You are an owner, not a hostage to the business. 
You want cash flow up, hours down, and a clean exit when you are ready.

I advise owners & CEOs of $1M–$25M service, manufacturing, logistics and home services companies get sale-ready in months, not years.

What you get
• Cash flow clarity, the 15 business drivers & value levers and a monthly score of what is and isn’t working. 
• Owner dependence reduced, SOPs, KPIs, and a real second-in-command
• Margin lift, quick wins in pricing, mix, scheduling, and collections
• Cleaner diligence, contracts tight, financials tied out, risks addressed
• Board-level guidance, 100 plus deals, portfolio company work, and exits

• Helped a precision fab shop lift margin 15 points in 90 days
• Cut an owner’s weekly hours from 65 to 20 with standard work and KPIs
• Turned a stalled deal into a signed LOIs in 45 days by fixing two red flags

For 25 years, I ran a single family office. I completed 100+ M&A transactions and raised over $1 billion in capital.

Want the Exit-Ready Checklist and a 15-minute readout… send a DM ‘Legacy’ or grab time on my calendar.

I've walked away from 1000s of businesses as a buyer…and as a seller. 

Here's what I learned: Most business owners build something valuable to them—but not to a buyer.

The hard truth? “The more valuable you are to the business, the less valuable the business is.”

Profitable companies with healthy margins that can't find a buyer

The difference between a sellable business and an unsellable one isn't revenue. It's not even profit.
It's whether the business operations and institutional knowledge can be transferred. 

This isn't theory. It's 25 years running a single family office:

   • 100+ M&A transactions completed
   • $1B+ in capital raised
   • Former CEO, CFO, Board Chairman & Director
   • Turned underperforming businesses into valuable assets

I grew up in family businesses. I know the pressure when everything depends on you.

I've been on both sides of the table in over 100 M&A deals.

As a buyer, I said no to thousands of businesses in the first five minutes.

As a seller, I positioned companies for maximum value and exited successfully.

Here's what I learned: 

Premium buyers don't just look at your financials.

They're pricing something deeper.

Four criteria separate businesses that attract serious offers from those that don't:

1. Transferable operations

Can the business run without you?

If you're the rainmaker, the relationship holder, or the one who knows where everything is, you don't have a business. You have a job.

Premium buyers pay for systems, not dependencies.

2. Documented processes

When I walked into a business as a buyer, I looked for proof the company knew how it made money.

If the owner said "it's all in my head" or "my team just knows what to do," I was already halfway out the door.

Buyers need to see the playbook. Without it, they're buying a black box.

3. Trained team that executes

A strong team isn't just talented people. It's people who can operate independently and consistently.

If your business falls apart when you take a two-week vacation, you're not ready to sell.

Buyers want to know the machine keeps running after you leave.

4. Predictable revenue streams

One-off projects and lumpy revenue are red flags.

Buyers pay multiples for predictability. Recurring contracts, repeat customers, or reliable deal flow all signal lower risk.

The more predictable your cash flow, the higher your valuation.

When you nail these four, three things happen:
~Your business becomes an asset, not a liability tied to your personal effort.
~You attract buyers who compete for your deal instead of negotiating you down.
~You walk away with real wealth, not just a modest exit that reflects all the risk you're leaving behind.

I've seen founders leave millions on the table because they waited too long to build these four things.

Don't be one of them.

Start now, even if a sale is years away.

The businesses that command premium valuations don't get built in the months before a deal.

They get built in the years of disciplined operation before anyone's watching.

Greg Head

I help executives break into private equity and leverage AI to accelerate Growth & Scaling, Improve Profits & Cash Flow | How to sell your business to PE | Owner/CEO who ran own businesses |100+ deals | $1 billion fund

The value creation advice that’s quietly killing deals:

“Clean up everything before you show anyone your business.”

That single sentence has cost owners millions in enterprise value.

Here’s the counterintuitive truth from working with family offices and private equity:

Radical transparency about problems builds more trust than trying to look flawless.

Sophisticated buyers have seen every issue you’re scared to show them:
~Customer concentration
~Messy ops and manual processes
~Sloppy working capital management
~Inconsistent reporting or weak forecasting

This is their day job. 

They expect imperfections.

What actually spooks them isn’t the problem itself.

It’s your attempt to hide it.

When an owner tries to:
~Gloss over operational challenges
~Hand-wave financial inconsistencies
~“Pretty up” numbers before a proper QofE

…you don’t look more valuable.

You look inexperienced with M&A.

What happens next:
~Red flags go up
~Diligence gets more aggressive
~Trust erodes
~Terms get worse (or the deal dies)

The owners who get the best outcomes do something very different.

They lead with structured honesty:
~“Here’s the issue we identified.
 ~Here’s why it happened.
 ~Here’s what we’ve already done.
 ~Here’s the plan and timeline to fully fix it.
 ~Here are the early results.”
T
hat approach does three powerful things:
→ Shows you understand your own business at a deep, operator level
 → Demonstrates real problem-solving capability (not just storytelling)
 → Builds confidence in your post-close leadership and execution

Buyers aren’t looking for perfect companies.

They’re looking for credible leadership teams who can navigate complexity without flinching.

Your ability to name, frame, and solve challenges is a competitive advantage in a process — not a liability.

If you’re prepping for an exit in the next few years, focus less on hiding the mess…

…and more on showing you’re the kind of operator who can clean it up.

👇 What’s one challenge in your business you’ve been tempted to hide?

 Reply with it, and I’ll tell you how a buyer is likely to interpret it in diligence.

Value creation isn’t about working harder. 

It’s about pulling the right financial levers.

Most owners obsess over growth.

The smart ones obsess over enterprise value.

There’s a difference.

Growth can destroy value when it’s:
~Unprofitable
~Unpredictable
~Dependent on the owner
~Burning cash to “hit a number”

Buyers don’t pay for “we grew fast.”

They pay for profitable, durable, repeatable performance.

In practice, that means building around the levers that actually move acquisition multiples:
→ EBITDA margin expansion
Improving contribution margin
Killing low-margin products / services that drag the blended margin down

→ Customer concentration reduction
Top 3 customers <20–30% of total revenue
No single relationship that can blow up the deal

→ Recurring revenue percentage increases
Contracts, retainers, subscriptions
Less one-off “hero projects,” more predictable revenue

→ Working capital optimization
Faster cash conversion
Cleaner balance sheet and fewer surprises in diligence

I’ve turned underperforming companies into highly saleable assets not by adding more hustle or headcount…

…but by letting the financials tell a different story.

That’s usually when owners realize their P&L is already telling a story to buyers.

Right now, that story either makes them:
~Lean in: “This will perform without the current owner.”
~Or check out: “This will be expensive and risky to fix.”

Every line item is either:
~Building toward a compelling acquisition narrative
~Or quietly undermining it

The companies that command premium valuations have financials that scream:

“This business is profitable, durable, and scalable without the founder.”

~ Predictable margins.
~ Diversified revenue.
~ Efficient operations.
~ Clean books.

That’s the language sophisticated buyers and family offices speak.

If the only thing a buyer could see was your last 12 months of financials…

👉 What story would they read?

Why perfection repels buyers — and profitable imperfection attracts them

Most owners think exit prep means “make the business flawless.”

So they:
~Polish every SOP
~Over-engineer systems
~Eliminate every inefficiency

Then real buyers show up… and get bored.

Because buyers don’t pay a premium for “nothing left to do.”

They pay a premium for clear value-creation levers.

The imperfections buyers like (🚀 upside):
~Owner still doing all sales → obvious case for hiring a team
~Strong inbound, no outbound → plug in a sales engine, lift revenue
~Manual, messy ops → low-cost automation to expand margin
~One core market, adjacent segments untouched → roll-out playbook

The imperfections buyers hate (🚨 risk):
~Sloppy or unreliable financials
~Customer concentration
~Compliance / legal issues
~Key-man risk with no transition plan

Exit prep isn’t “fix everything.”

Exit prep is:
~Remove risk
 ~Clean books, contracts, and liabilities. Stabilize the operation.
~Map the upside
 ~Identify 3–5 levers a buyer could pull in years 1–3 (pricing, channels, margins, markets).

Package the story

Show exactly where a buyer makes money after the acquisition.

You’re not selling a finished product.

You’re selling a credible growth plan someone else can own.

Perfection doesn’t sell.

Profitable imperfection with visible upside does.

👇 Drop ONE “imperfection” in your business below.

 I’ll reply with whether a buyer would see it as 🚀 upside or 🚨 risk.

Optimizing for metrics that actually drive enterprise value

If you’re running a family-led business doing $3M–$30M in revenue and you ever want to exit, you can’t afford to optimize the wrong numbers.

Most operators still chase:
🚫 Top-line growth at all costs
 🚫 “We hit $X million revenue” vanity milestones
 🚫 Headcount as a fake signal of scale
 🚫 Hustle + chaos disguised as momentum

But when a serious buyer looks at your business, they start with four questions:
1️⃣ Revenue quality
How much is recurring vs one-off?
Do your top 3 customers make up more than ~20–30% of revenue?

2️⃣ Margin quality
Is EBITDA margin in a healthy band for your space (e.g. 15–25%+)?
Are there obvious levers to expand margin post-acquisition?

3️⃣ Customer durability
Are there contracts, renewals, and switching costs?
Or could a competitor win them away with a discount and a smile?

4️⃣ Scalability of ops
Does revenue break every time you grow 20%?
Is the founder still the system, or do systems exist without the founder?

For the next 12–24 months, shift your focus to:
✅ EBITDA with margin expansion
Kill low-margin products / services dragging the blended margin down
Tighten pricing on your highest-value customers instead of discounting everything

✅ Durable, diversified customers
Move project work into retainers or longer contracts
Intentionally reduce reliance on any customer >20% of revenue

✅ Compounding revenue streams
Add recurring / subscription / maintenance / support layers where it makes sense
Make it easier for existing customers to buy more, more often

✅ Operations that scale without you
Document and delegate the 3–5 processes you still personally bottleneck
Replace “heroics” with simple systems and basic tooling

That’s where enterprise value gets built.

Not in the hype.

And not in the headcount.

Not in hustle culture theater.

In the metrics a buyer will actually underwrite when it’s time to write the check.

Being the youngest person in the room isn't the problem.

Thinking you need to prove you belong there is.

My first role out of MBA school was at Private Equity Firm as a deal & capital raising advisor that was mid-roll-up.

3 deals in due diligence.

4 LOIs active.

Integration planning already behind schedule.

My job was to support the VP leading it all.

He left/quit/asked to leave (I don't know what happened) at the end of Week 3.

Suddenly, I'm the one managing the team
→ sitting across from sellers twice my age
→ negotiating add-ons
→ explaining integration dependencies I barely understood
→ and trying to sound fluent in M&A vocabulary I had only seen in textbooks.

I knew the English language.

Just… not the version used in deal rooms.

No playbook.

No ramp.

Just pressure.

So like most young execs, I defaulted to the wrong instinct:

Over-explaining. Over-preparing. Over-justifying.

Trying to prove I deserved the seat.

It didn't work.

So I defaulted to the lessons learned growing uo watching the orginal Star Trek...don't be the expendable crew member who never got beamed back to the Starship Enterprise.

(Pro Tip: Look around your team, if you can't identify the expendable crew member it's probaly you)

Here's what did.

I stopped asking: "How do I prove I belong here?"

I started asking: "How do I create measurable value fast?"

That flipped how I spent my first 30 days in the 'seat'.

Instead of pushing new decks or "strategic recommendations," I ran a frontline immersion:
– Rode along with sales to understand the actual revenue engine
– Joined ops huddles to map where margin leaked
– Asked "show me" instead of "walk me through the org chart"
– Documented the top recurring operational bottlenecks we missed during LOI

We found one issue the team had normalized — a working-capital drag costing us weeks of cash conversion every month.

We fixed it.

Cycle time dropped.

The win showed up in KPIs within 30 days.

The sellers stopped questioning my age.

The team stopped waiting for someone else to make calls.

My boss's boss asked me to present the fix to the LP's and board.

The lesson stuck with me across 25 years and 100+ deals:

Young operators don't fail because they lack experience.

They fail because they optimize for looking credible instead of being useful.

Find the problem nobody's fixing.

Fix it.

The credibility follows.

It costs them millions.

And I made a career out of earning the millions doing what they should ahve done.

Most owners start exit planning 3 years too late.

WANTING to sell your business means nothing.

Your business has to be sellable…transferable…without you.

No one is going to pay millions for job-ball-and-chain.

Top reasons that kills most exits (and slashes valuations) long before the LOI:
~Revenue depends on the founder
~If you stop selling, the company stops growing.
~Financials are a "story," not a system

Buyers don't pay for chaos wrapped in spreadsheets.

No processes, no trackable & measured outcomes...just tribal knowledge

"John handles that" is not a scalable workflow.

Leadership team = you making all the decisions + some helpers

If you're approving everything… you're the bottleneck.

Owners think this is like selling a house.

“I’ll start when I’m ‘ready’ to retire.”
“I’ll hire a broker to list it and see what happens.”

Retirement delayed until…???

Buyers don't care when you're ready.

They care when the business is transferable.

The exits that command premium multiples all share the same pattern:

~Owner optional operations
~Predictable revenue
~Not chaos financials
~Transferable systems

Leaders who can make functional decisions so the operations run the company.

The exits that fall apart?

They wait until the last chapter to do what they should have done years ago (and leave meat on the bone for those that will).

How and what do you think Private Equity does to be so successful?

They do what the previous owner should have done but did not.

You did all the heavy lifting, you are entitled to enjoy the business you always wanted…and deserve.

If you want a buyer to take you seriously, start designing the business now, not when you're tired, burned out, sick & desperate for a way out.

Because the real rule of exit planning is simple:
~You don't sell when you want to.
~You sell when someone else wants to buy what you've built…no take over a JOB!

Be honest…if you stepped away for 90 days, would your business run… or collapse?

If you want the same results as everyone else… keep hiring the same people they hire.

Most companies don't have a hiring problem.

They have a "stop hiring the same boring people" problem.

Everyone is playing from the same strategy and the same tired playbook:
“10 years of industry experience.”
 “Knows the space.”
 “Been in the role before.”

They are all watching what each other is doing...and analyzing...and dicussing...and trying to put their 'unique spin' on it so they can calim something new

They are reverse engineering “Best Practices”, which become the norm

They are going to the same conferences, reading the same industry information, and talking to the same industry ‘Experts’

Great.

That usually means:
• 10 years of recycled ideas
• 10 years of learning the wrong lessons
• 10 years of protecting the status quo
• 10 years of blaming the market instead of fixing the business

After operating and advising multiple companies:

~Industry veterans are often the biggest blockers of innovation.

~Every stagnant company I've ran, board director or advised had the same issue:

A leadership team full of "experts" who hadn't questioned their own assumptions in a decade.

And the leaders who actually moved the business forward?

The outsiders.

The ones PE, Board Directors, Investors or senior company leaders  fought me on.

The ones with "no industry background."

The ones who asked the dangerous questions:
"Why are we still doing it this way?"
"Who approved this process?"
"Why does this take 12 steps instead of 3?"

Those people don't come in with bad habits.

They come in with clarity.

If you really want to break a company out of its rut, stop hiring from its past.

Experience is the most overrated hiring metric in business.

Curiosity is the most underrated.

(Pro tip: If you want to have a ‘Innovative Culture’, hire curiosity and give people space to fail…over and over again.)

When I'm helping a CEO or Board rebuild a team, I'd rather hire someone with sharp thinking and zero baggage than a "20-year industry professional" who's spent their entire career recycling the same “Best Practices”.

If that triggers you, good.

It should.

Who's been more valuable in your company…the industry veteran or the outsider with fresh perspective?

LET THE DEBATE BEGIN

The Most Dangerous Number in Any Acquisition

Everyone asks the wrong question during a deal.

Most buyers obsess over:

"How much are they making?" (Profit)

"How do I finance the purchase?"

But after buying, selling & assessing thousands of deals, the smarter questions are:

"After debt service and post-close balance sheet: 

1. How do I survive the first 180 days after close? 
2. How close to the covenants will I be?"

First-Time Buyers:

Deals don't fail at signing.

They fail when the new owner runs out of cash while trying to operate the business they just bought.

Over the years I've found a consistent pattern:

Almost every owner underestimates their Day-1 liquidity needs by 20–40%.

In my experience:

Keep 3–6 months of operating expenses in accessible cash on Day 1.

If the business burns $500K a year, you don't just need the $500K to buy it.

You need $125K–$250K sitting ready to deploy the moment you take over.

Because in the first 6 months:
~Revenue will dip while you stabilize operations
~Customers test the new ownership
~Collections slow down
~Your assumptions break
~Payroll doesn't care that you're "integrating a new company"

Simple framework:

1. Model the first 180 days under three scenarios:
– Base case
– 10% revenue dip
– 20% revenue dip

2. Stress test fixed obligations:
Payroll, rent, insurance, vendor contracts, debt covenants.

3. Pre-set your emergency liquidity options:
LOC, reserve capital, or investor buffer.

4. Decide your "zero line" — the point you will not cross.

The owners who plan this way never panic.

The ones who don't? 

They spend their first 90 days putting out fires they didn't see coming.

I tell every buyer the same thing:
Closing the deal is the easy part.
Running & Operating the company is where you win or lose.

Build your working-capital plan before you sign, not after you inherit the problems.

Question for you:

If you've operated or acquired a business — how many months of liquidity did you plan for… and was it enough?

Last call: Exit Ready Bootcamp enrollment closes tonight.

If you’re a founder with a profitable business…
But you’re still the one:

1. Solving team issues
2. Closing client deals
3. Making key decisions
4. Holding everything in your head

Your business isn’t sellable.
Not yet.

That’s what this Bootcamp fixes.

Here’s exactly what you get:

> Live 60-min Working Session ~ Draft your 1-page Exit Thesis with me in real time — built around your ideal buyer, timeline, and exit goals.

> ExitWise Score Deep Dive ~ We’ll walk through a 5-question assessment live to see where your business is strong… and where buyers will hesitate.

> The 4 Exit Types Framework ~ You’ll learn the 4 ways founders exit (plus a 5th hybrid model), and map the right one for your business.

> The Sailboat Test ~ The framework buyers use to determine if your business works without you — and what gets you a 3–5x premium.

> Complete Exit Workbook ~ Templates, checklists, frameworks, and your custom roadmap to make your business actually sellable.

> Lifetime Access to Recording + Slides ~ Can’t make it live? You’ll still get full access to everything.

* It’s $97.
* It’s 60 minutes.
* And it could change how you exit forever.

This isn’t fluff. This is what I wish someone had given my family.

Join here → [Link in the first comment or on my website]
Enrollment closes at midnight.

After tonight, we lock the room.

Scale Growth & Profits, Improve Cash Flow, Legacy Exit Intensive for owners of $1M-$25M revenue businesses | Owner & CEO who actually ran his own businesses |100+ deals | $1 billion capital raised

Grateful for the mention and the kind words.

I’ve spent a lot of years in the trenches with business owners, helping them get unstuck, create real cash flow, and build companies that become transferable assets instead of stressful jobs.

If you are a founder who wants clearer direction or a trusted partner to think with you, happy to help however I can.

🚀 NEW MENTOR ALERT!
🔥 Introducing Greg Head — a powerhouse business leader and CEO on InzpireU!
With 20 years of executive leadership, Greg has built and managed multiple companies, overseen his own family office, and played a key role in scaling businesses across industries. His expertise spans high-level strategy, capital raising, board governance, and large-scale business transformation.

Throughout his career, Greg has delivered exceptional impact, including:
 • Leading 100+ mergers and acquisitions
 • Serving on over a dozen boards of directors
 • Raising $1 billion in capital
 • Transforming underperforming companies into profitable, growing assets

Greg’s experience makes him an invaluable guide for founders, CEOs, and entrepreneurs navigating complex growth, investment, or operational challenges.
Whether you're building, scaling, or restructuring, Greg is exactly the mentor you want in your corner.

🎯 Are you a founder looking for structured guidance?

 Scan the QR code and connect with our mentors today.
#Entrepreneurship #Founders #BusinessLeadership #CapitalRaising #MergersAndAcquisitions #StartupMentorship #InzpireU #LeadershipDevelopment #MentorshipMatters #BusinessGrowth #ScaleUp #CEOLeadership #ProfessionalGrowth #MentorNetwork

You don’t need to sell your business today.
But you do need to start preparing.

Because here’s what most founders do:

-They wait until they’re exhausted.
-Until they’re burned out.
-Until they’re desperate to get out.

Then they try to sell.
And realize they’ve built something completely dependent on them.

That’s not a business.
That’s a high-paying job — with no buyer.

The truth is, making your business sellable isn’t a quick pivot.
It’s a 12–24 month runway.

You need time to:

1. Transfer client relationships
2. Document critical systems
3. Build operational independence
4. Prove the business works without you

That’s what buyers are looking for.
That’s what gets you a clean, high-value exit.

And that’s exactly what we map out inside the Exit Ready Bootcamp.

60 minutes. Tactical. Live.
You’ll leave with clarity — and a custom exit roadmap.

Join here → [link in the first comment or on my website]
Monday is the last day to enroll.

If your business only works when you’re running at 110%... it’s not ready to sell.

Buyers don’t pay for burnout.
They pay for systems that run at 80% capacity... and still deliver.

Here’s what buyers actually want to see:

1. Consistent delivery without heroic effort
 2. Systems your team follows without your input
 3. You taking a 30-day break — and nothing breaks

Because in due diligence, everything looks better than it is.
So if your business is already tight and chaotic now?
They assume it’s worse behind the scenes.

That’s why I built the Exit Ready Bootcamp.

In 60 minutes, I walk you through:

1. How buyers evaluate risk
2. The 5-question Exit Score framework
3. What to fix first to build real transfer value
4. A live-built Exit Thesis you’ll use as your roadmap

Most founders wait too long to figure this out.
You don’t have to.

Join here → link in the first comment

1. Get clarity on your exit
2. Start removing yourself from operations
3. Build something buyers actually want

The trap of over-optimizing your business before exit

Harsh M&A truth:

Sterile, over-optimized businesses don’t attract strategic offers.

They repel them.

Buyers want:
 ✅ Obvious levers to pull post-acquisition
 ✅ Inefficiencies they can fix with capital or scale
 ✅ Growth upside they can unlock

You’re not selling a finished product.

You’re selling a platform for growth.

STOP trying to make your business look perfect.

START making it look scalable.

The best acquirers want room to play.

No upside? No premium.

👉 So what’s one “flaw” in your business that might actually be a selling point?

taplio

Greg Head's Linkedin Analytics

Greg Head

Performance ScoreGreg Head's LinkedIn Performance

Greg Head's Best Posts (last 30 days)

Ready to grow your LinkedIn presence?

taplio

.css-6ytdur{background-image:linear-gradient(284deg, rgba(39, 43, 72, 1) 0%, rgba(33, 47, 183, 1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Greg Head's Linkedin Analytics

Greg Head

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Greg Head's LinkedIn Performance

Greg Head's Best Posts .css-1emoo84{font-size:var(--chakra-fontSizes-md);font-weight:400;color:var(--chakra-colors-gray-600);}(last 30 days)

Ready to grow your LinkedIn presence?

Greg Head's Linkedin Analytics

Performance ScoreGreg Head's LinkedIn Performance

Greg Head's Best Posts (last 30 days)