The futons arrived as a problem with upholstery. Jeff Kolovson was still at Dartmouth, running a student furniture-rental company called Evolving Vox, when an order required sixty of them to be assembled in thirty-six hours. Sixty flat-packed promises. One and two-thirds days. Presumably very little sleep and rather too much confidence in the civilizing power of an Allen key.
The company lasted two years and sold for a profit. More important, it gave Kolovson an early encounter with a fact that would follow him through payments, food delivery, home buying, and wholesale commerce: a business is a promise attached to machinery. The promise may be elegant. The machinery rarely is.
Today Kolovson is a co-founder and the chief operating officer of Faire, the wholesale platform that connects independent brands with independent retailers. His public biography reads like an index of modern commerce - McKinsey, Square, Caviar, Opendoor, Faire - yet his work has remained curiously consistent. He finds the point where a system makes someone hesitate, wait, or give up. Then he tries to remove it.
Chapter one
The useful art of fixing what is stuck
Kolovson graduated from Dartmouth in 2009 with a degree in economics and political science. He worked in McKinsey's San Francisco office, then joined Square within six weeks of Max Rhodes, another consultant impatient to move closer to the building. Square in the early 2010s was a useful school: a software company whose little white card reader had to survive contact with counters, cash drawers, clerks, and actual customers.
Kolovson helped take Square's retail distribution from a handful of Apple stores to 15,000 locations across dozens of retailers. Next he started its platform team, opened the company's first APIs, and built the developer program. The sequence matters. First, make the object available. Then let other people build on it. Distribution and extensibility sound like different disciplines until one notices that both answer the same question: how does a useful thing travel?
When Rhodes moved to Caviar, Square's food-delivery business, operations were struggling to scale. He asked Kolovson to take over. Kolovson worked with the data science team and cut delivery times in half. The achievement is pleasingly unromantic. Dinner arrived sooner. In operations, the grand theory must eventually submit to the clock.
The Square years also assembled Faire's eventual founding team. Rhodes brought product judgment and the firsthand experience of selling umbrellas wholesale. Marcelo Cortes brought engineering. Daniele Perito brought data and risk expertise. Kolovson brought the instinct for partnerships, distribution, and systems that had to work outside a slide deck.
Chapter two
A detour with a return ticket
In July 2016, Kolovson left Square and began work on what became Faire. The four founders operated from a San Francisco coworking space, visited retailers, courted investors, built the product, and won a place in Y Combinator's winter 2017 class. It was the familiar startup tableau: conviction, caffeine, and a suspicion among the participants that the others might be the only adults present.
Then Kolovson left. Founding stories tend to be polished into straight lines, but careers are drawn in real time and real time has untidy handwriting. He joined Opendoor, where the operating scale was of another order. As the company grew from a few hundred employees to more than 1,000, he built its growth engine, led a 400-person organization across marketing, sales, business development, and customer operations, and helped expand operations from a couple of cities to more than twenty.
Evolving Vox turns furniture rental into a first lesson in logistics.
Square, its first APIs, 15,000 retail locations, and Caviar operations.
Work begins on Faire with three former Square colleagues.
Opendoor supplies an accelerated education in organizational scale.
Kolovson returns to Faire as chief operating officer.
Max Rhodes never stopped hoping he would return. In May 2019, Kolovson did, this time as COO. The departure had hurt, Rhodes wrote when announcing the return, but the Opendoor experience had become useful preparation. The loop closed without pretending the detour had been a mistake.
Chapter three
The economics of sleeping better
Faire's central problem is easy to describe and unpleasant to experience. An independent shop operates on thin margins and limited floor space. A new product may delight customers. It may also sit there, quietly converting cash into decorative anxiety. Traditional wholesale often demanded that the retailer choose in advance, order in quantity, and live with the result.
Kolovson frames Faire's job as reducing that fear. The platform offers eligible retailers sixty-day payment terms and free returns on opening orders. It uses aggregated data and machine learning to recommend products likely to fit a particular place or customer. It handles much of the administrative fog between a brand and a shop. Convenience is the surface benefit; underneath it sits a transfer of enough risk that a proprietor can try something new without betting the month's peace of mind on it.
This is the operator's version of empathy. It does not stop at saying a decision is difficult. It asks which term, rule, delay, or missing piece of information makes it difficult. Then it changes the architecture around the decision.
The marketplace has grown around that bargain. By 2023, Faire counted 700,000 retailers and 100,000 brands. By January 2025, brands had sold more than $7 billion in inventory through the platform and formed more than nine million new retailer-brand relationships. A November 2025 tender offer valued the private company at $5.2 billion. Valuations travel up and down with the weather. The more revealing measures are relationships formed, products moved, and shopkeepers who return to place a second order.
Chapter four
Global plumbing, local taste
Faire expanded outside North America in 2021. International growth exposed a productive tension in its mission. The company was building a global platform in order to help local businesses remain distinctive. The danger was obvious: build one enormous machine badly and every street begins to look the same.
Kolovson's answer was intensely local. Hire people who understand each market. Adapt currency, language, tax, search, logistics, and the selection of brands. Let a shop in France feel French even when its infrastructure reaches California. “If you get the team wrong,” he has said, “it doesn't matter what else you get right.” Headquarters cannot hop eight time zones every time context goes missing.
By June 2026, Faire's network outside North America included more than 100,000 retailers and 50,000 brands across over thirty countries in Europe, Australia, and New Zealand. Those retailers had formed more than one million relationships with brands and bought more than twenty-two million products. Twenty-six percent of brands on the platform shipped across borders, exporting to five countries on average.
The numbers describe reach, but the operating work hides in the seams. A price must appear in the right currency. Duties should be visible before checkout rather than arriving as an unwelcome epilogue. A search result must understand what a local buyer means, and a shipment needs paperwork that does not turn a candle maker into a part-time trade lawyer. In Kolovson's account of European expansion, each function had to reconsider the customer experience. International expansion demanded that the whole company look again at the product, far beyond simply translating its American version.
That distinction also explains Faire's interest in AI. Kolovson has recently discussed smarter product discovery: using the network's information to help a retailer find what her customers may love. The useful ambition gives a shopkeeper better odds, less clerical drag, and more time for the human work of noticing what belongs on a shelf.
He remains fond of a warning from a mentor: “The prize for winning the donut eating competition is more donuts.” Success creates work rather than abolishing it. A bigger marketplace brings more countries, edge cases, duties, recommendations, and relationships to get right. The joke is funny because every competent operator recognizes the pastry.
Kolovson's career can be read as a series of disappearing acts. The card reader becomes easier to find. The API becomes available. The dinner arrives sooner. The house-selling operation reaches another city. The wholesale order stops feeling like a wager. When this work succeeds, customers scarcely notice the machinery. They notice that they could act.
That may be the cleanest definition of operations: making the right things possible. The sixty futons were never the grand plan. They were simply due.