Cyrus Massoumi and the art of starting again

Cyrus Massoumi’s first startup began at the wrong end of a pair of shoes. His feet were size 13. Buying footwear online meant sending plenty of it back, and the early internet had made ordering rather easier than returning. In 1999, he founded OneSizeTooSmall to improve the process. The name had the pleasing advantage of explaining itself before anyone opened a pitch deck.

The company folded. Years later, Massoumi described errors beyond the collapse of the e-commerce market: he had addressed a problem customers ranked below winning new business, waited too long to raise money, and let employees work without pay. He regretted that last decision. His account gives the venture a more uncomfortable ending than the familiar startup fable in which failure arrives, teaches a lesson, and politely excuses itself.

“My first company was a failure,” he wrote. It is a useful place to begin with someone better known as Zocdoc’s co-founder and founding CEO. The first business left him with questions about customers, cash, and the obligations of a founder. Those questions would outlast the company. A shoe that does not fit is annoying. A business that does not fit its customers’ priorities is considerably more expensive.

The people at the next desk

His route to Zocdoc ran through several institutions and one shared desk. After graduating from Wharton in 1998, Massoumi joined Trilogy Software in Austin. There he worked alongside Nick Ganju, who would become a Zocdoc co-founder. After OneSizeTooSmall closed in 2001, he spent six months backpacking through China, considering what to do next. The pause sits between two very different chapters of his working life.

He earned his Columbia MBA in 2003, receiving the Heffernan Award for Outstanding Service, and went on to McKinsey. A project there brought him together with Oliver Kharraz. In 2007, Massoumi, Ganju, and Kharraz founded Zocdoc. Two future partners had come from previous workplaces, years apart. The founding team had a history before it had a company name.

That sequence makes a small argument for paying attention to colleagues before they become useful names in an address book. Massoumi’s career contains the expected degrees and consulting experience. It also contains the less tidy interval in China and an unsuccessful venture. Read together, the entries resist the flattering illusion that a successful founder was always following a successful plan.

Twenty chairs, then a company

At Zocdoc, advice from investor Vinod Khosla gave Massoumi a number to remember: 20. The first twenty employees, Khosla told him, would determine the character of the company. Hiring demanded attention to the qualities people brought with them, rather than a willingness to fill seats quickly. Massoumi returned to the advice publicly in 2014. A small early team could establish habits that survived its own smallness.

A number makes the principle tangible. Twenty people can know each other. They can observe who gets heard, who receives credit, and what happens when somebody raises an awkward objection. The next employee joins a workplace where those answers already have examples. Culture acquires a cast before it acquires a handbook.

Massoumi had also learned that a launch did not automatically produce customers. Zocdoc debuted at TechCrunch in 2007; the founders expected demand immediately. The first booking took days. In his later account, activity accumulated gradually before growth accelerated. He wished he had hired good people when he met them, even before an obvious opening existed. Both lessons require patience, although one concerns waiting for demand and the other concerns recognizing a person before a job description catches up.

A pizza restaurant’s contribution to recruiting

During a visit to Chicago as Zocdoc prepared to expand, Massoumi and colleagues met a restaurant server who remained helpful and composed under pressure. They were looking for an office manager and encouraged her to apply. By 2013, he was describing her ability to negotiate property deals and her contribution to the company’s culture. A pizza restaurant had supplied evidence that a conventional résumé might have missed.

He also admitted to an earlier recruiting mistake: passing on a business-development candidate whose qualities impressed him because the experience on paper seemed insufficient. The regret mattered to his argument. He had participated in the very screening habit he now wanted managers to question. It is easier to recommend an open mind after noticing where one’s own mind closed.

His phrase for the alternative was “hiring for intrinsics.” He emphasized curiosity, thoughtfulness, a willingness to speak up, effort, and interest in the organization’s purpose. Skills could be developed; these qualities required a different sort of examination. Zocdoc hired people with backgrounds in athletics, music, acting, science, and street canvassing. The recruitment philosophy widened the search without removing the need to judge candidates carefully. In this version of office life, serving dinner could be a relevant audition for organizing the people who ate it.

The $498 management decision

Another account of Massoumi’s management comes from Justin Welsh, who worked in Zocdoc’s sales organization. Welsh recalled joining the company at 28 and living on a friend’s couch in Brooklyn. After earning enough to rent a tiny East Village bedroom, he furnished it with an uncomfortable futon. One morning, Massoumi noticed how exhausted he looked and asked what was happening.

Welsh explained the sleeping arrangement. Massoumi handed him a check and told him to buy a bed, with a spending limit of $1,000. Welsh bought one for $498. Years later, he used the incident in a talk about sales culture. The purchase had remained vivid long after its immediate usefulness.

There is something wonderfully literal about this intervention. The employee’s problem involved furniture; the response involved buying furniture. The memory offers a narrow, concrete view of the relationship, and Welsh is the person telling it. It also supplies a counterweight to abstractions about valuing a team. A founder can spend a long time perfecting a statement about employee loyalty. An employee may remember the afternoon he was sent to a mattress shop.

When the founder’s chair disappeared

Massoumi led Zocdoc for eight years. His time as CEO ended in 2015, and the departure became the subject of litigation. He alleged that Kharraz, Ganju, and executive Nettana Samroengraja had committed fraud ahead of a board meeting that led to his removal. The complaint made his separation from the company a contested part of the story.

On April 14, 2026, a New York appeals court unanimously affirmed the judgment dismissing that complaint. The decision found no triable issue of fraud on the incidents he identified. It also said the directors were not required to warn him that the board might terminate him. The allegations did not become findings of wrongdoing.

The outcome belongs alongside his account of leadership. Building a company, recruiting its people, and remaining in charge of it are separate accomplishments. The founder’s attachment can continue after the authority ends. In Massoumi’s case, the next chapters involved investing and founding again, while the dispute over the old chapter continued for years. The career did not arrange itself into a clean succession of departures and fresh starts.

Ambition gets a quieter business card

With Indiegogo co-founder Slava Rubin, Massoumi built humbition, a venture firm whose name joins humility and ambition. By January 2019, the partners were investing from a $30 million inaugural fund. The premise grew out of their own experience: investors who had operated companies could offer advice that felt useful to founders facing the same kinds of decisions.

Massoumi pointed to Marc Benioff, Jeff Bezos, and the PayPal founders as helpful operator-investors during Zocdoc’s growth. Humbition aimed to connect that experience with a new generation of New York entrepreneurs. Its approach placed importance on the founding team, early traction, and an understanding of the economics of the business. It had already backed furniture company Burrow.

His investing life also reached beyond the firm. He was among the early backers of Urban Compass, the real-estate startup launched publicly in 2013. The shift from founder to investor changes which chair a person occupies at the table. It does not eliminate questions about hiring, focus, or whether customers will buy. For Massoumi, those questions arrived with memories attached. The fund’s deliberately modest-sounding name leaves room for considerable expectations.

A detour with a wagging tail

One of Massoumi’s ventures pursued a problem outside the usual telling of his career: lost dogs. Shadow brought owners, volunteers, and information about missing pets into a common network. In a 2020 interview, he described the business alongside philanthropy and his work at humbition as three strands of his activities after Zocdoc.

A Columbia biography described Shadow as a community of people searching and people finding, drawing on his previous experience building networks. The underlying task was recognizable even with different participants. Information could exist in several places while the person who needed it struggled to bring it together. Software offered a way to organize the search, while volunteers supplied the human attention.

Shadow closed in October 2021. A humane purpose did not guarantee that the company would last. Its place in the career is still revealing: Massoumi had taken a familiar organizing problem into a setting where the desired outcome was a reunion. Founders collect attempts as well as achievements. This attempt deserves its past tense, and its place between the better-known company names.

Back to Columbia, with revisions

On May 16, 2026, Massoumi returned to Columbia Business School as the distinguished speaker for its MBA and Executive MBA recognition ceremony. Twenty-three years separated his own MBA from this appearance. By then, he was founder and CEO of Dr. B and a founder and managing partner of humbition. Harvard’s Innovation Labs also listed him as an expert who could help founders with pricing, capital, market strategy, and hiring.

At Columbia, he described how his formula for success had changed. People remained central. Experience had brought a greater emphasis on focus, sufficient time, and alignment with purpose. The polished version was “Great people, purpose alignment, focus, and time.” He urged graduates to develop their own equation. Advice, in his telling, could be revised rather than preserved in glass.

That is a fitting destination for a story that starts with returns. The shoes sent back in 1999 led to a company that failed; colleagues from earlier jobs helped form a later team; a restaurant encounter changed someone’s career; a sales employee remembered a bed. These are the particulars behind an otherwise familiar list of founder titles. Massoumi’s career makes room for ambition, and keeps leaving evidence that ambition needs people, patience, and the occasional change of plan.

“Your formula absolutely needs to be your own.”

Cyrus Massoumi / Columbia, 2026