In the late 1970s, Gary Wassner sat on the floor of an office so new it still lacked furniture. Across from him was Betsey Johnson, a fashion designer with decades of success behind the scenes, who was taking a leap to open her namesake brand. “Gary,” she said, “I have all these orders, and I have no idea how to finance the business.” This conversation sparked a new vision for Hilldun, a family-run business Gary had only recently joined.
Hilldun’s story began in 1932, when department store owner Albert Greenberg had an epiphany. The United States was in the throes of the Great Depression, and the standard sales approach that had guided Albert was no longer the most profitable. He adapted to the times by introducing layaway. “He realized there was more money to be made in layaway than there was in actually selling clothes,” explained Josh Kapelman, Hilldun’s executive vice president and managing director. “That insight is really what gave birth to the business—it was always about understanding the financial side of retail and how critical timing and cash flow are, especially when the world is unstable.”
During World War II, the business pivoted again. With train travel across the U.S. restricted and store managers leaving to serve overseas, Albert decided to sell the company to a partner whose last name was Dunhill, which is a reversal of the compound Hildun. This gave rise to the firm’s name.
In 1952, Hilldun entered its next chapter when Marvin Wassner—Gary’s father—and Robert Greenberg—Gary’s uncle and Josh’s grandfather—took over management. For many years, Hilldun operated far from the runway, functioning as a real estate management and finance company. “It wasn’t always a ‘fashion finance’ business the way people think about us today,” Josh noted. “We were doing accounts receivable lending, chattel mortgages and property management—things with very little resemblance to our current model.”
Hilldun’s shift into fashion began when Gary joined the company, bringing a deep passion for art and a profound appreciation for the artist. It was this sensibility that changed the firm’s trajectory, steering it away from traditional real estate finance and into the world of fashion. Speaking to Gary’s mindset, Josh explained, “One of the things he has always said, and something we think about constantly, is that it’s not whether or not we like something personally; it’s whether there is a market for that.”
Jeff Kapelman, Josh’s father, joined the firm in the late 1980s, replacing Robert Greenberg. This began a major evolution. Hilldun pivoted one more time, moving beyond general financing and embracing factoring, including handling credit checks, payment collections and credit guarantees. This is necessary because a brand may have a high volume of orders, but retailers often pay on 30-, 60- or 90-day terms. While waiting for those payments, the brand still faces immediate costs, including factory labor, freight, rent and payroll.
“Factoring is really about timing,” Josh said. By turning future receivables into immediate liquidity, Hilldun provides the infrastructure that allows a brand to continue operating and growing without being at what Josh describes as “the mercy of payment timing.”
Today, the firm is run by Gary, now CEO, alongside his son, Cris Wassner, and Josh. Neither Cris nor Josh initially planned to join the family business; both were pursuing their own professional interests until their families invited them to help guide the company’s future. “For both Cris and myself, working with our fathers is and was an incredibly special experience,” Josh said. “You get to know your father in a different way and really respect the hard work they did over the years.”
Cris, who serves as managing director alongside Josh, was the first to join, bringing the skill set he gained in real estate to the firm. For Josh, his prior experience as an entrepreneur in the e-sports market also became an unexpected asset.
“When you build something from scratch, you learn very quickly that success and failure are rarely about the idea itself,” Josh reflected. “They’re about execution, cash flow, timing, discipline and the ability to make good decisions when things get hard.”
This entrepreneurial spirit influences how the team evaluates potential clients. They are not interested in the loudest story or the fastest growth; they are looking for durable, responsibly built businesses. “Our business is not about hitting home runs,” Josh emphasized. “It’s about hitting singles and doubles. It’s about being there, answering the phone, supporting your clients and putting one foot in front of the other. That’s how you build something that lasts.”
The trio’s partnership is built on an alignment of values and a difference in strengths. Gary maintains industry relationships, Cris manages risk and operations with a focus on structure, and Josh oversees long-term strategy and growth. “The important thing is that we don’t operate in silos,” Josh said. “We listen to each other. We debate. And we have to agree before we move forward on something meaningful.”
The company’s commitment to stability is reflected in its staff as well, with many of Hilldun’s 50 employees having been with the company for over two decades. “Our mailroom manager was hired by my grandfather,” Josh noted. “That kind of longevity is rare, and it matters because this business is built on relationships, and relationships are not built through turnover.”
The firm’s philosophy for client support is to nurture personal relationships alongside providing capital. During times of industry volatility—such as the COVID-19 pandemic— Hilldun acted as a steadying hand. “During COVID, we hosted Zoom calls where we brought together CEOs and chief merchants of major retailers to talk openly about how the industry could address the crisis without hurting independent brands,” Josh explained. “One of the key takeaways from that call was, ‘We are all in this together.’”
Josh believes that this support is critical to the future of fashion. When he looks at how the New York fashion landscape differs from other fashion capitals, it’s the entrepreneurial spirit that stands out. “One of the things that has always been so unique about the United States is that we have great entrepreneurial thinkers and creatives, and we are the builders of contemporary brands,” Josh said. “Europe has luxury. We have contemporary. We invented contemporary, and we sustain it.”
As they look toward the next several decades, Josh remains committed to the family legacy and the long-term view that has sustained Hilldun since 1932. The work remains deeply personal, as they find themselves involved in the day-to-day operations of their clients’ businesses, through both successes and challenges. “I’ll be sitting in my chair for the next 30 years,” Josh stated. “So shortsighted views have no place here.” With a portfolio of around 450 clients and an average relationship length of 11 years—and some decadeslong client relationships—Hilldun continues to prioritize continuity and discipline, even in an industry defined by the fast-paced cycle of trends.
