The Useless Heiress Is Actually A Bigshot - Chapter 191 - : Joining the Company

Xu Yiyang, who was only late in his life when he was middle-aged, returned to 1999 in a dream.

At the turn of the millennium and the turn of the century, he realized a truth:
Not only to be famous early, to start a business and make money, but also early!
………………
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- Description from Uukanshu

Damien Rothschild, an immortal who has lived life to the fullest for the past four hundred years, is visited by a mysterious woman who reveals the many depravities of his mischievous brother in another world.To save his brother, Damien must first travel to this other realm. However, the path becomes treacherous as he is tricked and loses everything he once had. Now, he must navigate this new world in search of his brother.This story follows a man who was granted the gift of immortality, allowing him to rise to the very pinnacle of the human race—until he was stripped of everything he held dear in a desperate attempt to save the only thing he ever truly loved.

Childhood sweethearts.
The most popular person in school is my childhood sweetheart.

- Description from Novelupdates

Luo Qiu became the boss of a ‘club’ by chance.

It was a weird club that sold strange items and with a servant girl that had 300 years of working experience. Countless people with dreams, hopes and ambitions came to the club to exchange anything precious they own for what they want. They would offer their lifespan, items, and even their soul. Every successful trade would increase Luo Qiu’s lifespan by a little.

“Tribute successful, your lifespan has increased by 99 years.”

As thus, Luo Qiu began his endless life as the club’s boss.