Starting to dive deep into Stein’s oeuvre, I wanted to understand more about her relationship with Picasso, like how much they influenced each other, did Stein start experimenting with language before or during their friendship, did they goad each other on, how valuable were Stein’s salons to his creative process, etc. Some bits are revealed in the book, that Pablo was a literary man and chose writers for friends instead of painters:

His friends in Paris were writers rather than painters, why have painters for friends when he could paint as he could paint.
It was obvious that he did not need to have painters in his daily life and this was true all his life.
He needed ideas, anybody does, but not ideas for painting, no, he had to know those who were interested in ideas, but as to knowing how to paint he was born knowing all of that.

She met Picasso in 1905 after she purchased one of his paintings (The Girl with a Basket of Flowers), and he asked her to pose for a portrait. She posed for him 80 times during the winter but left for Spain before painting her head, which he did from memory when he returned. He was again in Spain in 1909, and returned to Paris with the beginnings of cubism in some landscapes he’d done.

At this time (1908-1909) he liked to say and later too he used to repeat it, there are so few people who understand and later when every one admires you there are still the same few who understand, just as few as before.

At the beginning of the war (WWI), they spotted a camouflaged truck going by and Picasso was amazed, saying “yes, it is we who made that– that is cubism.” It was by way of Matisse that Picasso got into African sculpture, aside from which “no one had ever tried to express things seen not as one knows them but as they are when one sees them without remembering having looked at them.” The cubism of Picasso was an “effort to make a picture of these visible things and the result was disconcerting for him and for the others, but what else could he do, a creator can only do one thing, he can only continue, that is all he can do.”
When “the academy” compares Picasso to Raphael, Picasso complains, “They say I can draw better than Raphael and probably they are right, perhaps I do draw better but if I can draw as well as Raphael I have at least the right to choose my way and they should recognize it, that right, but no, they say no.”
As he starts to use more and more pasted paper in his pictures, Picasso said “paper lasts quite as well as paint and after all if it all ages together, why not, and he said further, after all, later, no one will see the picture, they will see the legend of the picture, the legend that the picture has created, then it makes no difference if the picture lasts or does not last. Later they will restore it, a picture lives by its legend, not by anything else.”
Stein details his progression from Toulouse-Lautrec period through Blue period, Rose period, Cubism, Surrealism and beyond. Picasso becomes famous, “So success had begun, not a great success, but enough success.” Hilarious story that at this point Picasso’s house is robbed and burglars took all his linen:

It made me think of the days when all of them were unknown and when Picasso said that it would be marvellous if a real thief came and stole his pictures or his drawings. Friends, to be sure, took some of them, stole them if you like from time to time, pilfered if you like, but a real professional burglar, a burglar by profession, when Picasso was not completely unknown, came and preferred to take the linen.

You can hear echoes of herself in this statement about genius:

Picasso only sees something else, another reality. Complications are always easy but another vision than that of all the world is very rare. That is why geniuses are rare, to complicate things in a new way that is easy, but to see the things in a new way that is really difficult, everything prevents one, habits, schools, daily life, reason, necessities of daily life, indolence, everything prevents one, in fact there are very few geniuses in the world.