A Journey Through Business, Change, and Growth with Entrepreneur Jill Dudzinski
The end of the year often brings reflection, a look back at achievements, and anticipation for what’s next. For Jill Dudzinski, entrepreneur and former owner of hello ruby, 2024 was a year of major transitions, personal growth, and new beginnings. In her conversation on Minimum Rage, she opened up about selling her beloved fashion truck, building a thriving local business collective, and her journey through various career paths that led her to where she is today.
This discussion highlights the realities of entrepreneurship, the balancing act of running multiple businesses while raising a family, and the importance of embracing change.
Selling a Business: The End of an Era
One of the biggest changes in Jill’s life this past year was selling her fashion truck, hello ruby. For nearly eight years, the business had been a staple in her life, but in December 2024, she finalized the sale and officially handed over the keys to a new owner in Vermillion, South Dakota.
For Jill, letting go of hello ruby was bittersweet. The process of selling took time, and she went through waves of emotions, but ultimately, she felt it was the right decision. As she put it:
“Everyone kept asking if I was sad, and of course, there were moments, but once I made the decision, I was ready. It felt like a weight lifted.”
While the business will continue under new ownership, Jill is now fully focused on her next venture, growing Local Collective, a business networking and support community she co-founded.
The Birth and Growth of A Local Collective
Jill’s transition away from hello ruby wasn’t about stepping away from business—it was about refocusing her energy. Alongside her friend Katie, owner of Little Mango, Jill had spent years organizing pop-up markets and networking events for small business owners.
What started as a simple collaboration turned into a full-fledged community called A Local Collective, which now has over 150 members. The organization offers:
- Monthly meetups and networking events
- An online portal for business resources
- Educational workshops and guest speakers
- Signature events like boutique warehouse sales and modern markets
Jill and Katie didn’t expect A Local Collective to grow so quickly, but the demand was clear. Small business owners wanted a supportive space to connect, learn, and grow together.
Managing both hello ruby and A Local Collective had become overwhelming, which was a big factor in Jill’s decision to sell the fashion truck. Now, she is able to fully commit to growing this business support network.
The Reality of Entrepreneurship: Learning on the Job
Despite major business success, Jill admits that she didn’t learn everything from school. While she studied marketing and merchandising at UNL, she believes most of what she knows about business came from trial and error.
“Going to school for business was great, but honestly, I learned more by just doing it. When you’re actually running a business, you have to figure things out in real-time.”
She also touched on the challenges of being a multi-passionate entrepreneur. Many business owners struggle with sticking to one idea, and she admitted that at times, she felt pulled in too many directions.
“You have to keep your head down and keep going. It’s easy to get distracted by new ideas, but sticking with your original vision is key.”
Jill’s Career Journey: A Look Back at Past Jobs
Jill’s entrepreneurial spirit didn’t start with hello ruby. Before launching her own business, she held a variety of jobs—many of which shaped her work ethic and understanding of different industries.
Early Jobs: Learning from Experience
Her first job was as a front desk check-in girl at Great Clips, where she quickly realized how loyal customers were to their hairstylists. She also worked at Perkins, describing the challenging nature of food service and her eventual decision to quit abruptly on Mother’s Day.
She later worked as a nanny, but looking back, she admitted she wasn’t always the most responsible babysitter, joking that she sometimes dozed off while watching the kids.
Pharmaceutical Sales: High Stakes, High Pressure
One of the more intense jobs Jill held was in pharmaceutical sales, where she worked with doctors to promote prescription medications. She recalled the pressure of memorizing medical studies, dealing with strict industry regulations, and trying to navigate conversations with highly knowledgeable physicians.
“Doctors don’t really want to be sold to. They already know their stuff. My boss would push me to deliver certain talking points, but I found that just building relationships was more effective.”
Lessons from Her Past Work Experience
Through all these jobs, Jill learned valuable business skills, customer service techniques, and sales strategies. She also discovered what she didn’t want to do, which helped her narrow down her path to entrepreneurship.
Launching a Podcast: Behind the Business
As she moves forward, Jill is also preparing to relaunch her podcast under a new name: Behind the Business.
Previously called Where There’s a Wheel, There’s a Way, the show originally focused on her experience running a fashion truck. Now, she’s shifting the focus to interviewing fellow entrepreneurs, sharing behind-the-scenes insights about their journeys, struggles, and successes.
Her goal is to showcase the real, unfiltered stories behind small businesses, offering inspiration and practical advice for aspiring entrepreneurs.
“So many people see the success of a business but don’t know what it actually takes to get there. I want to highlight the behind-the-scenes work and the ups and downs.”
The podcast will be part of the Herdat One Network, a local media collective focused on Omaha-based podcasts and community storytelling.
Advice for Aspiring Entrepreneurs
Reflecting on her journey, Jill shared key advice for those looking to start their own business:
- Have a plan, but don’t overthink it – It’s important to have a roadmap, but waiting too long to execute can be a mistake.
- Take advantage of free business resources – Programs like the Small Business Administration (SBA) offer valuable support and education.
- Network and connect with others – Meeting like-minded entrepreneurs can provide support, collaboration opportunities, and business growth.
- Be comfortable with uncertainty – Running a business means dealing with unknowns, last-minute changes, and unexpected challenges.
- Stick to your focus – While new opportunities can be tempting, staying committed to your original vision is often the best path forward.
Looking Ahead to 2025
As Jill steps into 2025, her focus is clear:
- Expanding A Local Collective to support even more small business owners
- Growing Behind the Business podcast to tell more entrepreneurial stories
- Continuing to advocate for local businesses and build strong community connections
Jill’s journey is a testament to the power of adaptability, determination, and learning from experience. Whether she’s selling fashion, organizing business events, or launching a new podcast, one thing is certain—her entrepreneurial spirit isn’t slowing down anytime soon.
For those interested in connecting with Jill or learning more about her ventures, follow her journey on Instagram and check out Behind the Business podcast when it launches in 2025.
This blog post is based on a transcript from the Minimum Rage podcast episode released on December 24th 2024.
The Minimum Rage podcast is hosted by two coworkers, friends, and, most importantly, girl bosses. Minimum Rage is for anyone who has left work in a fit of rage (literally or figuratively). Get ready for a rollercoaster of anecdotes as our hosts and guests reminisce about the challenges, quirks, and downright absurdities of their early part-time jobs. From crazy co-workers to strange encounters with customers, let’s clock in and explore the wild ride that is working for minimum wage.
Edited by Grace Dunbar
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