What started as a $5,000 side hustle in a one-bedroom Los Angeles apartment became a thriving six-figure e-commerce business—and a life-changing exit that gave one entrepreneur the freedom to choose what comes next.
When Samantha Hamilton launched Dottie for Running from her living room in 2015, she had modest expectations. “I genuinely thought if I sell 10 of these and get to go through the process of shipping and invoicing, that’s success in my eyes,” she recalls.
Ten years later, Hamilton successfully sold her business through Flippa, transforming a creative passion project into a profitable exit that allowed her to step fully into motherhood while keeping her entrepreneurial dreams alive.
The Unexpected Beginning: When Your Mom’s Sewing Skills Become a Business Model
Hamilton’s journey into entrepreneurship wasn’t carefully plotted, it emerged from the intersection of necessity, creativity, and community.
As Director of Sales for a contemporary women’s clothing brand, she’d accomplished everything she set out to achieve. But with relocating on the horizon and a desire to be her own boss, Hamilton needed a low-overhead business she could control completely.
The breakthrough came from an unlikely source: Run Disney races.
“My mom had made what ultimately became the prototypes for the original Dottie skirts—little princess-based tutus with huge bows on the back,” Hamilton explains. “I got stopped so much during races and asked about the skirts that it made me start thinking: is this the thing I can build a business around?”
With just $5,000 invested in materials, Hamilton opened her Etsy shop. Her strategy was deliberately small-scale and domestic, avoiding the complexity and costs of overseas production she’d managed in her corporate role.
Through her father’s connection to an entrepreneur outreach program at the University of Alabama, she found Miss Lily—a seamstress who would produce Dottie’s signature pieces until the very end. “Until my exit from the business, we were still working with the same lady,” Hamilton says, highlighting the power of building lasting partnerships.
Sell Your Online Business With Flippa
Access expert guidance and the technology you need to list, market and close your deal.
400,000+ Weekly Active Buyers
20+ Multi-language Brokers
Seamlessly Negotiate and Receive Offers
Integrated Legal, Insurance, Finance and Payments
Finding Your Niche: The Community That Changed Everything
Dottie for Running didn’t just find customers, it found its people.
The Run Disney community embraced the brand’s playful, character-inspired designs. Hamilton’s tutus with their distinctive huge bows became recognizable symbols within the tight-knit running community, creating what she affectionately dubbed “Team Butt-Bow.”
But the real transformation came during an unlikely time: the COVID-19 pandemic.
“While lockdowns were obviously a struggle for everybody, one silver lining was it really pushed people’s creativity and their need to connect,” Hamilton reflects. The Run Disney community rallied together online, with Hamilton’s ambassadors creating dancing videos, hosting games, and keeping spirits high during isolation.
When in-person races returned in 2021, the pent-up enthusiasm translated directly to sales. “Revenue quadrupled in those couple of years,” Hamilton says. “That’s when I felt like, hey, I have a legitimate business. We crossed the six-figure mark as far as annual revenue went.”
The Evolution: From Etsy to Shopify and Beyond
As the business matured, so did Hamilton’s approach to running it.
Etsy provided the perfect launchpad, offering built-in traffic and simplified backend operations that let Hamilton focus on production and customer service. “Being on that platform really helped establish my customer base and make me visible,” she notes.
By 2022, with a proven business model and established customer base, Hamilton made the strategic leap to Shopify. “I realized I have a quote-unquote real business here and an established customer base. That’s when we made the jump to taking more ownership and control.”
This transition represented more than a platform change—it signaled Hamilton’s growing confidence as a business owner, even as imposter syndrome continued to whisper doubts.
The Decision to Sell: When Life Changes the Business Plan
Hamilton never built Dottie for Running with an exit strategy in mind. “I never in a million years thought it would become the established business that it became,” she admits.
But life had other plans.
As a military spouse with a growing family—eventually three children under five—the demands of running an inventory-based business while moving every few years became increasingly challenging. “When I found out I was pregnant with my third, that was when I really started seriously looking into selling,” Hamilton explains.
The catalyst wasn’t desperation—it was clarity. She recognized she was getting in her own way, and the business deserved an owner who could take it to the next level while she focused on being fully present for her young children.
The Flippa Experience: Finding the One Right Buyer
Initial research into traditional business brokers proved discouraging. For a boutique business worth low six figures, the upfront costs of private brokers, lawyers, and accountants were hard to justify.
Friends who’d worked with Flippa recommended the platform, and Hamilton decided to explore. “Right off the bat, the valuation I was given was slap bang in the middle of the range I had in mind,” she says.
Her broker, Malia, set expectations perfectly from day one: “This is a niche business. You’re not going to get a thousand buyers. You just need that one buyer who gets it and understands it. So we’re looking for the one right buyer.”
That mantra proved prophetic.
Daily, Hamilton tracked interest through Flippa’s platform—watching clicks, NDA signatures, and inquiries roll in. Venture capitalists expressed interest in the established 10-year-old business, but most fell away when they realized Dottie wasn’t a turnkey, set-and-forget operation. It required a hands-on owner.
Then the perfect buyer appeared: a first-time business buyer who was already part of the Run Disney community and had heard of the brand.
“She understood that customer base already, so it took off that huge learning curve,” Hamilton explains. Better yet, the buyer was looking for exactly what Dottie represented—a passion project to pour her energy into as her own children were leaving the nest.
Negotiating with Confidence: Knowing Your Bottom Line
When the initial offer came in, it was close—but not quite close enough.
“I had a bottom line number in the back of my mind that I needed to be above for it to be worth parting with the business,” Hamilton says. “There’s an emotional element as well as practical.”
The initial offer didn’t scare her, but it did require a counteroffer. This is where having Malia as her broker proved invaluable. “She very much held my hand and said, ‘No, if you need to be here and they’re coming in here, then we’re just going to go back right here and I’ll take care of it.’”
The key insight? “You are running a business, you’re still running a business here,” Malia reminded her.
The negotiations moved quickly from there, with lawyers reviewing agreements and minor details being ironed out. From listing to close took just a couple of months—and 30 days to finalize once negotiations began.
The Emotional Journey: Letting Go and Moving Forward
Selling a business you’ve built from scratch involves more than financial calculations—it requires emotional preparation.
Hamilton knew she needed to be ready to let go completely. “You have to accept that if there’s a new leader at the helm, it’s going to look different from how you’ve been doing things,” she reflects. “You’ve kind of given it wings now, and it’s going to go and be its own thing.”
She intentionally didn’t load the contract with restrictions about keeping specific elements of the business. “I had very much already made sure I was emotionally prepared to truly let it go and let it be the new owner’s vision of what I’d built.”
The transition included personal touches that mattered deeply. Hamilton personally contacted longtime customers-turned-friends to explain this was a happy decision, not forced by circumstances. She ensured her team of seamstresses could stay on if they wanted. And she could finally tell her parents—who’d been helping with operations past retirement age—to actually go be retired.
The 90-day transition period included weekly video calls, with the buyer thoughtfully sending questions ahead of time. They even met in person for an inventory handoff and day-long operational review. “I think that was invaluable for both of us,” Hamilton notes.
Life After the Sale: Freedom to Choose What’s Next
Six months post-sale, Hamilton reflects on what the exit has truly given her: presence.
“I cannot tell you what it has meant to be able to be truly 150% present with my children at home, especially over the summer, and to not have any distraction in the background,” she says. “Time goes by so quickly. I’m very thankful to have this luxury.”
But the entrepreneur itch hasn’t disappeared. “I have 50 million ideas in my head,” Hamilton laughs. She and her husband have wisely set aside funds from the sale for her next venture—but with intentional timing. She’s waiting until her youngest enters full-time school and the family settles into a permanent location post-military service.
“I’m a business owner at heart. I’m a shop girl at heart. I love retail, I love buying, I love production,” she says. “I’d like to do something on a larger scale right off the bat. That’s the luxury this sale has afforded me—time to refine whatever that looks like.”
Lessons from a Decade of Entrepreneurship
Looking back on her journey from $5,000 investment to six-figure sale, Hamilton has hard-won wisdom to share:
Overcome Imposter Syndrome: “Don’t let imagery out there of multi-million dollar businesses make you think you’re not legitimate,” Hamilton urges. “If you’re a stay-at-home mom with a side hustle, you are a business owner. There is a place for everybody in this business world.”
Just Start: “You never know where it will take you. It doesn’t have to be a big budget idea—just find a way and let your creativity come through.”
Build Community: Dottie’s success came from genuine connection with customers. “One of the most wonderful things about this business is you get interactions with this customer base, and I have customers-turned-friends who have been with me since 2015.”
Don’t Wait for Perfect: Hamilton’s basic record-keeping was “more than enough” for the sale process. “Don’t let that put you off. I am not a business manager or accountant by any stretch, but my files were sufficient.”
Be Transparent: “The more you’re comfortable sharing with potential buyers who’ve signed NDAs, the better. It shows you’re serious and takes away initial questions and doubts.”
Know Your Worth: Understanding your bottom line and being willing to negotiate is crucial. “You have to take care of you. You are running a business.”
Redefining Success: From Revenue to Freedom
Perhaps the most profound shift for Hamilton has been her definition of success itself.
“I feel a lot more legitimized as a business owner now. I feel more accomplished,” she reflects. The sale gave her not just financial security, but personal fulfillment and confidence for whatever comes next.
Most importantly, it gave her choice—the ability to be fully present during a fleeting phase of motherhood while keeping entrepreneurial doors open for the future.
For the thousands of entrepreneurs running boutique businesses, building niche communities, and wondering if their “small” success really counts—Hamilton’s story offers a resounding yes.
“Great oaks grow from tiny acorns,” she says. “Everybody has to start somewhere. If it’s your vision and you’re doing well with it, stick to it. Who knows where it’ll take you.”