The real reason group trips fall apart isn't the itinerary — it's the math
Ran the numbers on my last 4 group trips. Every single one had the same failure point: not the flights, not the Airbnb drama — it was money math.
Here's the pattern I noticed:
1. One person always fronts the big stuff. Someone books the Airbnb on their card because it's "easier," and now they're a debt collector for the next 3 weeks.
2. Splitting "evenly" usually isn't fair. The couple who left early still owes for the full week. The person who skipped the fancy dinner still gets billed a 6th.
3. Nobody wants to be the one who brings up money. So debts sit for weeks. Friendships take the hit, not the wallet.
The fix isn't a better spreadsheet — it's removing the social friction of asking. If the app tracks it and shows a single settle-up number, nobody has to be the "bad guy" chasing Venmo requests.
That's the whole thesis behind what I'm building. If your friend group has ever had a trip where someone quietly ate a $200 loss rather than ask for it back — you know exactly what I mean.
