Behind the Business: A Fresh Start with Jill Dudzinski and Katie Lakin

The Behind the Business podcast, formerly known as Where There’s a Wheel, There’s a Way, has made its debut with an exciting first episode featuring hosts Jill Dudzinski and Katie Lakin. This episode dives into Jill’s transition from owning and selling hello ruby, the evolution of their business partnership, and the growing success of their collective events.

Jill and Katie’s candid conversation covers entrepreneurial lessons, the importance of community in small business, and upcoming plans for their local collective. If you’re a small business owner, aspiring entrepreneur, or just love hearing behind-the-scenes insights, this episode is packed with valuable takeaways.

 

A New Chapter: Selling hello ruby and Embracing Change

Jill Dudzinski, the former owner of hello ruby, opened up about selling the business and how that decision changed her life. She expressed excitement but also reflected on the mixed emotions that came with it.

“I built a business from the ground up and sold it. That’s a pretty cool thing,” Jill said.

While she’s happy with her decision, there’s been curiosity from the community. People often ask, “What’s the tea?” about why she sold the business. While Jill keeps some details private, she reassures listeners that she’s moving forward with new opportunities.

One major shift after selling hello ruby is that she can fully focus on local collective events, such as The Boutique Warehouse Sale and Modern Market, without the added stress of running a retail business.

 

The Boutique Warehouse Sale: Supporting Local Businesses

Jill and Katie discussed their Boutique Warehouse Sale, an event where local businesses gather to sell excess inventory at discounted prices. The event spans two weekends at Regency, providing a space for boutique owners to clear inventory, attract new customers, and prepare for the next season.

Katie pointed out that while the event brings in record-breaking sales, profit margins can be tight due to deep discounts. However, business owners see it as an opportunity to reinvest in new inventory.

Why This Event is Important for Local Shops

• Helps businesses move unsold seasonal inventory
• Offers customers high-quality items at great prices
• Creates a community-driven shopping experience
• Builds brand awareness for smaller boutiques

Regency, the venue for the sale, has been incredibly supportive, and the event continues to grow each year.

 

The Modern Market and Junk Stock: Building a Collective Space

Jill and Katie also touched on their Modern Market, an event hosted at their warehouse in Waterloo during the first weekend of Junkstock.

For those unfamiliar, Junkstock is a huge event showcasing vintage, handmade, and repurposed goods. However, Modern Market provides an alternative shopping experience focused on local boutique items and modern small businesses.

“We’re not trying to compete with Junkstock,” Katie clarified. “We just want to offer another option for people looking for something different.”

The downside? Outdoor markets bring unpredictable weather challenges, from wind to extreme temperatures. However, the team is actively working on permits and logistics to make the experience as smooth as possible for both vendors and customers.

 

Member Meetups: The Power of Small Business Community

One of the podcast’s biggest takeaways was the importance of networking for small business owners. Jill and Katie host monthly member meetups through their collective, allowing business owners to connect, exchange ideas, and support each other.

With over 160 members, the collective offers:

• Networking opportunities
• Educational workshops (bookkeeping, influencer marketing, etc.)
• Business mentorship and advice
• Exclusive member discounts

These meetups give small business owners a chance to talk through challenges, learn from each other, and find support in what can sometimes be an isolating journey.

 

New Initiatives: The Boutique Swap and Retail Roundtable

Jill and Katie are always thinking of new ways to support local businesses. One of their latest ideas is a Boutique Swap, allowing boutiques to exchange unsold inventory.

“If something isn’t selling in your store, maybe another shop can sell it better,” Jill explained.

They’re also reviving the Retail Roundtable, a workshop series featuring guest experts to help business owners with everything from bookkeeping to digital marketing. Past sessions have included discussions on:

Taxes and bookkeeping (partnering with local finance experts)
Influencer marketing – finding the right social media collaborations
Facebook and Google ads – maximizing online advertising
Shopify and Squarespace insights – building better e-commerce sites

With an increased focus on education and growth, these initiatives will equip small business owners with the tools they need to succeed.

 

The Evolution of Little Mango: A Shift to Custom Sportswear

Katie, the owner of Shop Little Mango, shared how her business has evolved over the years.

Originally focused on children’s clothing, Little Mango has now expanded into women’s apparel and customized sportswear. As a baseball mom, Katie saw an opportunity to create personalized apparel for parents supporting their kids in sports.

They recently launched the “Number One Fan” collection, which includes:

Customizable sweatshirts featuring a child’s jersey number
Embroidered hats with team colors
Baseball-themed jewelry and accessories

To kick off the collection, they’re hosting a Baseball Mom Party, where moms can browse samples, place custom orders, and prepare for the season ahead.

 

Challenges in Influencer Marketing: The Struggle for Authenticity

One of the most relatable and frustrating topics discussed was influencer marketing.

Both Jill and Katie shared negative experiences with influencers who:

Took free products but never posted about them
Over-promised and under-delivered on collaborations
Charged high fees without providing measurable returns

Katie emphasized that finding the right influencer is key—one who aligns with the brand’s values, audience, and style.

“The best influencer collaborations are with people whose audience truly trusts them,” she explained. “If their followers don’t actually engage with their recommendations, it’s not worth it.”

The takeaway? Choose influencers wisely, set clear agreements, and focus on genuine partnerships over vanity metrics.

 

Upcoming Events and Plans for 2024

Jill and Katie wrapped up the episode by previewing upcoming events, including:

Spring Modern Market – April 26 (Seeking sponsors!)
Summer Boutique Warehouse Sale – Last weekend of July & first weekend of August
Fall Modern Market – October 4
Retail Roundtable and Business Workshops (Dates TBD)

They’re also looking for more businesses to join their local collective, offering networking, education, and event opportunities.

 

Final Thoughts: Supporting Small Businesses Together

This episode of Behind the Business highlights the real, behind-the-scenes challenges and triumphs of running a small business.

Jill and Katie’s journey shows that entrepreneurship isn’t just about making money—it’s about building relationships, adapting to change, and creating a supportive community.

As they continue to grow their collective, they remain dedicated to helping local businesses succeed through collaborative events, education, and networking opportunities.

 

This blog post is based on a transcript from the Behind the Business podcast episode released on February 10^th 2025.

The Behind the Business podcast chats with small business owners, entrepreneurs, and all-around inspiring people. We’ll talk about what it’s really like to build something from the ground up—the highs, the lows, and everything in between. Whether it’s figuring out how to get started, creating a standout brand, or navigating the crazy challenges that come with running a business, these are the stories that don’t always get told.

If you love supporting small businesses, have a dream of starting your own, or just want to hear some inspiring and relatable stories, this podcast is for you. Grab a cup of coffee (or your favorite drink), hit subscribe, and join Jill for Behind the Business.

Edited by Grace Dunbar