Business builder and investor. 12+ businesses founded. Exited 5. 30+ years of experience. 200K+ readers.

Building beautiful businesses. I’ve spent the last 30 years leading, building, and growing my holding company. 

Entrepreneurship done right makes the world a better place.

My track record of success:
- Employ 600+ people
- Built 12+ businesses across multiple industries
- Audience in the hundreds of thousands
- Chili's & Subaru evangelist (unpaid)

Michael Girdley

Nobody’s talking about this country.
But they will be.

Let me show you why Argentina is one of the most underrated places to build offshore teams right now:

You can hire two fluent, professional Argentinian team members, with minimal to no accent, for the cost of one US employee.

We’ve brought on folks in sales, marketing, customer support. Basically every remote role you can think of.

The real advantage isn’t price though, it’s quality. You get way more firepower for the same budget.

And it’s not just anecdotal. The data backs it up:

• Salaries for highly skilled professionals are 40–50% lower than in the US or Europe

• The BPO sector exports over $3B a year

• 92% of the population is urban—hello, infrastructure and talent

• Same time zones as the US

• #1 in Latin America on the English Proficiency Index

• 3 million people speak and write English fluently

• English instruction starts young. Private schools are often bilingual by kindergarten. In public schools, it starts by Grade 3 or earlier. And almost every university program requires it.

• 24% of the country holds a university degree

I know offshoring used to be dominated by India and the Philippines.

But if you’ve ever struggled with the time zone gap, delayed responses, or odd working hours… this is your chance to fix it.

Book a free strategy call with Hire With Near here, my followers get 5% off their service: https://lnkd.in/gyY2ErV7

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These awards recognize outstanding people under 40 years old who are rising stars in the business community. They are among the most important awards we bestow because they call attention to the fact that a community needs a constant stream of leaders coming up today to stay strong and relevant in the future.

2014 Man of the Year

The San Antonio Business Journal announces the winners of its 2015 40 Under 40 awards.
A select panel of judges consisting of past 40 Under 40 award recipients chose the 2015 winners from more than 110 nominees.

San Antonio Business Journal 40 under 40

TechStars

SAPitch.com

Legacy Geekdom Fund

King William Association

Essential insights for business owners. Sign up and join 44K+ leaders reading my weekly letter.

Girdley's Letter

A 360 solution to find, hire, onboard, pay, and retain top Latin American talent. Fill open positions in under 21 days.

Build High-Performing Remote Teams for 70% Less

HoldCo Conference 2026

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The rise and fall and resurrection of LEGO

Today, LEGO is the most profitable toy company in the world. But just 20 years ago, it was losing $1 million a day, drowning in debt, and weeks away from collapse. This video breaks down the real story behind LEGO’s rise, fall, and legendary turnaround.

In the 1990s, LEGO chased trends, over-expanded into theme parks, clothing, and electronics, and completely lost focus on what made it special. Costs exploded, complexity spiraled, and profits disappeared. By 2003, bankruptcy felt inevitable. Then a bold leadership change forced LEGO to strip everything back to its core: creative play, disciplined design, and customers who actually wanted to buy the product.

This is a masterclass in business failure, turnaround strategy, brand focus, and leadership under pressure — with lessons for entrepreneurs, investors, and anyone building something long-term.

Subscribe for more breakdowns on iconic companies, business turnarounds, and investing lessons every week.

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

I put down a deposit on a Cybertruck back in 2019.

Thought it looked cool. A truck from Blade Runner. What's not to love?

Five years later, I still don't own one. And after digging into the numbers, I'm glad I passed.

Here's what happened when Tesla decided to build what they wanted instead of what customers needed.

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The launch was genius. November 2019, Elon literally broke the "unbreakable" glass on stage. Whether it was intentional or not, it created massive buzz.

200,000 people put down deposits within 48 hours. I was one of them.

Elon promised deliveries in 2021, a base price under $40,000, and 500 miles of range. Sign me up.

But here's the thing, according to the Walter Isaacson biography, Musk told his team he didn't care if anybody bought it. He wanted to build the Cybertruck because it was cool and it pushed the envelope.

When engineers created an alternative design that would be easier to manufacture, Elon said no. We're doing my vision.

That decision cost them everything.

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The radical design meant reinventing 100+ years of automotive manufacturing from scratch. New materials, new processes, new everything.

Meanwhile, Ford and Rivian beat Tesla to market by 18 months with conventional designs.

When the Cybertruck finally delivered in 2023, everything had changed:

The base price hit the low $60s — 50% higher than promised. A decently equipped one runs $80k+.

The range came in at 320 miles, not 500.

Quality issues plagued early models. Panels falling off. Stuck accelerator pedals. The kind of stuff you don't expect when you're paying luxury car prices.

And the world was different too. Pre-COVID, money flowed easily. By 2023? 

Inflation hit hard. Interest rates skyrocketed. What might've been a $1,000 monthly payment became $1,500.

Suddenly fewer people could afford an $80k truck.

—

Today they're selling about 1,400 units per month. Tesla projected 250,000 annual sales.

Both the GMC Hummer EV and Ford F-150 Lightning are outselling it — in some cases by over 50%.

The lesson? It's pretty straightforward.

You need to build what customers want, not what you think is cool.

Tesla's engineers got to play with revolutionary materials and space-age designs. But customers wanted a practical truck at the promised price with the promised range.

When you ignore that fundamental truth, it doesn't matter how innovative your product is.

What do you think... Is the Cybertruck a flop, or am I missing something?

—

I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

The rise and fall of Boston Market

Boston Market wasn’t just a chicken chain — it was one of the fastest restaurant explosions in American history. From a tiny shop in Massachusetts to the hottest IPO of the 1990s, Boston Market looked unstoppable… until a bizarre franchise-loan scheme, hidden losses, and years of mismanagement sent the company spiraling toward disaster.

This video uncovers how a risky growth model, chaotic expansion, private-equity cost-cutting, and rising competition from chains like Chipotle and even Costco rotisserie chickens pushed Boston Market from 1,200 stores to near extinction. It’s one of the wildest rise-and-fall stories in the food world — complete with lawsuits, unpaid employees, government seizures, and a brutal collapse that almost no one saw coming.

If you love business documentaries, brand breakdowns, or untold corporate failures, this deep dive is for you. Subscribe for more rise-and-fall stories every week.

16% of Cracker Barrel's regular customers disappeared after the pandemic and never came back. 

For a chain that once did twice the revenue per square foot of its competitors, that's not just a bad quarter, that's an existential crisis.

I took my 16-year-old son there last week.

We lasted 5 minutes before he said, "This place is giving me a migraine." We left.

Walking through that gift shop felt like stepping into 1975—Stanley cups with cutesy sayings, random knick-knacks everywhere, sensory overload from every direction.

Here's the thing: Cracker Barrel didn't fail because they stopped being what they were. They failed because they stopped paying attention to who was coming through the door.

How It Started:

In 1969, founder Dan Evans built restaurants along the new interstate system. Nostalgic country food. Walk through a gift shop to get to it.

Perfect for baby boomers road-tripping across America. Before Yelp or Google Maps, people wanted chains they could trust.

They grew 20% year-over-year through the 80s. By 2011, $2.4 billion in sales across 600 stores.

Where It Went Wrong:

The boomers aged out. Gen X and millennials didn't want heavy meals and Chinese tchotchkes.

But Cracker Barrel kept listening to existing customers who wanted bigger menus. The menu exploded. Kitchen staff got overwhelmed. Service suffered.
The corporate structure made it worse. Unlike Texas Roadhouse where managers own 10% of their location, Cracker Barrel managers just reported KPIs. No skin in the game.

And those 10,000 square foot stores on interstate exits? Once an advantage, now a liability. Massive fixed costs in the middle of nowhere.

The Perfect Storm:

By 2020, they had no takeout, no delivery, no digital offering, and no appeal to young people.

Americans now spend 70 minutes more per day at home than pre-pandemic. If you depend on road trips, that's a death sentence.

Then in 2023, new CEO drops $700 million on a rebrand. President Trump tweeted about how much he hated it. The stock dropped $100 million in days. A week later, they reversed it.

The Real Lesson:

The core problem for 30+ years? Insular culture.

They sat in boardrooms making decisions without understanding what was happening outside. An activist investor spent years trying to get on the board to push for changes. They fought him instead. They invested $133 million in a Gen Z concept instead of fixing their core business.

I'd bet their leadership wasn't spending real time in stores. Because if they were, they wouldn't have made these mistakes.

The same thing that creates your advantage often becomes your disadvantage

Ever watched a business you loved refuse to adapt until it was too late?

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

In 2021, I started my own WeWork called The Rainwater.

I didn't want to make money.

I wanted to create my dream workspace.

And be surrounded by inspiring peers.

Speaking of inspiring peers...

If you are a professional in San Antonio, I have something for you:

We have an open office to rent in our coworking space. 

It's near the Zoo and Brackenridge Park. Stunning venue.

If you are interested, DMs are open!

A "Degentrepreneur" is a bro who made his riches in a business like vape shops, crypto casinos, or prediction markets. See also: lime-colored Lambo.

Any other businesses I need to add to the list here?

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

99.9% of the people talking about this issue so much could 10x any potential savings if they spent that time on a side hustle.

The same goes for the never-ending rent vs buy arguments here. People love to organize their nickels when they should be hunting dollar bills.

Thoughts?

—

I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

The rise and fall of CarMax: From used-car king to 75% stock crash

CarMax completely changed how Americans bought used cars. No haggling, full transparency, massive scale — and for decades, it worked. By 2021, CarMax was generating over $32 billion in revenue and selling 1 out of every 25 used cars in the U.S. It looked like one of the most durable retail businesses ever built. Then the cracks started to show.

In this video, we break down the rise and fall of CarMax, from its early dominance and COVID-era boom to the strategic missteps that left it vulnerable. We’ll cover shifting consumer behavior, rising interest rates, EV disruption, online competitors like Carvana, and why CarMax’s once-bulletproof model may no longer fit the future of car buying.

This isn’t just a story about cars — it’s a case study in how great businesses fail to adapt, and how success itself can become the trap.

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

Are you an accounting or audit pro who wants to be a CEO? With equity, salary, and reduced downside risk? And more leads than you can handle? 

Have a founding CEO role available. DMs open.

(I appreciate any interaction for reach if you could! This is one that LinkedIn will bury!)

Michael

The rise and fall of DeLorean Motor Corporation: What destroyed the $100M dream

The DeLorean DMC-12 is one of the most recognizable cars ever built—but behind the stainless steel and gullwing doors is a business disaster few truly understand. This video breaks down the rise and fall of DeLorean Motors, from John DeLorean’s meteoric climb at General Motors to one of the most infamous collapses in automotive history.

We explore how ambition, ego, government money, and impossible engineering decisions turned a revolutionary idea into a financial nightmare. From missed deadlines and exploding costs to the shocking FBI sting that ended everything, this is a case study in leadership failure, startup mismanagement, and how hype can’t save a broken business model.

If you’re interested in business stories, automotive history, or real-world lessons on entrepreneurship and risk, this deep dive delivers the full picture—without nostalgia goggles.

Subscribe for more data-backed breakdowns of iconic companies, failures, and investing lessons every week.

Want to test-drive a car without pushy salespeople?

1) Go to Hertz.
2) Find the car you like. Keys will be in it.
3) Drive it around their parking garage (no exit).
4) Park car.

Most people think they know what happened in 2023. One Instagram post, massive boycott, company learns its lesson, right?

Wrong.

Here's what really killed Bud Light — and it wasn't what you think.

The Slow Decline Nobody Noticed:

By 2023, Bud Light had been bleeding market share for over a decade. They'd cut $300M+ from marketing budgets after a 2008 acquisition. Craft beers were exploding (breweries went from 2,000 to 10,000 between 2010-2020). Gen Z was drinking 20% less than Millennials at the same age.

The brand was already in trouble.

But leadership was obsessed with chasing new customers instead of keeping the ones they had.

The Fatal Mistake:

When that controversial partnership happened in April 2023, it wasn't the partnership itself that destroyed them.

It was how they responded.

They went silent. They fired people. They issued a non-apology that satisfied nobody. And in doing all that, they sent one clear message to their existing customer base:

We don't really want you anymore.

Sales dropped 36% in three weeks. Customers switched to Coors Light and Miller Lite — both up 8-15% — and never came back.

The Real Lesson:

I've seen versions of this pattern dozens of times (though never at this scale). Companies get so focused on growth, new markets, and "evolving their brand" that they forget the people who already love them.

Your existing customers aren't a given. They're a gift.

And when you make them feel like you'd prefer different customers, they'll find a company that actually wants them.

The mission of your company isn't to impress your marketing team or chase trends. It's to delight the customers you already have — consistently, reliably, year after year.

That's hard to do for 20+ years. But the companies that pull it off? In-N-Out, Chick-fil-A, Costco — they print money.

The ones that take their customers for granted? Check the chart.

What's your take on the Bud Light fiasco?

The rise and fall of MTV: How a $400M empire collapsed.

MTV didn’t just play music — it created modern pop culture. From turning Michael Jackson and Madonna into global icons to defining what young America watched every night, MTV once controlled the cultural monoculture. But just a few decades later, the channel that launched music television stopped playing music entirely.

This video breaks down the real rise and fall of MTV — not the nostalgic version, but the business reality. Why music videos were never profitable, how reality TV quietly saved the network, and why shows like The Real World, Jersey Shore, and eventually Ridiculousness replaced the very thing MTV was built on. We also look at how YouTube, streaming, and the collapse of cable finished what success had already started.

The data tells a different story than the myth. MTV didn’t die because it abandoned music — it died because the monoculture died. And once young viewers left cable, there was no coming back.

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

When your $50k/year employee arrives at work in a $120,000 car.

Peloton went from a $50 billion valuation to losing 97% of its stock value.

Here's the thing: this wasn't just about COVID. It was about forgetting what business you're actually in.

In 2012, John Foley had a problem. He loved spin classes but didn't have time for them. So he built a $2,000 connected bike that brought the experience home. 

His target market? High-earning, time-crunched achievers who wanted a status symbol in their house.

And it worked. By 2019, they had 100,000 subscribers and went public at a $4 billion valuation.

Then COVID hit.

Suddenly everyone was trapped at home. Gyms were closed. Peloton's revenue doubled in spring 2020. They cracked 1.1 million subscribers by summer. The stock market valued them at $50 billion—higher than Ford and Kraft Heinz combined.

Let's be real: a bike with an iPad attached was worth more than companies making millions of cars and feeding America.

So what did Peloton do? They went all in. Bought an equipment maker for $420 million. Built a factory in Ohio for $400 million. Predicted they'd eventually have hundreds of millions of households with Pelotons.

But here's where it all fell apart: COVID was a one-time event, not a permanent shift. The people who wanted Pelotons already bought them. The world went back to normal. Suddenly they had 120,000 unsold bikes sitting in warehouses and a factory in Ohio that never produced a single piece of equipment.

Revenue dropped from $4 billion to $2.8 billion. Stock down 98%. The founder was out.

The fundamental mistake? Mistaking a niche luxury product for a mass-market necessity.

I don't own a Peloton. Never have. But the people I know who use them? They absolutely love it. That loyal, dedicated user base was always Peloton's real asset. Not the hardware. Not the factory capacity. The community.

When you have a niche product that serves a specific customer incredibly well, don't let an external shock make you believe everyone in the world needs what you're selling.

That's when you over-invest, over-promise, and set yourself up for a painful correction.

What do you think? What's the biggest lesson here?

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

My mom had a stack of those 20% off Bed Bath & Beyond coupons on the kitchen counter.

I swear they arrived in the mail every single day.

She'd drag me to the store as a kid, and I remember thinking it was the most chaotic place I'd ever seen. Stuff piled floor to ceiling. Blenders next to bath mats next to kitchen knives. It was organized chaos.

But my mom loved it. She'd go in with no plan and leave with a full cart, feeling like she won some kind of game.

Last year, all 1,500 stores closed forever. Bankruptcy. Gone.

Here's what killed them:

They didn't get the internet.

The founders literally said this. "We just didn't get the internet."

While Amazon was learning e-commerce and Target was pouring billions into omnichannel, Bed Bath & Beyond kept doing more of what had always worked. 

More coupons. More cluttered stores. More of the same.

By the time COVID hit, they had no way to serve customers who couldn't come into stores. The pandemic should have been HUGE for a homegoods retailer. Instead, it finished them off.

They treated the business like a piggy bank.

Get this: they spent $11.8 billion on stock buybacks. They even borrowed money to buy back shares.

That's money they could have used to build an actual e-commerce platform. Or weather tough times. Or invest in the business.

Instead, it went straight to shareholders and management pockets. Including deals where the founders' kids started companies and Bed Bath & Beyond conveniently bought them out.

They removed what customers loved.

In 2019, new management tried to "targetify" the chain. They cut 200 stores. Removed beloved brands. Got rid of those famous coupons.

Customers had been trained for 30+ years that shopping at Bed Bath & Beyond was a game. When they stopped letting people play, people stopped coming.

The ironic ending:

You know what Bed Bath & Beyond is now? An e-commerce site. 

Overstock.com bought the name for $21.5 million and rebranded itself.

The company that couldn't figure out e-commerce finally became an e-commerce company. It just had to die first.

Bottom line:

The founders who perfectly read the market in the 1980s completely missed the next wave. Financial engineering replaced reinvestment. And removing what made customers happy killed what was left.

This is one of those cases where the business had every chance to survive. 

They just chose wrong at every turn.

What's your take on this?

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

I used to love Chipotle.

Like, really love it. I'd stand in those famously long lines at lunchtime just to watch them make my burrito bowl right in front of me. It felt like real food, not the microwave TV dinner I'd get at McDonald's.

That was the magic of Chipotle. Steve Ells borrowed $1,000 from his parents in 1993 and did something miraculous — he took fine dining preparation and put it into a fast food format. Fresh ingredients, no frozen crap, visible kitchens. 

Customers went crazy for it.

McDonald's certainly did. They invested $360 million in 1998. By 2005, Chipotle had grown from 16 restaurants to over 500. Revenue went from $1.8 billion in 2010 to $4 billion by 2015. The chain opened a restaurant every two days.

Here's the thing: the strength that built Chipotle is exactly what killed it.

In 2015, they'd grown so fast they couldn't keep the food safe anymore. E.coli outbreaks. Salmonella. Hundreds of people got sick. Stock dropped 20%. They lost $600 million in revenue in 2016 alone. Eventually paid the biggest foodborne illness fine in history — $25 million.

Both co-CEOs got pushed out, including founder Steve Ells. The board brought in Brian Nichol from Taco Bell to fix things. And he did — sort of. He modernized tech, fixed food safety, brought in standardization. The kind of factory-level processes that McDonald's and Taco Bell use.

The numbers looked amazing. Stock up 700%. Profits up 700%. Revenue doubled by 2023.

But there was a problem.

All that efficiency destroyed the value proposition. The generous portions got smaller. The friendly environment became impersonal. Prices went up while quality went down. Nichol eventually admitted 10% of restaurants were deliberately skimping on ingredients to maximize profits.

Customers noticed. Today, Chipotle's net promoter score is 17. In-N-Out Burger's is 63. Same-store sales are down 5%. Local Chipotles near me have 2.5 to 3.5 star reviews. That's terrible.

The lesson here? Be careful how you fix a failing business. Brian Nichol ran the Taco Bell playbook at Chipotle. But Chipotle isn't Taco Bell. What built the brand was that generous, welcoming, fresh-food experience. The turnaround fixed operations but killed the soul.

Sometimes when you save a business, you lose what made people love it in the first place.

*I know this graphic is a little older. Currently, Chipotle stock is back in the gutter.

What's your take on Chipotle?

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

The days of Gen X or Boomers being OK with doing things "just because of tradition" are over.

My #1 advice for working with Gen Z:

You must explain the *why* things are being done at work a certain way -- or at all.

I got this idea while reflecting on my latest round of interviews. I hope this helps someone.

What has been your experience?

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I run an annual conference for business owners in Sundance, Utah. It’s all owners, operators, and investors sharing real deal structures, holdco economics, and what's working now.

Join us in February!

Click the link in my bio to check it out.

Clayton Smith

Father/Husband/Son/Brother
Servant Leader
Growth Driver
Brand Builder
Culture Champion

Co-Founder

dumptd is the first commercial construction and demolition waste diversion marketplace, allowing developers, waste producers, haulers and other stakeholders real-time diversion tracking to achieve green building certifications, promote sustainability and achieve ESG goals.

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