When a business owes you $50,000, $100,000, or more, “collections” isn’t just about being right. It’s about being strategic—because the fastest way to lose money is to spend months litigating and then discover the debtor is judgment-proof.
This guide walks Florida businesses through a practical playbook to collect a six-figure invoice (or defend against one), from the demand letter stage all the way through post-judgment collection.
Step 1: Before you send anything—confirm your proof and your leverage
The biggest mistake creditors make is sending a strong demand with weak evidence. If the debtor decides to fight, you want to be able to prove the basics cleanly.
Your “six-figure” proof file (assemble this first)
- Signed contract / proposal / MSA (and all addenda)
- The scope of work and any change orders
- Invoices and a clean account ledger
- Proof of delivery/performance (emails, photos, completion sign-offs, timestamps, job logs)
- Proof the debtor accepted the work or product (approval emails, usage, turnover, move-in, punchlist acceptance)
- Any payment history and promises to pay
- Any dispute communications (complaints, defect claims, “we’ll pay when…” excuses)
Reality check: is there a collectability path?
For six figures, you should ask early: How do we actually get paid?
Look for:
- A personal guaranty (this often changes everything)
- A solvent company with ongoing receivables
- A stable operating business (not winding down)
- A landlord/tenant context with a real entity and assets
- Insurance that might respond (rare for pure contract debt, but sometimes there’s a coverage angle)
If the debtor is a thin LLC with no assets and no guaranty, the strategy may shift toward an aggressive pre-suit resolution push (or deciding not to throw good money after bad).
Step 2: The demand letter that actually works (without backfiring)
A demand letter is not a “venting” letter. It’s a leverage document designed to make the other side choose one of two paths:
- Pay/settle on reasonable terms now; or
- Spend more money later and face worse consequences.
What your demand letter should include
- A short, businesslike statement of the agreement and the amount due
- A simple payment deadline (usually 7–14 days depending on circumstances)
- A list of attachments that prove the debt (invoice + ledger + key contract pages)
- A settlement option if you’re willing (for example: discounted lump sum, short payment plan, or equipment return)
What to avoid in a demand letter
- Threats you can’t (or won’t) follow through on
- Overstating facts (“fraud,” “theft,” etc.) when it’s really a contract dispute
- Emotional language or personal attacks
- A 10-page brief that teaches the debtor how to defend the case
A tight demand is often enough to trigger payment if the debtor believes you have (a) proof, and (b) the willingness to escalate.
Step 3: Choose the right “lane” — settlement, suit, or hard leverage
At the six-figure level, you generally have three lanes. The mistake is treating them like “preferences” instead of strategic choices. Each lane has a different goal, timeline, and cost profile—and the right lane is usually determined by collectability risk and delay risk.
Below is a practical way to choose.
Lane A: Pre-suit settlement (fastest dollars, least cost)
Goal: get paid (or mostly paid) quickly, with enforceable terms, without pouring money into litigation.
This lane is best when:
- The debtor is still operating and cares about business reputation, vendor relationships, or credit
- The dispute is mostly “timing/cashflow,” not a full-blown defect/counterclaim war
- You have good proof and want to convert it into cash quickly
- You want to preserve a relationship (or at least avoid scorched-earth conflict)
What “good” pre-suit settlement looks like (in six-figure disputes):
- A clear number, a clear due date, and terms that actually protect you
- A short payment plan (not a “forever” plan) with teeth if they default
- Confirmed terms in writing, not “we’ll get you next month” verbal promises
Tools and terms that often move money in Lane A:
- Lump-sum discount with a tight deadline (“Pay $X by Friday, release follows.”)
- Short payment plan with:
- automatic default provisions,
- attorney’s fees/costs provisions where appropriate, and
- clear “no further extensions” language
- Stipulated judgment structure (commonly: they sign it now; it’s filed only on default)
- Security when available (for example: confirmed receivable assignment, agreed-upon collateral, or structured releases tied to payments)
Red flags that mean Lane A may be a trap:
- They refuse to provide any documentation (ledger disputes, “we paid” claims without proof)
- They want a long plan with no protections (“we’ll pay $1,000/month forever”)
- They keep requesting more time but won’t sign anything enforceable
- You see signs of distress (vendors unpaid, moving locations, changing entities, shutting down)
If Lane A is working, you should see progress fast: documents exchanged, numbers narrowed, terms drafted, and money moving.
Lane B: File suit early (when delay makes collection harder)
Goal: stop the debtor from controlling the timeline—and use the court process to create pressure, structure, and consequences.
This lane is not about “being aggressive for ego.” It’s about recognizing that delay is the debtor’s friend when:
- you suspect they are running out of money,
- they are moving assets/closing accounts,
- they are hiding behind silence, or
- they only pay when forced.
Lane B is best when:
- You’ve been stalled with excuses (“next week,” “need one more invoice,” “waiting on funding”) and nothing changes
- The debtor is going dark or dodging accountability
- You suspect asset dissipation, shutdown, or restructuring
- You need formal tools to force the truth (documents, sworn testimony, corporate records)
What filing early can accomplish (practically):
- It puts the dispute on a structured timeline with deadlines
- It forces the other side to take the claim seriously (especially where attorney’s fees are in play)
- It creates leverage for an early business resolution (settlement often becomes more rational once there is real risk)
Common “six-figure” reasons to file sooner rather than later:
- The debtor is a thin entity and you need to locate assets/receivables
- The debtor has a history of nonpayment with others
- The dispute is heading toward a counterclaim no matter what—so you want to control the forum and framing
A helpful mindset:
If the debtor is not negotiating in good faith pre-suit, a lawsuit is often the tool that converts “endless discussion” into a decision.
Lane C: Harden your position before suit (when facts are messy)
Goal: reduce risk before you step onto the litigation track—because the facts, documents, or narratives need tightening first.
This is the lane many smart business owners choose when they suspect a lawsuit will be fought hard, and they want to avoid stepping into a counterclaim ambush.
Lane C is best when:
- There are competing stories about scope, defects, offsets, credits, or “who agreed to what”
- You suspect the other side will claim “defective work” or “we had to hire someone else”
- Your file is incomplete or scattered, and you need to build a clean proof package
- The debtor is threatening a counterclaim or already lawyered up
What “hardening” looks like (without overcomplicating it):
- Organize the proof file into a clean timeline (contract → performance → acceptance → invoice → nonpayment → communications)
- Identify the exact point of dispute (scope? price? quality? schedule? payment terms?)
- Demand specifics in writing:
- “What exactly was defective?”
- “When was it reported?”
- “Who fixed it?”
- “What did it cost?”
- “What payments do you contend were made, with proof?”
- Gather third-party proof where useful (building logs, vendor invoices, emails with project managers, delivery receipts, photos, timestamps)
Why Lane C often wins later:
When you enter litigation with a clean timeline and the other side is still operating with vague accusations, you shift the case from “stories” to “documents.” In six-figure disputes, that often dictates who gains leverage early.
Lane C red flags (when you shouldn’t wait):
- You believe assets are disappearing or the business is shutting down
- You have strong proof already and the only reason for delay is “hope”
- The debtor is weaponizing delay to force you into a discount
A simple way to choose the lane
Ask these questions:
- Do I believe the debtor can pay if pressured?
If yes → Lane A or Lane B. If no → you need a collectability-first strategy. - Is time helping me or hurting me?
If delay hurts collectability → Lane B sooner. - Is the dispute truly factual/technical, or is it just stalling?
If factual and messy → Lane C to tighten the record.
Most six-figure matters start in Lane A, but the winners know when to switch lanes quickly—before delay becomes irreversible.
Step 4: Lawsuit strategy — win fast and make the case “uncomfortable” for the debtor
Many business owners assume “winning the lawsuit” equals “getting paid.” Not necessarily. In six-figure cases, your litigation strategy should be built around two goals:
- Prove liability efficiently, and
- Increase the pressure to resolve before fees and exposure balloon.
Early leverage tools that matter
- Identify the cleanest claim(s): breach of contract, account stated, unjust enrichment (depending on facts)
- Demand the documents that kill common defenses: “proof of payment,” “defect evidence,” “credits,” “rejection communications”
- Pin down the story early through written discovery and targeted deposition topics
A word about counterclaims and “defect” narratives
In many invoice disputes, the debtor’s playbook is:
- “Work was defective”
- “We paid someone else”
- “We had to fix it”
- “Offsets exceed your invoice”
That doesn’t mean they can prove it. But it means you should plan for it and force them into specifics.
Step 5: The part most firms don’t write about—actually collecting after judgment
This is where business owners get frustrated. Post-judgment collection is often where the money is won or lost.
Think like this:
A judgment is a legal “IOU” with teeth. Collection is the process of finding where the money is and using lawful tools to reach it.
Common post-judgment paths include:
- Garnishing bank accounts (when you know where they bank)
- Garnishing receivables (when they’re paid by third parties)
- Discovering assets through post-judgment discovery
- Negotiating a structured settlement backed by enforceable terms
The best time to plan for collection is before you file suit—because your pleadings, strategy, and discovery can be designed to identify assets early.
Step 6: The “cost versus collectability” decision tree (simple but powerful)
Before you spend heavily, ask:
If the answer is “YES” to any of these, the case is often worth pursuing:
- There’s a personal guaranty
- The business is clearly operating and solvent
- There are known receivables/customers
- There are admissions in writing (“we owe it but…”)
- The dispute is narrow and your proof is clean
If the answer is “NO” to most of these, you may need a different approach:
- Pre-suit negotiated resolution with meaningful protections
- A quick lawsuit to force transparency (not a multi-year war)
- Or a business decision to stop bleeding money
Common settlement structures that work in six-figure disputes
- Discounted lump sum paid quickly
- Short payment plan with default provisions
- Stipulated judgment held in escrow and filed upon default
- Confidential settlement terms (when reputational risk matters)
- Mutual releases that end the dispute cleanly
The best settlements are the ones that are enforceable and reduce the risk of “re-litigation.”
FAQ: Six-figure invoice collections in Florida
What if the debtor claims they already paid?
Then the case becomes document-driven. Payment defenses live or die on bank records, receipts, confirmations, and ledger consistency. A creditor should demand proof and test it against the invoicing timeline.
What if the debtor says the work was defective?
Defect claims require specifics—what was wrong, when it was reported, what opportunity to cure existed, who fixed it, and what it cost. Vague complaints are not proof.
Should I wait and “be patient” if they keep promising to pay?
Not for six figures. Delay can make collection harder. If you want to be patient, do it with a strategy: written confirmation, structured payment terms, and clear consequences for nonpayment.
Can I collect from the owner personally?
Sometimes—especially with a personal guaranty. Without one, trying to reach the owner individually is typically harder and fact-dependent. (We cover guaranties in a separate article.)
Talk to a Florida business attorney before you spend months chasing the wrong strategy
Six-figure collections require a plan. The best outcome usually comes from combining:
- strong documentation,
- a leverage-driven demand letter,
- a litigation approach designed to resolve early, and
- a post-judgment collection strategy that’s built in from day one.
Douglas Firm represents Florida businesses in high-value collection matters and business disputes—both enforcing payment rights and defending lawsuits. If you want an assessment of your proof file and collectability options, we can review the documents and map the most practical path.
Disclaimer: This article is general information and not legal advice. Results depend on the specific facts and documents.