Q: How’d COVID impact your business?
  A: Terrible. We haven’t lost any employees, but we’ve had staff who’ve lost family members to COVID.

> you absolutely have to be involved in all levels of your business if you want to be successful

But it does sound like your dad is a very effective delegator and has given a lot of autonomy to people in the business - a skill you definitely need to be highly sucessfull in business.

So, maybe... stay involved at all levels, then find people who are good at a role (that you trust) and give them autonomy... and the you don't have to stay in the weeds for all roles any more?

To the parent comment's point, maybe the receipt checking part could have gone that route, but there was never any one who was right for a role like that in the business?

It would be interesting to learn what his red flags are (for errors and fraud), what his markers for attention are (good customers and staff).

I wonder if some of this could be scripted or otherwise encoded. At a minimum it might help him out.

I am a highly anxious person, and it can be debilitating.

But when you're talking about taking payments and arranging the collection of tax, I reckon it's wise to treat your anxiety like a colleague. Give it the best chair; make sure it has lunch, and not too much coffee. And listen.

If your dad loves the work, okay cool. But your effective implication is you cannot have anyone else do this, which is obviously absurd because there are companies much much larger than either of ours that pull it off.

The key point is not "the owner has to do it", it's someone has to be held responsible for this.

For smaller businesses, it's likely the owner. For someone like your dad's, it's usually someone else. Even a solid bookkeeping system would have picked up what OP missed.

> you develop a sixth sense for problems

100% agreed, but for the owner/operator it's usually all things, but for the person who is responsible, it's usually a lot more of the minutiae.

It's literally impossible to be the master of all things.

Bookkeeping is different, though. He's actually been defrauded by a bookkeeper in the early 1980s. I don't know the details but she was siphoning money from the business in some scheme, probably a 1981 version of OP's Stripe API issue. If you simply trust a person like this and don't verify regularly, the mistakes and frauds happen. Receipts is where the rubber meets the road for a retail biz and I just don't see a substitute for an owner who cares and checks.

I think that's it really - you need to have checks and balances on all things (including yourself imo as the boss).

Personally I would not want to be double-checking receipts every day (and with 100 employees, the volume is likely significant), but if he enjoys it, that's all that matters eh!