
From teen mom to roofing mogul: how Diane Hendricks built a $22 billion empire
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Learn more@concur.com It's 2009 in rural Wisconsin. A woman brushes snow off her coat as she enters her quiet, empty home. She flicks on the lights and steps into the home office of her husband and then pauses, reminding herself he's gone. She walks over to his messy desk. She moves past a statue of Ronald Reagan on horseback, a sculpture of construction workers perched on a beam above New York, and stacks of blueprints. She eyes the pile of unopened mail and then picks up the top envelope. Inside is a letter addressed to her, asking to meet and discuss the possible sale of the business. Not their business anymore. Her business should she? She gazes at the family photos lining the walls, taking in images of her seven children and 17 grandchildren. In that moment, she makes a decision. And she's doing it all for them.
Simon Jack
Welcome to Good Bad Billionaire, the podcast where we take the world's richest people and find out how they made their money.
Zing Singh
My name is Zing Singh and I'm a journalist, author and podcaster.
Simon Jack
And my name's Simon Jack and I'm the BBC's business editor.
Zing Singh
You've probably never heard of her, but.
Simon Jack
That woman standing in her late husband's office in rural Wisconsin would go on to become the richest self made woman in America. Diane Hendricks has a fortune of $22 billion.
Zing Singh
Oh, talk about big money. She Built her fortune through ABC Supply, the U.S. s largest distributor of roofing supplies, which she co founded with her husband in 1982.
Simon Jack
A teenage mother who left school at 17 and a two time cancer survivor, she's been called the most successful female entrepreneur in American history by forbes.
Zing Singh
At the 2024 Republican National Convention, she stood on stage and said, I'm living proof the American dream is possible. With hard work and deter.
Simon Jack
Also one of the Republican Party's biggest political donors. In 2024, she poured millions into Donald Trump's re election campaign.
Zing Singh
But before the headlines, before the billions, before all the roofs, let's rewind to where the dream really began.
Simon Jack
So Diane Hendricks was born Diane Marie Smith on 2 March 1947 in Mondovi, Wisconsin. Age nine, she and her family moved to a 200 acre dairy farm in Aseo, Wisconsin. A small rural town. By the nineteen fort, Wisconsin was known as America's Dairyland. Dairy farming provided families like hers with a steady modest income.
Zing Singh
So really, American heartlands?
Simon Jack
Yes, I can picture this in my mind. I've probably got it wrong, but I've got a picture.
Zing Singh
The grassy fields, the cows. Diane was the fourth of nine daughters. She said she loved her childhood. She was playing with her eight sisters, she was eating homegrown vegetables. And she said, I wish every child could be as loved as I was.
Simon Jack
I wish every child would eat homegrown vegetables as well.
Zing Singh
Yeah, she sounds like she was quite a special child in that regard. Diane loved being outside, but she said her dad didn't believe in girls doing farm work like milking cows or driving tractors because he didn't consider it safe. So he told her girls did housework.
Simon Jack
By 10 years old, Diane had decided that being a farmer's wife or farming was not for her. Instead, she dreamt of becoming a businesswoman who lived in a city, had a car and wore a blue suit.
Zing Singh
But in 1964, Diane got pregnant at the age of 17 and her high school asked her to leave. She admits she was only an average student, but she was determined to get her high school diploma. So she studied at home. And when the students left for the day, she went back to the school to hand in her work or take tests. And she said it was embarrassing, but it was okay. And a year later she got that diploma.
Simon Jack
So a bit of persistence, a bit of grit there, her parents encouraged her to marry the father of her son. So in 1965, the young couple moved with their baby to Janesville, which was then a booming industrial city in southern Wisconsin. Her husband worked in a Chrysler plant while she worked on the assembly line of a Parker pen factory. Remember Parker pens? But Diane quit after three months and got a job selling new build homes for a local builder. And that was a role that didn't require a license at that time.
Zing Singh
And while she was working, she started studying for a real estate license because she was determined to carve out a future on her own terms. Now, three years later, however, the marriage had fallen apart. She told the New York Times in 2009, I knew I had to find a way to support myself alone. I filed for divorce a week after I was 21. So imagine being a young single mother in the 60s in America.
Simon Jack
Yeah. And in a pretty conservative kind of background in those rural communities as well. Can't have been easy at that time. So yeah, you know, at this point things are not going great for Diane Hendricks.
Zing Singh
No, they really weren't. But she was still trying to, you know, get somewhere in real estate, wasn't she?
Simon Jack
She was trying to make her mark. She still needed to take on other jobs though. She spent a year working as a Playboy bunny in the Wisconsin branch of the Playboy Club. Diane has no shame about this. She says you gotta do what you gotta do sometimes.
Zing Singh
So around this time, Diane sold two houses to a roofing contractor called Ken. This is quite the meet cute. So they talked on the phone. He tried to set her up on a blind date with his friend, but they got on so well that she decided to go on a date with Ken instead. And she later told Forbes that by the time they met in person, she'd fallen for him. When Ken walked up the steps, she smiled and said, you're due.
Simon Jack
That's nice. There is something sweet about this. Ken was 27, she was 21. The pair though apparently were kindred spirits. He'd aspire hired to be an architect, but he too left school at age 17 after his ex wife got pregnant. Ken also took on jobs simultaneously to support his young family. He joined his father in the roofing business. He drove a repair truck for a local energy company. And whilst driving for that energy job, he'd make a note of houses needing roof repairs and then go back after his shift and offer to repair them on the weekends.
Zing Singh
Ken was always looking for ways to get more work. So for instance, when hailstorms hit towns, roofers usually hiked up their rates. Should make sense, right?
Simon Jack
Yeah. And hail is a massive problem in U.S. farmlands. You go crop and hail damage is like a real hazard to some of the crops and Indeed, to homes. But Ken decided to take an insurance person out to dinner and offered to keep his normal rates if the insurers offered him the contract for all the damaged houses. So when houses get damaged, they call the insurance company. The insurance company called Ken. He's got the inn to do that at a pre agreed rates. So when the next storm hit, Ken would be the first choice. Soon he won contracts to repair Ruth at military bases and Kmarts, for example, across the country. And by 1971, he built a business with 500 roofers working for him and had $7 million in annual sales.
Zing Singh
Pretty good business that is not bad going. Now, Diane says she and Ken started working together within weeks of that first date. They began by reading up on real estate, and then they bought $10,000 fixer uppers near Beloit College. And during the harsh mid winters, you know, when there probably wasn't that much construction work going on, they tapped Ken's roofing crew for help while Diane handled most of the painting and fin touches herself. In her words, I cleaned a lot of toilets. Over three years, Diane and Ken purchased 100 homes. She rented them to college students, and she reinvested that rental income to finance each new property. So clearly a couple with business on the mind.
Simon Jack
Yeah. And so buying places, fixing them up, selling them on, using that money to buy more, growing organically like that. So they were snapping up properties in the early 70s. This is right in the middle of a recession, actually. And house buying had slowed during that because loans were hard to get. But renovators like Ken and Diane, they could buy homes cheaply with, with cash initially. They could fix them up, as I say, and then use that as, use that property as collateral to buy more. With fewer people able to buy, the need for rental homes also went up. So you can't afford to buy, you have to rent. That gives them an income because they've got the rental properties. And rising inflation pushed property values higher over that time, helping their investments grow even as interest rates were going up. Quite. You know, this was the 1970s. We had inflation shocks. It was, it was actually a pretty tough time. And it's quite interesting when we look through all of our billionaires, quite a lot of them have thrived and prospered or certainly emerged from recessions when other people have been killed off. If you can get through a recession, you're in a great position.
Zing Singh
Right. And it's about holding your nerve as well. Right. It's not just about, you know, being able to buy things. It's about knowing that while everyone else is suffering pain, you're going to grit your teeth and get through.
Simon Jack
Yeah, exactly.
Zing Singh
Now, Diane and ken married in 1975. So, you know, clearly the business and romantic partnership worked out. They were blending not just their work lives, but also their family. So, you know, deep breath, because this is going to be complicated. Ken brought four children from his first marriage. Diane brought her son from her first marriage. Together, Diane and Ken had two more children, which meant they had a bustling household of seven. Oh, my God, that sounds exhausting. When each child graduated high school, their graduation presence included $100, a bag of nails, and a hammer.
Simon Jack
Really?
Zing Singh
I'm sure it felt really poignant.
Simon Jack
This is the path we've chosen for you.
Zing Singh
Maybe if you grew up in a construction family, you'd think, God, this is being handed the sword in the stone. But, you know, a bag of nails and a hammer, I'd be like, mom, can I not just get a nice necklace?
Simon Jack
Yeah. But they were in the family business, right?
Zing Singh
Yeah, exactly. So at one point, five of the seven kids held Vice President Rose in the family business. Diane has since instilled that intense work ethic into her 17 grandchildren, too. She said, they've all worked. My grandchildren know I'm not happy unless they've got a job, too.
Simon Jack
Why don't you just give me some of your $22 billion? And why are you making me come work?
Zing Singh
There's a saying in Hong Kong where the first generation makes the money, the second generation holds onto the money, the third generation loses it.
Simon Jack
Yeah. By the late 1970s, Diane was running their house renovation business, managing student rentals, overseeing a store that sold carpets and home appliance to other landlords, all while Ken traveled the country building his roofing business. So they're a busy couple, but Ken.
Zing Singh
Was on constant months, long road trips, and they were becoming unsustainable with that very large family. And the sharp rise in mortgage rates in 1979 began to impact their refurbishing business. So Diane and Ken started looking elsewhere. They started exploring new opportunities, because when.
Simon Jack
Ken had traveled the country for roofing jobs, he'd kept running into the same problem. The roofing supply industry was a mess. Rupert had to juggle multiple suppliers, travel long distances to pick up materials, deal with terrible service. As Ken told the Washington Post, you could spend half your morning waiting for a sales clerk who knew more about lawn furniture and than vinyl siding, whatever vinyl siding is. Diane later said, over time, we realized there needed to be a distribution chain that could offer contractors Access to specialized products from manufacturers across the country. Get this stuff organized.
Zing Singh
Diane and Ken also wanted to raise the professionalism in roofing, which had a bad reputation. So the industry was basically unregulated. So that opened the door to a lot of so called cowboy contractors who cut corners. And because most homeowners unfortunately cannot easily inspect a roof, many people were just unknowingly ripped off. And that in turn dragged down the reputation of even the hard working, honest constructors, which, if you've ever tried to refurb a house anywhere in the world, you know, it's a problem everywhere.
Simon Jack
Roofers also had a lot of downtime. When it rains, you can't work. So as Ken said, some spend a lot of time in the pool hall. But it angered him that roofers like his father and his workers were treated like low lives. Diane told cnbc, we felt like roofers weren't being treated with respect. That was part of our goal to build a company would help the guy in the pickup truck and provide service and respect to everyone. So they started a roofing supply wholesaler. It's quite interesting this, because putting the workman first, it's a smart move. It's basically they're the people who are going to be your customers. They're the people who are going to improve the reputation of the industry. So I think that kind of customer focus might have been unusual at that time.
Zing Singh
Yeah, especially I think, because a lot of our billionaires don't really cite respect, you know, as one of the reasons for motivating them to start a new business. It's quite unusual. It must be born out of, you know, both of their backgrounds, really, from quite humble backgrounds.
Simon Jack
But as we will see, it worked a treat.
Zing Singh
Yeah, that's right. Because by 1982, there was another recession in the United States. It was starting to bite back then, but they were undeterred. They were confident their supplies company would work. And they were so confident that they offered everything they owned as collateral for a massive bank loan of $900,000 to buy three struggling building supplies businesses. Bank in Janesville could not get behind the idea. Diane says that Ken had described himself as an entrepreneur to the bank, but the bank explained to Ken it meant risk taker. And they didn't do business with risk takers.
Simon Jack
Well, entrepreneurs, we know famously Dan Quail said the French don't even have a word for entrepreneur.
Zing Singh
That's very good.
Simon Jack
But anyway, entrepreneur these days trips off the tongue pretty easily. In fact, if you're not an entrepreneur and you live in Silicon Valley, then what the hell are you? But entrepreneur was probably something that was not welcomed with open arms. So very different time. So anyway, they asked a different bank. They asked their small bank in Beloit, Wisconsin, and this bank agreed to grant the loan. And American Builders and Contractors Supply, better known as ABC Supply, was launched at the end of 1982. They had three locations and sales of $4 million a year. They were expanding quickly. They acquired struggling distributors, they open new branches wherever they saw demand. And within two years, only ABC Supply had 25 locations with sales of $82 million. That is an extraordinary growth from 4 million to 82 in two years.
Zing Singh
Wow. I mean, it certainly is something. When ABC Supply was founded, Ken Hendricks with CEO and chairman Diane was executive vice president, also company secretary. And on the board, Ken was listed as sole owner. So we don't know exactly how much Diane earned, But by the mid-1980s, she was almost certainly a millionaire. And later, when she asked if she and Ken ever planned be billionaires, she answered no, but we wanted to be millionaires.
Simon Jack
Yeah. And they are there in the mid-1980s. And Doug, here we have the Limu Emu in its natural habitat, helping people customize their car insurance and save hundreds with Liberty Mutual. Fascinating. It's accompanied by his natural ally, Doug. Uh, limu is that guy with the binoculars watching us. Cut the camera. They see us. Only pay for what you need@libertymutual.com Liberty Liberty Liberty. Liberty Savings Ferry. Underwritten by Liberty Mutual Insurance Company and affiliates. Excludes Massachusetts.
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Zing Singh
Mmm.
Simon Jack
I love ravioli otante. Since when do you speak Italian?
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Well, you can predict the future.
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What message? Oh, hey, we all got bonuses.
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Simon Jack
I don't have kids. You don't say SAP Concur. Helps your business move forward faster. Learn more@concur.com so let us go now from a million to a billion. After this strong start, ABC's growth soared. By 1987, it had 50 locations, 600 employees, $183 million in revenue. It was ranked number one on Inc. Magazine's list of fastest growing companies. Ken at this time, was the company's public face. Diane was managing the finances and the family. But both were laser focused on maximizing the income and profit of the business. Ken concentrated on keeping costs down by negotiating bulk discounts. He used renovated trucks to deliver suppl recycling pallets, blah, blah, blah. Lots of small marginal improvements, cost cutting measures to make the business leaner and more profitable.
Zing Singh
And America was going through a home building boom at the time, wasn't it?
Simon Jack
Yeah, it was the early years of the Reagan administration. And there was a newfound confidence, in fact, in the US after the kind of the decade of the Vietnam War, you'd had the oil shocks, you had the high inflation of the late 70s, when basically the US was not a very happy place. The arrival of Reagan seemed to chime with a number of different things in terms of financial deregulation and all that kind of stuff, which gave America a more confident posture. And that was reflected in things like you need confidence to build bunch of houses. And that's what we were seeing.
Zing Singh
Yeah, you need confidence to know that you can build them, it'll get finished and people will buy them. So Diane looked at starting new companies that could service those building contractor companies. In 1986, she launched a company called American Patriot Insurance Agency to sell insurance policies to contractors to help them save on workers compensation costs. By the 90s, they'd also expanded into a trucking business, window manufacturing, a roofing products brand. So really trying to do this full 360 deal. And they also gave free seminars to customers on how to use new materials. They produced advertising signs for contractors to publicize their own businesses. So the idea was if all these customers who were buying from ABC were doing well, so would the Hendricks.
Simon Jack
That's so interesting about things like you Know, seminars on how to use new materials, all that kind of stuff. Helping the contractor, that's now common practice, you know, for building supplies, whatever. It was kind of novel at the time. Yeah. That they were saying we, you know, here's some new stuff, here's how to use it. We're not only the place where you buy it, you're the place where you learn new skills.
Zing Singh
A one stop shop.
Simon Jack
And probably now is a good time to try and give an insight into what Diane Hendricks is like. Diane, the person she named her insurance company American Patriot and that is telling. She doesn't share much personal detail, but her love for the US is pretty loud and clear. She told Forbes magazine, I love this country. I'm just so blessed to have been born in America. I've never had a door that didn't open for me. And she doesn't reveal much about her pastimes. But we know that her and Ken like motorcycling. She likes Harley Davidsons. Who doesn't if you're a motorcyclist? And she still loves the outdoors. Her property is home to three retired Budweiser horses. These are large working horses who used to pull the promotional beer wagons. We have a similar thing in the UK with these old sharks horses. A quiet nod though to her appreciation for American tradition.
Zing Singh
Now let's go to 1997. ABC Supply has 160 outlets and a 25% share of the market. But it wasn't all plain sailing. So Diane and Ken now needed to refinance the bank loans they used to grow ABC Supply. So the company issued a 10 year $100 million bond at a high 10.6% interest rate. Now those interest repayments meant that although ABC supply sales passed 1,098, they actually made a of 2.6 million that year.
Simon Jack
Okay, so basically their financing cost, the interest they're paying is outweighing some of their, the income they're getting. So pushing them to a net loss. So they needed to return to profitability. So for the first time they looked outside. They brought in an outsider to help. And that outsider was called David Luck. In 1998 he came in, he was a former chief executive of a national tire retailer and he was made president and chief operating officer at abc. And Luck said he wanted to shift the company's focus away company from the, from getting big to becoming the best. And he achieved this by sort of streamlining the infrastructure. He also gave more autonomy to staff, added more employee training programs which reduced staff turnover. And if you're gonna Bring in someone, someone whose surname is Luck. Sounds like a good idea.
Zing Singh
Yeah. What's that phrase? Normative determinism.
Simon Jack
Normative determinism. You are what you're called. Yeah. You become what you're named.
Zing Singh
Yeah. Well, I mean, David Luck luckily worked for them because by 2004, ABC Supply had successfully paid off the bond three years ahead of Sched. With Luck running the day to day business at ABC Supply, the Hendricks could focus on their other ventures, of which there were a staggering 30 of them. So under Hendrik's holding, they ran businesses from manufacturing steel and aluminium products to E Waste Management. And they also refocused on Beloit. You remember that struggling city where they bought homes in the 1970s that also was home to the bank that gave him that first loan?
Simon Jack
Yeah. They'd already transformed a semi abandoned diesel engine plant into ABC's headquarters. But apparently on a whim, in 2001, they bought Beloit Corp's million square foot former paper making foundry for $7 million. That company had gone bankrupt a few years before, costing the City an estimated 3,000 jobs from the plant and the supporting businesses in the supply chain. They turned the foundry into the ironworks. It was called a space that leased offices, workshops, retail space, the local businesses. Kind of a familiar idea now, that sort of thing. Ken often invested in these companies himself to persuade them to stay in Beloit, which helped preserve local jobs. So really, I mean, you know, it reminds me of something like where, where one family or one business becomes synonymous with, with the town. In the UK we have a place called Padstow where there's a chef, a restaurateur called Rick Stein, who basically, you know, has taken over the town and employs everyone there. And it's called Padstein. And I think it's, I think, I think it's a similar thing here.
Zing Singh
Yeah, And I mean, the Hendricks were praised for reinvesting in Beloit, but there were also a few dissenting voices. So some business owners took issue with their projects, particularly when they moved the police station, library and other city services from the business district to a then vacant mall that they own on the outskirts of town. The editor in chief of the Beloit Daily News, Bill Barth, said it's a very small sliver, but you do hear the occasional comment, why don't we just rename it Hendricksville? And yeah, it does seem like, like, you know, Rick Stein and Padstow aside, in America you can really just remake a town in your own image.
Simon Jack
Yeah. What about Walmart? Sam Walton on Bentonville?
Zing Singh
Yeah, yeah, I Feel like it must feel very good on the Eagle to know that you can walk out of your car into a town and think to yourself, I own this town.
Simon Jack
Yeah, but let's return to the business. In 2007, it was the 25th anniversary of ABC supply revenues by now $3 billion. Ken was named Entrepreneur of the Year by Inc. Magazine, and he appeared on Forbes billionaire list for the first time. A net worth of three and a half billion.
Zing Singh
Then, on the 21st of December, 2007, Ken came home from a business dinner. He went to check on renovations him and Diane were undertaking on their new home. And as he inspected a floor above their new garage, he fell through. And this is really tragic. He died in the hospital that night of a trauma to the head from the fall. I mean, Diane deeply missed Ken, didn't she?
Simon Jack
Yeah. She said, I can count on my hand the number of nights I wasn't with him in those 40 years. She buried him in a pasture next to her home. It reminded her of Ken campsites they visited when they went on their motorcycle trips together. So a very sad story, but just.
Zing Singh
A month or so after Ken's death, a rival company made Diane an offer to buy ABC Supplies. So, you know, people were already circling the business. And this is where we actually found Diane at the beginning of this episode, because they assumed that she would want to sell up. But instead, in March 2008, she promoted David Luck to CEO and made herself chairwoman. She worked from home. She asked staff to attend meetings at her house. She told Forbes, I had to put the grief aside, then revisit it after the meetings. The first year was about making it through the day.
Simon Jack
But she also admitted she was scared. She's 61 years old. This was the first time she lived on her own. She hired security guards to patrol her 200 acre wooded estate. She learned to shoot. First a handgun, then a shotgun. She now uses that for hunting wildfowl on her land. So a real, you know, new chapter for her.
Zing Singh
Oh, definitely. But she also had bigger issues to contend with. So she was now in charge of the company during the 2008 financial financial crisis. And that hit the housing market and linked industries hard. ABC Supply sales declined 10% between 2006 and 2009. So together with David Luck, Diane decided to cancel her and Ken's Plan to hit 5 billion in sales and 500 stores by 2010. Instead, they closed the doors on 30 outlets.
Simon Jack
Yeah, so the 2008 crisis was actually rooted in the housing industry. Lots of risky loans have been given to people who really had no business or ability to repay them. And when house prices stopped going up, up, those loans all went bad. Those loans have been parceled up and sold right across the global financial system and kept propping up. No one knew which bank had grenades somewhere hidden in their balance sheet. And the whole thing came to, you know, it was a, I mean I remember this very well, as if it was yesterday actually. I'm getting ptsd. No, not a flashback, flashback to the financial crisis, but it hit the housing market very, very hard. But Diane had been through recessions before and knew that there could be opportunities if she was brave enough. Arrival. Bradco supply, which had 130 stores and sales of one and a half billion dollars, had recently been sold to a private equity group, a little buyout group, and had an uncertain Future. In early 2009, Hendricks chairperson and David Luck began holding meetings with Bradco to discuss a buyout. Now, to fund the purchase, Diane would have to take on an investment partner to, you know, put in extra money and give up 40% of her shares in her business. And she admitted this was very painful to do as she and Ken had always had full ownership of the companies. She said, I felt I risked the company that I wanted my children to run when we're not here. But she knew Bradcoe and felt the acquisition, in her words, had to be done. It was do or dive. She didn't buy Bradco. A rival would. An ABC Supply then could lose its place at the top or even be swallowed up themselves.
Zing Singh
Yeah, so risky business. A deal was eventually struck where if Diane was able to deliver the return in five years, she'd be able to buy those shares back and she'd did it within three years. So by 2012, ABC Supply had 450 branches in 45 states. Revenue was exceeding $4.6 billion. And in 2013, Forbes estimated her net worth to be 3.8 billion. The first increase since she had solely helmed the company.
Simon Jack
So let's go beyond a billion. It was around this time, 2012, that Diane Hendrick's political donations started making the headlines lines. She'd been interested in politics since the 80s, but her support wasn't really known beyond Wisconsin. In May 2012, a documentary filmmaker released footage of Diane speaking with then recently elected governor of Wisconsin, Scott Walker. And she asked if he can make Wisconsin a completely red state, Republican state, and work on these unions and become a right to work state. Now, right to work states or right to work laws are still seen as pro business because Essentially, it's a right to hire people who aren't members of a union. That's really what it is. And it's generally seen as weakening union control over some industries and gives companies the right to hire people who aren't members of union, who don't pay dues to the union and ending what used to be closed shop, as they call them, kind of arrangements. But they can lead to lower wages, fewer benefits of workers due to that weakened union power. On the other hand, they tend to be in states which are very pro business and have kind of all sorts of incentives for businesses. So they tend to do a little bit better economically, those states. So it's a, you know, it's a bit of a balance.
Zing Singh
Right. And Walker did introduce a bill called Act 10, which limited the ability of public workers to bargain over wages. This actually resulted in protests in the state and there was a recall election in 2012. Diane went on to donate half a million dollars to that recall election campaign, which Walker successfully won, and he remained governor of Wisconsin.
Simon Jack
Meanwhile, Diane has continued to grow ABC Supply through some large scale acquisitions, some geographic expansion. In 2016, another important acquisition, they bought one of the largest distributors of gypsum, wallboard and ceiling tiles for nearly $700 million. That added another 136 store locations. At the time of recording, ABC Supply has over a thousand locations and over 20,000 employees. Employees.
Zing Singh
So pretty huge. Yeah.
Simon Jack
Big Enterprise.
Zing Singh
And in 2022, Diane said the company she started with Ken was actually five times bigger than when he was alive. She's also invested a further 85 million in renovating Beloit buildings. And in 2025, this is quite a development. She made the leap to reality TV star alongside her daughter, Konya Hendricks Sher. Now the pair helm the A E reality show Betting on Beloit, which follows their attempt to renovate and flip some of the worst home in that town. Rob Gerbert's, the CEO of her real estate firm, said, the things she's done, I'm not sure Ken would have done. I don't know if he'd want to go on a reality show, to be honest.
Simon Jack
But she's well and truly out of the shadow. She's built a business and taken it onto new heights after his death. So now we've learned about how she made her many billions. It is time to judge her. And in this section, what we do is we look at a number of categories like wealth, philanthropy, controversy, their power and legacy. Score them between naught and 10, 10 and then ask you to decide Whether they are good, bad, or just another billionaire. So let us start with wealth.
Zing Singh
Well, she was actually named the second richest self made woman on earth by Forbes in 2025 though, which is not bad going.
Simon Jack
That's pretty good.
Zing Singh
Yeah. And remember, self made means she doesn't have a single penny or cent of inherited wealth. She's made all that money by herself.
Simon Jack
So on wealth, and not only that, we often look at, you know, how far they've come, you know, on the journey. And she was one of, you know, lots of kids growing up on a rural dairy farm eating homegrown vegetables. Teenage pregnancy.
Zing Singh
Yeah. Divorced by 21, had to strike out on her own.
Simon Jack
Amazing. Really shows real grit and determination and could have wavered after the love of her life and business partner died, but she kept going. So, you know, a lot of grit there as well. So I'm gonna for wealth. Given the fact that she's the second richest self made woman on the planet, I'm gonna give her an 8.
Zing Singh
Yeah, I think an 8 out of 10 is pretty much where I land as well. And also, I mean that rags to riches journey that is that, you know, she talks about her being the embodiment of the American dream. Wisconsin farm girl turned billionaire. That is quite the tagline.
Simon Jack
I wonder if those kids are still using their hammer and the nails that they got or whether they're living it up in a billionaire lifestyle style. So eight for each of us on that controversy. What kind of scrapes or controversial things has she been involved in?
Zing Singh
So in 2016, the Milwaukee Journal Sentinel, a local paper, reported that Diane didn't pay state income tax between 2012 to 2014. And the company's tax director later explained that the move wasn't illegal because the company had changed its tax status from a C corporation to an S corporation, which meant it was allowed to opt out of certain tax requirements with the state, including on payments made to Diane, as long as federal taxes were fully paid.
Simon Jack
Oh, for a proud Wisconsinian.
Zing Singh
Yeah.
Simon Jack
This seems like a move that would have been unpopular in her local area, let's put it that way.
Zing Singh
Yeah. Wiggling out of tax requirements through administrative bureaucracy never goes down well.
Simon Jack
In 2016, the UK paper, the Guardian, shared leaked court documents naming Diane Hendricks as a major donor whose large contributions, half a million dollars, for example, raised concerns about wealthy donors having too much influence in elections. Well, twas ever thus, was it? It not.
Zing Singh
Yeah. And those documents actually came from a Wisconsin Supreme Court investigation into corporate money's impact on politics. The investigation was actually ended in 2015. Because the court said prosecutors overreached and the campaign laws were unclear.
Simon Jack
Yeah. Spoiler alert. Corporate money's impact on politics. It has some impact, yeah.
Zing Singh
Well, I don't think Diane is an outlier in that regard.
Simon Jack
Okay, so controversy, controversy. I've just. I'm not finding much in here that is an outlier to most billionaires attempts to influence politics. I can think of quite a few. So I'm going to give her a middle of the pack here. I think there's nothing, you know, give her a five for controversy, if that.
Zing Singh
A solid five out of ten. Yeah. Typical billionaire behavior, I think, especially after doing so many episodes on what billionaires get up to when it comes to politics. She strikes me as very firmly middle of the road with what she uses her money to do.
Simon Jack
Yeah.
Zing Singh
Five for me, I think.
Simon Jack
Okay, philanthropy. This is how much you've given back. Most of Diane's philanthropy is done through ABC Supply and the Hendricks Family Foundation. And to date, ABC Supplies donated $65 million to the charitable foundation to support communities, mostly in Beloit.
Zing Singh
Sometimes she donates money directly to causes, so she's given 1.75 million to the University of Wisconsin for breast cancer research in 2015. There's less information out there about these direct donations, though.
Simon Jack
They also help fund the Beloit International Film Fest, which held its first event in 2006. And she's also produced and given money to various films, including An American Carol, a 2008 satirical comedy about an anti American filmmaker who's out to abolish the July 4th holiday visited by three ghosts who try to change his perception of the country. I have not caught that film.
Zing Singh
I must say, to admit, I. I didn't hear about this film either.
Simon Jack
I'm sure it was being shown on repeat at a cinema in Beloit. I think in total, though, 65 million is a big number, but it's not as big as 22 billion. So that's 22,000 million. Better than some, much worse than others. I would give her a three.
Zing Singh
And I would give her. Yeah, I think a three out of ten.
Simon Jack
Power and legacy. She's clearly had an enormous legacy locally on Wisconsin and in, of course, in Beloit. Some have said that Diane's funding played quite an important role in turning Wisconsin red for Trump's 2016 victory. That's a surprise. The state historically leaned towards the Democrats. In fact, Wisconsin is one of those hot states whenever there's a U.S. election, it's like, which way is Wisconsin gonna go? So it's really important.
Zing Singh
Yeah. A bellwether state.
Simon Jack
Yeah. Diana's worked with conservative fundraising groups like the Koch Network. You may remember we did an episode on David Koch, very important Republican donor. So she's working with them. And in 2022, Forbes EST, Diana donated more than $40 million since 1992 to Republican candidates and causes.
Zing Singh
So if you were in the Republican Party and your secretary cordon said, diane Hendricks is on the phone, you would.
Simon Jack
Definitely pick up, you take that call. And also, as we were saying, huge legacy in Beloit. Some say positive, others question whether it's got a little bit out of hand.
Zing Singh
Yeah, this is a funny quote. So a New York Times reporter interviewed Diane, described it as if she and ken were playing SimCity with Beloit when they arrived. SimCity being that computer game where you build your own city.
Simon Jack
Yeah, but the ironworks, remember, they turned an old factory into this kind of commercial offices, leasing, all that kind of stuff. It's bought over 1500 jobs to the city. She's funded a new stadium in beloit called the ABC Supply Stadium, estimated to have cost $37 million. So power and legacy, clearly an absolutely massive person in Wisconsin. And actually, because of Wisconsin's importance in many presidential elections, it creeps into a national picture as well. She's also, you know, blazed a trail for roofing supply magnates everywhere. You know, this is really making money the old fashioned way. Nuts and bolts and rivets and gypsum and blah, blah, blah, and vinyl siding and what have you.
Zing Singh
Well, in a way, it is really a sign that you can still make tons of cash the old fashioned way.
Simon Jack
Yeah, yeah.
Zing Singh
You don't need to be doing fiddly bits of code or creating AR glasses or anything. Some people will just always need a roof over their heads.
Simon Jack
So power and legacy I'm going to give her because of her massive wealth and you know, cause all politics is local in a way. I'm gonna give her a seven for parallax. Right.
Zing Singh
Oh, I was actually gonna go with a seven because in a way it's kind of funny. Other than the reality TV show, which, you know, I feel like if you're into reality tv, you might have heard of. It's quite interesting that she kind of stays in the shadows, you know, like both you and I hadn't really heard of her.
Simon Jack
Right.
Zing Singh
And still she's managed to wield enormous influence over, you know, her state, her hometown, US Politics. I feel like I've talked myself into giving her an eight out of ten.
Simon Jack
Okay, wow. Okay. So seven from me, eight from you and just a final reflection, I mean, you said you summed it up well there. It's an incredible rags to riches, not rags, but, you know, very humble origins to massive super wealth. And did it done in a pretty home spun sort of way. Making things like you say, making money in a way the old fashioned way. I think it's a, you know, it's a riveting tale.
Zing Singh
Literally riveting.
Simon Jack
Yeah, well, I didn't even mean that. Riveting tail. I'm not sure Rufus is going to get in trouble saying we don't use rivets anymore. Stupid.
Zing Singh
Wow. Apologies to any roofers listening in. It's such a fascinating one because it kind of shows you that if you are looking for a way to make money, sometimes it pays not to be distracted by the flashy new thing on the block. Yeah, yeah, because she certainly wasn't.
Simon Jack
This is the nuts and bolts of the US economy and they've made money, lots of money in it.
Zing Singh
Lots and lots of money.
Simon Jack
So we are then going to ask you, is Diane Hendricks good, bad or just another billionaire? What do you think?
Zing Singh
That's right. Email goodbadbillionairebc.com or drop us a text or WhatsApp to 001-917-686-1176 and tell us what you think.
Simon Jack
That's good bad billionaire. All one word@BBC.com or 006861176 and please include your name because we may read out your message on a future episode.
Zing Singh
We've actually had some feedback on one of our earlier billionaires, Evan Spiegel. Dominic has emailed in saying dear Simon and zing, I'm an ardent follower of good bad billionaire. Thank you very much. If only to understand the motivation of these entrepreneurs for wanting more and more wealth but not wanting to pay any taxes. In your latest episode you featured even Spiegel of Snapchat fame and I count him as just another billion billionaire. He came from a wealthy family, he had one idea and has since sat back on his laurels. Brutal Dominic. He has shown no world conquering ambitions and not particularly evil. Well, that's Dominic on Evan Spiegel.
Simon Jack
However, Cynthia from Sao Paulo, Brazil disagreed. She thinks Evan Spiegel bad billionaire. Just my opinion. Three exclamation marks. Congratulations for all the solid researching in the way you both conduct the podcast extending to the entire time team. Love it. There are some smiles elsewhere in the studio here. Thank you Cynthia for that from Sao Paulo.
Zing Singh
And if you are listening to this from Beloit, please let us know what you think.
Simon Jack
We'd love to know. What do you make of Diane Hendricks?
Zing Singh
Let us know. So who do we have on the next episode? It's someone you've actually met a few.
Simon Jack
Times and had to sort of lecture him a little bit about not advertising his own company on national television. He's bold, ruthless when it comes to cost cutting. He is Michael o'. Leary. Not the first founder of Ryanair, but undoubtedly the person that everyone identifies with, that local stone.
Zing Singh
That's Michael o'. Leary. On the next episode of Good Bad Billionaire.
Simon Jack
Good Bad Billionaire is a BBC World Service podcast produced by Tamsen Curry. The researcher is Maria Noyen, the editor.
Zing Singh
Is Paul Smith and it's a BBC Studios audio production for the BBC World Service. The commissioning editor is John Lennel.
Simon Jack
Sam.
Podcast: Good Bad Billionaire – BBC World Service
Hosts: Simon Jack (BBC Business Editor), Zing Tsjeng (Journalist & Author)
Date: November 3, 2025
Episode Theme: An in-depth look at the life, business journey, and impact of Diane Hendricks – the richest self-made woman in America, founder of ABC Supply, and a major political donor. The hosts evaluate her as a “good, bad, or just another billionaire” by examining her wealth, power, philanthropy, controversies, and legacy.
The episode profiles Diane Hendricks, tracing her journey from humble beginnings on a Wisconsin dairy farm, through personal and business adversity, to becoming a billionaire business leader in roofing supply. Hosts Simon Jack and Zing Tsjeng dig into her entrepreneurial grit, her family values, her ambitions, and her controversial political activity – ultimately inviting listeners to weigh in: Is she good, bad, or just another billionaire?
[03:16] – [06:26]
“I wish every child could be as loved as I was.” – Zing Tsjeng [03:53]
“…it was embarrassing, but it was ok.” – Zing Tsjeng [04:30]
[06:26] – [11:02]
“It’s about holding your nerve…grit your teeth and get through.” – Zing Tsjeng [09:22]
[11:17] – [15:13]
“We felt like roofers weren’t being treated with respect. That was part of our goal: to build a company that would help the guy in the pickup truck…” – Diane Hendricks, as quoted by Simon Jack [12:16]
“The bank explained to Ken [that entrepreneur] meant risk taker…and they didn’t do business with risk takers.” – Simon Jack [13:35]
“That is extraordinary growth from $4m to $82m in two years.” – Simon Jack [14:46]
[17:15] – [24:32]
“If all these customers…were doing well, so would the Hendricks.” – Zing Tsjeng [19:30]
[22:28] – [24:04]
“It reminds me where one family or one business becomes synonymous with the town.” – Simon Jack [23:01]
“Why don't we just rename it Hendricksville?” – Bill Barth, Beloit Daily News [23:31]
[24:32] – [25:57]
“I can count on my hand the number of nights I wasn’t with him in those 40 years.” – Diane Hendricks, via Simon Jack [24:54]
[28:26] – [34:42]
“…if you were in the Republican Party and your secretary said Diane Hendricks is on the phone, you’d definitely pick up.” – Zing Tsjeng [36:42]
“Wiggling out of tax requirements through administrative bureaucracy never goes down well.” – Zing Tsjeng [33:30]
[30:02] – [31:04]
[34:43] – [38:28]
[31:31] – [38:28]
“She was one of lots of kids growing up on a rural dairy farm…divorced by 21, had to strike out on her own. Amazing.” – Simon Jack [31:46]
On risk-taking and grit:
“I wish every child would eat homegrown vegetables as well.” – Simon Jack [03:55] “You gotta do what you gotta do sometimes.” – Diane Hendricks, via Zing Tsjeng [05:51]
On family values:
“When each child graduated high school, their graduation presents included $100, a bag of nails, and a hammer.” – Zing Tsjeng [10:02]
On business motivation:
“We felt like roofers weren’t being treated with respect...to build a company that would help the guy in the pickup truck and provide service and respect to everyone.” – Diane Hendricks, via Simon Jack [12:16]
On legacy in Beloit:
“Why don't we just rename it Hendricksville?” – Bill Barth, Beloit Daily News [23:31]
On adversity and resilience:
“I had to put the grief aside, then revisit it after the meetings. The first year was about making it through the day.” – Diane Hendricks, via Zing Tsjeng [25:25]
Next Episode Preview:
The next episode will focus on Michael O’Leary of Ryanair, promising more debate on cost-cutting, company culture, and airline dominance.
End of Content Summary