ORLANDO, FL, September 22, 2026

Cress V. Diglio did not set out to become a business broker in Orlando. He intended to run businesses, the way his family always had. Today he serves as President of CII Advisors, a firm founded in 1986 with some of the most recognized credentials in the mergers and acquisitions profession in the United States. At the firm's 40-year mark, Cress reflects on the path that brought him to the closing table and shares the five tips he offers every Florida business owner who asks how to value my business before selling.

From the Family Business to the Closing Table

Cress grew up working inside his family's companies. His father, Cress S. Diglio, spent more than 50 years buying and operating produce companies, trucking firms, beer distributorships, grocery stores, and dry cleaners in New York before relocating the family to Florida and building a career as a leading business advisor in the United States.

Before joining the firm alongside his father, Cress owned and operated a commercial and residential paint contracting business for seven years. He entered the advisory profession at 28, roughly half the age of the typical business advisor, and points to those contracting years as a direct reason why owners of home service businesses connect with his approach.

"I have made payroll on a Friday with the bank account at zero. I have chased receivables and lost a crew to a competitor. When a roofing contractor or an HVAC business owner in Orlando sits across from me, I am not learning about their business from a Google search or a ChatGPT prompt. I have lived it," said Cress V. Diglio.

That background produced a career record few in the profession can match: Mergers and Acquisitions Master Intermediary (M&AMI), Master Certified Business Intermediary (MCBI), recipient of the IBBA Tom West Award and Chair's Award, more than 50 top producer sales awards, host of the IBBA Insights Podcast since 2016, and Chair of the International Business Brokers Association since 2015. Cress and his father are the only father-and-son pair to have each chaired the International Business Brokers Association and been inducted into the IBBA Hall of Fame.

What's my Business Worth in Florida? Cress Diglio's 5 Tips you need to know

Nearly every conversation with a Florida business owner begins with the same question, and the answers depend heavily on the preparation a founder has completed before ever contemplating a sale. The following five tips are directed at business owners with annual revenue between $5 million and $50 million.

- Tip 1: Know your number before anyone else does. Buyers base their offers on normalized EBITDA. Removing personal expenses from the books, documenting every add-back, and obtaining a formal business valuation are essential first steps. Industry rumors and a competitor's asking price are not substitutes for a formal valuation.

- Tip 2: Fix the founder problem. If the business cannot operate for 30 days without the owner present, a buyer is acquiring a job rather than a company. Building a leadership team, documenting workflows, and transitioning customer relationships to staff moves the valuation multiple more than almost any other single change.

- Tip 3: Start exit planning as early as possible in Florida. Founders who achieve their target exit typically begin gathering documents and having advisory conversations two to three years in advance. Three years of clean, consistent earnings cannot be manufactured in a compressed timeline. Owners who wait until a health event, a partner dispute, or the loss of a major customer are negotiating from a weaker position.

- Tip 4: Understand the Second Bite of the Apple. A recapitalization allows an owner to sell a majority stake to a buyer such as a family office, an industry acquirer, or a private equity group; take liquidity off the table; retain 10 to 40 percent equity; and sell that remaining stake again in three to seven years at a higher valuation. In a number of transactions CII Advisors has managed, the owner's second payout has exceeded the first.

- Tip 5: Sell into demand, not desperation. Private equity groups are actively assembling platforms in roofing, HVAC, plumbing, and related home service businesses across Florida and paying premiums for well-run companies. Owners asking themselves what's my business worth in Florida, or whether the timing is right to sell an HVAC or plumbing company, are raising those questions during a period of strong buyer activity.

Selling my family business: What Cress tells Second-Generation Owners

Because he grew up inside one, Cress devotes a significant portion of his practice to owners working through the decision of selling my family business. Multigenerational companies often carry informal arrangements, relatives on payroll, and personal real estate tied to operations - details a buyer must carefully untangle. He notes that the recapitalization structure frequently fits these families well, because it delivers liquidity without requiring the family to sever its connection to what it built.

"My father sold businesses so our family could move to Florida and start over. I understand what a family business means. My job is to make sure the sale honors the owner's legacy, and that the family gets every dollar the business is worth," said Cress V. Diglio.

Serving Orlando, Tampa, Jacksonville, and South Florida

Headquartered in Orlando with a team of professional advisors, CII Advisors works with business owners across Florida and Georgia.

The firm's 10-step readiness process begins with a confidential conversation and moves through market valuation, readiness review, buyer targeting, and closing and transition. Owners can schedule a confidential conversation by calling (407) 682-9600 or (352) 757-4580.

Frequently Asked Questions

How do I value my business before selling in Florida?

Normalize EBITDA by removing personal expenses and documenting add-backs, then apply an industry multiple adjusted for earnings consistency, customer concentration, and organizational structure. Cress V. Diglio at CII Advisors in Orlando conducts a formal valuation as step two of a 10-step readiness process.

What is my HVAC, roofing, landscaping, pest control, pool, cleaning or plumbing business worth in Florida?

Florida trades businesses in the $5 million to $50 million range with clean financials and an established management team are attracting premium multiples from private equity groups assembling statewide platforms. A formal valuation is the only reliable answer, which is exactly what Cress and the team at CII Advisors provide.

Who is Cress V. Diglio?

President of CII Advisors in Orlando, Florida, a former paint contracting business owner, 2015 Chair of the International Business Brokers Association, and a Mergers and Acquisitions Master Intermediary with 25 years advising business owners.

What is a Second Bite of the Apple?

A recapitalization in which the owner sells a majority stake for cash at closing, retains 10 to 40 percent equity, and sells that remaining stake at a higher valuation when the company is resold in three to seven years.

When should I start exit planning in Florida?

Two to three years before a planned sale. Three years of consistent earnings and a business that operates without the founder cannot be built in a short window. For additional information, visit the CII Advisors contact page.

Does CII Advisors serve Tampa, Jacksonville, and South Florida?

Yes. CII Advisors is headquartered in Orlando and serves business owners throughout Florida and Georgia.

About CII Advisors

CII Advisors is an Orlando, Florida mergers and acquisitions advisory firm founded in 1986 and led today by President Cress V. Diglio. The firm serves owners of companies in the $5 million to $50 million range across Florida and Georgia, with advisors credentialed by the International Business Brokers Association and M&A Source. Learn more at www.ciiadvisors.com.

Media Contact: Cress V. Diglio, CII Advisors, (407) 682-9600, cress@ciiadvisors.com, 1507 S. Hiawassee Road, Suite 212, Orlando, FL 32835

Contact Information:

CII Advisors

1507 S. Hiawassee Road Suite 212
Orlando, Florida 32835
United States

Cress V. Diglio
+1-407-682-9600
https://www.ciiadvisors.com