OK, so I do have myself to blame partly for this, but I'm seeking advice on how to fix it.

I run a small complementary health practice with 15 - 20 practitioners in it. They all get invoiced every fortnight and for the most part pay me on time. Except one guy.

I used to work in the building the same days as him. We were very friendly with each other - had a laugh and a joke. He has a defunct email address that he never checks so I used to give him payment reminders in person, and would usually pay while I was there with him. He was often late but he always paid, and because I was there it wasn't a huge hassle to tell him in person when bills were due.

I asked him to set up a direct credit to which (a few weeks later) he said that he tried but there was an issue at the bank that he couldn't seem to fix so couldn't set it up (I called bullshit, but whatever - he never set a regular payment up). When I brought it up to him again saying that I didn't want to have to remind him constantly, he said that he gets paid from other jobs sporadically so a direct regular payments wouldn't work for him. I asked him to simply pay on time, and not outsource his reminders to me. Nothing changed.

Since the start of this year, I'm no longer in the building with him on the same days. So I set up Stripe in Xero so that invoices could be sent directly by SMS to his mobile. No excuses right? Wrong. He seems to just completely ignore them, and continues not to pay me on time until I remind him via written text.

So this is what happens each and every invoice: SMS goes out when it's issued: no payment. SMS goes out a week later when it's due: no payment. SMS goes out when it's 7 days overdue (and another fortnightly invoice has been issued): no payment. I send a text saying 'this invoice is 7 days overdue, please pay now to avoid late fees': sometimes payment, and sometimes an incurred late fee and another text the following week before eventual payment (and now behind on the second invoice sent). Rinse and repeat until you want to vomit...

It's driving me insane to have to do this over and over, but this person is not an insignificant part of my very marginal business, and I really cannot afford to lose him.

I've added SMS reminders, pestered him with SMS reminders every day when a bill is overdue (which is a pain for me because I can't set up auto SMS reminders in Xero), added late fees (for which he has now had to pay quite a few).

I'm at my wits end, short of threatening to kick him out (which I don't want to do), I'm not sure how to make this stop. I think my next move would be to escalate late fees for him only (incur them quicker, and make them higher) - but the law seems a bit vague on what is 'reasonable' here.

Thanks for reading if you got this far! Any help appreciated.

And just FYI - I have tightened up my boundaries immensely since starting the business and everyone has responded to that really well. I don't have any other issues with payments except this one guy.

OK, so I do have myself to blame partly for this, but I'm seeking advice on how to fix it.

I run a small complementary health practice with 15 - 20 practitioners in it. They all get invoiced every fortnight and for the most part pay me on time. Except one guy.

I used to work in the building the same days as him. We were very friendly with each other - had a laugh and a joke. He has a defunct email address that he never checks so I used to give him payment reminders in person, and would usually pay while I was there with him. He was often late but he always paid, and because I was there it wasn't a huge hassle to tell him in person when bills were due.

I asked him to set up a direct credit to which (a few weeks later) he said that he tried but there was an issue at the bank that he couldn't seem to fix so couldn't set it up (I called bullshit, but whatever - he never set a regular payment up). When I brought it up to him again saying that I didn't want to have to remind him constantly, he said that he gets paid from other jobs sporadically so a direct regular payments wouldn't work for him. I asked him to simply pay on time, and not outsource his reminders to me. Nothing changed.

Since the start of this year, I'm no longer in the building with him on the same days. So I set up Stripe in Xero so that invoices could be sent directly by SMS to his mobile. No excuses right? Wrong. He seems to just completely ignore them, and continues not to pay me on time until I remind him via written text.

So this is what happens each and every invoice: SMS goes out when it's issued: no payment. SMS goes out a week later when it's due: no payment. SMS goes out when it's 7 days overdue (and another fortnightly invoice has been issued): no payment. I send a text saying 'this invoice is 7 days overdue, please pay now to avoid late fees': sometimes payment, and sometimes an incurred late fee and another text the following week before eventual payment (and now behind on the second invoice sent). Rinse and repeat until you want to vomit...

It's driving me insane to have to do this over and over, but this person is not an insignificant part of my very marginal business, and I really cannot afford to lose him.

I've added SMS reminders, pestered him with SMS reminders every day when a bill is overdue (which is a pain for me because I can't set up auto SMS reminders in Xero), added late fees (for which he has now had to pay quite a few).

I'm at my wits end, short of threatening to kick him out (which I don't want to do), I'm not sure how to make this stop. I think my next move would be to escalate late fees for him only (incur them quicker, and make them higher) - but the law seems a bit vague on what is 'reasonable' here.

Thanks for reading if you got this far! Any help appreciated.

And just FYI - I have tightened up my boundaries immensely since starting the business and everyone has responded to that really well. I don't have any other issues with payments except this one guy.

... Do supermarkets have THREE different cheese sections all placed in different parts of the building?!

Is the fancy cheese allergic to the block cheddar?

I could kind've understand fancy in one place, and the boring cheese in another (still stupid, but I sorta get it). But THREE different cheese sections?

WHY oh lord WHY.