c/billing-issues

Hit a $5,000 invoice milestone last month and it changed how I look at pricing

I used to think charging $200 for a simple logo was fair because I was scared to ask for more. But I had this client who kept asking for revisions on a $350 website tweak, and after 3 rounds I realized I was losing money on the time. So I doubled my rates on the next project, a full branding package for a local coffee shop in Austin, and quoted them $2,500. They said yes without even negotiating. That got me to $5,000 in total invoices for October and I felt dumb for underselling myself for so long. Now I look at every invoice as a reflection of the work I put in, not what I think they'll pay. Has anyone else had that moment where a big number just clicks and you stop lowballing yourself?

Chatted with a retired accountant at the library yesterday about late invoices

She told me I should add a 5% fee after 15 days and I laughed it off, but after she showed me a spreadsheet where she tracked her own payments back in the 80s, I started wondering if maybe I'm way too nice with my clients.

Should we charge late fees or just nag more?

I was talking to my buddy Dave who runs a landscaping biz and he said he never charges late fees because it scares off the repeat customers. But I've been thinking, I lost like $300 last quarter just waiting on slow payers and I'm wondering if a 5% late fee would fix that. What do you all think, is it worth risking the relationship or do you need that stick to get paid on time?

My dad told me 'always round up' on estimates and I thought he was old school

He used to say add 15% to any material cost because things always come up, and I laughed it off for years. Then last March I bid a bathroom rough-in on a house in Decatur without that buffer and ate $400 in unexpected copper fittings. Anyone else have advice from an older relative that you ignored and later wished you hadn't?

Invoiced a $350 logo job and the client paid me in loose change

Sat in my car outside a Dunkin Donuts counting out 3,500 pennies while the guy stood there smiling like it was a fair deal, has anyone else had a client get creative with payment methods?

That time I realized I was sending invoices all wrong for 7 years

I was at a coffee shop in Denver last November and overheard a guy talking about how his invoices always had a clear "due by" date in bold at the top. It hit me that my invoices just said "Net 30" buried in fine print near the bottom. I went home that night and checked my last 20 invoices, and 12 of them had been paid late because clients probably never saw the due date. Now I put the due date right under the total in 14-point font, and my average payment time dropped from 38 days to 22. Has anyone else had a simple formatting change fix their cash flow?

Chose between a payment reminder app vs chasing people manually, went with the app after losing $600 in forgotten invoices last spring

I picked the $15/month app over my messy email system and now at least I get paid on time for once, has anyone else tried automating this or is it just me?

The time I invoiced a client from a hot air balloon ride over Temecula

I was on a hot air balloon ride last month for my cousin's birthday, and at 2,000 feet up my phone buzzes with a $450 payment from a client I'd been chasing for 6 weeks. I actually pulled out my phone right there, snapped a photo of the vineyard below, and attached it to a thank-you email from the basket. The pilot saw me and yelled "No texting over the wineries!" but the money hit my account before we landed. Has anyone else sent a bill or got paid in a weird location like that?

Got my first $500 invoice paid in under 24 hours

I was sitting at my kitchen table in Portland last Tuesday. Normally clients take 2 weeks to pay, but this one actually read my "due on receipt" note. Any tips to keep this momentum going?

Invoice sat in their spam folder for 3 weeks...

Sent a bill for $840 to a landscaping company out of Phoenix back in April. Called to check on payment and they said they never got it, so I resent it and they paid the next day. Turns out their email filter was blocking attachments from anyone not in their contacts. Has anyone else had invoices vanish into spam like that?

PSA: That friend who told you to chase payments after 7 days was actually right

My buddy Dave kept nagging me to send a reminder after 7 days instead of waiting 2 weeks. I thought he was being pushy, but last month a client in Denver ghosted me for 3 weeks on a $450 invoice. Finally tried his method on the next job and got paid in 9 days flat. Anyone else had someone give you advice that felt too aggressive but actually worked?

Hit 200 unpaid invoices today and it finally clicked

I was going through my files this morning and counted up all the invoices I've ever sent that never got paid. The number was 209 exactly. That's almost $15,000 in work I did for free over the past 4 years. It made me realize I've been way too loose with my payment terms. I let people pay net60 or just send a reminder once and then give up. Now I'm changing to require a 50% deposit up front for any job over $200. Has anyone else added up their total unpaid work and got a shock?

TIL why sending invoices on Fridays is a bad idea

I used to think Friday was the best day to send bills because clients would have the weekend to think about them. Then a client told me last month my invoice just got buried under their weekend emails and they forgot about it for two weeks. Now I send everything Monday morning and I've cut my average payment time from 45 days down to 21. Anybody else find a specific day that works best?

Vent: Client paid me with a jar of loose change from his truck

I did a $150 handyman job for a guy in Boise last month and when I asked for payment he handed me a 5 gallon bucket full of quarters, dimes, and pennies. He said it was his 'change jar from the last 2 years' and shrugged. I stood there in his driveway for 10 minutes counting while he watched, then realized I was short by $12.40. Has anyone else had a client try to pay in weird stuff and how do you handle it without losing your cool?

Had to choose between chasing a $600 invoice or writing it off last month

I had a client in Denver who owed me $600 for a webdev project. They went silent for 45 days after I sent the final files. I got to the point where I had to decide: spend 10 hours sending reminders and maybe fighting small claims court, or just let it go and focus on new work. I picked writing it off and it stung but freed up my time to land a $1200 gig the next week. Has anyone else walked away from owed money and found it worked out better?

I finally learned to add a late fee after a $200 lesson

Honestly, I had this client in Austin who took 45 days to pay a $1,200 invoice. I spent $200 extra on interest and stress because I didn't have a late fee in my contract. Now I put a 5% monthly late charge on every bill and it's cut slow payers by half. Has anyone else had luck with a specific penalty that actually works?

Last Tuesday was a nightmare with a client who took 90 days to pay a $450 invoice

I finally got paid yesterday for a job I did back in January. This client kept saying 'the check is in the mail' every time I called (which was like 8 times). I sent them a final notice with a late fee attached and suddenly they magically found the money. What really got me was they had the nerve to ask for a discount on the next project. Has anyone else had a client who pays super slow but still wants special treatment?

Debate: Should you send a reminder before the invoice is even due?

I had this situation last month with a client in Portland who always pays exactly on the due date, never late but never early. I sent a friendly reminder 3 days before the invoice was due and they got weird about it, saying it felt pushy. But then I have another client who literally said 'if you don't remind me I will forget' after I let one slide. Which side do you fall on? Do you nudge people before the deadline or just wait and see?

Appreciation post: Finaly tried invoice reminders instead of waiting forever

I used to just send a bill and cross my fingers but last month I started using a simple automated reminder system for a client in Phoenix who was 45 days late on a $3k commission. The reminder email went out twice a week and they paid within 5 days, which is way better than my old approach of nagging them myself. Has anyone else seen a big difference between using reminders versus just chasing people manually?

Tried sending a bill with a hand-drawn cartoon and the client actually paid faster

So last month I had this small roofing job for $350 and the guy kept ignoring my emailed invoices. Out of frustration I drew this silly cartoon of a sad roofer holding an empty wallet and scanned it into the invoice. He emailed back laughing and paid within 6 hours. I mean it probably only works for certain clients but maybe adding a little humor helps. Has anyone else tried something weird to get a slow payer to cough up cash?

Found a trick that gets slow payers to send money within 24 hours

Had this one client in Dallas who was always 45-60 days late. Emails, calls, nothing worked. Then I tried sending a quick invoice through Square with a 2% discount if they paid within 5 days. They paid in 3 hours. Now I offer it to anyone who's been late more than once. Works about 70% of the time. Has anyone else tried early payment discounts?

Lost 3 clients after switching to net-60 payment terms

Back in March I changed my invoicing from net-15 to net-60 because three bigger clients asked for it. They said it matched their accounting cycle. Fast forward to July and I'm still waiting on payments from two of them. One guy actually laughed when I called to follow up and said 'oh we pay on 90 days now, sorry.' That's $4,200 total sitting out there. I switched back to net-15 for all new clients last week and already lost a potential project because they wanted net-60. Anyone else had a client stretch terms way past what you agreed on?

QuickBooks auto-pay setting that saved me 2 hours of follow-up every week

Found this by accident about 3 months ago when I was setting up a new account for a landscaping job in Phoenix. Under the recurring transactions menu there's a toggle for "auto send payment reminder" that I never noticed before. Set it to 3 days before due date and 1 day after. Now clients pay on time like 80% of the time. Has anyone else found hidden settings in their billing software that made a big difference?

My payment gateway just failed on a $12,000 closing

I was closing a deal on a house in Maplewood last Wednesday and my credit card reader just died mid-transaction. The buyer was literally holding the card out and I had to ask them to write a check like it was 1995. I always thought having a backup plan was overkill, but now I carry a paper invoice pad and a mobile square reader in my car at all times. Has anyone else had a payment system go kaput right when you needed it most?

Tried sending invoices with Venmo links and got paid 3x faster...