From Playboy Bunny to Billionaire

Many business owners centralize decision-making, stifling responsiveness to local customer needs. They often focus on price wars or generic offerings. They neglect the tailored service that builds sticky relationships. They fail to invest in understanding their customers’ pain points. Which only leads to commoditized businesses with no differentiation.

Not Diane Hendricks. She’s a female billionaire who owns a roofing company. She’s the sole owner and chair of ABC Supply. Which is one of the largest distributors of roofing materials in the United States. She’s the richest self-made woman in America with a net worth of about $21 billion.

Hendricks prioritized understanding and serving contractors’ needs. Not only does ABC Supply offer roofing products. Her company offers solutions. Which includes fast delivery, reliable inventory, and expert advice. What did she do differently? She empowered branch managers to make decisions tailored to local markets.

The results? Agility and customer loyalty. ABC Supply’s decentralized model ensures branches act like local businesses. They do this while benefiting from national scale.

Many business owners shy away from acquisitions. This could be due to risk aversion or lack of capital. They miss opportunities to consolidate fragmented markets. They pursue misaligned acquisitions, diluting focus or over-leveraging finances.

Integration failures. Cultural clashes. Redundant operations.

These are common when owners lack the same disciplined approach to post-merger execution. They lack the disciplined approach of Diane Hendricks.

Her aggressive acquisitions expanded ABC Supply’s geographic footprint and product offerings.

Hendricks co-founded ABC Supply in 1982. That’s when Ken and Diane Hendricks acquired three failing supply centers from Bird & Sons.

In 1984, Ken and Diane acquired 13 former GAF stores as part of a larger expansion strategy. Which included also acquiring stores from other distributors.

Ken and Diane had experience as roofing contractors. But with this acquisition, they disrupted the building materials distribution business.

Ken’s childhood experiences working with his contractor father inspired him. Suppliers often gave indifferent treatment to contractors. Suppliers failed to meet their practical needs. That bothered him.

Ken and Diane’s guiding principle for ABC Supply was to treat contractors with respect. They provided the products and services necessary to help contractors’ businesses thrive.

She took full ownership after her husband’s death in 2007.

Since taking full control, she’s overseen the acquisition of competitors. As well as complementary businesses (e.g., L&W Supply in 2016). Hendricks integrated them to enhance scale while preserving operational efficiency. She targeted businesses that aligned with ABC’s core strengths.

Many business owners overextend their finances. They chase growth with unsustainable debt or bloated overhead.

They often lack the discipline to reinvest profits, allocating strategic capital. They’re not proactive about cutting costs. They leave their companies vulnerable to market shifts. Others prioritize flashy expenditures (e.g., lavish offices) over operational resilience.

Not Diane Hendricks. She maintained tight control over costs. She keeps ABC Supply lean even as it scaled to over 900 locations. She avoided excessive debt. She funds growth through cash flow and selective borrowing. Which insulated the company during economic downturns like 2008.

In 2010, she gave up a 40% stake in ABC Supply to a financial backer. It was during her company’s major acquisition of Bradco Supply. It was the only way to finance the deal, with the condition that she could buy it back within five years.

In less than four years, she reclaimed full ownership, repurchasing those shares. As of now, she controls all shares of ABC Supply.

Her modest upbringing rooted her frugal mindset. Which translated into a culture of efficiency.

Many business owners chase short-term profits. They cut corners on quality or investment to boost margins. They sell too early or go public before they’re ready. They lose control to external pressures. Diversification into unrelated fields often dilutes expertise.

This is a trap Hendricks avoided. How? By staying laser-focused on roofing and siding distribution.

ABC Supply is a private company. Hendricks kept it that way for a reason. It allows her to focus on long-term growth rather than quarterly earnings pressures. She made heavy reinvestments in the business.

Expanding branches. Upgrading technology. Training staff.

While resisting the temptation to cash out or diversify into unrelated ventures. Her commitment to the core business kept ABC focused and dominant.

Many business owners neglect culture, leading to high turnover or disengaged employees. Micromanagement or distrust erodes morale. While others fail to align incentives with long-term goals. Scaling without a unifying culture often fragments organizations.

This is something Hendricks avoided through personal engagement and clear values.

Many business owners either resist change, or lose their competitive edge. They cling to outdated models. They make radical pivots. Failure to balance innovation with core strengths often leads to missteps. For instance, they over-invest in unproven tech. They abandon loyal customers for new markets.

Not Diane Hendricks. She navigated industry changes.

Economic cycles. Supply chain disruptions. Technological shifts.

She did this by adapting ABC’s operations while staying true to its core mission. For example, she embraced e-commerce and logistics tech to enhance efficiency. But didn’t chase trendy diversifications like unrelated construction sectors.

Many business owners crumble under pressure. They lack the grit to push through setbacks. They may delegate too much. They lose touch with the business, or give up when faced with personal or market challenges.

Not Diane Hendricks. Her hands-on leadership and unwavering commitment set her apart.

About her personal story — did you know she was a Playboy Bunny in the late 1960s? After becoming a mother at 17, she worked as a Playboy Bunny waitress at the Lake Geneva Playboy Club. This was in Wisconsin. She worked there to support herself and her child, rising from a single mother to billionaire.

Diane Hendricks defied expectations in a male-dominated industry. Her perseverance and tenacity set the tone for the company’s resilience.

I like you,

– Sean Allen Fenn

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Methods of Prosperity newsletter is intended to share ideas and build relationships. To become a billionaire, one must first be conditioned to think like a billionaire. To that agenda, this newsletter studies remarkable people in history who demonstrated what to do (and what not to do). Let me know how I can help you out. For more information about the author, please visit seanallenfenn.com/faq.