Selling a Business for Retirement in Florida: 2026 Owner Guide

You built the company. You are somewhere between 58 and 68. The work still gets done, but you are the one who does most of it, and every year you tell yourself you will start planning the exit next year. That is the single most common conversation we have at CBH Business Group, and it is the one that costs Florida owners the most money. A retirement-driven exit is different from an opportunistic one. An opportunistic seller can wait for the right buyer, the right cycle, the right multiple. A retirement seller has a clock — health, energy, a spouse who is already done, a lease renewal, a partner who wants out. Buyers can smell that clock, and a seller who is negotiating against their own calendar loses leverage on price, on terms, and on how much cash actually shows up at closing. The good news: a retirement exit planned 18 to 36 months out is one of the strongest positions in the market. Florida is a net importer of buyers. Private equity search funds, family offices, out-of-state strategics chasing Sun Belt growth, and SBA-backed individual buyers are all actively looking for exactly the profile that a 60-something owner-operator has built — an established business, real customers, real cash flow, and an owner who is motivated but not desperate. This guide covers what a retirement exit actually looks like in Florida: the timeline, the money, the tax picture, and the mistakes that turn a good business into a hard sale. ## Why Retirement Sellers Get Underpaid The business is usually fine. The problem is almost always structural, and it comes from the same habits that made the business successful in the first place. - **Owner dependency** — After 25 years, the relationships, the pricing decisions, the key vendor accounts, and the institutional knowledge live in one person's head. A buyer is not buying a business at that point. They are buying a job that requires your specific network to function, and they will discount heavily for it. - **Deferred investment** — Owners approaching retirement stop spending. The trucks get older, the software stays legacy, the sales hires never happen. Revenue flattens for three years running, and a buyer prices flat revenue as declining revenue. - **Messy financials** — Personal expenses run through the company, cash transactions never quite make the deposit, and the tax returns are optimized to minimize income. All of that is legal and common. It also makes it very hard to prove what the business actually earns. - **A hard deadline** — Announcing that you must be out by December is the most expensive sentence in a negotiation. Buyers slow down, re-trade on price, and push more consideration into earnouts and seller notes. - **No successor conversation** — The son-in-law who "might want it" is not a plan. Ambiguity about who takes over freezes the process for months while the family works it out on the buyer's clock. Every one of these is fixable. Most of them take 12 to 24 months to fix properly, which is exactly why the planning window matters more than the market timing. ## What Your Business Is Actually Worth Value in the lower middle market is driven by adjusted earnings and by risk. Adjusted earnings — SDE for smaller owner-operated businesses, EBITDA for companies with real management in place — is the starting number. The multiple applied to it is where all the negotiation lives, and the multiple is a direct function of how much the business depends on you. Here are the general ranges we see in the Florida market. Treat these as market context for planning, not as a quote on your specific business.

Adjusted EBITDA / SDE	Typical buyer	Common multiple range	What drives the top of the range
Under $500K	Individual buyer, SBA 7(a) financed	2.0x – 3.5x SDE	Recurring customers, transferable licensing, real books
$500K – $1M	Individual or small search fund	3.0x – 4.5x SDE	A working manager, low customer concentration
$1M – $3M	Search fund, family office, regional strategic	4.0x – 6.0x EBITDA	Management depth, documented systems, growth trend
$3M – $10M	Private equity platform or add-on	5.5x – 8.0x EBITDA	Scalability, contracted revenue, clean quality of earnings
Over $10M	PE platform, national strategic	7.0x – 12.0x+ EBITDA	Market position, margin profile, management that stays

Notice what happens between the $1M and $3M rows. The jump is not about size alone. It is about whether the company runs without the owner. A business doing $1.2M in EBITDA with a general manager in place will often clear a higher multiple than one doing $1.6M where the owner is still the head of sales, operations, and purchasing. For a retirement seller, that gap is the entire retirement plan. ## The 24-Month Retirement Exit Timeline The owners who get paid the most start roughly two years out. Here is the sequence that works. ### Months 24 to 18: Get honest about the numbers Have a broker's opinion of value done. Not a rule-of-thumb from a competitor who sold last year, and not a number from a friend at the country club. A real valuation tells you whether the business supports the retirement you have in mind, and it gives you 18 months to close the gap if it does not. This is also the point to clean up the books: separate personal expenses, document the add-backs you intend to claim, and put the accounting on a system a buyer's accountant will recognize. ### Months 18 to 12: Build the second layer Promote or hire the person who can run daily operations. Move your name off the key customer relationships. Write down the processes that only exist in your head — pricing logic, vendor terms, how you bid a job, how you handle the difficult account. Buyers pay for documented process because it converts your experience into an asset they can actually acquire. ### Months 12 to 6: Fix the risk flags Address customer concentration if one client is more than 20 percent of revenue. Renew or extend the property lease so it transfers cleanly. Confirm that licenses, permits, and certifications can move to a new owner — in Florida this matters enormously for contractors, healthcare practices, insurance agencies, and title companies, where a qualifying license holder may need to be part of the deal structure. Settle any partner or family expectations in writing before a buyer is at the table. ### Months 6 to 0: Go to market Confidential marketing, buyer screening, offers, letter of intent, due diligence, and close. A well-prepared Florida business typically takes six to ten months from launch to closing. Due diligence alone runs 60 to 90 days once an LOI is signed, and any surprise found there costs weeks and usually costs price. ## The Tax Picture for Florida Retirees Florida gives you a structural advantage that owners in most other states do not have. - **No state income tax** — Florida imposes no personal income tax, so the gain on a business sale is not taxed at the state level for an individual seller. A California or New York owner selling the same business can lose a significant additional share of the proceeds to state tax. This is a real, quantifiable reason buyers and sellers both keep relocating here. - **Federal capital gains still apply** — Long-term capital gains rates plus the net investment income tax still hit the federal side. The deal structure determines how much of the price is taxed at capital gains rates versus ordinary income rates. - **Asset sale versus stock sale** — Most lower middle market deals are asset sales, which buyers prefer for liability and depreciation reasons. Asset sales require allocating the purchase price across asset classes, and that allocation drives your effective tax rate. It is negotiable, and it is worth negotiating. - **Installment treatment on seller notes** — If part of the price is paid over time, the gain on that portion may be recognized as payments are received, which can matter for a retiree managing income across tax years. - **Retirement account and estate coordination** — The sale is often the largest liquidity event of your life. It should be planned alongside your estate plan and your retirement income strategy, not after the fact. Get your CPA and your estate attorney involved before you sign a letter of intent, not after. Tax structure is far easier to shape while terms are still being negotiated. Nothing here is tax advice for your specific situation — it is the framework we see play out in Florida transactions. ## Structuring an Exit You Can Actually Retire Into Retirement sellers care about two things beyond price: how much cash arrives at closing, and how long they have to stay. Most deals in this size range are not all cash at close. Expect a structure combining cash at closing, possibly an SBA-backed loan on the buyer's side, a seller note, and sometimes an earnout or a small rollover equity stake if a private equity buyer wants you invested in the next chapter. The mix is negotiable, and the mix is where a retirement seller either protects their outcome or gambles it. A few principles worth holding: - **Weight the deal toward cash at close.** Every dollar in an earnout is a dollar that depends on someone else running your company well. - **Keep the transition period defined.** Three to twelve months of transition support is normal and reasonable. An open-ended commitment to "stay on as needed" is not. - **Understand the non-compete you are signing.** It is standard, it is enforceable in Florida within reasonable scope and duration, and it should be scoped to the business you actually sold. - **Model the after-tax, after-fee number.** The headline price is not the retirement number. Net proceeds after taxes, transaction costs, debt payoff, and working capital adjustments is the number that funds your life. ## Frequently Asked Questions ### How long does it take to sell a business in Florida? From launch to closing, six to ten months is typical for a well-prepared business. Add another 12 to 24 months if the company needs preparation work — cleaning up financials, reducing owner dependency, or addressing customer concentration. Owners who plan for a retirement date and start the preparation two years ahead consistently get better outcomes than those who go to market in the same quarter they decide to retire. ### Can I sell if I am still the one running everything? Yes, but expect a discount and a longer transition commitment. Buyers price owner dependency as risk. If you can install a general manager and shift key relationships even 12 months before going to market, that single change often moves the multiple more than another year of revenue growth would. ### Will my employees find out before the sale closes? Not if the process is run properly. Business sales are marketed confidentially — buyers see a blind profile with no company name, sign a non-disclosure agreement before receiving details, and are screened for financial capability before any deeper information is shared. Employee and customer notification is planned deliberately, usually close to or at closing. ### What if my kids might want the business? Have that conversation before you go to market, in plain terms, with a real answer. A family transition and a third-party sale are both good outcomes, but they are different processes with different timelines, financing, and tax treatment. Ambiguity is what kills deals. An internal transition or management buyout can also be structured to give you liquidity while keeping the business in the family. ### Is 2026 a reasonable time to sell in Florida? Buyer demand in Florida remains strong across the lower middle market, driven by population growth, SBA acquisition lending, and private equity appetite for Sun Belt add-ons. The bigger variable for most retirement sellers is not the market cycle — it is whether their own business is prepared. A prepared business sells well in most markets. An unprepared one struggles even in a strong one. ## Start the Conversation Before You Need To If retirement is somewhere on your horizon — this year or five years out — the most valuable thing you can do right now is find out what your business is actually worth and what it would take to close the gap between that number and the one you need. CBH Business Group is a Florida M&A advisory and business brokerage firm working with owners of businesses in the $3M to $50M revenue range across Miami, Tampa, Orlando, Jacksonville, Fort Lauderdale, Naples, Sarasota, Palm Beach, and Central Florida. We were recognized among the Top 50 Brokers in Florida in 2024 and 2025, named Million Dollar Producer in 2024 and 2025, and ranked the #1 Top Dollar Producer in Central Florida in 2025. Start with a free, no-obligation valuation: https://cbhbusinessgroup.com/valuation-calculator Or have a direct, confidential conversation with Jesse Hastings about what a retirement exit would look like for your business. Book a time at https://calendly.com/jesse-cbhadvisory or call (407) 908-3845. The conversation is confidential, and it costs nothing to know your number.