Cress V Diglio, P.A.

Cress V Diglio, P.A. President CII Advisors. Past Chairman, IBBA, Lifetime Master Certified Business Intermediary, M&AMI Cress V.

Diglio is a highly accomplished M&A advisor with over 25 years of experience specializing in the lower middle market. Beginning his career in 1999 at the age of 28, Cress has since become a nationally recognized leader in business sales, serving as President of CII Advisors, a respected business advisory firm with a legacy spanning more than four decades. Under Cress’s leadership, CII Advisors has

grown into a powerhouse of experienced M&A professionals, collectively closing over 500 transactions totaling more than $500 million in enterprise value. His firm specializes in the sale of privately held companies with revenues ranging from $5 million to $50 million and EBITDA of $1 million or more. Cress has successfully sold businesses across virtually every industry, with a focused expertise in sectors such as home services, construction, roofing, HVAC, plumbing, landscaping, windows and doors, glass, pest control, and property management. His deep understanding of these industries and their business dynamics enables him to deliver optimal outcomes tailored to each unique situation. What truly sets Cress apart is his personal dedication to every client’s engagement. He is known for being hands-on throughout the entire process, employing a skilled M&A team to meet the rigorous demands of each transaction—never delegating key responsibilities to junior associates. Cress is a skilled negotiator, meticulous in detail, and deeply empathetic to the emotional and financial complexity of selling a business. He understands that for most entrepreneurs, the sale represents the culmination of a lifetime of hard work, and he strives relentlessly to help each client realize the maximum value for their business. Cress is widely respected for his integrity, transparency, and client-first philosophy. He fosters a collaborative team atmosphere, working closely with clients and their legal, financial and other trusted advisors to ensure a smooth and successful transaction. His distinguished career has earned him numerous accolades, including induction into the IBBA Hall of Fame (Class of 2025), Lifetime Master CBI, M&AMI, Fellow of the IBBA, Fellow of the M&A Source, and recipient of the prestigious CII Rolex Award. He has been named CII Advisor of the Year, honored multiple times by the Transworld President’s Club, and awarded the Sunbelt Largest Transaction Award (2010), Tom West Award, IBBA Chairman’s Award, and both Gold and Platinum Club distinctions from the M&A Source. Diglio brings a rare combination of experience, heart, and high-performance results to every engagement. For business owners seeking a trusted, capable, and caring advisor, Cress stands as a benchmark of excellence in the M&A industry

Twenty-five years to build it. Ninety days to protect it.There’s a strange pattern in M&A that catches even seasoned own...
08/26/2026

Twenty-five years to build it.
Ninety days to protect it.

There’s a strange pattern in M&A that catches even seasoned owners off guard.
The years spent building a business get treated with total discipline.
The final stretch before selling it often doesn’t.

Burnout sets in.
Owners take the first offer just to be done.
They skip the prep work that due diligence requires because they’re mentally already done with it.
Every one of those shortcuts quietly costs money, often more than the owner realizes until it’s too late to renegotiate.

A few months of intentional preparation before going to market can be worth years of what was actually built.
The exit deserves the same discipline as everything that led to it.

08/26/2026

Twenty-five years to build it.
Ninety days to protect it.

There's a strange pattern in M&A that catches even seasoned owners off guard.
The years spent building a business get treated with total discipline.
The final stretch before selling it often doesn't.

Burnout sets in.
Owners take the first offer just to be done.
They skip the prep work that due diligence requires because they're mentally already done with it.
Every one of those shortcuts quietly costs money, often more than the owner realizes until it's too late to renegotiate.

A few months of intentional preparation before going to market can be worth years of what was actually built.
The exit deserves the same discipline as everything that led to it.

Before you accept the first offer on your business, read this.Here’s something buyers don’t advertise: Their opening num...
08/20/2026

Before you accept the first offer on your business, read this.

Here’s something buyers don’t advertise:
Their opening number is almost never their real number.

1.
That first offer that lands in your inbox isn’t a compliment on your business.
It’s a test to see what you’ll accept.
Owners who sign it as is rarely find out what was actually on the table.
Owners who push back almost always close higher.

2.
Then comes the letter of intent, which feels routine but quietly locks in the terms that shape everything after it.
Most of the real negotiation happens here, long before an attorney ever reviews a page.

3.
After that, due diligence turns into a search for reasons to lower your price.
Anything undocumented or unclear becomes leverage.

4.
And through all of it, the buyer’s team has done this dozens of times.
If your side of the table is an attorney who’s never run an M&A deal, that’s not a fair fight.

A 30-minute conversation before you sign anything could change how this entire deal ends! 📞

08/20/2026
One buyer negotiates. Multiple buyers compete.There’s a quiet difference between selling to the first offer and selling ...
08/17/2026

One buyer negotiates.
Multiple buyers compete.

There’s a quiet difference between selling to the first offer and selling into a room where buyers know they’re not the only ones bidding.

One buyer sets the terms because they can.
There’s no pressure, no urgency, no reason to sweeten the deal.
Bring a second qualified buyer into the picture and the entire dynamic flips.
Offers improve.
Timelines shrink.
Buyers start selling themselves on why they deserve the deal.

That competitive tension doesn’t happen by accident.
It’s built through structured outreach and timing long before a single offer hits the table.

08/17/2026

One buyer negotiates.
Multiple buyers compete.

There's a quiet difference between selling to the first offer and selling into a room where buyers know they're not the only ones bidding.

One buyer sets the terms because they can.
There's no pressure, no urgency, no reason to sweeten the deal.
Bring a second qualified buyer into the picture and the entire dynamic flips.
Offers improve.
Timelines shrink.
Buyers start selling themselves on why they deserve the deal.

That competitive tension doesn't happen by accident.
It's built through structured outreach and timing long before a single offer hits the table.

08/13/2026

Property management is worth more than most of its owners realize.

Most property management owners think of their business as a service they run day-to-day, not as an asset that's part of a $115 billion market.

But strategic acquirers and private equity groups don't see it that way.

They see fragmented markets ripe for consolidation, and Florida happens to sit right in the middle of that opportunity.

The interesting part isn't that the market exists.

It's that most owners in this space have never stopped to ask whether their business is actually built to capture a piece of it, recurring contracts, retention rates, and operational systems that don't rely entirely on the owner.

That distinction is usually the difference between an offer and a premium offer.

They tried it alone first.Steve’s family had been trying to sell their business independently.Without a structured proce...
08/11/2026

They tried it alone first.

Steve’s family had been trying to sell their business independently.

Without a structured process, a prepared data room, and professional buyer outreach, the right buyers never came to the table.

CII Advisors came in, repositioned the deal, and closed it at a higher price than Steve was asking on his own.

In his words: “He is consistent, honest, and very professional. We can’t imagine having done it without him.”

Selling a business isn’t just about finding a buyer.

It’s about finding the right buyer, and knowing how to position the deal so they see the full value.

A question worth answering now: what will you do the Monday after you sell?Most business owners spend years preparing fo...
08/07/2026

A question worth answering now: what will you do the Monday after you sell?

Most business owners spend years preparing for the sale itself.
Fewer spend any time preparing for what comes after.

The deal closing is the final step of one chapter.
It’s also the first day of a new one, and that transition catches a lot of owners off guard.

The identity, the routine, the sense of purpose that came from running the business doesn’t disappear the moment the wire transfer clears.

CII Advisors works with owners on both sides of that line, the deal itself and what comes next, because a successful exit isn’t just about the number.

It’s about being ready for the life on the other side of it.

Address

1507 S. Hiawassee Road Suite 212
Orlando, FL
32835

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