This hackathon (lablab Band of Agents Hackathon, 6/12-19) is about multi-agent enterprise workflows. That means building a multi-agent system where agents can coordinate with each other, pass context, and split up work to complete a task.
Honestly, what I wanted to build at first was a solo founder architecture — like a "one person can run a whole company" universal assistant. Slack messages get automatically routed, meetings get auto-summarized, to-dos get scheduled, client replies get drafted for you.
Sounds cool, right?
But after doing some market research, I found out it's already a red ocean. Notion, Lindy, Relevance AI, all those GPT-wrapped solo founder assistants — every solo founder I know already has 2-3 tools on their desk. Giving them another one just makes them annoyed TT
So I went back to find a problem again...
Finding the Gap from Family Background
My mom's a finance accountant, did it her whole life. My aunt is too. I used to run a small trading company in Korea, doing cross-border procurement.
So in our family, we have a common language when it comes to "not getting paid back"~
When I was doing trade, the hardest part wasn't getting orders or shipping — it was collecting payment.
Time zone is the first enemy — if the client's in Europe and I'm in Asia, by the time I wake up they're off work, by the time they're at work I'm asleep, one email exchange takes at least 48 hours. The second is phone collection calls — you don't know when the right contact at their company will pick up, don't know if they'll be friendly or annoyed when they do, don't know what words you can say and what words will make them blow up... the psychological pressure is really high. The third is legal — if there's a problem with a cross-border invoice, do you look at the buyer's local law, the seller's local law, or the arbitration clause in the contract? Just figuring that out takes a whole week.
Going back and forth, it's really annoying.
And usually the ending is: you grit your teeth and write the email yourself, make the call yourself, get angry yourself, deal with it yourself, and decide for yourself whether to just let it go.
So I interviewed my mom and aunt, asking how they handle overdue payments in their companies now.
The answer was consistent: no good tools. Either they manually track with Excel, or they hand the case to a lawyer, or they just swallow the loss and move on. Nothing in between.
No One in the Middle
I also browsed r/smallbusiness and r/sweatystartup on Reddit for posts about "customer won't pay". Hundreds per week.
"Customer says cash flow issues, already dragged two months, every chase is met with 'next week', next week becomes the next week after that"
"40K invoice, customer suddenly says quality issues, but the acceptance form was already signed"
"Don't want to tear things apart, but this money is my next month's rent"
The common thread in these stories: the money isn't big, but it's life or death for the person.
What about lawyers? Lawyers' contingency starts at 30-40%, and lawyers only want cases in the five figures. Five thousand, eight thousand, twenty thousand — these cases, lawyers just think are too much trouble.
What about collection agencies? True, there are a lot in the US. But their business model is "dumbly take all cases and run them through the same process". $2,000 case and $20,000 case use the same SOP — call, send letters, report to credit bureau. The result is two extremes: either they use brute force methods to recover the $2K (FDCPA complaints and TCPA fines flying everywhere), or the case gets stuck in queue for six months with no one touching it.
No one in the middle.
Middle is exactly those cases my mom and aunt encounter at work.
Middle is exactly those cases I encountered when running my trading company.
Middle is every small business owner posting hundreds of times a day on Reddit.
"Finding the Right Person Matters More Than Doing Things Right"
"Can I build an AI collection system that only helps these people?"
This idea spun around in my head for a night. But I didn't jump straight into building, because I knew once I start, I'll get stuck in product design and lose the ability to ask myself questions.
So I first gave myself 2 questions:
First question: How do you know which cases you can help and which you can't?
Second question: For the ones you can't help, what do you tell them?
These two questions hit hard.
Because most of these systems are designed around the thinking "we take all cases — the agent runs anyway, so we don't have to do work". But applying this logic to collection becomes just like existing collection agencies — take a $2K case in, recover $500, subtract fees client gets $200 — worse than not chasing at all.
So I decided, the first agent in this system isn't writing letters or making calls — it's looking at the real shape of this debt first, and picking the path that makes the most sense.
I called this agent Pre-flight.
What Pre-flight Looks At: Not Invoice Amount, but Outstanding
Here's a line we keep saying in our demos:
"Lawyers look at gross. We look at outstanding."
Take a real case from our canonical fixture: a $47,300 gross invoice, with the customer already having paid a 50% deposit at order. Outstanding balance is $23,650. A lawyer glances at the gross, sees nearly $50K, and says "cross-border litigation is too expensive, drop it." But for us, $23,650 lands right in our sweet spot.
So when Pre-flight gets the contract and invoice, it does two things:
- Extract contract clauses — governing law, forum selection, late fee, arbitration clause, deposit % (§6.1). Market research tells us roughly 70% of cross-border contracts don't even have a governing law clause — just surfacing that to the client is already educational value.
-
Compute outstanding, route into three paths —
outstanding = gross × (1 − deposit %). Routing runs on this number, not the big number printed on the invoice.
The three paths are clean: under $3K goes Lite (simple email + payment link); $3K–$40K is the sweet spot and runs the full In-Spot pipeline (letters + calls + tone escalation, with a final legal step only if nothing else works); over $40K we don't run the system at all and refer you to an attorney.
Three Paths: Lite / In-Spot / Attorney Recommended
Path 1: Lite (outstanding under $3,000)
The amount is too small to make a full pipeline worth it. So this path does only the simplest thing: Diplomat sends one friendly reminder email with a multi-channel payment page attached (credit card, Stripe, ACH, wire — all on the same page, the customer picks whichever they prefer).
No calls, no attorney letter. If unpaid after 7 days, the case closes.
If they pay, we win. If they don't, we'll tell you directly: "Pushing this one further isn't worth it. Small claims court or writing it off is the better path. Here's why."
Not fun, but honest.
Path 2: In-Spot (outstanding $3,000 ~ $40,000)
This is the sweet spot. The middle band lawyers won't touch and collection agencies will mess up. Recoverflow's full 8-agent crew runs, escalating step by step from light to heavy:
- First letters (Diplomat — friendly reminder, formal notice, all the way to an attorney-backed demand letter, with the tone graded by stage)
- In parallel, calls (Voice Agent — real two-way conversation that can understand "pay you next week" and follow up with "which day, in what form")
- Throughout, Tone Coach watches in the background for any wording that might cross an FDCPA red line
- Concierge routes every external action to you for approve first
- If the case is still unpaid by Day 60, Escalator is the one that pushes it up to the formal attorney-backed demand letter step
This path is Recoverflow's main stage — later diary entries will break each agent down one by one.
Path 3: Attorney Recommended (outstanding over $40,000)
For this band, our answer is direct: don't use Recoverflow — go find an attorney.
A contingency attorney (around 33%, no upfront) usually works out cheaper than us at this size, plus they have subpoena power to check the other party's assets and bank accounts. That cross-border enforcement muscle is something we just don't have.
So for cases like this, Pre-flight doesn't spin up the 8-agent flow. It tells you directly:
"We'd recommend you find a cross-border commercial collection attorney for this one. Here's a vetted list we've put together in CA / NY / DE, and roughly what their contingency structures look like."
We take zero referral fee. The list goes out as-is, no strings attached.
For cases over $40K, the most valuable thing we can do is honestly tell you "we're not the right tool here".
The Cost of Being Honest with Small Businesses
I know this design isn't pretty from a business model perspective.
If I forced every Lite case into the full pipeline and kept Attorney-bound cases for ourselves instead of handing over the referral list, revenue could triple. But the result would be going back to the old collection-agency way — ugly with small clients, useless to big clients.
That's not why I built this system.
I want to build something a small business owner would willingly recommend to their friends.
When you think about it clearly, a lot of cases that seem "should take" are actually "shouldn't take".
Truly good products were never about covering everything — they actually cut to the pain point and really solve it!
After interviewing my mom and aunt, I decided on this problem...
How the Whole System Is Thought Through
Back to the hackathon theme — multi-agent enterprise workflows, meaning letting multiple AI assistants divide labor and collaborate to complete a business task.
What I wanted to build isn't "one super AI that chases payments for you" — it's a small team: each agent (think of it as an AI assistant that only does one thing) only does one thing, does it really well, then passes context to each other and coordinates with a state machine (a little notebook tracking where this case is in the process).
The whole Recoverflow has 8 agents, split into three layers:
Layer One — Gatekeeper
- Pre-flight: The first agent to see a case. Doesn't write letters or make calls. Does two things: extracts contract clauses (governing law, deposit %, etc.), and routes by outstanding into Lite / In-Spot / Attorney Recommended. This whole diary entry has been about this one agent.
Layer Two — Doers
- Investigator: Looks up your history with this customer, finds patterns (do they always drag? Any emergencies? Did the contract miss the late fee clause?)
- Diplomat: Writing letters. From friendly reminders, formal notices, to final demand letter — tone escalates as the case progresses
- Voice: Making calls. Two-way conversation, can understand "pay next week" and also press for "which day, in what way"
- Payment: After they agree to pay, Stripe checkout link / wire transfer guidance all in one
Layer Three — Guardians
- Concierge: Your approve button. Every external action — Pre-flight routing, Diplomat's letter, whether Voice calls, whether Escalator escalates — all gets sent to you to press yes before going out
- Tone Coach: Watching in the background constantly. Every sentence Diplomat writes, every word Voice says gets checked by it — crossing FDCPA red lines or too aggressive tone gets blocked and rewritten in real time
- Escalator: The escalation layer when case enters escalation (e.g., the other party is completely unresponsive, going lawyer route)
The core idea of this architecture: doers need to be strong, but more importantly, gatekeeper and guardian need to be hard.
Most agent system designs are "give doer a super strong prompt, expect it to get there in one go". But this system's bet is exactly the opposite — I'd rather Diplomat writes so-so, as long as Tone Coach is always on guard; I'd rather the process be one step slower, as long as Concierge shows you every step; I'd rather Pre-flight spend the extra 5 seconds computing outstanding and route the case onto the right path than force every case into In-Spot just for revenue.
Because in collection, one mess-up isn't "the user finds it unhelpful" — it's FDCPA complaints, it's getting resented by clients, brand trust goes to zero.
That's also why the problem is called Recoverflow instead of Collector — what I want to recover isn't just the money, but the dignity small business owners get worn down by during the collection process.
Next entry I'll write about how our Voice Agent changed from "one-way notification" to "two-way real conversation" — in between I made a phone call myself and hit a bug, and rewrote the prompt on the spot for two hours.
That's another interesting story...
Originally published at Judy AI Lab. Visit for more articles on AI engineering and development.
