For me, it’s $8,000. No biggie.
Wrong forum. This is an IMHO thread.
In any case, $1800. I had just received payment for a new PC I was about to sell to a customer. I was on my way to the distributor to pick it up.
If it had been a check, I would have just cashed it at the customer’s bank and turned it into a cashier’s check, but it was actually a safer trip to the distributor than the bank, so I just rolled on out.
Only £500, but through a truly scary part of Manchester. My landlord had made a fuckup with postdated cheques, but realised straight away and was good enough to sort out cash for me to be able to stop them bouncing.
Probably about $10,000 but I run the deposits for a small business to the bank everyday so I’m no stranger to having semi-large amounts of cash in the car with me by myself.
$6-10 thousand in cash and checks every Monday morning for several years. Not a big deal after the first couple weeks, really. I’d park my car where I had a clear view of it before leaving the station and payed attention to what was going on around me, but that was about the only special precaution I took. That was a good 12 years ago now.
$12,000. A friend’s father won it on a basketball game bet. He was carrying it in a gym bag and showing it to people. He was in his seventies and kinda frail. I suggested he put it in the bank, but it was a weekend. I took it home with me, then met him the following week at his bank.
Only $300 for me, and I was still pretty nervous that I’d lose it. Or more, really, the thought that if I lose it, its gone forever. I am a child of debit 
About $750, I think.
I think that most that I ever had at one time was about $17,000 in cash and checks. About $12,000 of it was cash.
Approximately $18k.
It was for a previous job, where I was manager of one store and covering for a manager on vacation at another - I had to pick up the daily cash for both stores for Friday & Saturday one week. One store got $4k every day, the other got $5k.
About $15,000. It was two weeks of per diem for a large crew I had working for me. I gave out half on the first day of the rotation and had to carry the remaining $7500 on me until the second half of the rotation started.
I kept it in my lunchbox.
I’d be packing.
$16,000 cash. Mainly $20s and $50s. It was kinda heavy really, in a big fat bank bag. No lock.
£2,500 in travellers cheques on a 3 month stint in Bahrain.
Wasn’t going to exchange them at an exhorbitant rate and I didn’t like the idea of leaving them in the hotel ‘safe’.
Used my cash card the entire trip and claimed back the exchange and commission for using it in the local ATMs
Kept them secure in my Man-Bag by my side at all times.
Oddly enough I only ever used said bag in the Middle East.
I only ever went to the toilet sans bag when a collegue was still sitting in the bar.
Otherwise it went with.
Using it back in the UK would probably have generated a good head kicking on general principle and the theft of meh cheques.
Cashiering for the service department of a Ford dealer, 25k. One busy day’s cash and check deposits. I had written up the deposit, too, yuck. Cash paid for car service is usually filthy.
I think it was about £3,000 - the deposit for a car I was buying. Maybe I dreamed this part, but I’m sure I remember switching from boxer shorts to Y fronts for the day, so I could stash my wallet in my undies without it falling out.
1800 in cash. Poker game.
$20,000, for work, once, I was a little bit scared.
Once Mr. AdoptaMom built a turnkey house for our neighbor across the street. We lived in the boondocks back then and our neighbor would walk over every Friday morning with that weeks draw in a brown paper sack. Usually around $5K, but a couple of times it was closer to $15K. That’s the year we bought a fire proof safe.
Whatever one term’s tuition plus room and board was when I was in college. Probably two grand, two and half, maybe.