Hey all,

I used to run a personal branding agency and at one point we were handling 36 clients. Then I moved into the software world and started working with IT audiences. I am honestly enjoying that switch a lot more.

Two days ago I met three agency founders at Starbucks. Just a casual chat. One of them said something that hit me hard.

He said he feels bad asking clients for payment. Even after the work is done he feels awkward to send a reminder. He worries the client might get hurt or churn.

Immediately the other two said they also feel the same.

That took me back to my early agency days. I used to feel the exact same way. Instead of saying
"Hey the invoice is pending"
I used to send a simple
"Hi"
just to stay in the client's radar without sounding pushy.

Later we hired someone whose only work was payment reminders.

After that Starbucks chat I realised this might not be a small thing. A lot of agency owners seem to have this emotional block around payments even when they are 100 percent justified in asking.

So I started building a small automation tool for my own curiosity. It sends invoices and payment reminders automatically through email and WhatsApp so the owner does not have to do the awkward part manually.

I have not priced it or launched it. I just want to understand if this is actually a universal pain or if it is something only a few founders deal with.

My question for the community:

Do you feel the same discomfort sending payment reminders
If yes, how did you handle it
Did automation solve it for you or did you hire someone

I am not here to sell anything and there are no links. Just talking to other agency founders because this topic is not discussed enough.