Shaul Olmert and the trouble with a good story

Shaul Olmert once carried business cards that offered an unusually efficient introduction. They contained the results of personality quizzes: Spider-Man, a pirate, Tokyo, the Big Lebowski. Most people settle for a title and a telephone number. Here was a founder who could apparently supply a previous life and a suitable city as well.

The cards were an advertisement for Playbuzz, the company he co-founded with Tom Pachys. They were also a neat little joke about identity. Ask a few questions, receive a flattering answer, pass it around. A person becomes legible to friends in seconds. The business grew around that small, pleasurable transaction.

Years later, Olmert would take up the same subject in a less cooperative format: the novel. His second, Gutfreund, appeared in 2026. Its central character carries the weight of family, childhood and friendship. There is no convenient results card at the back. For a founder associated with fast answers, this is an interesting choice of work.

Between the quizzes and the books sits a career in games, television, startups and now AI. The recurring concern, as he has described it, is giving people ways to express themselves. Following that concern produces a more revealing portrait than simply counting the companies. It also explains why a supposedly frivolous quiz and a carefully written novel can belong to the same working life.

The pupil who became the partner

Before the funding rounds, Olmert taught computers. One of his pupils was Pachys, whom he met when the boy was 12 and he was 22. Olmert encouraged Pachys’s parents to pursue university study for their son. Later, he invited the young programmer to New York to gain experience; Pachys spent about a month sleeping on his couch. They subsequently worked together at SundaySky.

Playbuzz brought that relationship into a different arrangement. Pachys initially joined as an employee, then became co-founder as his responsibility grew. In October 2019, when Olmert stepped down as chief executive, Pachys succeeded him. A relationship that began in a classroom had become a business partnership and, eventually, a succession.

Other jobs supplied different kinds of schooling. Olmert studied interactive telecommunications at New York University, and worked in digital media at Oberon Media, MTV Networks, SundaySky and Conduit. At MTV he was a vice president responsible for digital products and online gaming. These were jobs at the meeting point of entertainment and software, where a familiar character had to become something an audience could actually play.

The titles mattered to him. Looking back on corporate life, he described the appeal of a good position and the eventual need to ask what he wanted to make. One test was whether he could explain his work to his children with pride. That is a demanding audience: children are famously unimpressed by reporting lines.

A little game with a large audience

Playbuzz was founded in 2012; its public site launched in December 2013. Its tools let publishers and other creators assemble quizzes, polls, lists and similar interactive pieces, then share or embed them. The distinction mattered. A successful item could travel beyond the company’s own site, and a publisher could use the machinery without building it.

By November 2014, Playbuzz had reached the top of the Facebook publisher-sharing rankings, with approximately nine million shares. Those are historical sharing figures, rather than a measure of today’s business. But they help explain the sudden attention around a young company selling something that looked suspiciously like a pleasant way to avoid work.

There was a serious publishing argument underneath the amusement. Readers encountering stories through a phone or social feed could arrive at almost any page first. A publication had to earn their attention there. Olmert advocated varying formats to suit that environment: an interactive piece could ask readers to take part, making the encounter more personal than a paragraph they merely passed over.

A quiz result gives its owner a small conversational object. Sharing it invites agreement, argument or the discovery that one’s friends have all been assigned the same fictional character. That is an editorial reading of the appeal, rather than a scientific account of personality. The result need only be interesting enough to start the exchange.

When the founder leaves his own story

Growth gave Playbuzz a larger operation to manage. By the time Olmert’s departure as CEO was announced in October 2019, it had raised nearly $70 million and operated internationally. The business had also been changing, expanding from interactive formats into branded content for commercial partners. A restructuring in June 2018 had cut 25 jobs from a workforce of 180.

The announcement said Olmert would become president while Pachys took over as CEO. By September 2020, Olmert described Playbuzz as continuing without his involvement. The company became EX.CO. His place in its history is as co-founder and former chief executive, a distinction that matters when a company keeps evolving after the person leaves.

His account of starting again was strikingly specific. After leaving, he wanted quiet. Later, he began missing product checks, the morning look at usage and revenue, and exhausted meetings rescued by somebody’s new suggestion. He missed belonging to a shared undertaking. It was the work, in its ordinary and repetitive details, that pulled him back.

The next company had a name designed to invite disbelief: Flying Pigs. Olmert and Ilan Leibovich founded it in 2020, with Piggy as the product. Olmert explained the name through the familiar phrase about impossibility. After years of presenting a company to investors, he had chosen to put the objection right on the stationery.

“I simply wanted quiet.”

Shaul Olmert · on leaving Playbuzz, 2020

The pitch deck becomes the demonstration

Piggy asked a practical question. If people already made expressive things on their phones, why should a document or presentation require them to return to the conventions of the desktop? The app offered mobile creation for presentations, invitations, school projects and other documents, using the visual and interactive vocabulary people knew from social platforms.

In November 2022, Piggy announced $7.7 million in seed funding led by Insight Partners, with Remagine Ventures and Stardom Ventures among the participants. Olmert said the company had used a Piggy-made overview deck with investors. That gave the pitch an appealing economy: the sales presentation could also serve as the product demonstration.

The ambition extended beyond making an existing page fit a smaller screen. Piggy incorporated media and interaction, with recipients able to view shared creations without registering or downloading an app. Olmert discussed mobile résumés as one possible use: applicants could present themselves through video and other expressive elements, rather than relying entirely on a conventional document.

By a July 2024 interview, he was describing his newer work under the name KwaKwa, a platform for short mobile courses. His public promotion invited people to turn expertise into a course using an interface familiar from social apps. Documents and courses are different products, but the underlying question remains recognizable: what would people make if the tools felt natural to them?

An answer that takes 215 pages

Alongside the products came fiction. His first novel, The Dream Sellers, was published in Hebrew in 2021. It follows a startup founder, Gadi Hasson, through the promises and pressures of the technology business. A world Olmert knew professionally became material for a story about what ambition asks of the people pursuing it.

There is an obvious temptation to treat a founder’s novel as a collection of disguised office gossip. The more useful distinction is between a business account and fiction. Fiction can give room to a person’s competing loyalties without having to finish with a lesson for the next board meeting. A character is allowed to remain inconvenient.

Gutfreund, his second novel, runs to 215 pages. It begins with an incoming call bearing the name of Yiftach, more than a decade after Yiftach’s death. Its protagonist, Zohar, is a factory worker with a very different earlier life: a promising student, the son of a prominent figure, and a childhood friend still attached to what that friendship meant.

Olmert described spending five and a half years working on the book. In announcing it, he recounted his daughter asking what occupation she should put down for him on a form. He acknowledged the discomfort of being without a job title, even by choice. The question he had once asked himself about explaining his work to his children had acquired a rather literal sequel.

He also writes book recommendations at Sipur Tov, a Hebrew-language reading blog. The activity places him on the reader’s side of the transaction as well as the author’s. It is a useful detail in a career so closely concerned with audiences: sometimes the job is simply to read somebody else’s work and decide what to say about it.

Back to the business of participation

In September 2026, Cesura AI announced Olmert as its CEO, joining co-founders Yuval Haber and Itai Hochman. The company builds a platform for simulation-based training, assessment and research. Its stated ambition is international expansion and wider access to simulations across languages. Here, participation means practicing an encounter rather than clicking through a quiz.

The appointment adds another medium to the sequence. Games turn a viewer into a player. Publishing tools turn a reader into a maker. Simulations let somebody rehearse a situation. The novel asks for a different participation again: attention sustained long enough to enter another person’s life. That connection is a reading of his career, but it fits the choices he has publicly described.

There is room in this portrait for less solemn preferences. He has named Homer Simpson as an inspiration, declared his enthusiasm for peanut butter, and said he speaks fluent Yiddish. None is a business strategy. Together they offer some relief from the immaculate founder biography, in which every childhood hobby must foreshadow a funding round.

Olmert’s own record supplies a more interesting ending than a victory lap. There is a former student running the company they built, a new CEO role, and a book whose central friendship resists a quick description. The old business cards could tell you that he was Spider-Man. The subsequent years have given him quite a bit more to write on the other side.