest risks lead to the biggest rewards, and that the only way to create something truly unique is to trust yourself and take that first step—even if you’re not sure where the path will lead.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
My name is Dawn Pilpel, and I was born and raised in Toronto, a city that fueled my love for art and fashion from an early age. Growing up surrounded by the energy and diversity of Toronto, I developed a passion for creativity that has been the driving force behind everything I do.
My journey into this industry started when I worked as a buyer for a specialty boutique in Ohio. That experience opened my eyes to the business side of fashion and inspired me to create something uniquely my own. With a background in philosophy and sculpture, I decided to combine my artistic sensibilities with a bold and innovative vision: transforming everyday, utilitarian objects into extraordinary pieces of wearable art.
This vision led to the creation of my jewelry line, where I use common metal components like nuts, washers, and hardware to craft handmade designs that challenge the ordinary. Each piece is infused with a story and held to the highest standards of quality. What sets my work apart is this ability to take the overlooked or utilitarian and turn it into something meaningful and beautiful.
Recently, I expanded my creative offerings by introducing prints of my original drawings. Inspired by the vibrant colors of the world and the people I meet every day, my art is a celebration of life and individuality. Whether it’s a bold piece of jewelry or a striking print, everything I create carries my personal motto: “Grab life by the nuts.” This mantra reflects my belief in embracing life with courage, humor, and a sense of adventure.
What I’m most proud of is the connection my work creates with others. Whether someone is wearing one of my designs or displaying a piece of my art in their home, I love knowing that my creations bring joy, spark conversations, and inspire confidence. At the heart of my brand is a commitment to originality, craftsmanship, and a playful approach to life.
For those new to my work, I want you to know that iWEAR …do you? isn’t just about fashion or art—it’s about celebrating individuality and seeing the beauty in the unexpected. My hope is that through my designs, you’ll feel inspired to express yourself, embrace your uniqueness, and approach life with a sense of creativity and boldness.
How’d you build such a strong reputation within your market?
I believe my reputation within the market has been built on a foundation of honesty, loyalty, and genuine connections with my customers. Over the past 20 years, I’ve made it a priority to not only create quality products but also to foster trust and strong relationships with the people who support my work.
One of the key factors has been my ability to listen. Being a good listener allows me to connect with a wide variety of people—young and old, from all walks of life. It’s important to me that every customer feels seen, heard, and valued. I’ve always taken the time to understand what they’re looking for and how my creations can bring joy or meaning into their lives.
Loyalty is another cornerstone of my reputation. From my very first customer to my most recent, I’ve always stood behind everything I create and sell. I hold myself to the highest standards, ensuring that every piece I make reflects the care and dedication I put into my craft. Customer satisfaction isn’t just a goal for me; it’s the driving force behind everything I do.
I’m proud of the trust I’ve earned over the years. Whether it’s through my handmade jewelry, original art clothing, art prints and greeting cards, I’ve built a reputation for delivering not just products but also an experience of connection and authenticity. My customers know they can count on me—not only for high-quality creations but also for a genuine commitment to their happiness and satisfaction.
Can you tell us about what’s worked well for you in terms of growing your clientele?
The most effective strategy I’ve used to acquire customers has been a combination of adaptability, persistence, and a genuine passion for connecting with people. Over the years, I’ve made it a point to learn every aspect of the wholesale and retail business, which has given me a deep understanding of how to reach and resonate with different audiences.
Traveling along the East Coast of the U.S. and Canada, I’ve worked tirelessly to sell my products and expand my reach. I’ve embraced every opportunity to introduce my work to new markets, whether it’s at conventions, markets, or other venues where I can meet new customers face-to-face. Each new location offers a chance to connect with people from different cultures and backgrounds, which not only helps me grow my customer base but also fuels my creativity and inspiration.
What has truly set my strategy apart is my unwavering dedication. I’ve never given up, even when the path was challenging. I’ve poured my heart and soul into this business, constantly pushing myself to explore new opportunities and never settling for less. For me, the potential to grow and reach more people is always there, and that belief keeps me motivated to keep going.
This approach—of being open to new experiences, meeting people where they are, and putting my all into every interaction—has been instrumental in building a loyal and diverse customer base. It’s not just about selling products; it’s about creating connections, sharing my passion, and inspiring others through my work.
Contact Info:
- Website: https://www.iweardoyou.net
- Instagram: @iweardoyou
- Facebook: https://www.facebook.com/iweardoyou
- Twitter: @iweardoyou
- Other: https://www.grablifebythenuts.com
