Diane Hendricks has spent nearly five decades building one story that keeps getting bigger: from a teenage single mother working odd jobs in rural Wisconsin to the wealthiest self-made woman in the United States.
According to Forbes‘ 2026 billionaires list, Hendricks is worth $22.3 billion, making her not just the richest self-made woman in America but also the wealthiest resident of Wisconsin. Her path there, however, included a stint as a waitress at a Playboy Club, decades of hard manual labour, and the sudden loss of the husband who built the business alongside her.
A dairy farm childhood and an early start in life
Hendricks was born in 1947 in Mondovi, Wisconsin, and raised in Osseo, Wisconsin, one of nine sisters, according to Bloomberg’s profile of her. Her early life was shaped by hardship rather than privilege.
As reported by CNBC, Hendricks became pregnant at 17 and finished her final year of high school from home before getting married. The marriage did not last, and within a few years, she found herself divorced and raising a child on her own, a mother of seven children in total, with no college degree and few obvious paths to financial security.
The Playboy Bunny years and a career in real estate
To support herself and her son, Hendricks worked a string of jobs, including a stint on the assembly line at the Parker Pen Company in Janesville, Wisconsin, and a year as a waitress, known as a “Playboy Bunny,” at a Playboy Club in the late 1960s, as she has confirmed in interviews cited by CNBC and other outlets.
Far from hiding this chapter, Hendricks has spoken about it openly, telling reporters it was simply one of many jobs she took to get by. It was during this period, she has said, that she first became drawn to business and real estate as a way out of financial instability.
At 21, she earned her real estate broker’s licence and began buying run-down houses, fixing them up herself, and renting them to college students—an approach that taught her the basics of property management and renovation long before she entered the building supply industry.
Building ABC Supply with Ken Hendricks
Hendricks’ fortunes changed after she met roofing contractor Ken Hendricks in the mid-1970s; the two married in 1975, according to Bloomberg. Together, the couple continued investing in rental properties around Beloit, Wisconsin, reportedly buying and renovating roughly 200 older homes over a few years.
In 1982, they took a bigger leap, purchasing three struggling building-supply stores and launching what would become ABC Supply, a wholesale distributor of roofing, siding, windows and related materials.
Their model focused on buying directly from manufacturers and offering a level of customer service that was, as Forbes has described it, unusually strong for the industry at the time. Within five years, the company had grown to around 50 locations and roughly $140 million in sales, according to figures reported by AOL and Forbes.
Taking over after tragedy and becoming sole owner
The business continued expanding through the 1990s and 2000s, crossing $1 billion in annual sales by 1998, according to ABC Supply’s own company history. But in 2007, Ken Hendricks died after a fall at the couple’s home, leaving Diane Hendricks to take over as chair of the company.
Rather than step back, she pushed the business forward, even navigating a period of significant headwinds: ABC Supply’s sales declined 7% between 2006 and 2009 as the Great Recession hammered the real estate market. She then led what Forbes has called the two largest acquisitions in ABC Supply’s history: the purchase of rival distributor Bradco in 2010 and building-materials distributor L&W Supply in 2016.
In 2013, she bought out minority stakes held by private equity firms Advent International and Apollo Global Management, along with Bradco Supply, in a deal valued at about $1.4 billion according to Moody’s Investors Service, becoming the sole owner of ABC Supply.
America’s richest self-made woman in 2026
That consolidation paid off. ABC Supply’s revenue has more than doubled in recent years, climbing from $12.1 billion in 2020 to $20.7 billion in 2024, according to figures reported by BizTimes and the National Roofing Contractors Association.
The company now operates more than 900 branches across the US and Canada and employs roughly 20,000 people, making it one of the largest privately held companies in the country, according to Forbes’ rankings of America’s biggest private firms.
Hendricks, now 79, has topped Forbes’ list of America’s Richest Self-Made Women for nine consecutive years through 2026, and her current net worth of $22.3 billion also places her among the world’s billionaires, according to Forbes. Beyond ABC Supply, she controls Hendricks Holding Company, a portfolio of businesses with stakes in 18 companies spanning trucking, insurance, manufacturing, real estate, and recycling, as reported by Bloomberg.
Hendricks has said she has no plans to slow down or sell the company, telling Forbes in 2022 that ABC Supply is “not a company that’s ever going to be for sale” and that she intends to pass it on to her children.
For a woman who once cleaned toilets in rental properties and waited tables in a bunny costume to make ends meet, her trajectory stands as one of America’s most striking rags-to-riches stories. She built it not on inheritance or a single lucky break, but on decades of hard physical work and a refusal to step away when tragedy struck.