Alex Cyriac and the value of an old friend

Before Alex Cyriac had a co-founder, he had a friend who gave him a hard time about sports. Shobin Uralil was the athletic one, at least in the friendly account Cyriac later offered of their childhood. Years before there was a company to run, the future partners had already established a useful entrepreneurial tradition: one of them could be relied upon to keep the other’s ego in check.

By 2016, they were building Lively together. Cyriac became CEO; Uralil became COO. Their business would require software, capital, employees, and customers willing to trust a new name. The relationship between the founders, however, came with a much longer operating history. Their parents had known each other before either of them was born.

It is an unusually human starting point for a software company. A founder can spend months looking for the right partner, checking references and comparing ambitions. Cyriac’s story begins with someone whose family had been showing up at the same gatherings for years. There was plenty left to discover about building a business. There was less mystery about the person on the other end of the phone.

The friend before the founder

Cyriac grew up in Southern California and moved to the Bay Area after college. Uralil lived across the country. They saw each other at weddings, birthdays, and other events, the sort of occasions where the grown-ups talk and the children gradually become grown-ups themselves. Their friendship survived the distance.

As adults, they also had opportunities to observe each other working. While Uralil was involved with an earlier startup in Boston, his visits to San Francisco included stays with Cyriac. Cyriac later described being impressed by the effort he saw his friend put into that earlier business. His respect for Uralil had a basis in experience before the two began working together themselves.

“Shobin to me is the definition of grit.”

Alex Cyriac, 2018

Their shared family history later became the subject of a joint podcast conversation. It gave the partnership a context wider than a cap table: mutual respect, family expectations, and years of watching each other make decisions. Those ties do not remove the risks of starting a company. They offer a different way of assessing the person who will share them.

A department of one

Cyriac studied computer science at the University of California, Santa Barbara. His early career moved through programming, implementation, payments, and business development. Eventually, at Justworks in New York, he became head of operations. That progression put him close to both the machinery of a service and the people expected to use it.

A contemporary account of Justworks at the beginning of 2015 supplies a particularly good detail. Cyriac was the “one-man operations team.” Customer experience had its own department of one, Marc Rosenberg. The grand organizational chart, at that moment, would have required very little paper.

Justworks grew from roughly 20 people to more than 75 during 2015. The retrospective describes the work behind that expansion: closing out the previous year, processing paperwork, handling rising volume, and getting ahead of the next problem. These are the jobs that make growth possible without usually becoming its publicity photograph.

For a future founder, such work offers a demanding education. A customer buys an outcome. Inside the company, delivering it may require several systems and several people to agree. When a department consists of one person, the distance between discovering a problem and becoming responsible for it can be admirably short.

The first believers

In mid-2016, Cyriac left his job to pursue Lively. Uralil was still in Boston. There were engineers to find and a product to build. The company’s beginning involved the familiar startup imbalance: conviction had arrived before most of the practical arrangements.

Cyriac’s first two calls for advice were to former bosses. Both offered to invest. Another early backer, PJC, knew Uralil through his previous company. The founders’ working relationships were becoming part of their new company’s financial foundation.

There is a distinction between knowing someone socially and having watched that person do the work. These early investors had some of the latter experience. Their willingness to back a new venture suggests why the less visible years of a career can matter when someone finally decides to put a new name on the door.

The transition also involved a household. Cyriac has publicly thanked his wife, Jenita, for supporting the decision and accepting its financial and personal demands. That acknowledgment belongs beside the investor names. A startup consumes hours that had other uses, and the people making room for those hours are part of its beginning.

Lively joined Y Combinator’s Winter 2017 batch. Uralil moved to San Francisco that January, and the product launched in March. By 2019, the company had 28 employees working opposite the city’s ballpark. A friendship had become a workplace, with all the obligations that change entails.

Owning the machinery

The founders made an early decision to build their own underlying platform. Licensing someone else’s technology would have been the easier way to get a service running. They chose the work of owning it.

Uralil has explained that choice in terms of the customer’s experience. When the company depends on someone else’s system, a problem can trigger a handoff. The customer waits while one organization consults another. Building the software internally gave Lively more control over what happened next.

That is a practical expression of a service philosophy. Customers rarely care who owns the code until ownership determines who can fix something. An attractive interface can make a good first impression. The machinery underneath it becomes more interesting when a person needs an answer.

In October 2021, Lively announced an $80 million Series C led by B Capital Group, with Telstra Ventures and Costanoa Ventures participating. The company put its total funding above $120 million. It also described plans to invest in the platform and develop more relationships with financial institutions.

A financing announcement is a snapshot of what investors are prepared to support. The continuing test comes afterward, when employees have to turn resources into a service people can use. For Cyriac, whose earlier work included keeping an operation running, the distance between the announcement and that daily work was familiar territory.

The problem with being nice

Cyriac’s account of company culture contains a revealing complication. Lively’s people were nice to one another. Sometimes, he wrote, that made difficult conversations harder to have. Accountability became an explicit value in response.

It is a useful admission. Pleasantness can keep a meeting comfortable while leaving a problem intact. A company needs some way to tell the difference between being considerate and avoiding the subject.

In his 2023 description of Lively’s values, Cyriac also discussed manager reviews and passing on skilled candidates whose values did not fit. The list was meant to affect decisions. The cost of a principle becomes clearer when it changes whom a company is willing to hire.

His earlier explanation of hiring puts structure around that intention. A values interview involved two people from other teams asking a consistent set of questions. Candidates could be asked about occasions when they showed integrity or held themselves accountable. The process gave interviewers something more specific to examine than whether the conversation felt agreeable.

He also described training for managers on feedback and one-to-one meetings. The reasoning is recognizable to anyone who has been promoted and discovered that doing a job well does not automatically teach you how to help someone else do it. Management needs practice, too. A new title is an inexpensive substitute for preparation, and a rather costly one afterward.

Ten years, and still building

By 2026, Lively was still led by its two founders. Its leadership team also included Luke Surazski overseeing product and technology, Theodore Bangura as chief financial officer, and Shannon Duncan leading operations and services. Cyriac’s old department-of-one days were well behind him.

In June, Lively announced Axis, the next evolution of its proprietary platform. The company described AI capabilities intended to connect information and reduce administrative work. Its product and technology chief explained the ambition through ordinary tasks: answering account questions, identifying recurring errors, and helping administrators understand what needs attention.

The announcement extended the earlier decision to own the software. Once again, the question was how much work the system could take off the person using it. The technology had changed; the customer still wanted to finish a task without conducting a tour of the company’s internal arrangements.

Lively appeared on the Inc. 5000 in 2024, 2025, and 2026. Those listings mark a company that has moved beyond its earliest experiments. They also bring the story back to the partnership that made those experiments possible.

Cyriac and Uralil began with a long acquaintance, different working experiences, and the willingness to build together. A decade later, their names remain alongside each other. The childhood sports commentary has acquired a considerable amount of software around it. Somewhere inside the larger company is the same simple advantage: when Cyriac calls his co-founder, he already knows who will answer.