connor, firstly, places a lot of value on "the old ways," which he gets from romanticizing his father's past. "i'll never understand dad until i shit in a bucket." he mistakenly thinks that logan will appreciate a remnant of rural, traditional childhood - sourdough starter. he's obsessed with history and he runs a ranch so he can larp being a blue-collar bootstraps man full time. he wants to go to a "real bar, where men have dirt and blood on their hands, like in the movies." he wants to badly to not be the out of touch, spoiled rich boy who never had any real experience, who has nothing to show for his life that isn't his dad's money. and it's just not possible.

similarly, kendall stakes his ideal of "realness" in victimhood. he's more disillusioned with logan's backstory than connor is (at times) but ultimately, he wants the same thing. to be able to rewrite his life and believe that he started from nothing. he identifies with the underdog and with the marginalized to a sometimes delusional and fetishistic degree - just watch his very first scene in the show, lmao. he's aware of the evil that his dad has done and, as his heir, he wants to believe that he is a product, rather than a producer, of the fucked of world. because those affected are the real people.

shiv, meanwhile, doesn't look to logan's beginnings but his present when she thinks of what is real. unlike her brothers, she really did make her own pile. she existed, for some time, as separate from the company, with an independent career that, like logan's, involved influencing politics. the only trouble is that there are still many part of a Real Person that she just doesn't have, like the ability to have healthy relationships. even when she tries. her efforts themselves aren't a failure as much as they just ring hollow.

and roman... well, roman just already is the worst parts of logan. the ones logan himself doesn't like and can't stand to see reflected in his own son. he's the youngest [brother], the weak dog, the sexually dysfunct. he got sent off to military school--he experienced something that connor would have enviously considered real life, because his dad had done it too, and it did not help him. everything about him is an overt product of abuse, and it does not make him feel any more real. it didn't make him stronger. unlike his siblings he has never specifically wanted to be unlike his father, but also does not seem to emulate anything about him in particular, either. being physically around his father was all he wanted, and he was aware of it.