Framing Your LOI: Two Offers and Smarter Seller Financing in Southwest Florida
When you’re ready to submit a Letter of Intent (LOI) to buy a business, most buyers stick to one number, one structure, and then brace for weeks of back-and-forth. That single-offer approach often stalls momentum; and worse, it can get bogged down in terms that may not even be the seller’s real priorities.
In Southwest Florida, where many businesses are closely held and owner-operated, especially in Naples, there’s an opportunity to make your LOI not just an opening bid, but a tool for clarity and trust. The method? Present two genuine offers in your initial LOI.
Example structure:
Offer A: Higher total enterprise value but less cash at close, with the balance paid through seller financing and/or earnouts.
Offer B: Lower total enterprise value but more cash at close, minimizing post-sale payment risk for the seller.
Why it works:
Restores seller control – This is particularly important in our local market where many sellers are first-time exiters. Giving them a choice between two real offers makes them a decision-maker, not just a respondent.
Reveals priorities quickly – In Naples, some owners care most about a clean break; others want maximum price, even if it means some payments come later. Their choice tells you which way they lean.
Shows the trade-offs in plain view – The “your price, my structure” principle is easier to grasp when both options are side-by-side.
Speeds up the deal – Many sellers simply choose one offer outright rather than entering prolonged, positional negotiations.
Going deeper on Offer A: the seller financing and earnout levers
Seller financing isn’t just “we’ll pay you later.” It’s a flexible set of tools that can help bridge valuation gaps and align incentives. In Naples and broader Southwest Florida, where seasonal swings, tourism exposure, and customer concentration can be factors; structuring these terms well is critical. Many buyers only consider EBITA or Net Income based earnout rules, simply because they were unaware of other options. Get creative, as long as a seller agrees, anything you can put into a contract can be the rules to the earnout.
Beyond standard EBITDA-based earnouts, you can tie payments to:
Revenue from the largest customer(s) – Reduces the buyer’s risk if key relationships don’t hold after transition.
Gross profit targets – Protects both sides from revenue growth that comes with eroding margins.
Post-sale retention milestones – Especially relevant if the seller’s relationships with staff or key accounts are critical to the business.
Seasonal performance windows – Useful in industries with heavy Q1/Q4 reliance in Southwest Florida, ensuring earnout metrics match local demand patterns.
The art here is to make the targets meaningful enough for the seller to stay invested in the business’s success post-closing, while still being achievable under the buyer’s management.
Local reality check
In Naples, I’ve seen family-owned businesses where the seller opted for the “more cash now” option because it removed post-sale uncertainty. Others have gone with the higher total value, knowing they could help ensure performance metrics were met. In both cases, the two-offer LOI kept the conversation productive and the relationship intact.
Bottom line
Framing your LOI as two ready-to-close offers; especially when one incorporates thoughtfully structured seller financing, gives you better insight into the seller’s motivations, reduces wasted time, and often results in a smoother closing. In the Southwest Florida market, where relationships and reputation matter just as much as numbers, this approach can be the difference between a signed deal and a slow fade into “we couldn’t get there.”
