rant · moment 18 of 19
Hitting Bottom Selling Mortgages on Long Island
from #182 - Beware the Villas | The Tim Dillon Show · #182
2 min
Tim describes bottoming out at 25 selling subprime mortgages in a dying post-crash office on Long Island, drinking heavily and living rent-free after defaulting on a house he bought at 22.
- Tim had to bottom out first, which he connects to Gary Vee's philosophy about failing enough.
- Tim hit a wall at 25: drinking every night while working a job that no longer exists.
- The job was selling mortgages in 2009, right after the financial crisis—insane timing.
- The office was decrepit, windowless, on Long Island with fruit flies and ceiling leaks.
- All the mortgage guys had vanished; their Porsches and Maseratis were repossessed or gone.