How 750 entities turned the Kanter family into a family office

Josh Kanter has run the family operation for almost 25 years and serves as president of Chicago Financial, but a quarter-century ago he would not have described what he was doing as running a family office. It was, he says, three people with the same last name working together, and what eventually forced the label — and the structure behind it — was an inventory rather than a windfall.

Kanter came to the family's affairs as a lawyer rather than an investor, trained in corporate and securities law, and had represented the family's venture funds, several portfolio companies, and the family itself while his father, Burton Kanter, practiced tax law and his brother ran the venture portfolio where the family invested directly alongside two funds the father and brother operated together. When his father was diagnosed with cancer in 2000 and the family understood he would die, Kanter left his practice to help, spending 18 months learning from him the estate planning, insurance planning, and administrative plumbing that family offices run.

Eighteen months covered less than he needed: Kanter says that within minutes of his father's death, people began asking questions he could not answer, the first being why the family had 750 entities. The tax department was filing 750 returns a year for the family. That question, in his telling, is the moment the office became one — it grew out of the level of complexity rather than the size of the balance sheet.

A structure of that size implies a standing load — filings, registrations, accounts, signatory lists, and books for entities that may not trade in a given year — that must be maintained whether or not anyone is making an investment decision. Kanter's point is not that the family was short of assets, but that a structure assembled deal by deal and fund by fund over decades had stopped being legible to the person who inherited responsibility for it; the number he could not explain was the number of things requiring explanation.

The adversarial thread is part of that inheritance: Kanter describes a dispute with the IRS that was already 22 years old when he joined the family business and ultimately reached the U.S. Supreme Court, running 33 years from start to finish. The interview does not say how the case ended or what it cost, and Kanter does not attribute the length of the fight to the entity count, but the detail establishes that a meaningful share of the structure he inherited was shaped by a legal contest as much as by investing.

His stated goal was to simplify — to move the family toward a structure that was more economically efficient — and that work was also what let him advise other families, applying what he describes as the intersection of his legal training and his knowledge of family dynamics and governance. The simplification came first, and the outside practice followed it, not the reverse.

The family still runs through three branches — Kanter, his brother and his sister, an artist — and he describes the sibling relationship as collaborative, built on complementary skill sets, with his brother handling investing and Kanter handling everything else, especially the legal work. A brother would bring him a medical device deal, and Kanter would skip the science and ask about the structure. There are seven grandchildren in the next generation, though the interview does not describe how responsibility for the structure passes to them.

That is where the Kanters' experience cuts against a position this publication has taken: we have argued that the next governance crisis for expanding families will be asset illiquidity rather than succession, but Kanter's story points to an earlier and cruder failure mode, one that arrives before anyone has to sell anything — a family that cannot account for its own entities. Complexity of this kind is a governance problem in its own right, paid for in staff time, filing costs and the legal work of unwinding it.

The investing posture is the other piece worth flagging: the Kanters were direct venture investors at a time when that was less common, a version of the direct-principal turn this publication has described, with family capital writing its own checks rather than only committing to funds. The interview does not size that portfolio or say whether the family led rounds or took board seats, but for the operations side, direct investing and entity sprawl are the same problem seen from two ends: each deal can add a vehicle, and each vehicle adds a return, an account and a signatory to a list someone has to maintain.

Kanter now spends part of his time with other families on governance and dynamics, which is where the 25-year arc leaves him, though the account does not report whether the entity count at Chicago Financial came down or how far the simplification ran. What it establishes is that the office he runs today began with a question he could not answer in the minutes after his father died, and that the work of answering it has occupied two decades, at home and now for other families.