CATSKILL, N.Y. — Rob Kalin made the bed he sleeps on, the cob oven for the bread he bakes with near religious fervor, the progressive preschool his twin daughters, Zia and Kora, attend on the onetime dairy farm he bought three years ago and his own underwear.

In the five years since Mr. Kalin was forced out of Etsy, the global online crafters’ marketplace he founded in 2005, which went public last year, he has been trying to make a life here that matches his values. In a former mill and furniture factory in two 19th-century buildings that stretch from Main Street to the Catskill Creek behind it, he has assembled a small community of artisans engaged in the same challenge.

Whether he and they can make a living doing so, and at the same time raise the fortunes of their adopted town, is still being debated, he said.

“There’s two very different versions of value,” Mr. Kalin said. “There’s the Walmart and McDonald’s version, which is price and convenience, and then there’s values, and that part is really hard. We’re not purists. We are trying to be practical. But this is a challenge.”

Mr. Kalin, 36, is still the soft-spoken D.I.Y. evangelist he was 11 years ago when he and two friends, Chris Maguire and Haim Schoppik, created their handmade community in his Brooklyn apartment. (By the time he left Etsy in 2011, it was a venture capital darling with revenues over $40 million.) The other day, he was standing in the storefront of the mill buildings he bought out of foreclosure a few years ago, the fallout of a failed condominium project, without knowing exactly what he may do with them.

“What’s a good use for buildings like this in a town like this?” he asked himself. “I’m still figuring it out.”

The property he has named the Catskill Mill is enticing and deceptive looking: The modest storefront on Main Street unfolds into a 20,000-square-foot warehouse connected by a steel-truss bridge enclosed in glass to a 55,000-square-foot warehouse on the creek. Mr. Kalin’s initial thought was to create Catskill-branded products: objects like housewares and furniture made from local materials.

Who would make them, and how local is local? Should the place be a co-op, or would craftspeople work for Mr. Kalin? He and Trevor Babb, an artist who was living in California, spent a week camping in the desert talking it through, and then Mr. Kalin persuaded Mr. Babb to move here.

Mr. Babb and Mr. Kalin are kindred spirits. Mr. Babb, 38, makes cunning Old World “disaster kits” — steamer trunks and wooden boxes filled with supplies, tools and materials, like seed libraries — for the end times; he calls them “fantastical provisions for the post-apocalyptic homestead.” In 2009, when he had a show of this work in Red Hook, Brooklyn, Mr. Kalin bought a piece called “Shelter,” a sculptural object made from a large hunk of wood embedded with axes, picks and machetes, and they became friends. Mr. Babb also makes exquisite leather luggage.

Mr. Kalin makes refined wood furniture of Shakeresque simplicity, and extremely high-end horn speakers and other bespoke stereo componentswith Jeffrey Jackson, 43, an engineer and hi-fi designer from Memphis, who moved his entire family (and his collection of World War II-era electron tubes and other audio arcana) here to collaborate with Mr. Kalin.

“Jeffrey is one of a half-dozen people who understands this stuff,” said Mr. Kalin, introducing Mr. Jackson, a lanky man with a shock of curly brown hair.

Mr. Kalin can seemingly make anything. (Well, knitting still confounds him, he said, as do bagels.) Not too long ago, he made a unisex tunic he colored with cochineal — a carmine dye yielded by insects that live on cactuses, a favorite of the Aztecs — in shades from bubble-gum pink to a dark royal purple.

He made the tunics for friends, enjoying the intimacy of fitting a garment to a loved one, and he made one for himself, hoping it would give him a more Roman silhouette, he said. “But it ended up looking like a shift dress.” (Photos he sent prove otherwise: In purple knee socks and scuffed leather boots with straps and buckles, he looked rather like an extra from “Ben-Hur.”)

Mr. Kalin has had a foothold here since 2008, when he began renting a 1920s duck hunter’s camp on a finger of land overlooking the Hudson as a weekend place. Not that he got up here much. In Brooklyn, he was sleeping on the floor of the unheated warehouse that was Etsy’s office. In 2009, when he was first able to sell his stock in Etsy, he bought the house with the proceeds. By then, he was dating Layla Delridge, who was working on a D.I.Y. sewing website in the same building as the Etsy office.

Mr. Kalin has been on his own since he was 16, when he left home to work in a photo shop (he wanted to be a photographer) and live in an artist’s squat with an uncle in Boston. His parents were divorcing, and he was bullied in school. He did return to high school and is proud to tell you he graduated with a D average.

Afterward, he spent a year at the School of the Museum of Fine Arts, Boston, while sneaking into art and design courses at M.I.T. using fake ID cards he and a friend had made for themselves. (He crashed classes at Harvard, too, because there was a girl there he was interested in, but found them too boring to continue.)

He later moved to New York and worked at the Strand bookstore and for a construction company, among other jobs, while sneaking into night classes at the New School. Eventually, he graduated from N.Y.U.’s Gallatin School of Individualized Studies with a concentration in classics. When he and a classmate, Mr. Maguire, made a website for the founder of Getcrafty, a how-to site for the booming indie-craft movement, Mr. Kalin had an idea to create a digital marketplace for these new makers.

As for the name Etsy, its origins are still a mystery. It has been reported that Fellini’s “8½” will yield a clue, or that the name is a play on the Latin for “What if?” (Et si?) Mr. Kalin remains mischievously closemouthed. “Gee, I plumb forgot,” he said.

Either way, Etsy was perfectly tailored to the movement at the time: an agora for the whimsical and the twee (crocheted toilet paper, anyone?), as well as for the useful and the beautiful, like handmade clothing, ceramics and furniture. (Perhaps inevitably, Regretsy, a blog parodying its most out-there wares, like felted vulva necklaces, appeared.) Along with a virtual storefront, Etsy offered its sellers skill- and community-building workshops and residencies.

While its community grew exponentially each year, and Mr. Kalin and Mr. Maguire were joined by Mr. Schoppik and Jared Tarbell, Etsy soon struggled under the ambitious idealism of Mr. Kalin, always an eccentric chief executive. In 2008, he hired Maria Thomas, a senior vice president for digital media at National Public Radio, to help focus the business; he then stepped aside and offered her his job.

Two years later, he stepped back into the role, only to be fired by his board in 2011.

“Rob is more of an artist than an entrepreneur, but the two are similar and related,” said Fred Wilson, a founder of Union Square Ventures and an early investor in Etsy. “They both require risk taking and doing things differently.”

Five years ago, Mr. Kalin said, he could have talked about being “sacked for days.” “Now, I’m just really grateful for my experiences with Etsy, and I’m so glad I’m not the C.E.O. of a publicly traded company,” he said. “I got off the ride not when I thought I would, but I take a very karmic view of things. If the universe gives you a hint and you don’t listen, it gives you a kick.”

Mr. Kalin and Ms. Delridge moved here full time the year he was fired and got married; their daughters were born in 2012. The couple are now separated, and Ms. Kalin runs an avant-garde fashion boutique in Hudson, N.Y. “We are trying to be kind to each other and just be good parents,” Mr. Kalin said. “Having kids is a gigantic emotional reset. It’s been a clarion call for me to try and figure out the way I want to live my life for my kids.

This town of just under 12,000 has welcomed Mr. Kalin and his collaborators, said Kay Stamer, the executive director and founder of the Greene County Council on the Arts. After the blows of the last recession, “we are on the upswing again,” she said. “Not the least of it is thanks to Rob and Trevor and company, who have opened their hearts and space to us.”

The town may still be searching for its cultural identity, said James Male, the principal of House Hudson Valley Realty, but Mr. Kalin has been a course correction for the place. “The cultural identity that it’s wrapping its arms around now is crafts, the arts and dance,” Mr. Male said. Last year, his office sold a 19th-century former lumberyard complex to the American Dance Institute, now based in Maryland, which plans to turn it into a performance space and artists’ housing, opening in 2018.

Mr. Male and an associate, Michele Saunders, have been selling Main Street properties to artists relocating from SoHo, Brooklyn and Beijing, he said, with prices about half what they are in nearby Hudson. “My clients who want to be ‘over there’ don’t want to be in the hubbub of Hudson,” he said. “People who could live anywhere they want choose to live in Catskill, because it’s still under the radar. It also has a great food truck.”

Not anymore. In 2013, Mr. Kalin bought a food truck and hired a chef to create a Vietnamese menu for it, as a way of sticking his toe into the waters of food service.

“But it was hard to make money,” Mr. Babb said. “We had all these limitations. We need to use locally sourced materials. We need the packaging to be compostable. We need to pay everyone a living wage, and we need to keep the prices low so everyone in Catskill can afford it. Which is basically impossible economics.”

They ran the truck for two seasons, a humbling experience, Mr. Kalin said, recalling mishaps like the night the truck broke down minutes before a benefit. “We made amazing food and fed a lot of people we cared about, but even in its best month, it lost about two grand,” he said.

All during this time, Mr. Kalin, Mr. Babb and others were working to clean and stabilize the mill areas. They were trying various scenarios: Could they make and sell local products under one house brand — clay, leather, textiles and wood, for example?

“We had a metal shop for about a minute,” Mr. Kalin said, but it was too noisy, and metal is tricky to source locally.

They hired Margot Becker, a 29-year-old fiber artist who lives across the river in Hudson, as a consultant to set up some looms for them and work through, as she put it, “some fiber-processing ideas: What does it mean to make something from start to finish? What does it mean to be a hand artisan, and how does one make a living? Also, how do you fit that into Catskill, whose economy isn’t New York City? Paying the right amount for a woven thing that’s been made from start to finish is a huge luxury.”

Kurt Holsapple, 65, a local furniture maker who met Mr. Kalin when he built him a kitchen, came on board as well, to the delight of the everyone. Mr. Holsapple, a free spirit and charmer who describes himself as “dyslexic and colorblind, with a touch of Asperger’s,” makes graceful wooden furniture and fine art from natural materials that look like miniatures by Robert Smithson. The recession here had hit him hard.

“I went into foreclosure while I was doing Rob’s kitchen,” he said. “I was picking up side jobs, but I couldn’t make enough to pay my taxes, so I just gave up on paying my mortgage. When Rob found out, he was just setting up the mill and said, ‘Let’s invite Kurt.’ I had $200 when I came in. I do feel very lucky to be here, because at my age, he’s giving me a chance to not worry about making money for a few years.

“Rob is a patron, in a sense. This has been like going back to college, but I’m the old fart.”

Three years ago, Mr. Kalin bought a former dairy farm on 300 acres near his property. With a group of parents, he created a preschool there. In the cathedral-like Dutch barn he is restoring, he hoped to put an elementary school, but adhering to building codes would have meant destroying the character of the old timber framing, so he is searching for other options.

In 2014, he bought another property, a ravishing but derelict 1812 brick townhouse that’s nestled behind Main Street and across from the warehouse on the creek.

“We went through 18 different possibilities,” Mr. Babb said of the house. “It’s a bakery! No, it’s a bakery and a cafe and a fine-dining restaurant. No, it’s none of those things. It’s an elementary school. No, it can’t be that because it’s too close to a local bar. O.K., it’s just a house, but who’s going to live there? O.K., I’ll live there! But Rob’s like, ‘You can’t live there; you can’t be a plantation owner. It can be a guesthouse. No, you can’t have an empty guesthouse, you can’t not rent it out. O.K., it’s a B&B, and oh, it’ll be like a showroom, too. Wait, it can’t just be a retail setting, that’s too tacky. …’ This is how we think.”

The plan now is to turn the house into a B&B filled with goods that have been made by Ms. Becker, Mr. Holsapple and others, so that guests can live with the wares of the Catskill Mill. Dishware and other ceramic pieces — including the sinks — were made by Asia Sosnowski, a 27-year-old ceramist, from clay dug out of Mr. Kalin’s land. Sconces and chandeliers are being designed by Laleh Khorramian, 42, who also makes handmade garments like mommy/baby quasi-space-age resort wear.

Mr. Kalin commissioned these pieces — furniture and towels and rugs and ceramics — from their makers and may commission more, he said, though the present arrangement has the artisans concentrating on their own work in studios set up throughout the Main Street warehouse.

On a recent afternoon, Mr. Kalin had made enough bread to send a few loaves home with a photographer and a reporter, who were eating handfuls of it and standing around an elegant butternut dining table and benches. The furniture was made by Mr. Holsapple and Mr. Kalin, and set in the mill’s storefront.

Mr. Kalin disappeared to find wrapping for the bread and was gone a bit longer than you would expect it to take to find a suitable container. As it happened, he was making bread bags, which he sewed from muslin scraps and then signed, faintly, with his initials.

“At one point, I created too much here,” Mr. Kalin said, noting his habit of stretching himself too thin. “A friend said, ‘When the phone rings, you always answer it.’ But if you aim too high and try to come in a little bit lower, you’re still way up in the clouds.”

A version of this article appears in print on May 5, 2016, on Page F14 of the New York edition with the headline: After Etsy, Scratching an Itch. Order Reprints | Today’s Paper | Subscribe

By Penelope Green