Harnessing AI to Drive Growth for Optimal Exits for Digital Businesses ◆ Strategic M&A Specialist ◆ Follow & Subscribe for Unique Strategies on Maximizing Your Digital Business's Potential and Profit ◆ Link in Profile

𝐑𝐞𝐬𝐮𝐥𝐭𝐬-𝐃𝐫𝐢𝐯𝐞𝐧 𝐃𝐢𝐠𝐢𝐭𝐚𝐥 𝐌𝐚𝐫𝐤𝐞𝐭𝐢𝐧𝐠 𝐄𝐱𝐩𝐞𝐫𝐭 & 𝗠&𝗔 𝐌𝐚𝐫𝐤𝐞𝐭𝐢𝐧𝐠 𝗔𝗱𝘃𝗶𝘀𝗼𝗿

With over 20 years of experience in the digital business arena, I've developed a deep understanding of how to navigate the challenging landscape of mergers and acquisitions (M&A). 

My passion lies in helping small to medium-sized eCommerce and SaaS businesses scale, exit, or acquire with success.

Whether you're looking to increase market share, add profits, bring on talented individuals, or scale your enterprise, I'm here to guide you through the process with minimal stress and risk. 

I employ a diverse range of funding strategies and focus on creating value for our investors and partners.

In my role as a Sell-side Advisor, I help online business owners (< than $10M) who are interested in selling all or part of their company assets navigate the process, including:

✅ Developing a selling strategy
✅ Marketing the business for sale
✅ Negotiating the deal
✅ Handling due diligence

As a Buy-Side Advisor, I work with companies to determine if a growth-through-acquisition strategy is right for them and, if so, the best time to execute an acquisition and how to make it happen. 

I have over 230 different funding strategies for acquiring businesses without using up cash reserves.

I believe in the power of growth through acquisition and am committed to saving jobs and growing companies. 

If you're considering buying or selling a business, or want to learn how to grow your current business through acquisition or strategic investment, I would love to connect with you.

SPECIALTIES
◆ Facebook Ads Media Buyer Specialist
◆ International Speaker
◆ ClickFunnels 2 Comma Club Award Recipient 
◆ Amazon Seller 
◆ Shopify Expert

💬 Want to chat? Go here to set up a time: https://skrpmedia.com/info

Steve Kilberg

Jon Stoddard

Most people who want to buy a business never do.

They get stuck chasing bad deals.
They waste time on YouTube.
They don’t know how to raise money.
And they quit—right before something great shows up.

That’s exactly where I was years ago.

I chased deals. Made mistakes. Lost money.
Eventually, I built a system that worked—and started helping others skip the mess.

Now? I help first-time buyers close million-dollar businesses the right way.
No fluff. No “guru” hacks. Just real strategy, real coaching, and real closings.

Over the last 12 months, I’ve helped real people go from stuck and spinning to confident business owners.

Here’s what that looks like:

👉 Tom looked at 50+ businesses in 2 years—no progress. We found a 20-year-old security firm with $750K in profit. He bought it 6 months later.
👉 Henry had a $27M deal but no clue how to raise capital. I introduced the right investors. He closed it.
👉 Scott faced a choice: safe vs. scalable. We pressure-tested the upside. He picked the growth play—and won.
👉 John was a sourcing machine but couldn’t value a deal. We stress-tested it, and he landed a $1M cleaning products company.

What made the difference?

✅ Deal Flow – finding real, fundable deals (not broker junk)
✅ Deal Review – spotting red flags and pricing smart
✅ Deal Financing – structuring with SBA and investor capital

This 3-part framework is called the Acquisition Engine™—and it powers everything inside the DealFlowSystem Business Buying Academy.

It’s a practical, proven system built for first-time buyers ready to stop spinning their wheels and start closing real deals.

Who I work best with:
✅ First-time buyers
✅ Professionals tired of starting from scratch
✅ Entrepreneurs ready to skip the “YouTube wormhole” and get serious

If you’re ready to stop guessing and finally buy your first million-dollar business:
👉 Take the free Business Buyer Readiness Assessment: www.dealflowsystem.net/bbr-score

You’ll learn where you’re strong, where you need help—and exactly what to do next.

Let’s build your Acquisition Engine™ and get you across the finish line.

CEO of Stack Acquisitions 

StackAcquisitions.com   We acquire great companies.   And we help other companies acquire great companies.    We always offer fair, fast and friendly terms.   Buying or selling,  we only work with people we like.

Thought Elon overpaid for Twitter at $44B?

Let’s put numbers on it — before opinions.

THEN (2022–early 2025):
• Twitter/X purchase price: $44B
• Private market marks afterward: ~$33B equity
• Enterprise value (incl. debt): ~$45B

At the time, critics said:
“Social media company. Declining ads. Bad deal.”

NOW (2025–early 2026):
• xAI (the company behind Grok) raises capital at $80B → $200B+ valuations
• Early 2026 private funding round reportedly prices xAI around $250B
• X is folded into xAI as the real-time data + distribution layer

Key point most people miss:

Grok isn’t a company.
It’s a product inside xAI.
X isn’t the business — it’s the infrastructure.

So the $44B wasn’t for a social network.
It was for:
• Distribution
• Data
• Attention
• Optionality

Same asset.
Completely different valuation lens.

This is why amateurs argue price.
Professionals argue what the asset unlocks.

Think about that before calling a deal “overpriced.”

Valuation now $250B

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Advisor

How to Buy a $1Million Dollar Business

Host of Top M&A Entrepreneurs Podcast

Investment Advisor

We help first-time buyers become the kind of person who can confidently find, fund, and close their first business

I lost a prospect this week.

They chose another program because it had:

• a bigger team
• more “support staff”
• more structure
• more visible systems

On the surface, that feels safer.

But here’s what I shared with them — and it’s something every serious business buyer needs to hear:

You don’t buy a business with a support department.
You buy a business with judgment — and that’s built in one-on-one mentoring, not ticket queues.

Account managers don’t see through inflated add-backs.
Support teams don’t negotiate seller notes.
Systems don’t tell you when to walk away.

You negotiate from real cash flow —
the kind lenders trust,
that defines risk, exposure, and what a deal is truly worth.

Buying a company is not a customer-service experience.

It’s a series of irreversible decisions made under pressure.

And those decisions can’t be outsourced.

If bigger teams created great buyers, private equity would be run by help desks.

It isn’t.

It’s run by a few people who know when to lean in — and when to walk away.

Next...

When a Service Business Is Way Overpriced — and the Seller Is Offended
This happens more often than people admit.
You look at a service business.
 The seller is proud.
 The broker is optimistic.
 The asking price is… ambitious.
And the numbers?
 They’re quietly telling a very different story.
Let’s walk through how experienced buyers think about this—and what the smart play actually is.

I see people on X who’ve bought and sold more businesses than I have.
That part doesn’t bother me. They earned that experience.

Where I disagree is when experience is treated as a substitute for education.

Here’s the part most people miss:

Buying and selling businesses teaches you.
Teaching teaches patterns.

I’ve spent years watching first-time buyers look at hundreds of deals, talk to lenders, get rejected, overpay, or walk into risk they didn’t even know existed.

At this stage of my life, I’m not interested in proving I’m tougher than anyone.
I’m interested in helping people avoid mistakes that can’t be undone.

Those are two very different goals.

If I made $100,000 last year
but spent $110,000 to do it…

I didn’t make money.
I lost it.

That’s why buyers don’t start with revenue.

This might sound uncomfortable, but it’s honest.
Most advice online comes from survivors.

You rarely hear from:
• the buyers who overpaid
• the ones whose SBA loan buried them
• the families who took on risk they didn’t understand

I work with those people before they become cautionary tales.

That changes your perspective.

I don’t teach buyers how to be heroes.
I teach them how to stay solvent, sleep at night, and live with their decisions.

At 64, I don’t care about upside stories.
I care about downside protection.

Buying a small business looks simple.

Lower price.
SBA loan.
“Owner retiring.”

But here’s the real risk:

You become the shock absorber.

One employee quits.
One customer leaves.
One truck breaks.

How to find these:
• BizBuySell
• Local business brokers
• Listings with SDE (not EBITDA)

How brokers signal it:
• Heavy owner add-backs
• “Owner works 40–60 hours”
• “Easy to run” language

Art of the Deal here:
You pay only for proven cash flow
and push uncertainty into:

– Seller notes
– Earn-outs
– Long training periods

You don’t buy growth stories.
You buy stability.

People think starting a business is safer.

No debt.
No seller.
No bank.

But you’re risking:
• Time
• Savings
• Years of trial and error

Buying the right business isn’t risky.

Buying the wrong one is.

Big difference.

Banks don’t want the business to barely survive.
They want it to pay the loan and still pay you to live.
Take too much salary and the deal fails.
Take too little and your life does.

How a First-Time Buyer Screened Deals (And the Red Flags They Didn’t Expect)

When people talk about buying a business, they often jump straight to valuation models and financing.

But for one first-time buyer, most deals were won—or lost—long before that.

The real work happened during screening.

Over time, this buyer realized their process naturally broke into tiers, each designed to eliminate risk early—before spending real money or emotional energy.

Here’s how they approached screening, and the red flags they learned to watch for along the way.

View newsletter: Top M&A Entrepreneurs Podcast

When people talk about buying a business, they often jump straight to valuation models and financing. But for one first-time buyer, most deals were wo

Open article: How a First-Time Buyer Screened Deals (And the Red Flags They Didn’t Expect) by Jon Stoddard • 3 min read

How a First-Time Buyer Screened Deals (And the Red Flags They Didn’t Expect)

My student was stressing about the LOI she’s about to send…

“Jon, this business isn’t perfect. What if it’s not enduring?”

So I sent her this.

10 billionaires who made their defining move buying BROKEN businesses — not perfect ones:

1. Warren Buffett — Berkshire Hathaway
Bought a dying textile mill everyone hated.
Killed the core business. Recycled the cash into insurance.
Lesson: The asset isn’t the business — it’s the trapped capital.

2. Carl Icahn — TWA Airlines
Bought a bankrupt airline with labor wars + debt.
Sold routes. Extracted value from a corpse.
Lesson: Distressed ≠ worthless. It means mispriced.

3. Wilbur Ross — Steel & Coal
Bought bankrupt mills no one wanted.
Rolled them up. Sold for $4.5B.
Lesson: You don’t need innovation. You need restructuring.

4. Sam Zell — Distressed Real Estate & Tribune
Bought collapsing newspapers + busted property.
Flipped after normalization.
Lesson: Buy when blood is in the streets.

5. Mitt Romney — Bain Capital
Bought bloated, failing manufacturers.
Cut fat. Sold cleaner versions.
Lesson: Control beats creativity.

6. Kirk Kerkorian — MGM
Bought ugly Vegas casinos in decline.
Consolidated. Modernized.
Lesson: Ugly assets become gold with patience.

7. Harold Hamm — Oil Fields Everyone Abandoned
Bought declining fields nobody wanted.
Applied new drilling tech.
Lesson: Fixing beats finding.

8. Henry Kravis — RJR Nabisco
Bought a bloated corporate dinosaur.
Largest LBO in history.
Lesson: Big companies rot just like small ones.

9. Sheldon Adelson — Sands Casino
Bought a failing Vegas convention hotel.
Rebuilt the model. Expanded to Macau.
Lesson: Business models fail before assets do.

10. Stephen Schwarzman — Blackstone
Bought distressed real estate post-2008.
Rented for cash flow. Sold for billions.
Lesson: Distress is leverage — if you have patience.

Bottom line for business buyers:

You are not hunting unicorns.

You are hunting mispriced problems.

And the more “unendurable” it looks to everyone else…
the better your odds are.

Everything look good in the CIM, and financials...until we found a 5 Star Terrible Google Review - on their website. 

And it was not linked to a business’s Google Business Profile

Buyers love revenue.
Banks love timing.
If your cash is stuck for 55 days and you burn $4,000 a day, that’s $220,000 you must have.
Not “should.”
Must.

Sellers sell stories.
Banks fund systems.
The Working Capital Peg is how you force the story to survive the system.
If it can’t, the deal was never real.

Deal flow is boring by design.
It’s calls, follow-ups, nagging the broker, reviewing CIMs, waiting waiting waiting, spreadsheets, and silence.
Then suddenly… opportunity.

Expect polished CIMs.
Expect optimistic projections.
Expect prices that assume perfect execution.

Your job is to separate signal from story.

The real skill isn’t finding opportunities.
It’s killing bad ones fast before they waste months of your life.

Most people look at a business and ask,
“How much money did it make?”

That’s the wrong first question.

Profit doesn’t tell you if a business is healthy.
It only tells you part of the story.

Service businesses usually need two months of expenses.
Construction needs three to five.
Product businesses must front inventory before sales.
Seasonal companies fund the entire off-season in advance.
If you don’t know which one you’re buying, you’re guessing with your future.

People romanticize off-market deals.
Then they send 50 letters and quit.
Real off-market deal flow is boring, lonely, and slow. 
And numbers,  big numbers for cold leads.  
It works only because most people won’t outlast the silence.
That’s your edge.

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