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

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Legacy Geekdom Fund

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Girdley's Letter

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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.

—

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.

—

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?

—

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?

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

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.

—

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.

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.

CEO @ Pioneer Capital Advisory LLC / Managing Partner at SMB Business Plans LLC / I help business buyers get funded with SBA 7(a) loans / $65 million closed in ‘23 / aiming for over $100 million in ‘24

My team at Pioneer Capital Advisory LLC helps business buyers with navigating the SBA financing process 

We have helped business buyers close over $120 million of SBA 7(a) financing in 2025 alone, and over $250 million since May of 2022

We take a team approach to your deal to help you every step along the way

Email: matthias@pioneercap.com

If you have an opportunity under LOI, please reach out to my team via email at deals@pioneercap.com

Schedule a call with us:https://www.pioneercapitaladvisory.com/

Matthias Smith

Life update:

My wife and I welcomed our first child early last Thursday morning. I am incredibly grateful and excited to step into fatherhood and to embrace everything that comes with it.

I will be taking approximately six weeks of paternity leave while my team at Pioneer Capital Advisory LLC  continues to run point day to day.

If you have a deal under LOI and are exploring acquisition financing, please reach out to my Head of Business Development, Rafael McFerran-Lopes  at rafael@pioneercap.com.

If you are a current client and need assistance during this time, please contact my COO, Valerie Stash  at valerie@pioneercap.com.

I plan to be “back on the ice” in the later part of February to enjoy quality time with this little dude

Matthias  Smith

My team helps self-funded searchers and independent sponsors finance business acquisitions | President / Owner @ Pioneer Capital Advisory | Over $124 million of SBA 7(a) financing facilitated in 2025

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I couldn’t agree more with Eric’s post.

Seven figures of personally guaranteed debt is real leverage, and with that leverage comes very real risk. Too often, people focus on the upside without fully appreciating how unforgiving the downside can be when things don’t go as planned.

One of the most underrated risk mitigants in a business acquisition is proximity. Being able to see what’s happening in the day to day of the business matters far more than many buyers realize. When you are physically present or at least deeply embedded operationally, issues surface faster, problems get addressed earlier, and bad surprises are less likely to compound quietly in the background.

Distance adds friction. Friction delays information. Delayed information increases risk. That is a dangerous combination when you are personally guaranteeing a large amount of debt.

Leverage can be an incredible tool when paired with the right structure, the right business, and the right level of operational visibility. But pretending those risks don’t exist, or that they can be fully papered over, is how people get hurt.

Thoughtful leverage beats blind optimism every time.

graphical user interface, text, application

I saw a post earlier today from Rory Tyer, Executive Coach that stopped me in my tracks.

Rory and his wife are navigating an incredibly difficult stretch right now as their newborn may need to spend an extended period of time at MUSC in Charleston. In the midst of everything that comes with caring for a child in the hospital, they are also trying to solve for short term housing so they can be close and flexible as needs arise.

Rory is also a former client of Pioneer Capital Advisory LLC, and beyond that, someone I have a great deal of respect for. Situations like this are a reminder that even the most capable, thoughtful people can find themselves needing help in moments that truly matter.

If anyone in my network has a connection to a short term or month to month rental in or very close to Charleston, or knows someone who might, I know it would mean a great deal to their family. He can be reached via DM on here. 

Thinking of you, Rory, and sending strength to you, your wife, and little Ruby as you focus on what matters most right now.

$255M+ closed across 115+ business buyers.

We publish our numbers because we’re proud of them.

Ask your SBA broker for theirs. If they can’t tell you, ask why.

If you already own a business and are considering buying another one, expansion acquisitions are worth a serious look.

Here’s why.

In a standard SBA 7(a) acquisition, you are typically required to inject at least 10% equity. On a $2,000,000 deal, that is $200,000 of cash out of pocket.

But if your acquisition qualifies as an expansion acquisition, that equity requirement can go to zero. In the right structure, 100% financing becomes possible, allowing you to preserve capital for working capital, growth initiatives, or liquidity.

So what actually qualifies as an expansion acquisition under SBA rules?

Three boxes must be checked.

First, the current business and the acquisition target must share the exact same 6 digit NAICS code. Broad industry overlap is not enough. The match must be precise.

Second, ownership must be identical. How the entities are structured matters, and the ownership percentages must line up exactly.

Third, both businesses must be borrowers on the loan. They go on together as co borrowers.

One important update that opens things up even further.

As of September 30, 2025, the SBA eliminated the geographic proximity requirement. The target business no longer needs to be in the same geographic area as your existing operation. That change meaningfully expands the universe of viable expansion opportunities for business owners looking beyond their immediate market.

This is not theoretical.

Over the last year, my team at Pioneer Capital Advisory LLC has helped a handful of former clients successfully complete expansion acquisitions using this structure. When done correctly, it can be a powerful tool to scale without tying up significant personal capital.

That said, the details matter. NAICS classification, ownership structuring, and borrower setup all need to be right, and lender interpretation can vary. This is the kind of strategy worth discussing early with your lender and advisor before you get too far down the road.

If you are considering an expansion acquisition and want to talk through whether it fits your situation, feel free to reach out to my Head of Business Development, Rafael McFerran-Lopes, at rafael@pioneercap.com.

Here’s the guidance for anyone interested in reading further:

naggl.org/wp-content/upl…

There’s no shortage of loan brokerage firms popping up right now.

That’s a good thing. Competition sharpens the market, and I welcome it.

But if you’re a business buyer, there’s an important distinction worth paying attention to before you sign an engagement letter.

Not all principals in this space come from the SBA world.

And that matters more than most people realize.

SBA financing is not a theoretical exercise. It isn’t won on slide decks or generic deal experience alone. 

It’s built on lender relationships, pattern recognition, and hundreds of small judgment calls that only come from actually doing SBA deals end to end. Over and over again.

Big law deal experience does not translate directly to SBA deal experience. The rules are different. The risk framework is different. The lenders are different. The execution bottlenecks are different. And the margin for error is dramatically smaller.

When something goes sideways in underwriting or late in the process, what saves a deal isn’t pedigree. It’s knowing which lender will flex, which credit officer will engage, and how to structure around the issue without blowing up the timeline.

If you’re working with a firm on SBA financing, make sure they’ve actually lived in this ecosystem. Make sure they’ve facilitated deals, navigated credit committees, and closed transactions through real friction.

That’s the know-how you’re expecting when you sign up.

And it’s the difference between a deal that closes and one that quietly dies.

Proud to share the loan approval for a commercial printing company acquisition that Pioneer Capital Advisory is honored to support.

This transaction includes a $2.621 million SBA 7(a) acquisition loan, thoughtfully structured to support both the purchase of the business and the buyer’s long-term operating needs. Approvals like this are the result of disciplined underwriting, proactive communication, and close coordination across all parties involved.

A sincere thank you to Natalie Beane and the team at Provide, powered by Fifth Third, for serving as the lender on this transaction. Their professionalism, responsiveness, and collaborative approach were instrumental in getting this deal approved.

In 2025, my team at Pioneer Capital Advisory LLC had the privilege of helping 51 business buyers successfully close $124 million of SBA financing. We take seriously the responsibility of guiding buyers through complex acquisition financings and are grateful for the trust placed in us by both our clients and lending partners.

I have included links in the comments for those who are pre LOI and interested in connecting with my team for an introductory conversation, as well as for buyers who are under LOI and looking for financing guidance as they move toward closing.

Excited to support this buyer through the final stages of the transaction and to continue helping acquisition entrepreneurs step confidently into ownership.

SBA loan refinances are quietly becoming one of the most misunderstood tools in the lower middle market financing world.

Most business owners assume that once they close an SBA loan, that capital structure is effectively locked in for the life of the loan. In reality, SBA refinancing can be a powerful way to fix structural issues, improve long term economics, or clean up legacy debt; but only if it is done correctly and within very specific SBA rules.

At Pioneer Capital Advisory LLC we have recently started taking on SBA refinance engagements more actively. We are seeing increased demand from business owners who want to proactively strengthen their balance sheets rather than wait for pressure points to emerge.

Here is the critical distinction. SBA refinances are not simple rate shopping exercises.

Under current SBA guidelines, an existing SBA loan can only be refinanced with a new SBA loan if several conditions are met. In practical terms, that typically includes the following:

- The refinance must provide a clear benefit to the borrower such as improved cash flow, longer amortization, or removal of structural risk
- The existing SBA loan must generally be seasoned for at least six months
- The new loan cannot be used to take cash out or increase overall leverage beyond what SBA allows
- The refinance must replace eligible debt only; no new uses of proceeds can be layered in
- The business must continue to meet SBA eligibility requirements related to size, ownership, and operations

In addition to SBA policy requirements, there is an important lender reality that business owners should understand early in the process.

Most banks want to see at least two full years of filed business tax returns from the date the acquisition financing closed before they will seriously entertain an SBA refinance. Even if a refinance is technically allowable under SBA rules, lender credit committees typically rely heavily on post acquisition operating history and tax returns to get comfortable approving a new SBA loan.

These rules exist for a reason. SBA refinancing is intended to stabilize small businesses and improve long term durability; not to re lever companies or mask weak fundamentals.

Where we add value is helping business owners determine whether a refinance is realistically viable before approaching lenders; structuring the transaction so it fits squarely within SBA policy; and positioning the opportunity with lenders that are actively executing SBA refinances today.

If you are a business owner carrying an SBA loan and wondering whether your current structure is still the right fit; or if you simply want an informed conversation about refinancing options; we are happy to help.

If you are interested in exploring an SBA refinance, please reach out directly to our Head of Business Development, Rafael McFerran-Lopes, at rafael@pioneercap.com to coordinate a conversation.

One of the commonly overlooked things that I see business buyers looking past in the early stages of the deal process is business license qualification 

If you’re acquiring a company that requires specific licenses to operate, its mission critical to understand what the requirements are to be a qualifier for the specific type of license 

While there are specific rules that states and municipalities have, the SBA loan program and banks can and often have more stringent requirements

A couple of key factors to contemplate specifically:

-Does the license qualifier need to have direct industry experience?

-Is the qualifier of your license someone that has economic motivation to stay post closing? For example, if there is a key employee of the business qualifying the license and that person leaves, what is your back up plan?

Buying a business with SBA financing is complex. It does not have to be confusing.

Last year alone, we helped 51 business buyers successfully close $124 million of SBA acquisition loans. That brings our total to $255M+ closed across 115+ business buyers.

At Pioneer Capital Advisory LLC, our focus is simple. Help serious buyers navigate SBA financing with clarity, speed, and realistic expectations.

Our lead positioning message says it best:
$255M+ closed across 115+ business buyers with one of the most transparent track records in SBA acquisition financing.

If you are actively pursuing an acquisition and want experienced guidance through the SBA process, we are here to help and support you.

I have included a Calendly link in the comments to coordinate schedules for a call.

Happy to talk through your deal, timing, and financing options.

My team at Pioneer Capital Advisory LLC is currently advising on the acquisition of a food and beverage distribution business that serves international airline routes from the U.S. to Europe, and is seeking to partner with a senior lender on the transaction.

About the Business:

The company has been operating for over 20 years, developing, sourcing, and distributing food and beverage products to airline caterers at major U.S. international airports. Product categories include dry goods, baked items, proteins, beverages, desserts, and meal components.

Once a product is approved and spec’d into an airline’s menu, it typically remains in place for years due to strict specification requirements and long procurement cycles. Several customer placements have been active for more than 20 years.

The business operates an asset light model, with manufacturing, warehousing, and transportation fully outsourced. This structure supports stable EBITDA margins of approximately 20% with minimal capital expenditure and working capital requirements.

Financials (2025E)
Revenue: $17.0M
EBITDA: $3.5M
EBITDA Margin: 20.6%

Transaction Overview:

Purchase Price: approximately $15.0M (4.3x EBITDA)
Senior Secured Term Loan: $9.0M
New Equity: $5.0M
Seller Rollover: $1.5M (10%)

The seller is rolling equity and will remain involved post close, which is viewed as a strong signal of confidence in the business and its future performance.

Growth Thesis:

The growth plan focuses on increasing wallet share with existing airline customers, expanding into adjacent end markets such as cruise lines, theme parks, and QSRs, and developing proprietary food products that carry higher margins.

If you are a lender active in the lower middle market and this opportunity may fit your portfolio, a conversation would be welcome.

Pablo Redondo  
Senior Associate
pablo@pioneercap.com

Rafael McFerran-Lopes  
Head of Business Development 
rafael@pioneercap.com

One thing I see trip buyers up over and over again has nothing to do with the quality of the business.

It’s what their balance sheet looks like the day after closing.

Post close liquidity is one of the most common friction points in SBA backed acquisitions. Not because the business is flawed, but because the buyer shows up to closing with almost no margin for error. On paper, the deal works. In real life, the transition period is rarely that clean.

Banks are not just underwriting historical cash flow. They are underwriting you. Your ability to handle timing gaps. Your ability to fund working capital. Your ability to absorb the inevitable surprises that come with taking over a business.

Cash after close is not idle. It is not dead money. It is operational insurance.

Two buyers can acquire the exact same business with the same SBA loan. One walks in calm, confident, and able to make thoughtful decisions. The other feels pressure immediately. The difference is not intelligence or effort. It is liquidity.

The buyers who think about this early tend to have a very different experience. They model ownership from day one, not just the path to getting a deal across the finish line. They structure transactions more intentionally. They evaluate financing options realistically. And they avoid the late stage underwriting surprises that slow deals down or kill momentum.

It also shows up in how lenders perceive them. Buyers who understand their post close liquidity come across as more credible and more prepared. There are fewer open questions around capitalization, which means fewer delays once the deal is under LOI.

Getting to closing matters. But what matters more is being able to operate from a position of strength once the ink dries.

If you are serious about buying a business with SBA financing, spend time upfront thinking about what your liquidity looks like on day one. That single decision will shape your first year of ownership far more than the purchase multiple ever will.

It was truly an honor for our team to have the opportunity to work alongside Shawn and support him through the financing process for his business acquisition.

Transactions like this are never a solo effort. This was very much a team win, with thoughtful coordination and execution across our organization. Huge credit goes to my Chief Operating Officer, Valerie Stash, Andrea Parada, our Head of Closing Operations, and Fernanda de la Peña Tapia, our Financial Analyst, for their diligence, communication, and commitment to keeping every detail of the process moving smoothly from start to finish.

Helping acquisition entrepreneurs navigate financing is exactly why we do what we do. Supporting buyers through complex timelines, lender requirements, and closing logistics takes experience, consistency, and a team that stays engaged well beyond the initial lender introduction.

If you are looking to buy a business in 2026, our team would love to connect and see if we can support you through the process. Please feel free to book a call using the Calendly link in the comments.

We have recently started helping clients facilitate refinances of existing SBA loans, and we’re seeing strong interest from business owners looking to improve structure, terms, or long-term fit.

A few high-level cliff notes on what typically makes an SBA-to-SBA refinance eligible:

• The existing SBA loan must be current and have been current for at least the past 12 months.
• Most SBA lenders want to see at least two full financial periods with filed business tax returns showing profitability.
• The refinance must meet a clear SBA justification, such as an inappropriate maturity, over-collateralization, or other terms that are no longer reasonable.
• In most cases, the new SBA loan must provide at least a 10% improvement to the borrower’s installment payment, unless a specific SBA exception applies.
• The debt being refinanced must be business debt and properly reflected on the company’s financials and tax returns.

If you’re a business buyer contemplating refinancing your existing SBA loan with a new SBA facility and want to understand eligibility, timing, and lender expectations, please reach out to my Head of Business Development, Rafael McFerran-Lopes, at rafael@pioneercap.com.

One of the most powerful and often misunderstood uses of SBA 7(a) financing is the expansion acquisition.

At its core, an expansion acquisition allows an existing operating business to acquire another business as a natural extension of what it already does. This isn’t a new operator taking on unfamiliar risk. It’s a proven management team scaling a model they already know how to run.

Historically, the SBA has distinguished expansion acquisitions from “new businesses” based on a few core factors:

- identical ownership
- the same six-digit NAICS code
- operational integration through a co-borrower structure

But in practice, geography often complicated things. Many lenders treated expansions as eligible only if the acquired business was located within a “reasonable” distance of the existing operation. That interpretation created friction, especially for operators looking to expand across state lines or into adjacent regions.

That friction has now been meaningfully reduced.

A recent SBA Procedural Notice updating SOP 50 10 8 removed the geographic limitation from the definition used to distinguish a business expansion from a new business. In plain terms, location alone no longer determines whether a transaction qualifies as an expansion.

Under the revised framework, when an existing business acquires another business with

- the same six-digit NAICS code
- identical ownership
- a co-borrower structure

The transaction can be treated as a business expansion, even if the new location is outside the original geographic footprint.

This distinction matters. Expansion acquisitions are generally viewed as lower risk than true new businesses. They benefit from established management, proven operations, and systems that can be replicated. As a result, they often avoid the additional equity requirements and heightened scrutiny that apply to new business transactions.

For operators pursuing growth through acquisition, this update meaningfully expands what’s possible with SBA financing.

If you’re interested in having a conversation about expansion acquisitions and how SBA financing can support that strategy, please reach out to my Head of Business Development, Rafael McFerran-Lopes, at rafael@pioneercap.com

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