About
Built by operators, for operators.
BookThemTwice is a product of West Egg Enterprises, Inc., the company behind Cashflow Diary — short-term rental education and consulting founded by J. Massey. Cashflow Diary has trained thousands of STR operators on running their properties as a real business, not a side hustle.
BookThemTwice is the automation Cashflow Diary operators kept asking for: a simple way to keep their own record of every guest and bring them back for a direct rebooking, instead of losing that relationship to whichever platform the original reservation came through.
What we believe
The guest relationship belongs to the operator who delivered the stay — not to the platform that happened to process the booking.
What we build
Systems that run automatically after checkout, so rebooking doesn't depend on an operator remembering to follow up.