Hey friends đź‘‹
It’s a story old as time. You walk on stage to pitch your startup, and the speakers start blasting “Loser” by Beck. (Literally.) Then investors tell you your market is too small — for a company whose customer base is, quite literally, everyone.
This week we finally brought Phillip Mason into the studio. Yes, that Schmillip. He’s the founder and CEO of LilyPay (ShmillyPay?), a payments and financing platform for the death care industry — about 200 families served and 225 funeral home partners in a year and a half.
So naturally we spent the whole hour on his losses.
It’s an in-person founder psychology episode: how to hear “no” without rewriting your pitch after every call, when a dozen investor conversations start to look like a story, and why the hardest decisions are the ones the data won’t make for you.
Plus, the question nobody has a clean answer to—how do you stay delusional enough to start and grounded enough to survive it?
(Phillip’s answer involves… Chumbawamba, apparently?)
In Frivolous Thoughts, JDM hands out gel cubes, Cameron rides into Deadwood, and Phillip defends the South’s claim to Kentucky.
As always, thanks for listening.
—Cameron and JDM
