From a basement studio to a 6-figure e-Commerce brand: How a creative side hustle became a successful Shopify brand
From a basement shelf to a thriving eCommerce leader, Anna and Santiago built their brand through community trust, relentless testing, smart reinvestment, and disciplined growth.
Industry
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Meet the brand founder
Long before it was a serious eCommerce operation, the store started as something much simpler: a working artist sharing her craft online.
In 2009, Anna Wilinski was already a professional face painter. She had started at eleven years old, visiting nursing homes with her mom, performing as a clown, painting faces at birthday parties and community events. When YouTube launched, she became one of the first face painters to upload tutorials. She wasn’t thinking about building a retail empire — she was simply sharing what she loved.
Then opportunity knocked.
A face paint brand trying to break into the U.S. market noticed her videos. They reached out and asked if she would use their products in her tutorials and help sell them online. Anna agreed, and with the help of a friend, she launched the first version of their online store.
Santiago Massano entered the story in 2010. Once his work authorization came through in the United States, he began helping Anna improve the store’s design and online presence while looking for work himself.
What started as a creative outlet slowly began turning into something bigger.
The first real win
The turning point wasn’t a viral spike or a huge ad campaign.
It was customers.
They began noticing something powerful: people inside Facebook groups were recommending their store over much larger, established competitors. Word spread organically within tight-knit face painting communities.
Then came the inventory crunch.
They couldn’t keep products in stock. So they made a bold move: they borrowed $5,000 from their in-laws and tripled inventory.
Sales poured in.
They paid the loan back in about a month.
That was the moment they realized this wasn’t just a scrappy side hustle. It was a real business with real demand.
They quit their school jobs to focus on growth — all while participating in the Habitat for Humanity program that would eventually allow them to purchase their first home.
How the business runs today
Today, Santiago’s role looks very different.
He no longer picks and packs orders or restocks shelves. Instead, he focuses on growth:
Sourcing new products
Expanding into new markets
Improving marketing strategy
Optimizing UI, UX, and SEO
Hiring and HR management
Taxes and legal oversight
Every morning starts with emails — especially those requiring owner-level attention. Then comes time spent answering questions on Reddit and Facebook, staying connected to the professional face painting community.
His calendar might include meetings with:
A web developer
An SEO and paid ads specialist
A CPA
A lawyer
He frequently studies new regulations, import laws, and tax requirements — often attending seminars or consulting specialists to stay compliant.
The work is more complex now. The early days were simpler, even if they were harder physically.
But one thing hasn’t changed: he still makes time to stay close to customers.
Leveraging experts, agencies & apps
The decision to bring in outside experts came in stages.
First, a web designer — when it became clear competitors’ websites were outperforming theirs visually and functionally.
Then an SEO expert — after Santiago reached the limit of what he could self-teach.
Then a paid ads manager — after several failed campaigns despite taking online courses.
Then a CPA and lawyer — when growth made “winging it” too risky.
Their early taxes were recorded in a notebook. A professional CPA eventually implemented QuickBooks and created clarity around income and expenses. A lawyer helped structure the business as an LLC to protect personal assets.
The biggest growth drivers?
Their web developer and SEO/paid ads agency. A well-designed, conversion-optimized website turned traffic into customers. But surprisingly, their CPA ranks just as high — because organized financial visibility allowed strategic growth.
On the Shopify side, several apps are mission-critical:
Searchanise – Nearly 30% of homepage clicks happen in the search bar. Accurate search dramatically improves conversions.
Order Printer Pro – Custom invoices organized by SKU streamline warehouse picking.
Bundle Builder – Roughly 10% of sales come from product bundles.
Growave – Loyalty, reviews, wishlist, Q&A — critical for SEO and retention.
Each tool was added after careful testing.
But not every hire worked out.
They once hired an SEO agency that relied heavily on questionable link-buying tactics. They hired web designers who were cheap — and the results reflected the price. They hired CRO consultants who promised massive growth and delivered little beyond suggesting free shipping and coupon codes.
The lesson: your website is everything. Invest accordingly. And always understand enough about the task before outsourcing it.
Big challenges
Scaling brought new complexity.
Sales tax laws changed, requiring collection in over 15 states. New FDA regulations affected products. Tariffs shifted import costs. Inventory planning became reactive when sudden policy changes forced rushed purchase orders.
Logistics added pressure. USPS, their primary carrier, reduced distribution centers and pickup times, making it harder to maintain fast, affordable shipping.
Then there’s HR — hiring well, managing people fairly, and sometimes letting someone go.
Growth didn’t just mean more revenue.
It meant more responsibility.
Advice to brands on their way to 7–8 figures
Santiago’s advice is pragmatic and experience-driven.
Start early with a good lawyer and CPA. Organization isn’t glamorous, but it’s foundational.
Don’t delegate too quickly. Learn the task first. Understand what it requires so you can:
Evaluate fair pricing
Ask the right questions
Measure performance properly
Avoid debt if possible. Grow with your own capital, even if that means working extra jobs early. If things go wrong, you won’t be buried in loans. If things go well, you keep your profits.
Invest in a professional website and real SEO as soon as you can afford it. Word of mouth isn’t enough. The internet is too big to rely on luck.
And when hiring experts, don’t hire blindly or cheaply. Learn enough to spot unrealistic promises. Know what good work looks like.
What’s next for the brand
Now, the focus shifts toward innovation and profitability.
Santiago is investing heavily in developing new products that solve real problems within the face painting industry — solutions he believes don’t yet exist or aren’t optimized.
At the same time, he’s focused on increasing profitability and automating operations to simplify day-to-day management.
The basement studio is long gone.
But the mindset that built it — relentless learning, customer proximity, disciplined reinvestment — remains intact.
What started with one shelf in a drafty living room has become a sophisticated, multi-layered eCommerce operation.
Built not on hype.
But on trust, persistence, and a willingness to sweat — sometimes literally — to test which paint lasts longer.
Meet the experts behind brands like this
Scaling a Shopify brand takes more than a good idea — it takes the right people, systems, and partners at the right stage. Meet the experts who support brands like this on shopexperts.com