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It’s about a half-hour walk from the IRS Chief Counsel's Office in Washington, D.C., to the corner of First and M streets, Northeast—but for Isaac Stein, it’s a world away. Dressed in a suit and tie, his usual work outfit at the office, he now mans a cart, dishing out hot dogs and advice under the shade of an umbrella. It’s been his daily routine ever since the federal government shut down in October, and Stein found himself out of a job—at least temporarily. But far from being a sob story, this is the story of how he fulfilled his childhood dream. Stein’s Hot Dog Cart Origin Story As Stein tells it, he was a tall kid and in seventh grade was recruited to play basketball. He likes the game, he explains, but while on the team, he found something that he liked doing even more. Each year, as part of a community event, the teachers would play ball in a sort-of knock-off version of the Harlem Globetrotters in the school gym. Of course, he says, his team attended the game. But while the other boys were more interested in the game, Stein was excited about something else: his shift at the concession stand. Each member of his team was required to do a short shift—but at the end of his, Stein didn’t want to give up his shift. “I had way more interest selling chips and soda than I had in the game,” he says. He immediately fell in love with the idea of connecting with the community and talking to people and learning about their lives. “And so I knew when I was when I was 12,” he says, “that I wanted to experience that again.” There are no formal educational paths to manning concession stands or hot dog carts. So after a stint in college in Chicago, he eventually went to law school at the University of Arizona. There, he met a professor who taught federal tax and ERISA employee benefits. (ERISA, the Employee Retirement Income Security Act of 1974, is a federal law that sets minimum standards for most private-sector retirement and health plans to protect participants.) That professor, Stein says, “was one of those rare leaders where you think, wow… I’m now absolutely fascinated by the subject material.” So, he says, he signed up for more of those classes. During law school, he snagged an internship at the IRS, which eventually led to a full-time job with the IRS Chief Counsel. About IRS Chief Counsel IRS Chief Counsel, a position dating back to 1866, serves as the chief legal advisor to the IRS Commissioner on all matters related to the interpretation, administration, and enforcement of tax laws, as well as other legal issues. The Chief Counsel, which reports to the IRS Commissioner and the Treasury General Counsel, provides legal guidance and interpretive advice to the IRS, the Treasury, and taxpayers. Attorneys in the Chief Counsel's Office serve as lawyers for the IRS. They provide the IRS and taxpayers with guidance on interpreting Federal tax laws correctly, represent the IRS in litigation, and provide all other legal support required to carry out the IRS’s mission. Before any cuts at the IRS, the Chief Counsel organization had approximately 2,600 employees. (The office has been shedding attorneys in 2025, losing nearly 13% of its staff due to resignations and firings from January to June 2025.) Stein’s IRS Career Stein’s first day at the IRS Chief Counsel’s office was September 12, 2022. It was love at first sight. Being a junior attorney can be hard—your knowledge base is necessarily limited—but Stein says that his work colleagues immediately made him feel welcome. “Being surrounded by people who want to help, who want to answer your questions, and who are also very passionate about the subject,” he explains, “is super helpful.” He was lucky to find mentorship opportunities with senior attorneys and settled in nicely early on, continuing to focus on ERISA and employee benefits. Those opportunities paid off, and he was able to expand his footprint at IRS Chief Counsel, including serving as the principal author of Notice 2024-63, which provided guidance for a new opportunity for taxpayers created under SECURE 2.0 Act that allows employers to make matching contributions to retirement plans based on employees' student loan payments. The match amount is calculated as if the employee contributed their loan amount to the plan, even if they did not make any elective contributions. (You can read more about it here.) The Hot Dog Cart Rolls Out Rolling out a hot dog cart is quite a shift from writing IRS guidance—and Stein obtained his permits for the cart before the shutdown began on October 1, 2025. Stein was one of the thousands of IRS employees that were furloughed as a result of the shutdown. According to the IRS shutdown contingency plan, about half—34,429 of the total employee population of 74,299—of the IRS workforce were subject to furlough. That employee count already reflects a decrease in the IRS workforce—by comparison, in 2024, the IRS relied on 90,516 full-time equivalent staff. So, did Stein set up the cart in anticipation of the shutdown dragging on? “Oh, I'm not nearly that smart,” he says. The timing just worked out. That passion for serving food and making people smile that he got a taste of at age 12? It had never really gone away. Initially, the cart was intended to be “a backyard art project.” Then, he started batting the idea around a bit: What if he could make it work? He loved the idea of using some artistic expression to customize every detail and picked up the cart in August. The menu, the umbrella, the stickers? “It’s all part of the stick,” he explains, “And the fun that I'm going for.” Even the motto ( “The only honest ripoff in D.C.”) and the name, Shyster’s Dogs, were all in fun. Shyster is a slang term for a dishonest or unscrupulous person, especially a lawyer who uses deceptive or unethical practices. In his case, the name belies the fact that he’s a lawyer running a business which, he says, “wholly correctly follows all relevant permits and codes.” There were, he noted, a lot of local regulations—he knows firsthand about government red tape—to sort out. Even before buying the cart, he explains, there was work to be done. You can't, for example, file for a health inspection until the cart is registered with the Department of Motor Vehicles (DMV), which requires an emissions inspection—even though the cart doesn't have a motor. Stein got it to the DMW by pushing it three and a half miles each way before his day job at the IRS. He was fully permitted by the third week in September and had planned on operating on the weekends—then the shutdown happened, causing him to change his plans. The experience, he says, has given him a deep appreciation for all of the back-end work that has to happen to successfully operate a business. The experience, he says, has given him an immense respect for small business owners. Hot Dogs Equal Happiness The choice of a hot dog cart over, say, pretzels was deliberate. “Hot dogs are an emotional food,” he explains. “Everyone has their own unique and special connection to it—often it is linked to someone's first experience at a baseball game, or the first time that they went to the beach.” Stein wants buying a hot dog to be a reminder of that joy. “Part of what I'm trying to bring to people,” he says, “is unadulterated happiness.” You can’t order the wrong dog, exactly, but Stein does have a favorite: mustard and sauerkraut. “I just assert that my preferences are correct,” he says, adding, “I often thank them for their compliance, which has gotten a couple of chuckles.” Stein was ultimately motivated to roll out the cart because he wanted to create an in-person space where people could connect. That has meant even more since the shutdown—now in its fifth week—began. “I’ve really been overjoyed at the organic interactions that people have been having just hanging out for a hot dog,” he says, “I’ve interacted with a lot of interesting, accomplished people.” Those people include his work colleagues and members of the tax community who have shown up to offer support. Even though Stein’s goal was to create that in-person space, Stein has become something of an online celebrity. He’s amassed over 5,000 followers on Instagram, where he documents his journey and has become something of a celebrity in the tax community, inspiring selfies and posts on Linked In. Now, Stein is even selling merch, including stickers, while noting that a full 50% of the after-tax profit from sales will go to charities that support DC, regional, and national food banks; support services for adults and children on the autism spectrum; and support research into rare forms of cancer. Each of those issues, he says, is important to him. What’s Next For Stein? So, is being a hot dog cart owner—rather than, as my fellow tax attorney referred to him, “the world’s most famous tax attorney”—Stein’s new future? Not exactly. Stein is eager to return to the IRS Chief Counsel office, emphasizing that his goal is to start working as soon as he’s called in. “I'm very much looking forward to it,” he adds. But he’s not hanging up his hot dog tongs just yet. He plans to keep the cart open on Fridays and weekends, as he originally intended. ForbesConfirmation Hearing Set For Trump’s IRS Chief Counsel Nominee Donald Korb
