Changing the Conversation

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Growing up as the daughter of two immigrant physicians, Ayesha Mahapatra always assumed she would follow the familiar path laid before her. After all, medicine ran deep in her family—especially on her mother’s side—and she remembers relatives fully expecting she would eventually put on a white coat.

She excelled in the sciences, but she also possessed something else entirely: a fierce love of debate, a sharp analytical mind and a tendency to challenge assumptions with clarity and confidence.

“I liked talking, I liked poking holes in arguments, and I loved advocating for myself,” she reflects. “I think it drove my parents absolutely bananas, but it was empowering for me.”

Eventually, the realization hit her that while she respected the medical profession, she did not want the decade-plus commitment it required. A deeper look at her strengths—writing, speaking and critical thinking—led her toward a different calling. She enrolled at Princeton University as a U.S. history major, diving into rigorous research and writing, and later took a constitutional law course that opened her eyes to the world of legal strategy.

“From that point, I realized I really enjoyed the analytical side of the law and how it helps you break down complex problems into something actionable,” she shares.

Law school followed, and with it came early experiences that shaped her career trajectory. Mahapatra found herself drawn to labor and employment, antitrust and corporate law, and she began her career as an associate at Littler Mendelson, where she thrived.

“I really enjoyed the work,” she shares, remembering what it felt like stepping into high-stakes matters where clarity and composure mattered most.

Her shift in-house came when she joined Young’s Holdings, stepping into a world she describes as “a deep dive into alcohol beverage law overnight.” The company’s portfolio spanned multiple operating entities, including real estate, fine wine and spirits importers, and major brand suppliers, and the complexity of the regulatory landscape proved both challenging and exhilarating.

“Alcohol distribution law is unusually intricate due to the post-Prohibition structure that handed control to states and even individual municipalities,” she describes. “It’s very local, very specific and wildly different from state to state. That’s just the bargain of Prohibition. Lifting the ban required embracing local control, and now we live with a patchwork of rules county by county.”

At Young’s, she quickly took ownership of litigation and employment matters, joining the HR leadership team and working daily with business partners across multiple states. The shift from firm life to having a single, embedded client changed her understanding of legal partnership. She learned that while statutes provide black-letter rules, real-world application rarely feels black-and-white.

“You learn that law in isolation doesn’t always work,” she explains. “The question becomes: how do I help the business navigate risk while still achieving its goals? That’s where you start building real trust.”

That foundation became pivotal when Young’s Holdings sold half of its Young’s Market Company business to Republic National Distributing Company (RNDC) in 2019. Mahapatra worked on the deal itself—effectively helping facilitate a transaction that would eventually reshape her own future.

Realizing the consolidation meant her existing role would change, she started taking a closer look at RNDC’s leadership, culture and trajectory. Mahapatra connected with RNDC’s general counsel, Alan Rosenberg, whose background leading large publicly traded company legal teams offered mentorship she recognized as invaluable. The opportunity to learn from someone with deep operational experience across complex business structures proved too compelling to pass up.

“It was an incredible opportunity for me to be mentored and learn from somebody who’s done this before,” she shares. “Alan wears multiple hats every day. Watching him navigate those dynamics has taught me so much.”

RNDC’s structure, she notes, is unlike anything she experienced before—where Young’s operated under a single-family ownership model, RNDC is driven by multiple family ownership interests navigating governance through collaboration and balance.

“It’s fascinating because you’re constantly working to help align different perspectives so the business can continue to move forward,” she says.

Her leadership approach is rooted in authenticity and empathy—qualities she spent years honing.

“I’m very authentic to who I am,” Mahapatra shares. “I lead empathetically first, and I ask a lot of questions. People are motivated differently, the same way everyone has different love languages. Listening helps you figure out what support each person needs.”

That philosophy has guided her through some of the most rapidly shifting moments in alcohol distribution, especially as new categories like non-alcoholic beverages and hemp-derived THC products disrupt traditional markets.

“Balancing innovation with regulatory risk isn’t about dampening enthusiasm but grounding it,” she explains. “There are prohibitions in federal law that conflict with what states are allowing, and you have to tread carefully. Our job is to bring excitement down to earth—propose strategies that allow innovation but don’t jeopardize the core of our business.”

She points to RNDC’s cautious, strategic pilot programs in select states as an example. When sales teams push aggressively into emerging markets, she sees her role as providing reality, not restriction.

“My job is not to say no, it’s to provide paths forward,” she shares. “The best advice is the advice people feel like they came to themselves.”

Earning that level of trust across a company operating in nearly 40 markets stands as one of the accomplishments she values most.

“Getting the business to see legal not as an impediment but as a partner has been huge,” she says. “I get a lot of calls now where people say, ‘I spotted an issue and wanted your take.’ That’s when you know you’re making an impact.”

Outside work, Mahapatra rebalances through family, and life with 13-year-old twin boys brings energy and hilarity in equal measures. A former college volleyball player and lifelong sports fan, Mahapatra also spends weekends coaching from the sidelines, exploring museums, traveling and introducing her kids to live music.

Looking ahead, Mahapatra remains energized by the work in front of her and the continued evolution of RNDC.

“I’m excited about where we’re headed,” she says. “The industry is changing so quickly and finding solutions that help the business grow while staying thoughtful and strategic—that’s the part I love most.”

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