I Turned My Disney-Inspired Running Skirts into a Profitable Side Hustle and a $120,000 Exit

What if you could turn a hobby into a six-figure business, grow it while raising three kids and living overseas, and then sell it for $120,000?

Samantha Hamilton did exactly that with her former Disney-inspired running skirt business, Dottie for Running.

What started as a mom-made tutu she wore to races turned into a thriving e-commerce brand serving a passionate niche community.

In this episode, Samantha shares how she identified the opportunity, navigated the challenges of production and growth, and ultimately prepared the business for a successful sale through Flippa.

Tune in to Episode 702 of the Side Hustle Show to learn how to:

Turn a niche passion into a six-figure side hustle selling Disney-themed running skirts
Build brand loyalty and community through ambassadors and social media
Scale handmade products while keeping production lean and quality high

Table of Contents show

Finding the Intersection: Running, Disney, and Fashion

Back in 2015, Samantha was working a corporate fashion job in Los Angeles and getting into distance running. She and her mom designed custom tutus with signature big bows on the back for her to wear to runDisney events.

The response was immediate. People stopped her mid-race asking where she got her outfit.

About the Dottie — Image: dottieforrunning.com

That’s when the lightbulb went off. Samantha saw an opportunity at the intersection of three things: her fashion background, the growing runDisney community, and a product people were actively seeking.

The key insight: Look for overlaps between your interests and existing demand. Bonus points if you can piggyback on an established trend or community. The runDisney events provided built-in marketing and a ready audience of potential customers.

Solving the Production Challenge

One major hurdle was production. Samantha didn’t want to tie up capital in overseas manufacturing or wait months for container ships. She also couldn’t rely on her mom to sew every order.

So her solution is connecting with local seamstresses in Alabama through university programs.

Many factories in the region had closed, leaving talented seamstresses looking for work. However, Samantha’s dad worked at the University of Alabama and helped make connections, so this approach gave her several advantages:

No minimum order quantities
Quick turnaround times
“Made in USA” credibility
Support for other small business owners
Flexibility to scale up or down as needed

The original seamstress, Miss Lily, stayed with the business until the day Samantha sold it. She created the first pattern from scratch using just sketches and Samantha’s mom’s prototypes.

Navigating the Disney IP Question

One concern many people have when selling Disney-inspired products is intellectual property. How did Samantha handle this?

She was careful to use “inspired by” language rather than claiming any direct affiliation and never used Disney imagery or character names in her marketing. She consulted with lawyer friends who confirmed that this approach provided protection.

The magic words “inspired by” allowed her to create products that referenced Disney themes through colors, designs, and style without crossing legal lines. Think of it like fan fiction for fashion.

Disney did decline her application to sell at their race expos, saying the products were too similar to what they sold in parks. But they never sent a cease and desist letter for her online sales.

Getting Those First Customers

Samantha’s first sales platform was Etsy. She chose it because the handmade nature of her product fit the platform well, and Etsy drives organic traffic to new sellers.

Her initial goal was modest: ship one skirt per month. Within weeks, she was shipping one per week without any major marketing push.

Her early marketing strategy included:

Grassroots outreach: Attending runDisney races armed with business cards and flyers. When people asked about her skirt, she now had somewhere to send them.
Social media giveaways: Instagram was relatively new, and giveaways were effective for building followers. She’d offer free skirts for likes, follows, and shares.
Direct customer connection: With a small business, she could personally respond to every customer and learn where they heard about the product. This feedback helped her focus her marketing efforts.

Building the Ambassador Program

A few years into the business, Samantha created Team Buttbow, her ambassador program.

Initially, she reached out to runDisney influencers offering to send them products in exchange for promotion. But within a year, the dynamic flipped and people started applying to become ambassadors.

Every September, Samantha opened applications and selected a diverse group. Half had large followings and high engagement, while the other half were emerging influencers with compelling personal stories.

The program was entirely product-based — no cash commissions. The ambassadors received free skirts and the prestige of being part of the team. For many, being selected became a point of pride rather than just a way to earn affiliate income.

This organic community building turned customers into evangelists. It also meant Samantha wasn’t the only face of the brand, which made the business more sellable later.

The Post-COVID Boom

Throughout its history, Dottie for Running grew steadily at about 30% year over year. But in 2021, something changed.

When runDisney announced the return of in-person races after COVID shutdowns, demand exploded. Samantha had her first six-figure quarter in sales.

This surge presented a new challenge. For the first time, she was getting disappointed customer emails because items were selling out. Her lean, made-to-order model suddenly couldn’t keep up.

She adapted by implementing a hybrid approach:

Pre-orders for new designs: Customers could order based on photos and samples, with an 8-week ship time.
Stock for proven sellers: Princess-themed and classic character designs were kept in regular inventory.

This flexibility allowed her to meet demand without overcommitting to inventory or overwhelming her seamstresses.

Pricing Evolution and Margin Management

Samantha started by pricing skirts at $69 plus flat-rate shipping. She admits this was probably too low.

“I would have swallowed some of the imposter syndrome and made sure I was priced competitively but making sure I was able to comfortably take care of everything and truly draw a profit right off the bat,” she reflected.

Her initial pricing strategy was simple: cover expenses and keep it under $100 to make it an appealing price point. Only after a couple of years did she sit down and properly evaluate whether the pricing supported sustainable growth.

By the time she sold, skirts were priced between $100 and $130. Several factors drove the increase:

Fabric costs rose significantly
Hidden overhead costs added up
She valued her own time more appropriately
The brand had established enough loyalty to support higher prices

The seamstresses were always paid per unit, and Samantha made sure they were compensated fairly. This was a priority even though it represented a large portion of production costs.

The Tech Stack

Samantha kept her tech stack deliberately simple:

Etsy -Provided built-in traffic and credibility for a handmade product. She eventually put it in vacation mode but never fully closed the store because she was “terrified of losing all that data.”
Shopify – She transitioned to Shopify as the business grew. It offered more control over the website design, better reporting capabilities, and a more professional storefront. Once the brand had enough name recognition, she moved all sales there.
Instagram and Facebook – Instagram was the primary social media platform. Samantha hired a social media manager to help tie everything together, including setting up a Facebook shop. However, Instagram remained the main driver of engagement and sales.
Google Sheets – For tracking client preferences and organizing production.
Social media management – She eventually hired help for this, which was crucial as the business scaled.

The Decision to Sell

By early 2024, Samantha was facing a crossroads. Within a few months, she had her second child and the family was preparing for an international move back to the States from Germany, where her husband was stationed.

“I could see where I was sort of cutting corners a little bit, like kind of going into survival mode where I was having to choose between the customer service, like my customers and my children essentially,” she explained.

She realized she couldn’t be everything to everyone. Small business owners aren’t Amazon or Target — they can’t be available 24/7 despite wanting to give perfect service.

At the same time, she could see what the business could become with the right owner. Someone with more time and energy could take it further than she could while managing three young children and military life.

Another factor was the business’s 10-year anniversary approaching in 2025. A decade felt like a meaningful milestone and a natural ending point.

Preparing for the Sale

Samantha initially explored working with private brokers but quickly learned that route was expensive and time-consuming. For multimillion-dollar sales, hiring your own accountant and lawyer makes sense. For low six-figure deals, the costs can eat too much of the proceeds.

Friends who had sold a small business recommended Flippa, an online marketplace for buying and selling businesses. The platform offered several advantages:

All-in-one service: Legal contracts, buyer vetting, and escrow services were all handled through Flippa.
Pre-qualified buyers: Buyers had to sign NDAs before seeing detailed financials, and Flippa verified they had funds available.
Lower fees: Compared to private brokers who might charge 10-15% or more, Flippa’s commission structure was more reasonable for smaller deals.
Broker support: Samantha worked with a dedicated broker, Malia, who understood the niche nature of the business and knew how to market it effectively.

Finding the Right Buyer

Malia set realistic expectations from the start. “You’re not going to get hundreds of buyers because it’s such a niche business,” she told Samantha. “But that’s okay, because you just need that one buyer.”

The listing went live on November 2nd. For a couple of months, there was interest from venture capitalists and investors, but those conversations didn’t go anywhere. They wanted a turnkey, absentee-owner situation, which wasn’t realistic for a business built on personal relationships and hands-on management.

Then in early February, the right buyer reached out. She was a runDisney runner and Disney fan who understood the product and community. She was also approaching empty-nester status and looking for a project to call her own.

Samantha with Cara, the new Dottie for Running owner

“From those initial conversations, it just kind of felt like we understood each other and she got the vision,” Samantha said.

By April 23rd, all the paperwork was signed, final assets were transferred, and the sale was complete. The entire process from listing to closing took about five and a half months.

What’s Next for Samantha?

Samantha promised herself and her husband she’d take at least a year to focus on being a stay-at-home mom. After years of balancing business ownership with raising young children, she wanted to be fully present.

That said, she admits the entrepreneurial bug is hard to shake. “Once you sort of get the bug for being your own boss and having your own business, it’s hard to get away from that,” she said.

Whatever comes next will likely involve her love of retail and pretty things. But for now, she’s enjoying the luxury of time with her children and planning a celebration beach vacation with her husband.

Samantha’s #1 Tip for Side Hustle Nation

“Just do it.”

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