Tax season has a talent for arriving like an ambush everyone scheduled months ago. The receipts are somewhere. The books are almost current. The clever decision that might have saved money expired in December. For a solo consultant or realtor, the annual ritual can expose a strange gap: you own a business, yet you do not have the finance department that businesses are supposed to have.
Shahar Plinner has spent his career inside that gap. He is a tax and accounting entrepreneur, an immigrant from Israel, a Seattle MBA, the builder and seller of a traditional firm, and now the co-founder and CEO of Formations. His second company is organized around a compact proposition: a business of one is still a business. It needs structure, books, payroll, tax work and advice that arrives before a deadline becomes a eulogy.
An immigrant learns the American tax code
Plinner arrived in the Seattle area in 2005. His earlier working life had been in Israel, including several years in the family insurance-adjusting business. The move replaced one intricate rulebook with another. He entered U.S. taxation, studied for an MBA at Seattle University from 2008 to 2011, and found a profession where ignorance could be perfectly legal and surprisingly expensive.
In 2009, he started GPL Tax & Accounting. Over the next 13 years, the practice grew to roughly 3,500 clients. Those clients gave him more than scale. They gave him repetition: thousands of variations on incorporation, payroll, deductions, benefits, bookkeeping and the blank look produced when a professional explains in April what should have happened the previous autumn.
The self-employed cases held his attention. Corporate employees inherit a financial apparatus: withholding, payroll, benefit choices and people paid to remember dates. Independent professionals inherit a login page. The freedom is genuine; so is the administrative solitude. Plinner came to believe that this population was not failing to use the system. The system was failing to meet them where they worked.
“The biggest tax mistake isn't paying taxes. It's paying more than you legally owe because nobody helped you plan.”Shahar Plinner
The clue was hiding in the calendar
Formations launched in 2020 with co-founder Uri Bar-Joseph. Its early thesis joined two pains. Accountants lacked an efficient system for serving solo businesses continuously; solo owners lacked coordinated support for the decisions scattered across their year. Entity formation, bookkeeping, payroll, business and personal returns, and tax planning were treated as connected jobs rather than neighboring errands.
There is a product lesson in the sequence. Software often makes an existing task faster. Formations tries to make the task happen at a more useful moment. A dashboard can display that cash is short. Planning sets aside money before it becomes short. Filing software can report an entity choice. Advice can test that choice while it can still be changed. In taxes, timing is not a convenience bolted onto the product. Timing is part of the product.
Investors saw a large market in that missing layer. Formations announced an $8 million Series A in April 2022. The financing brought its reported total funding to $15 million. That same year, Plinner sold GPL. The chronology matters: Formations was not an escape from accounting. It was the attempt to turn what a local practice had taught him into repeatable infrastructure.
The company’s timing was unusually theatrical. It launched as the pandemic pushed more work, more paperwork and more professional life onto screens. A service designed to operate digitally no longer needed to persuade customers that remote financial work was possible. Yet Plinner and Bar-Joseph resisted making the human professional disappear behind the interface. In later conversations about their AI tax assistant, MAX, they returned to the same division of labor: technology can surface information and handle repetitive production, while complicated cases still require an expert who understands context.
That hybrid is operationally awkward, which may be why it is interesting. Pure software enjoys clean margins but asks the customer to interpret the output. A conventional firm provides interpretation but carries a staffing pyramid, seasonal bottlenecks and a patchwork of systems. Formations sits between them, attempting to standardize the back office without standardizing every owner. It is less elegant than declaring that software will eat accounting. Tax lives in the inelegant details.
One career, two operating models
The bill at the family table
Founders enjoy retelling the years of strain once those years have acquired an exit. Plinner’s version is less lacquered. He has written about lying awake at 2 a.m., mentally running payroll again. He remembers the employee who quits during tax season, a familiar client leaving, the cash-flow squeeze and the pressure that moves into the house without paying rent.
His three children learned the sentence “Daddy is in tax season.” His wife, Ortal, carried more at home while he carried the firm. In his telling, entrepreneurship is not a private wager. The whole family absorbs the volatility. It is a bracing addition to the founder ledger, where sacrifice is usually counted only when the founder makes it.
He would build again. He would not build the same machinery again. That distinction now shapes his most interesting idea for the accounting profession. Plinner calls it the “Accountant of One”: a solo accountant or fractional CFO using automation, AI and shared infrastructure to serve far more clients than a conventional independent practice could support.
His argument begins with a change already moving through the profession. Large firms are merging. Private equity is consolidating practices. AI is lowering the cost of compliance work. The traditional career ladder assumed that more clients required more preparers, then more managers, then more partners. If production becomes cheaper, that pyramid need not be the only shape. An experienced accountant might instead remain independent, select a niche and use a common operating layer for the jobs that do not require a personal relationship.
Plinner’s number is deliberately provocative: he imagines a strong professional serving as many as 1,000 clients with the economics of a multimillion-dollar firm. It is a forecast, not a reported Formations result. The practical insight is smaller and immediately useful. Before hiring another person, identify which work needs judgment and which work merely needs reliable machinery. Hiring is sometimes growth. Sometimes it is a receipt for a system nobody built.
“The future will be built around leverage.”Shahar Plinner
The phrase sounds like a software pitch until Plinner explains what should remain stubbornly human. Production work can be automated. Trust cannot. A machine may categorize the transaction, but a professional still interprets the owner’s messy ambitions, weighs risk and takes responsibility for a recommendation. His preferred future is neither the lonely practitioner rebuilding every system nor the faceless platform treating expertise as a nuisance. It is an expert with machinery.
Useful complexity
Plinner’s public writing has become more direct about that balance. When the bookkeeping service Bench abruptly closed in late 2024, he argued for “tech-enabled services” and a diverse ecosystem of providers. He also offered migration and filing help while naming competitors that might suit different customers. The gesture fit a philosophy he phrases as giving more than you ask for. It also acknowledged an inconvenient truth: no single product is right for every complicated financial life.
He is equally candid about his bias. Formations, he says, is for owners who want strategy throughout the year and operational work handled with them. His comparisons allow that DIY software can suit a simple situation, a traditional CPA can earn the fee on genuinely complex work, and software-led competitors may appeal to owners who want greater automation. A founder explaining where the product does not fit is doing something rarer than marketing. He is reducing future disappointment.
At home, the person behind the tax thesis is less abstract. He enjoys sporting events and time with Ortal and their three children. He speaks Hebrew. He has belonged to Entrepreneurs’ Organization since 2014, and colleagues have described the humor he brings to a subject usually delivered with the bedside manner of a stapler. In 2025, he spoke publicly about the loneliness of entrepreneurship and the instinctive decisions that changed his path.
The ambition now is bigger than filing returns and more modest than abolishing tax confusion. Plinner wants solo owners to have the advantages of an organized business without first becoming a large one. He wants accountants to apply judgment without rebuilding the same operational stack every generation. Both aims depend on turning hard-earned expertise into something other people can use before the clock runs out.
That is the appealing contradiction in his second act. Formations is built around one-person businesses, yet its promise is company: a system watching the year, a professional in the corner, a decision made while it is alive. Independence, Plinner’s career suggests, becomes more durable when nobody has to practice it entirely alone.