Shai Stern keeps finding business in the paperwork

The pizza arrived because the paperwork could not wait. In the early days of Vintage Filings, Seth Farbman was pinned to his desk by SEC deadlines. Shai Stern brought food. Their business began in Farbman’s basement in 2002, with a couch, long hours, and the sort of appetite that makes a delivery receipt look like an operating expense. The task was electronic regulatory filing. The working conditions were rather less electronic.

It is a useful opening scene for Stern’s career. There would be acquisitions, payment platforms, board seats, and another company to start. Yet the recurring subject was already present: a customer had something necessary to get done, and the process was consuming too much attention. Stern has spent much of his working life close to that predicament. Bureaucracy, it turns out, has excellent repeat business.

Pizza before the deadline

Farbman remembers Stern as the force on the sales side of Vintage. The division of labor mattered. Winning an account meant making a promise that someone else, often someone working through lunch, had to fulfill. Between the basement and the eventual buyer lay the less picturesque business of doing that again tomorrow. A deadline offers limited patience for entrepreneurial charm.

By April 2007, PR Newswire had announced its acquisition of Vintage Filings. Stern would continue as chief executive; Farbman as president. The combination joined filing work with the distribution of corporate information. A public company could have its disclosures prepared and delivered through a broader service. Stern’s company had found a buyer whose existing business gave the service another route to customers.

His earlier experience had already placed him inside the machinery of public companies. As a vice president at American Stock Transfer Company, he worked on business relationships and share balances. He also helped grow its stock-plan operation. These were jobs in which the record and the relationship had to agree. A friendly conversation was useful. The figures still needed to be right.

That combination helps explain the industries he kept choosing. A filing service sells completion. A transfer business handles records people depend upon. The customer may never develop a romantic attachment to either activity, but will certainly notice when it goes wrong. For an entrepreneur prepared to care about the details, indifference elsewhere can leave room.

A school leaves the story, then returns as a client

Stern’s education has an unusually tidy sequel. He attended Yeshiva University and left without finishing. Writing in April 2026, he recalled the disapproval that accompanied his decision to go to work roughly thirty years earlier. His parents gave him a practical advantage: two years living rent-free in his grandparents’ apartment while he found his footing.

Years later, Yeshiva became a client of Vcheck, the due diligence business with which he was involved. Stern called his father to enjoy the reversal. The institution he had left was now paying the company. There is pleasure in a story that allows a parent to replace an anxious question with a smile. Stern’s telling gives the family’s help a place beside his own decision.

The connection between support and work appears elsewhere in his career. The early partnership with Farbman depended on complementary contributions. His latest business includes people he already knows and trusts. Read across those episodes and a consistent preference emerges: he likes building in company. Even the basement story contains two founders, a couch, and somebody making sure lunch happens.

The check takes the scenic route

At CheckAlt, Stern found a durable disagreement with the prevailing mood. Paper checks were widely treated as an activity on its way out. He paid attention to the people and institutions still using them. His observation was simple: people don’t change behavior so quickly. An industry can be unfashionable while its customers remain quite busy.

The interesting complication was that some checks began their lives online. Someone instructed a bank to make a payment electronically. Behind the screen, systems failed to connect in a way that would complete the transfer digitally. A paper check emerged and went into the mail. Progress had acquired an envelope. The payer’s experience of clicking a button concealed the recipient’s experience of waiting.

Stern discussed that detour repeatedly during his CheckAlt years. In an October 2024 conversation, he argued for upgrading the systems that turned electronic instructions into mailed checks. The approach put the intervention behind the customer’s existing behavior. People could keep doing the familiar thing while the infrastructure did a more sensible job of carrying it out.

CheckAlt expanded through purchases that added processing and software capabilities. ERAS came from Diebold in 2014. Klik Technologies came from MUFG Union Bank in 2016. U.S. Dataworks followed in 2020, acquired from The Bankers Bank of Oklahoma. The sequence brought different ways of handling receivables into the same business.

The U.S. Dataworks deal is particularly revealing. It added technology for institutions and business customers that wanted to capture payments internally, including on-site and remotely. CheckAlt could serve customers seeking outsourced processing while also accommodating those who wanted more control themselves. A business owner’s preference could become a product requirement, rather than an inconvenience to be argued away.

Stern’s own geography changed during that period of building. In a 2024 interview, he described moving back to New York after fifteen years in Los Angeles, with recruiting a stronger team central to the decision. He spoke warmly about having colleagues with different areas of expertise. Growth required people who could do work he could not reasonably do alone.

The business behind the business

Payments were one part of a broader career in corporate services. At Vcorp, where Stern served as co-chairman, the work included the legal and administrative requirements around companies. Wolters Kluwer acquired the business in October 2016. Its announcement described a firm of twenty-two employees joining CT’s services. Small teams can occupy useful positions in very large administrative systems.

Vcheck brought another version of necessary work: background investigations and due diligence. Sunstone Partners announced a strategic investment in November 2021, supporting technology development and expansion. Across these businesses, the subject changed from a filing to a payment to an investigation. The purchaser still wanted something dependable, delivered with less effort on their side of the desk.

By 2025, Stern was ready to return to the beginning of that process. He has described wanting to work more closely on building again after his years at CheckAlt. Leaving the company in capable hands mattered to him, as did choosing trusted collaborators. Patrick Law and Rachel Book were part of the CheckAlt leadership he credited with carrying the business forward.

Gotavi is the resulting venture. Its proposition gathers the work of starting and operating a business: formation, compliance, insurance, payments, and related tools. Technical co-founder Elishah Herman brings technology and data experience from HSBC. Co-founder Michelle Miklosey leads the customer experience. Eli Stern works on sales and partnerships. The arrangement gives distinct responsibilities to the people around the founder.

The attraction is easy to understand if you have ever opened a business and discovered that opening it was merely the first item on the list. Each additional service comes with another relationship, another request, another place to look. The founder becomes the person responsible for joining everything together. Gotavi’s ambition is to take on more of that coordination.

The next meeting should remember the last one

Stern’s public writing gives this business argument a more personal voice. In September 2026, he began an essay with Oreos, moved through AI responsibility and vendor meetings, and arrived at basketball. He admitted to having new cookie flavors shipped home for his children and taking variations into the office. The administrative specialist has room for a biscuit department.

The vendor stories were sharper. One arrived unprepared and spoke about its own merits instead of the customer’s requirements. Another missed a meeting, then sent automated follow-ups asking to meet. Stern’s verdict was compact: You cannot automate your way around basic human courtesy. Anyone who has received an enthusiastic reminder from someone who missed the appointment may appreciate the distinction.

“You cannot automate your way around basic human courtesy.”

Shai Stern, September 2026

For a founder selling connected tools, this is a useful standard to be held to. A platform may collect the tasks, but service depends on remembering the person carrying them. The promised convenience has to survive the handoff between a sales conversation and the work that follows. Otherwise, the customer has simply purchased a more elaborate way to explain the same problem twice.

Stern’s career gives that test some weight. He has worked around obligations that businesses cannot wish away, and through several changes in how those obligations get handled. His present ambition brings many of them together. The next chapter will be measured in completed tasks and customers whose working days become easier. The paperwork remains. He is still looking for a better way to get it done.