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

How do you turn a billion-dollar business into a disaster in just three years?
Ask Topgolf.

Topgolf is in serious trouble. Sales down 10% year-over-year in established markets. Stock dropped 40%. The company is literally splitting itself apart to survive.

Here's how it happened:

Started in the UK around 2000. Private equity brought it to the US. People loved it—especially millennials looking for group activities that weren't just another bar.

By 2019, Topgolf was doing $1.1 billion in revenue and growing 30% annually.

Then Callaway (the golf equipment company) made a massive bet. They bought Topgolf in 2020, renamed the whole company, and borrowed hundreds of millions to build 10 new locations a year.

Each location costs $15-40 million to build. But they were doing $15-20 million per year in revenue. The math looked good.

Post-COVID, things got even better. People were desperate for in-person experiences. Fresh air. Group activities. Topgolf crushed it.

But here's where it all went wrong:

Problem #1: Consumer behavior normalized faster than expected. Turns out people's COVID habits weren't permanent.

Problem #2: Inflation hit. Average spend per person is $36. They wanted $650 just to reserve a bay on a Tuesday afternoon for a corporate event. In an environment where wages aren't keeping up? That's a tough sell.

Problem #3: It became a fad. People tried it once or twice and moved on. The repeat business never materialized the way they needed.

Problem #4: Interest rates skyrocketed. All that borrowed money to build new locations? Now it's crushing their free cash flow.

Problem #5: Competitors figured it out. Guys are putting the same tracking tech in strip mall driving ranges for $100K instead of $15 million.

The lesson? You can't count on a fad to become a permanent behavior change. 

And you sure as hell can't borrow hundreds of millions betting that it will.

They're splitting up the company now, trying to save what they can.

Will Topgolf survive? Probably. But this is a masterclass in what happens when you grow too fast, borrow too much, and mistake temporary consumer enthusiasm for permanent market demand.

What's your take—have you seen this pattern play out in other businesses?

—

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 here to check it out: https://lnkd.in/dCJnMh7i

Small private colleges are so cooked:

I literally advised my kids not to apply to my alma mater, where I had a great experience, BTW.

But this price is insane.

Speaking for well-off parents, we get no financial aid or discounts. You might get a small "scholarship," but it's a joke.

Mrs. G and I are ambivalent about our kids attending college now. The ROI has shifted from when we were young – and the world is a much different place.

How are you approaching this?

The rise and fall of Hollywood

For nearly a century, Hollywood was the global capital of entertainment — the place where dreams were made, and where 90% of the world’s box office revenue once flowed. 

But today, that empire is crumbling. The movie industry has lost a third of its workforce, and soundstages across Los Angeles sit empty. What happened?

In this video, we trace the entire rise and fall of Hollywood — from the Edison patent wars that started it all, to the golden age of cinema, to the streaming revolution that’s now destroying it. 

You’ll learn how technology, politics, and changing audience tastes all collided to end a hundred-year reign of power.

This isn’t just a story about film — it’s about how entire industries can collapse when they stop listening to the audience.

Follow for more honest breakdowns of business, culture, and media every week.

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Thinking back to when Jaguar had a 97% sales crash. One of the most spectacular brand collapses I've ever watched in real time.

Some good business lessons here:

• The Complacency Trap

For decades, Jaguar was synonymous with British elegance. Enzo Ferrari supposedly called the E-Type "the most beautiful car ever made." Their founder's motto was "copy nothing."

But heritage became a cage. By the 1970s and 80s, Jaguar was selling old-fashioned cars to old customers. Young buyers? They went elsewhere.

First lesson: Even legendary brands die if they stop evolving. Being badass for 20 years doesn't give you a free pass for the next 20.

• The Execution Disaster

When Ford bought Jaguar in 1989, they tried to copy BMW's playbook — go downmarket with a cheaper sports sedan to capture volume.

They totally screwed it up.

The X-Type was basically a rebadged Ford Mondeo wearing a Jaguar badge. Traditional buyers hated it. The younger buyers they were targeting? Not impressed either.

Lesson two: Copying a competitor's strategy without understanding WHY it worked is a recipe for disaster. They alienated their loyal customers and attracted zero new ones.

• The Brief Comeback

Fast forward to Tata Motors buying Jaguar in 2008 for just $2.3 billion (half what Ford had spent). They caught the luxury SUV wave at the perfect time. The F-Pace, E-Pace, and electric I-Pace were hits.

US sales more than doubled from 2015 to 2017. Global sales hit 180,000 in 2018 — an all-time high.

But beneath the surface, Jaguar was losing money on every car. Land Rover's profits were subsidizing the whole operation.

Lesson three: Don't let parts of your business quietly become money losers. The best operators jump in and fix it or cut it. Jaguar just let it rot.

• The Rebrand Catastrophe

By 2020, Jaguar made a radical bet: shut down ALL production, go completely electric, and rebrand as an ultra-luxury player.

Then in November 2024, they launched their rebrand campaign.

No cars. Just androgynous models in wild outfits on Mars-like settings with taglines like "live vivid." They killed the iconic leaping cat logo for a minimalist wordmark.

Even Elon Musk roasted them, asking "do you sell cars?"

The timing was brutal. They designed this campaign during peak 2020-2022 when over-the-top fake stuff was everywhere. But by late 2024? People were tired of that. We wanted authenticity.

And Jaguar delivered the opposite.

• The Final Lesson

You have to read the room. Don't tell the world something when they want to hear something else.

As a potential customer, I'd love to buy a Jaguar built with care and soul. 

Instead, they're pitching a $200,000 electric GT wrapped in the most manicured, fake, over-the-top campaign imaginable.

Their first new car launches late 2025. They're starting from scratch with burned dealers and confused customers.

I'm not sure they can pull it off.

What do you think, can Jaguar survive this rebrand?

Michael

At one company, a person stole hundreds of thousands of dollars. I’ve been robbed by people who have been with me for years.

So I asked an auditor: 

"What's the #1 way to prevent theft as a business owner?" 

He said: 

"Simple. Each month, review every transaction. Don't hide that you're doing it."

What’s your take on preventing employee theft in your businesses?

The Rise, Fall, and Comeback of Best Buy (How It Outsmarted Amazon)

Best Buy was supposed to die. Circuit City, Fry’s, RadioShack—all gone. 

In 2012, analysts called Best Buy “the next retail bankruptcy.” Instead, it pulled off one of the most incredible comebacks in business history.

This video breaks down the Rise, Fall, and Comeback of Best Buy: how a tornado sparked its superstore model, how showrooming nearly killed it, and how CEO Hubert Joly turned it all around with price-matching, vendor partnerships, and the bold “stores-within-a-store” strategy.

From near-death to a $47B powerhouse—this is the playbook every operator and investor should study.

—

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!

Shoot me a DM if this is up your alley.

He knew he wasn't supposed to say it because people wanted to hear it was all. After all, he was so smart and outworked everyone else, right?

However, while that stuff was necessary, fortune plays a significant role in making any fortune.

Luck played a huge factor in this founder's life-changing outcome.

"I was at the right place at the right time near the right people."

I've talked to tons of successful founders.

Same pattern every time.

—

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 here to check it out: https://lnkd.in/dCJnMh7i

The rise and fall of Spirit Airlines: A billion-dollar mistake.

Spirit Airlines went from flying gamblers to Vegas to becoming the most profitable airline in America by 2015.

 But less than a decade later, the same ultra-low-cost model that made Spirit a phenomenon also pushed it into two bankruptcies and a fight for survival. 

In this breakdown, we dig into the business decisions, competitive pressures, and strategic missteps that transformed Spirit from an industry disruptor into a cautionary tale.

We’ll cover how Spirit’s unbundled pricing changed air travel, why competitors copied and undercut its model, how overexpansion and fragile operations triggered its collapse, and what its second Chapter 11 filing means for the future of ULCCs. 

Whether you’re into airline strategy, business case studies, or investing lessons, this story is packed with insights about temporary vs. durable competitive advantages.

If you enjoy deep-dive business analysis like this, follow for more investing and company breakdowns every week.

How do you screw up a business that sells 30 cents of coffee for $5?
Starbucks found a way.

CEO fired. Thousands of stores closing. And somehow they're also opening thousands more.

Let me explain what's actually happening:

Starbucks grew from 4,000 stores in 2000 to 40,000 today. That's insane scale. 

And they nailed three things:

1. The "Third Place" concept — Home, work, and Starbucks. Americans lost their community gathering spots (church, Elks Lodge, whatever). Starbucks filled that void perfectly. Clean bathrooms, good Wi-Fi, friendly baristas.

2. Premium real estate domination — Starbucks outbid everyone for the best locations. When you're selling a commodity (coffee with sugar), location is everything.

3. Achievable luxury — Millennials lived through 2008. Couldn't afford houses. But a $5 Starbucks cup? That was their daily luxury flex.
This flywheel worked beautifully. Until it didn't.

What went wrong:

Not one big mistake. A series of small bad decisions that compounded:

• Menu got too complex — Prep times increased 60%. Coffee needs to be convenient. Waiting 10 minutes for a triple-shot-whatever kills that.

• Lost the "third place" vibe — Locked bathrooms. Tired stores. I stopped going to my local Starbucks because it literally smelled like an airplane bathroom. One near me turned into a homeless shelter.

• Inflation crushed their customers — $5 coffee became $7. Your salary didn't go up. Do the math.

• Competition exploded — Luckin Coffee in China. Dutch Bros raised hundreds of millions. Seven Brew. The pie got divided fast.

• Leadership chaos — CEO lasted 15 months before getting fired. That tells you everything about board panic.

The turnaround plan:

They brought in Brian Niccol. This guy fixed Chipotle when everyone thought it was dead.

Here's what he's doing:

• Simplified the menu by 30%
• Returning to the "third place" model — more seating, better vibes
• Closing underperforming locations
• Opening premium locations strategically

And here's the paradox I mentioned: Growth hides problems.

Keep the top line growing and investors give you time to fix profitability. That's why they're still building stores even while closing others. Smart.

The real lesson?

Big problems that take years to create take years to fix. You can't turn around a 40,000-location chain in 6 months.

Brian knows this. He's playing the long game.

Early signs look promising — same-store sales flattening out, international decline shrinking from -4% to -1%. Green shoots.

But they're not out of the woods yet.

Bottom line: When you're selling a commodity product, you can't let complexity, bad locations, and poor experience kill your core value prop. 

Starbucks forgot that. Now they're remembering the hard way.

What's your take — will Starbucks pull off the turnaround, or is the third place concept dead?

Follow Michael Girdley for more business content ✅

The rise and fall... and rise again of the Las Vegas Sphere

When the Las Vegas Sphere opened, it was supposed to be the future of live entertainment — a $2.3 billion tech wonder built to change concerts forever.

Instead, it became one of the biggest financial disasters in Vegas history. Between construction delays, massive losses, and an empty calendar, many thought the Sphere was doomed.

But then came the comeback no one saw coming. In this video, we dive deep into how James Dolan and his team completely flipped the script — transforming the Sphere from a money pit into one of the most profitable venues in the world. 

From U2’s residency to the jaw-dropping Wizard of Oz 4D experience that sold out for months, this is the story of how Vegas’ wildest idea was finally saved.

If you love stories about business turnarounds, innovation, and redemption, you’ll want to see this one through to the end.

Follow for more deep dives into business, tech, and comeback stories every week.

—

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!

Shoot me a DM if this is up your alley.

Here's how Dave's Hot Chicken went from a $900 parking lot popup to a $1B exit in seven years.

They rode a wave instead of creating one

Nashville hot chicken was already trending. These guys didn't try to invent something new — they just brought it to LA where people were hungry for it.

Smart move #1: Find a trend and ride it hard.

They started smaller than small

Most restaurant founders go rent a space, borrow from family, rack up debt. 

These guys spent $900 on folding tables, a tent, and a portable fryer.

No credit cards. No business permit. Just a parking lot and chicken.

First night? Made $40.

Then a food writer showed up. Next night, 70 people in line. Within weeks, they each had $10K in their pockets — more money than they'd ever seen.

They made one thing really, really well

Look at Chick-fil-A. Raising Canes. In-N-Out. They all do one thing incredibly well.

Dave's kept it simple: chicken tenders, sliders, a few sides. That's it.

When you're not complex, you can't screw up in complex ways.

They knew what they didn't know

These guys were smart enough to recognize their limitations. So they brought in:

Samuel L. Jackson (and other big names for cache)
Bill Phelps (restaurant scaling expert)
Drake (to reach younger crowds)

Then they went all-in on franchising. Sold over 1,000 locations. Let other entrepreneurs bring capital and knowhow.

By 2023: $600M in revenue. 57% year-over-year growth. Spewing cash.
This week: Roark Capital bought them for a billion dollars.

The lessons:

Start small. Perfect your product before you scale. Ride trends, don't fight them. 

Know what you're good at, then find people to fill the gaps.

And for the love of God, focus on doing one thing really well instead of ten things poorly.

What's your take on this success story?

This graph has been on my mind a lot lately.

The main reason it's so hard to build or do anything physical in this country now is that we have so many on the payroll looking to keep themselves busy by saying no or creating hurdles.

A gerontocracy doesn't want change or disruption. So, they promote many people to prevent that from happening.

What's your take on this?

A $4 billion company just lost 90% of its value and nobody's paying attention.
The entire plant-based meat industry is collapsing.

Beyond Meat sales dropped 10% last year. Their stock? Down 90% from peak. 

And look, if you're in the food business and consumption drops 10% in a year, that's not a rough quarter. That's a disaster.

Here's what happened:

Back in 2009, Beyond Meat launched at the perfect moment. Millennials were coming of age. Social media was pushing environmentalism and health trends hard. And for the first time, fake meat actually tasted... decent.

The IPO in 2019 was insane. $4 billion valuation. One of the best-performing first-day IPOs of the decade. Burger King, Carl's Jr., everyone wanted in. Big money poured in. Billions.

They scaled like crazy — 13 suppliers at one point producing their product. 

Sales tripled in a year. The party looked like it would never end.

Then COVID changed everything.

People started questioning what they believed online. The original promises started falling apart:

• Plant-based meat isn't cheaper (10-50% MORE expensive)
• Environmental benefits? Mostly debunked
• Healthier? Social media flipped on that narrative too

By 2023, sales were down 30%. The fad was over.

The business lessons here are brutal:

1. Fads go both ways. Social media created the demand. Social media killed it just as fast.

2. Never scale expecting the music won't stop. Beyond Meat went from 13 suppliers to 1. That's expensive whiplash.

3. When you're riding a trend, build defensibility fast. Because when the trend turns, you better have something real holding you up.

The reality is they built a massive business on shifting consumer sentiment driven by social media. That's sand, not concrete.

Now here's the twist — the industry might not be dead. We're raising fewer cattle in the US than any time since 1951. Population has doubled since then. If beef prices spike, maybe plant-based meat gets its second act.

But they're going to have to rebuild trust they burned through the first time around.

Bottom line: Growth feels amazing. But sustainable growth beats explosive growth that implodes.

What's your take — is plant-based meat done, or just early to the party?

Older small business owners when the most recent existential "crisis" hits the company late on a Friday. (see meme below)

--

After a few years, you learn that business ownership is very different from how it's widely regarded.

Business ownership is actually a never-ending flow of crises, f-ups, and shit storms. That's the norm. It's never "all going great." 

"Going great" is just that the crises are all known and manageable.

Ironically, the only time you should panic is when there aren't any "disasters" right now. That means there are certainly problems in the company -- you're not aware of them yet.

—

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 trying to deploy customer-facing voice agents/AI in your company? Want to?

I'm helping a team working on this space. We'd love to talk to you. Maybe get work done for you on the cheap, too!

DMs open or email me michael at girdley dot com!

Family Office (Private)

I am exclusively engaged with a family office diversified in a variety of PE backed businesses.

Director | Special Projects

Momentous Ventures

Experienced Business Executive Consultant and Strategic Investor. I specialize in providing expert guidance to enhance business operations and efficiency. I’m also very passionate about investing in promising ventures that drive innovation and growth.

Principal

BILLY BRICKS

Investor & Partner

Penn National Gaming

During my tenure at PENN, I led the B2B division's transformation, overseeing various departments including Corporate Strategy, Licensing, Lobbying, Sales, Sales Operations and Training. Finding the best talent and promoting innovation we collectively built a sustainable & highly profitable operation. 

In a span of just two years, we doubled sales growth, increased EBITDA by $16M, and attracted top industry talent. Notably, we adopted a human-centric approach, reducing employee turnover to a record low and achieving the highest ever work-life satisfaction scores. Our focus on cultivating culture, partnerships, and creative strategies transformed the B2B division, establishing new standards of growth and excellence.

Director | Business Expansion

FUND Conference

Founder / Chief Marketing Officer 

Fund Conference connects early-stage companies with venture capital firms, angel investors, and industry experts.

As Founder, Chief Executive Officer & Chief Marketing Officer, I launched an annual conference in the greater Chicago metropolitan area and subsequently spearheaded a demand-driven expansion into the new markets of Austin, Denver, and Kansas City.  In this position, I lead a 15-person team.

My most notable accomplishments have included:

► Created environment of communication and collaboration, enabling companies exhibiting at Fund Conference to raise $390M+ in total equity funding. 

► Recognized as largest conference in U.S. focused on connecting entrepreneurs with venture capitalists and angel investors, averaging 1K attendees per conference. 

► Attracted large sponsorship from organizations such as Oracle, NetSuite, Microsoft, Insperity, JPMorgan Chase, Mass Mutual, Yodlee, and Polsinelli. 

► Launched unique podcast (The EcoSystem: www.fundecosystem.com), interviewing top venture capitalists and entrepreneurs and growing to 10K followers with just 8 months.

► Obtained media coverage from Entrepreneur, Chicago Tribune, 1871, DCEO, SBDC, ACA, and Goldman Sachs 10K Small Businesses platform.

Founder / Chief Executive Officer

Venture Connects

Venture Connects is a boutique investment banking firm (FINRA/ SEC Broker-Dealer) working with early-stage companies to develop strategy and operational infrastructure as well as raise mission-critical capital and structure M&A activity.

As Chief Executive Officer, I collaborated with senior management teams of 100+ companies (primarily technology-driven organizations) in developing and executing strategic roadmaps as well as in fundraising activities.

Some of the key ways in which I made a difference include:

► Successfully raised $110M+ in aggregate equity investment for client base from leading venture capital firms and attained millions in annual revenues.

► Represented Akouba Credit acquired by Velocity Solutions (HIG Capital portfolio company), WorkXO acquired by QuestionPro, BrandAmper acquired by The Muse, WeDeliver acquired by Deliv, and Tribe.do acquired by Peoplevine.

Chief Executive Officer

Tribe.do

ACQUIRED : October 2017 

Tribe is a collaboration platform for professional services firms. We allow anyone to easily capture and test their business process. 

Tribe helps you coordinate work with outsiders—clients, teammates, and vendors, all from a secure, shared workspace. Our platform is the first truly zero-adoption solution, allowing anyone to engage with the application through email with signing up. 

Member of the Techstars Chicago '15 class.

Silent Partner

AutoFlipr

Automotive Technology Services (AutoFlipr) was a technology platform enabling auto dealers nationwide to list their entire inventory on a single mobile app.

As Co-Founder & Chief Operating Officer, I developed, commercialized, and marketed an innovative mobile application (AutoFlipr), penetrating 10% of the entire U.S. auto dealership market within just 6 months while managing a 20-person team.

Co-Founder & Chief Operating Officer

The Secret Sauce

Secret Sauce is a global producer of award-winning barbeque sauce with distribution channels in 8 countries.

As Founder & Chief Executive Officer, I launched a global CPG company after winning 1st place at the American Royal World Series of Barbecue (the world’s largest barbeque sauce contest). In this organization, I led 12 employees.

My best achievements were:

► Attained $2M in peak annual revenues at 50%+ net margins.

► Obtained distribution in 660 retail stores across 8 countries (U.S., Canada, Singapore, Hong Kong, Tokyo, Thailand, South Korea, and Australia).

Founder & Chief Executive Officer

Verizon

Recruited & relocated to Chicago to lead the SMB B2B sales teams for Chicagoland & NW Indiana.

Took many underperforming teams to Winners Circle & President's Club (top 1%) within less than 2 years.

My best achievements were:

► President's Club (2008)

► Winners Circle (2008)

► President's Club (2007)

► Largest single customer acquisition in company history

Managing Director - B2B

Hey there - I’m RJ, an accomplished leader fervently dedicated to the evolution and expansion of businesses within diverse sectors. With a robust portfolio of leading B2B organizations for over two decades, my expertise lies in navigating new ventures and propelling organizations to unprecedented heights of success.

Central to my approach is a philosophy I term as 'PPP' – People, Process, and Profits. This guiding principle underpins my strategy, fostering growth, establishing structure, setting measurable KPIs, and ensuring scalable practices across various industries. My passion resides in transforming startups into pinnacle success stories or infusing established companies with innovative dynamism. My investment strategy mirrors this versatility, with a keen eye for ventures that promise substantial growth potential.

Holding an Executive Master's in Business from the prestigious Kellogg School of Management at Northwestern University, I blend academic excellence with practical leadership acumen. Originating from Kansas City, I have spent the last 15 years in Chicagoland, harmonizing my professional endeavors with the enriching experience of family life. Beyond the corporate realm, I have a penchant for profound discussions on business strategies, the intricacies of barbecue, or the latest in MotoGP & F1.

My leadership identity is deeply influenced by my Enneagram Type 3 and ENTJ traits, enriched further by Clifton Strengths in Executing, Influence, Relationship Building, and Strategic Thinking. I am perpetually in pursuit of collaborative opportunities and innovative ventures.

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Michael Girdley

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