Michael Girdley

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Michael Girdley Business builder and investor. 12+ businesses founded - fireworks, software, media, and more. Exited 5. 30+ years of experience. 300K+ readers.

24/09/2026

The Rise and Fall of the Tesla Cybertruck: 1 million preorders to failure.

Fast forward, and the Tesla Cybertruck is struggling. With recalls, pricing issues, and production delays, sales have fallen flat—just a fraction of what Tesla projected. Meanwhile, competitors like the Ford F-150 Lightning, Rivian R1T, and even the GMC Hummer EV have taken the lead. Explore the rise and fall of the Tesla Cybertruck—from the record-shattering preorder hype, to Elon Musk’s bold promises, to the harsh reality of recalls, price hikes, and customer disappointment. For those interested in EV trucks, Tesla news, Elon Musk business lessons, or why big launches flop, this analysis covers it all.

23/09/2026

HOW TIGER WOODS DESTROYED HIMSELF

Tiger Woods’ 2008 U.S. Open win is remembered as an incredible display of toughness. It also contains a much harder leadership lesson: resilience can become dangerous when you lose the ability to step back, manage your emotions, and decide when pushing harder is actually the wrong move. Tiger Woods built his career around extraordinary discipline, competitiveness, and an ability to perform under pressure. Those qualities helped make him one of the greatest golfers ever. But this story is about what can happen when the same traits that drive success get pushed to an extreme.

Tiger’s relationship with his father, Earl, the pressure and mental toughness of his childhood, and what changed after Earl died are key elements. The 2008 U.S. Open at Torrey Pines becomes the clearest example: Tiger played through a torn ACL and stress fractures despite doctors telling him not to play—and then won. That victory created a complicated lesson. The decision worked, even if the decision-making process behind it may not have been healthy.

That matters for executive leadership because results can fool us. A bad process can still produce a great outcome. Leaders have to separate the two. Winning after taking an unreasonable risk doesn't necessarily prove that taking the risk was smart, just as losing after making a sound decision doesn't necessarily make the decision wrong.

One of the most important leadership lessons is learning to lead yourself before you lead other people. That means recognizing when emotion is driving the decision, looking objectively at the facts, and knowing when persistence has crossed over into self-destructive behavior. Sometimes leadership means pushing harder. Sometimes it means having enough perspective to stop.

There’s also a leadership lesson in Earl Woods’ role. Parenting is its own form of coaching and leadership, and the way we develop people matters beyond their immediate performance. Whether you're raising a child, developing an employee, or scaling a team, producing extraordinary results isn't the only measure of successful leadership. The person you're helping create matters too.

22/09/2026

The Rise and Fall of Walgreens: from $100B to bankruptcy watch.

But now? The Walgreens collapse is in full swing. Their stock is down 90% from its peak. In 2025 alone, they’re closing 500 stores, and Wall Street’s wondering if they can even survive.
The rise and fall of Walgreens is compared directly to smarter competitors like CVS and Amazon PillPack:
- How Walgreens built a moat around real estate and pharmacy profits
- Why PBMs (pharmacy benefit managers) broke their pricing power
- How CVS Caremark and Aetna outmaneuvered them with vertical integration
- And why tech giants like Amazon are dismantling what's left of the business
This isn’t just a failing retail chain story — it’s a dive into missed opportunity, bad leadership, and disruption.

21/09/2026

THE RISE AND FALL OF FRIENDLY'S

Friendly’s grew from a Depression-era ice cream stand into a restaurant chain with roughly 850 locations at its peak. The analysis covers how Friendly’s built a beloved brand, why its competitive position deteriorated, and how ownership changes, financial engineering, bankruptcy, and COVID helped turn an American restaurant institution into a fraction of what it once was.

Friendly’s started in 1935 in Springfield, Massachusetts, when brothers Prestley and Curtis Blake opened an ice cream stand with money borrowed from their parents. Their proposition was simple: make an affordable treat accessible to everybody. After World War II, they expanded beyond ice cream into burgers, hot dogs, and other food just as suburbanization and car culture were transforming America. That tailwind helped Friendly’s grow first to 100 locations, then 200, then 500.

But that expansion also contained the seeds of a strategic problem. Friendly’s was simultaneously a restaurant and a dessert destination. As competition intensified, specialists attacked both sides of the business. McDonald’s, Burger King, and Wendy’s competed for inexpensive meals; casual-dining chains such as Applebee’s and Chili’s competed for sit-down occasions; and Dairy Queen, Baskin-Robbins, and Cold Stone Creamery focused on dessert. Friendly’s increasingly found itself stuck in the middle rather than dominating a category.

Ownership changed, too. Hershey’s bought Friendly’s from the founders for $162 million in 1979 and later sold it for $375 million. The chain eventually went public, and in 2007 Sun Capital acquired it for $337 million plus assumed debt. Cost cutting, sale-leasebacks, higher prices, and debt came at exactly the wrong moment, when Friendly’s needed investment in its stores, menu, advertising, and competitive position. By 2011, declining store sales and its debt burden helped push Friendly’s into Chapter 11 bankruptcy.

Friendly’s continued operating through the 2010s, but COVID struck a business built around in-person, sit-down dining and the soda-fountain experience. The company filed for bankruptcy again in late 2020, and the brand was subsequently acquired for $2 million. Some franchise locations survived, and Friendly’s-branded ice cream and treats remain on grocery-store shelves.

The rise and fall of Friendly’s is ultimately a lesson about competitive advantage and stewardship. A company can have enormous customer affection and decades of history, but nostalgia alone isn’t a moat. The exploration of Friendly’s story reveals what happened to the chain, why it declined, and what founders and operators can learn from a business that lost its differentiation while competitors became increasingly specialized.

20/09/2026

STARBUCKS IS STRUGGLING. WHY ARE THEY OPENING SO MANY STORES?

In this video, I look at:
• The hidden reasons Starbucks grew so fast (and what broke the model)
• How bad decisions, menu bloat, and inflation crushed their momentum
• Why the new CEO is betting big on more stores (and how it could actually work)
If you’re into business strategy, turnarounds, or want to learn from Starbucks’ mistakes, this one’s for you.

What do you think of Starbucks’ game plan? Drop a comment below.

19/09/2026

WHY NOBODY SHOPS AT MACY'S ANYMORE

Macy’s went from an $11 opening day in Manhattan to one of America’s most recognizable retailers, eventually generating roughly $28 billion a year in sales. I trace the rise and fall of Macy’s, what made the department store model so powerful, and why changing consumer behavior, strategic decisions, and financial engineering left the company struggling to adapt.

Macy’s story starts with Roland Macy, who failed at several ventures before opening R.H. Macy & Co. in Manhattan in 1858. The company embraced ideas that were radical for retail at the time: fixed pricing, a money-back guarantee, cash-only sales, aggressive newspaper advertising, and a huge selection of products under one roof. Over the decades, Macy’s became more than a retailer. Its Manhattan flagship, parade, and role in American culture turned the brand into an institution.

The department store model became especially powerful as America moved to the suburbs and malls became major shopping destinations. Macy’s and other department stores served as anchor tenants, benefiting from favorable rents while generating traffic for the smaller stores around them. Macy’s later pursued scale through consolidation, eventually replacing regional names like Marshall Field’s and Foley’s with the Macy’s brand. That created a national retail giant, but it also sacrificed some of the local loyalty those stores had spent generations building.

Then the economics changed. Mall traffic weakened, e-commerce made shopping dramatically more convenient, and discount retailers attacked department stores from below on price. Macy’s had also spent years leaning into deals, sales, and coupons. That left the company caught in the middle: Amazon and other e-commerce businesses could win on convenience, while discount retailers could compete more aggressively on price.

Financial engineering made those pressures harder to absorb. Macy’s had already endured a debt-heavy leveraged buyout and a 1992 bankruptcy. Decades later, activist investors began arguing that Macy’s real estate could be worth more than the retail business itself. Eventually, real estate investors pursued multibillion-dollar offers to take the company private. The conversation had shifted from how to grow Macy’s to what its underlying assets might be worth.

That’s the bigger business lesson in what happened to Macy’s. There wasn’t one decision that caused its decline. Changing consumer behavior, dying malls, e-commerce, discount competition, brand decisions, debt, and financial engineering accumulated over decades. The contrast with Dillard’s is especially interesting: while Macy’s went through ownership changes and financial maneuvering, Dillard’s remained family-controlled and managed its own decline with far less drama.

18/09/2026

The Rise and Fall of Subway: The $11 billion empire that crumbled.

I dive into the fascinating story of Subway — from its humble beginnings to becoming a global giant, and the lessons every entrepreneur can learn from its rise (and struggles). If you’re interested in business, franchising, or success stories, gain insights into one of the most famous franchises in history.

I’ll cover:
- How the $5 Footlong deal exploded in popularity
- Why Subway franchises actually lost money on the promotion
- The lawsuits and controversies that followed
- Why the $5 Footlong eventually disappeared
- What this marketing fail can teach us about business strategy

17/09/2026

Why did the beef industry take Oprah to court for $10 million? When Oprah Winfrey criticized beef on her show, cattlemen sued her, turning a defense of their industry into a high-stakes battle over reputation. Oprah's refusal to back down wasn't just legal; it was about maintaining trust with her audience.

16/09/2026

The Rise and Fall of NASCAR: How America's race lost its speed.

NASCAR once climbed from dirt tracks to America's #2 TV sport, powered by Winston Cup money, ESPN exposure, and larger-than-life stars—then it stalled out as viewership halved and sponsors left. The pivotal moments: the 1979 blizzard that supercharged Daytona's first live 500, the revenue split that favored tracks over teams, and a 2004 playoff reboot that confused casuals and alienated loyalists.

The "Car of Tomorrow," the Great Recession sponsor collapse, and why the fan base aged into its late-50s and 60s all played a role. NASCAR's comeback attempts include Next Gen cars, new faces like Bubba Wallace, celebrity owners (Michael Jordan, Pitbull), and a heritage nod with North Wilkesboro—essentially an F1-style playbook. Can it work? The data, incentives, and storytelling that built (and broke) the brand.

15/09/2026

Why isn't Rolex considered cool anymore? Rolex's rise from Hans Wilsdorf's wristwatch innovation to a $10 billion luxury giant illustrates a paradox: immense popularity diluted its exclusivity. Once a symbol of achievement, Rolex is now seen by some collectors as a "beginner's watch." The brand's success in creating demand through scarcity inadvertently shifted its cultural status.

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