Curtis Matsko and the art of outgrowing a good idea

Curtis Matsko had made a promise before he had settled on a product. His girlfriend disliked her job. He suggested she quit, help him start a company and trust his ability to sell things on the internet. In his telling, the next question was awkward: what, exactly, were they going to sell? A handmade leather journal eventually supplied the answer. It also supplied the beginning of Portland Leather Goods.

The story sounds tidier when told backward. The garage becomes an origin scene. The journal becomes an obvious first step. Yet the interesting part of Matsko’s career is how often he has had to revise something that was already working. A product can sell and still occupy too much of the founder’s attention. A company can grow and still need a different way of making things. The success is real; the instructions have expired.

A journal and a promise

Before leather entered the picture, Matsko had already spent time thinking about commerce online. He recalls a girlfriend working on an early online university newspaper in Missouri, and his interest in using the internet to sell. He says he wrote a book on the subject in 1995, then built a business operating websites and sold it to a publicly traded company in 2000. Portland Leather would be a later chapter in a longer entrepreneurial life.

His own description of the younger Curtis is less corporate. He grew up in Montana, the youngest of four boys, and remembers himself as competitive, energetic and inclined to make people laugh. Those qualities remain visible in his public appearances. He introduces an idea, interrupts it with a joke, then returns to the idea as though the joke had improved its balance sheet.

The company dates its founding to 2016. Matsko’s Portland garage was the workshop; journals were the opening product. There is something fitting about that choice. A journal is a container for plans that have yet to survive contact with Tuesday. Here was a founder selling people a place to write their next chapter while improvising his own.

The good idea that got in the way

Art festivals gave him a quick education in the difference between appreciation and a purchase. Matsko recalls taking his booth apart and rearranging it as he watched the flow of people, the light and the places where customers paused. The display was provisional. If shoppers liked something and walked out empty-handed, he wanted to understand why.

He also learned something inside the workshop. A part-time employee could make a taller, better stack of journals than he could. The comparison offered a fairly blunt performance review. He could contribute more by finding customers and building the business than by insisting on being its most productive pair of hands.

Leather totes presented another question. Personalization had given the journals extra appeal, but it also made each order more laborious. Matsko remembers spending too long expanding the familiar product before recognizing the opportunity in bags. The lesson has a particular sting: customers were buying what he made. He had evidence of success and still needed to change.

“I’m a marketer.”

Curtis Matsko, December 2024

The shift asks a founder to separate pride from attention. A good idea can deserve its place in the company without deserving every new machine, employee or hour. Matsko’s account includes money and effort spent on personalization before he pulled toward a more repeatable product. His judgment became better by encountering the cost of the earlier judgment.

Four thousand dollars, counted carefully

For someone who speaks readily about enormous businesses, Matsko retains a detailed memory of a much smaller number. He describes borrowing $4,000 to buy a clicker press as an early risk that frightened him. The machine belongs to a less glamorous category of entrepreneurial milestones: equipment that has to earn its place.

It is an instructive amount to put beside his current ambitions. In retrospect, an early purchase can look inevitable. At the time, the founder is making a bet with money that matters. The later company does not arrive to guarantee the loan. Matsko’s enthusiasm for taking risks grew out of decisions that demanded a practical answer, rather than a handsome slide about courage.

His personal website describes Portland Leather as a brand with more than $150 million in annual sales, built without outside investors. That is his account of the business. It also helps explain his preoccupation with profit. A company funding its own growth needs earnings for inventory, equipment and people. Growth consumes money before it gets around to looking impressive.

Portland, by way of León

The garage gave way to larger premises, including a former pole-dancing studio in Portland. Matsko remembers mirrors and purple paint. It is a pleasingly unceremonious stop between a home workshop and an owned factory. Business histories tend to skip the decorating.

Today the company operates The Studio in León, Mexico. For Matsko, owning manufacturing means being closer to the decisions that determine speed and cost. A different stitch, a new color or a revised product becomes work the company can organize itself. The control comes with the machines, the materials and the responsibility for the people doing the making.

He describes the workshop as a place where ideas can become prototypes, photographs and products quickly. The attraction is clear. If a business discovers that customers want something different, the ability to respond depends on more than the marketing department’s enthusiasm. Somebody has to change what gets made.

Portland remains in the name. Matsko has written about being challenged on that point, and treats the move as part of the company’s ongoing development. The question carries a familiar tension for a growing founder: how much of the beginning must survive? In his telling, the promise to customers concerns the product and its value. The address of the workshop can change while he works to keep that promise.

The customers name the unicorns

Some of Portland Leather’s vocabulary came from its customers. Matsko recalls unusual sample hides accumulating in the earlier studio, then being made into bags. Fans began calling these distinctive pieces “Unicorns.” The name stuck. A practical attempt to use material had acquired a little mythology.

That is the sort of detail a marketing plan can easily flatten. Customers had noticed something, given it a name and passed the name around. Their participation made the bags part of a shared conversation. Matsko likes to talk about stories, and here the story had other authors.

The conversation now reaches into product development. In June 2026, the company’s creator community lead, Wanda Avon, described customer requests for an east-west version of the Lola crossbody. The design team delivered the wider silhouette within months. She also described local fan groups, including one Jasmine Smiley established in Arizona after moving there.

The Gilbert store at SanTan Village was another expression of that relationship: a physical place for customers whose interest already existed. Choosing a location becomes a different exercise when a community has been asking for one. The company can hear enthusiasm before it signs a lease, although the shop must still earn its keep once the doors open.

For Matsko, this returns the business to an early advantage of the art-fair tent. People can tell the company what they want. The channel has changed, and the number of participants has grown, but the usefulness of an actual answer remains.

“The best marketing we have is our bag in someone’s hands; that’s it.”

Curtis Matsko, January 2025

A CEO with the volume left on

Matsko’s public persona has the conversational speed of somebody who expects an idea to improve if he keeps talking. His writing is crowded with exclamation marks, jokes and direct invitations to reply. It is easy to see why he would be uncomfortable with a version of executive life devoted to saying less, more solemnly.

On LinkedIn, he has recalled trying to behave like the CEO others expected him to be: slower, calmer, more conventionally reassuring. In his account, the change unsettled people. The person they knew had begun performing somebody else’s composure.

Mariana Patiño, his assistant and frequent conversational partner, has a visible role in his public work. Matsko describes an elaborate attempt at making videos that failed to capture what happened during an ordinary break. The casual conversation felt better. A laptop and more conversations followed.

His later writing argues for leaving room to stumble over a word, offer a thought in progress and sound like yourself. That preference suits him. The appeal of his appearances often lies in the small detours: a remembered mistake, a joke at his own expense, the next person bringing him back to the question. A polished script would have a great deal to tidy away.

The cap costs how much?

There is a useful counterweight to the large numbers in a video about shopping in Austin. Matsko was startled by a baseball cap priced at $38. He wondered how ordinary purchases had become so expensive. This was the same founder who could discuss a billion-dollar company valuation. The hat, apparently, required a separate committee.

He distinguishes his interest in company profit from an appetite for buying things. The distinction is personal rather than an accounting principle. He wants the business to grow and remain strong, yet describes little excitement about accumulating purchases. His irritation at the cap makes that view less abstract, and considerably funnier.

He has also described a different return on the hours spent online. People he met through LinkedIn became friends, and some traveled to attend his birthday party. In his account, that is a reason to keep showing up. A growing audience can make an entrepreneur more visible; an actual friendship gives him someone to invite.

The company continues to change, and Matsko continues to explain the changes with a mixture of arithmetic and jokes. The journal remains a useful beginning. It reminds us that he once had to answer a simple question about what he would sell. The harder questions arrived after customers said yes. They asked what he would make next, who should make it, and which successful habits he was prepared to put down.