Rob Kalin built Etsy. The workshop never left him.

Rob Kalin made his own furniture. He also made his own underwear, a detail that business profiles found considerably more startling. A chair is evidence of craftsmanship; apparently, making one’s undergarments suggests a position on civilization. For Kalin, both belonged to the ordinary pleasure of doing something yourself. That pleasure helped produce Etsy. It also posed a question that would follow him through the company and out the other side: could making things become a way to make a living?

His career has moved between the screen and the workbench, with occasional stops in the boardroom. The boardroom supplied money and complications. The workbench supplied the original reason for being there. To follow Kalin through the founding of Etsy, two terms as its CEO, and later experiments in Catskill is to watch those different rooms compete for his attention.

A shop for people who made things

Before the company, there was a succession of jobs. Kalin worked as a department-store cashier, in a camera shop, on demolition work, as a carpenter, and at New York’s Strand bookstore. He also worked for an elderly Viennese philosopher. It is a résumé with little respect for a straight line, but plenty of contact with materials, customers and the business of getting through a day.

He graduated from New York University in 2004, after an uneven route through higher education. The woodworker who emerged was trying to find buyers for his furniture. Existing online commerce offered reach, but Kalin wanted a setting that felt suited to the people making the goods. A handmade object could look rather homeless in a marketplace arranged around everything else.

Work on GetCrafty, an online community run by Jean Railla, put that frustration into company. Kalin and his collaborators could see other craftspeople asking where their work belonged. Here was a community that could exchange advice and encouragement, yet still needed a practical route to customers. A conversation about craft had revealed a problem in commerce.

Etsy launched in June 2005. Kalin worked on design; Chris Maguire and Haim Schoppik handled programming. Jared Tarbell was also part of the founding team. The first version came together in a Brooklyn apartment over a matter of weeks. Sellers received their own online shops. Someone with a small inventory could begin without commissioning an entire website or persuading a retailer to take a chance.

By October 2007, Etsy had 100,000 active sellers and half a million members, with more than a million items sold through the site. Those figures describe people finding an outlet as well as a company finding an audience. The appeal was understandable: the maker could stay visible, and the shop could remain theirs.

A nonsense word, a serious ambition

Even the name left room for invention. Kalin connected Etsy to watching Federico Fellini’s 8½, listening to its sounds and wanting a word whose identity could be built from scratch. In an early interview, he spoke about the film’s invented childhood words and their suggestion of magic. The name arrived without a tidy description of the business attached. It had the useful quality of needing an explanation.

Early Etsy made browsing part of that explanation. One interface let visitors choose goods by color, with animated pictures responding to a colorful grid. Shopping could involve curiosity and play. It suited a site where an object’s peculiar charm might be precisely what made it desirable. A very efficient search for something you already know you want leaves little room for falling in love with something faintly absurd.

But Kalin also wanted the business to become large. Years later, Maguire recalled disagreement within the founding team over taking investment and pursuing household-name scale. Maguire preferred a sustainable, interesting company. Kalin wanted a broader reach. That recollection complicates the easy picture of an artist merely carried away by commercial events. The ambition to grow was part of the original argument.

Small fish, expensive water

When Etsy announced a $27 million investment in 2008, Kalin explained its collective ambitions through Leo Lionni’s Swimmy. The children’s book follows small fish who organize into the shape of a larger one to protect themselves. It was an apt image for independent shops gaining strength together. It also left a deliciously awkward question floating nearby: what happens when the organization itself becomes very large?

Management changed as the company expanded. Maria Thomas succeeded Kalin as CEO in 2008; he became chief creative officer. He returned to the CEO position in December 2009. In July 2011, chief technology officer Chad Dickerson took over. Kalin’s title changed several times in six years, while the marketplace kept accumulating responsibilities that could hardly be settled with another design idea.

His sympathies remained plain. “I admire the makers of the world,” he said. Yet sympathy alone could not settle the practical tension inside handmade commerce. If one person makes every object, increasing demand eventually meets a stubborn physical limit. There are only so many hours available for cutting, stitching, packing and explaining why the parcel has not arrived.

The marketplace’s early rules made that limit consequential. Sellers who needed help producing more goods could find their growth at odds with the definition of handmade. To a customer, personal production might be the attraction. To a seller facing a large order, it might become an obstacle. The same promise could feel generous from one side of the transaction and restrictive from the other.

Scale brought another design problem: finding things. By 2012, Etsy was doing business in 150 countries. Its abundance could make browsing feel like discovery or like getting lost. The company had to help customers navigate while giving individual shops a chance to be seen. Gathering small businesses together was only the beginning; deciding how attention moved among them was an enduring responsibility.

The workshop gets an address

Kalin’s response to makers’ needs also took a physical form. Through Parachutes, he offered workspace and business workshops to a small group of Etsy companies. The experiment addressed the gap between being good at a craft and running the enterprise around it. A sewing machine does not automatically confer knowledge of pricing, bookkeeping or how to survive a quiet month.

He also saw possibilities beyond Brooklyn. When Etsy established support operations in Hudson, Kalin was interested in the effect jobs could have on a smaller town. Having a Catskill house made the location practical for him, and the train journey made it accessible from New York. Remote work, in this case, had a timetable and a station.

In 2013, Kalin and Trevor Babb opened the Catskill Mill project, bringing craftspeople into former industrial buildings. Woodworkers and ceramicists could use equipped spaces. A marketplace had helped people distribute their work; a shared workshop could help them produce it. The move shortened the distance between an idea about independent making and the sound of someone actually getting on with it.

“I’m an artist and the Web is my medium.”

Rob Kalin, 2012

The property changed hands in 2017, when Kalin sold the 50,000-square-foot Catskill Mill to Steve and Stef Halmos for $1.9 million. Their plans centered on an arts building with studios and programming. That sale belongs in the story, too. Projects acquire new owners and new uses; enthusiasm is seldom a permanent deed to a building.

Alongside these ventures was the smaller activity of learning another useful thing. An educator biography described Kalin making furniture, baking bread, learning to sew, and learning to farm outside Catskill. At Kite’s Nest, he taught a course called Give Me Shelter. The list has the appealing untidiness of someone for whom competence in one subject is an invitation to become a beginner in another.

Land, classrooms and a different kind of tool

Education became a more substantial undertaking through Catskill Montessori School. Kalin helped found it with Gaura and Narottama Tester. He brought land to the project and served as the initial board chair. The school opened in fall 2020, with 31 children in its first group and a practical emphasis on learning through the surrounding land.

The work was shared. Gaura brought educational leadership; Narottama helped build gardens, playgrounds and the physical setting. Kalin’s contribution gave the venture ground to stand on, quite literally. The school’s founding account remembers an open house with paint still drying and tables awaiting chairs. Institutions, like furniture, have a stage when their eventual usefulness requires a little imagination from everyone present.

His later technology work adds another object to this collection. In June 2025, a report linked Kalin’s startup Dopple Works to Loop, a handheld spatial-computing device resembling a magnifying glass. The proposed form put a display in the user’s hand rather than a headset over the eyes. Learning and play appeared among its intended uses. At that point, these were reported plans and public filings, with commercial execution still a separate question.

A firmer dated marker followed on June 9, 2026. A US design patent for a mobile computing and gaming device, assigned to Dopple Works, named Kalin alongside Geoff Chatterton and Gregory Fodor. A patent establishes a documented design contribution. It leaves the product’s reception to another day.

The shape of the career is pleasingly irregular: furniture, online shops, workshops, classrooms, a device to hold. Each carries a different version of the question that began in Brooklyn. What could someone do if the right tool, space or opportunity were within reach? Kalin has tried several answers. He has also kept the workbench available, which seems wise. There is always another joint to fit.