I've read two books in this genre lately (subject to be changed later as I remember more!) - but both just kind of 'touched' on the area.
The more recent
Brainiac: Adventures in the Curious, Competitive, Compulsive World of Trivia Buffs by Ken Jennings It's not 'sold' as a memoir, but he does manage to get a bit of his long Jeopardy! run into it. Suprisingly well written, I thought.
The other was
Managing Ignatius: The Lunacy of Lucky Dogs and Life in New Orleans by Jerry E. Strahan The author was (is?) the manager of Lucky Dogs and talks about all of the characters who have sold from the carts made famous by
A Confederacy of Dunces by John Kennedy Toole.
I'm also in the middle of (but not working on very hard)
Memories of the Old Plantation Home by Laura Locoul Gore. It's not particularly 'modern' in it's writing, and was a memoir written for her children, which is why I'm not working on it very hard. Laura Plantation gives a fantastic tour, though, based on the book.