Ben Kovler and the value of an unfinished puzzle

Before Ben Kovler had cannabis licenses to consider, he had a grandfather who would withhold the answer. Raymond Epstein supplied riddles at family dinners and on vacations. Young Ben wanted another, then another. Sometimes he solved one quickly. Sometimes the thing followed him around for weeks. When he asked to be put out of his suspense, his grandfather suggested a little more thinking.

Their collaboration became a book, Fundrum My Conundrum, published in 1992. Its origin story includes a note from Ben dated October 1991, thanking his grandfather for the puzzles and the company. Epstein, in turn, wrote about the pleasure of his grandson’s quick wit. Before the balance sheets and board meetings, there was a shared pastime, and an adult willing to let a child remain temporarily stumped.

Today Kovler is founder, chairman and CEO of Chicago-based Green Thumb Industries. He still invokes that early education. His instruction, in a letter about the company’s beginnings, is to ‘remove all assumptions.’ It sounds easy until an assumption happens to be convenient, lucrative or your own. A useful riddle has a way of making confidence look faintly ridiculous.

His career offers several opportunities to test that instruction: an investment conference whose proceeds leave the room for Chicago youth organizations; a cannabis business built around consumer brands; and, early on, a decision to surrender a license other founders might have framed. The interesting question running through them is how much opportunity a person should actually take.

The family had seen a prohibition end before

Kovler grew up in Chicago with a family history that made consumer brands something more concrete than a business-school diagram. His great-grandfather Harry Blum helped build Jim Beam after alcohol prohibition ended. His grandfather Everett Kovler later ran the business. The family sold it in 1967. A name on a bottle could outlast the people who developed it, provided customers kept asking for it.

There was another recognizable name in the family’s orbit. His father, Jonathan, was a managing partner of the Chicago Bulls during the 1970s and 1980s. The Kovler name also appears around Chicago’s civic institutions. This is a story with inherited access and business connections, and those advantages belong in the picture alongside the founder’s decisions. A head start still leaves choices to make.

At Pomona College, Kovler studied philosophy, politics and economics. He later earned an MBA in accounting and finance at the University of Chicago. Between those credentials lies an unusually apt combination for his eventual industry: questions about what people value, how rules get made and what a business can afford.

His working life included private equity in food, beverages and consumer products, and three years teaching math. The classroom is an intriguing stop on the way to a public-company office. Both jobs require an explanation that survives questions. A spreadsheet may forgive a muddled explanation rather more politely than a roomful of students.

“remove all assumptions”

Ben Kovler · Letter from the founder

Twenty licenses. One familiar pattern.

In 2013, Illinois adopted a cannabis licensing framework. Kovler read the legislation and saw a structure that reminded him of regional gaming: limited permission to operate, potential demand and a business whose prospects depended on understanding the rules. He investigated with a team, visiting Colorado and speaking with people in California. Green Thumb followed in 2014.

His phrase for the opening was ‘Prohibition 2.0.’ The family’s bourbon history gave the comparison personal resonance, but his business proposition was specific: ‘brands distributed at scale.’ Cultivation would put a product into the market. A recognizable brand might give a customer a reason to choose it again. Distribution would make that choice possible in more places.

That thesis also explains the distance between Green Thumb’s corporate name and the names on its shelves. RYTHM, Dogwalkers and Beboe address consumers; RISE is the retail chain. The corporate name does its work elsewhere. Plenty of shoppers have a favorite product without taking an interest in its parent company’s organizational chart. This is probably a blessing for everyone involved.

By 2019, Kovler was discussing how to develop Green Thumb’s existing 12-state footprint, with an emphasis on scaling and improving what was already there. Geography made an impressive list, but the work was inside each market. More locations create more chances to sell something, and more places where an ordinary operational mistake can spoil the promise.

The license he handed back

One early decision supplies a useful complication to the usual founder story. In 2015, Green Thumb won three of Illinois’s 20 cultivation licenses. Kovler worried about whether the company could afford to build all three facilities. He returned one license.

A limited license is precisely the sort of scarce asset that makes expansion sound inevitable. Winning three gives a founder an excellent sentence for a pitch. Giving one back invites a less glamorous conversation about construction costs, available money and what happens if the arithmetic refuses to cooperate. Kovler chose to have that conversation.

He recounted the episode in 2023 while discussing spending restraint, customer relationships and the limitations of judging a cannabis business by EBITDA alone. His argument was about the cash demands of operating a company. An earnings measure can help describe performance while leaving important bills outside the frame. The bills retain an irritating preference for being paid.

The episode does not establish that every subsequent decision was wise. It does offer a concrete example of restraint at a moment when expansion was available. For a former math teacher, the answer had to work after the celebration. An unused opportunity could be less costly than an underfunded commitment.

A second balance sheet, for Chicago

Green Thumb was not Kovler’s first attempt to organize people around an investment idea. In 2009, he and Ron Levin founded Invest For Kids. Its annual conference brings investment professionals together to share market views and ideas, with proceeds directed to organizations supporting young people in Chicago. The design puts the investment content at the center of the event.

The mechanism is worth pausing over. Attendees get something they want: ideas they can examine and potentially use. Local organizations receive funding. In their 2023 anniversary letter, Levin and Kovler committed to continuing to cover the operational expenses themselves, allowing conference proceeds and donations to support the mission. The expense line has benefactors of its own.

By October 2026, Invest For Kids reported $25 million raised and 123 nonprofits supported since inception. Its 18th annual conference was scheduled for October 28 at Chicago’s Harris Theater. Those are organization-wide results, built by co-founders, staff, speakers, donors and recipients. Giving the founder all the credit would make the arithmetic misleading.

One recipient makes the mechanism tangible. Working in the Schools announced in September 2025 that it had been selected for an estimated $200,000 grant. The organization provides literacy enrichment and mentorship in Chicago Public Schools. The money travels from an event about investing to the daily business of helping students read.

The teaching chapter in Kovler’s career makes this continuity particularly interesting. Years after leaving the classroom, he is still connected to educational work through a different set of tools. The conference does not require a financier to become a teacher. It asks whether the resources already assembled in a professional network can be put to another use.

The brand changes hands. The thesis stays.

The brand strategy has acquired a more complicated corporate structure. In August 2025, Green Thumb sold a subsidiary holding intellectual property for several brands to Agrify for $50 million in cash. Green Thumb also entered a licensing arrangement to continue manufacturing and distributing the products. Agrify subsequently became RYTHM, Inc.

Kovler serves as chairman and interim CEO of RYTHM as well as leading Green Thumb. The overlapping roles matter: the brand transaction was disclosed as a related-party deal. A consumer may need only recognize the package. A shareholder needs to follow the ownership, licensing payments and management responsibilities too. The familiar name on the shelf can conceal a less familiar route through the accounts.

RYTHM’s beverage business has also taken Kovler’s consumer thesis into recognizable Chicago settings. In May 2026, the company announced a multiyear partnership bringing RYTHM and Señorita drinks to Navy Pier. Its announcement also described availability at the United Center and music venues around the city. Distribution, in this version of the puzzle, includes the places people already go for an evening out.

The ambition is visible without assuming its outcome. A beverage at a concert or arena competes for a place in an existing social routine. Getting onto that menu is a distribution achievement; being chosen repeatedly is the consumer test. His original interest in recognizable brands now has a different sort of countertop on which to prove itself.

The next answer still has to add up

Green Thumb’s second-quarter 2026 figures show both the scale of the business and the friction inside it. Revenue reached $306.7 million, up 4.6% from a year earlier. Comparable-store sales fell 1.1%. The business could grow overall while established stores faced pressure. Both statements belong in the same sentence about progress.

The company reported $4.9 million in net income and $29 million in operating cash flow for the quarter, while spending $48.3 million repurchasing shares. It ended June with $283.6 million in cash. These figures describe different things, which is exactly why looking at several of them matters. A revenue headline cannot do the entire job.

By October 16, the company was announcing its 26th Florida location, in Belleview. Another results call was scheduled for November 4. The calendar carries on with its unromantic obligations: open the store, serve the customer, report the numbers, answer the questions. The original business idea becomes a succession of decisions that have to hold up individually.

Kovler’s early riddle book makes an unexpectedly good companion to that calendar. A puzzle promises that an answer exists, but it offers little sympathy for impatience. A company is less obliging: conditions change, other players move and yesterday’s answer may need revising. The habit that survives is the willingness to look again. Somewhere between a grandfather’s withheld solution and a cultivation license handed back, Kovler found a way to keep the question open.