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What’s it like to be an entrepreneur? It’s not what you see above. It’s more like the email below, which I just sent to my bank, and which will give you a small taste of the glory of entrepreneurship. I have removed the name in order to give my bank the benefit of the doubt. Depending on how they respond I may put the name back in.

Hi [name], I just had an interesting experience…

Over the past few days I’ve had a number of transactions that have been rejected. First it was a payroll tax payment made through Intuit/Quickbooks. Then it was a payment I made through Square Cash. Then a payment I made through Dwolla. And today it was a direct deposit I made through Intuit/Quickbooks. I spent a half hour or so researching this, trying to figure out what happened, then called [bank name] and spent a half hour or so on the phone with 3-4 different people and as many different departments, and the finally told me these transactions had been rejected because I have “[amazing add-on service]” on my account and I hadn’t gone in to approve these transactions, or I had rejected them. 
I had no recollection of ever hearing about [amazing add-on service] before, and I told them I had no idea what it was. I told them I had made transactions successfully through all these services before, even within the past month, and I had never had this issue previously. They told me it had only been activated within the past week or so, and that triggered something so I looked up this email and sure enough, it was activated on the 24th, the very day I sent you paperwork, ostensibly to cancel [amazing add-on service].
 
So it appears that [amazing add-on service] was not active on my account before (although apparently I was paying $10/month for it), but when I sent in paperwork to cancel it, it somehow got activated. As a result of this mishap, the following have happened:
 
1. I’ve spent at least an hour sorting this out, and I’m afraid I’ve probably got another 2-3 hours left, due to the matters below. I normally bill out at $200/hr for my time.
 
2. My bank account was disconnected from Dwolla and I have to go through the process of reconnecting it. This took a few days the first time around, submitting paperwork, etc. This is how I pay one of my contractors, so it affects my relationship with her when I don’t get payment to her in a timely manner.
 
3. Two payments I tried to make to a different contractor using Square Cash were rejected, so that’s affected my relationship with that contractor as well.
 
4. The tax payment that would have been on time is now late, so I’ll be getting a penalty for that. Not sure how much yet, I’m sure the IRS will let me know in a few months.
 
5. The direct deposit I made was a paycheck to myself, and my wife had initiated financial transactions based on that being in our account today which she is having to spend time canceling/reversing, etc.
 
6. Intuit charges a $100 fee for non-sufficient funds, and for the taxes and direct deposit they have now charged me a total of $200.
 
In other words, I’m out $200-300 in cash, I’ll probably end up spending around $600-$800 of my time on this to get it all sorted out, and it’s resulted in a number of non-cash costs.
 
I’m not angry, I’m not blaming you because I have no idea who’s responsible, except that it appears to be [bank name]. I did get the [amazing add-on service] service cancelled today when I called in, but I would like to know what happened so that I can make sure it never happens again, and I would like to know what [bank name] is going to do to compensate me for the costs I’ve incurred.
 
Thanks!
I really am not angry. I’m actually somewhat amused. Situations like this are fascinating to me and would be almost entertaining if I were the only one inconvenienced by their occurrence.
Did I need to spend time on this today? No. As a business owner I have a long list of things I would have preferred to spend my time on, like getting a decent night’s sleep, seeing as how I was taking care of this from Hong Kong and it’s now after midnight here. This is a small glimpse of the reality of what it’s like to be an entrepreneur, and on days like this I sometimes dream about how nice it would be to work for someone else in a standard 9 to 5.