On August 27, Sheridan Clayborne, the 21-year-old founder of fintech startup Lendtable, found himself at the Sway House in Los Angeles, home to six of TikTok’s biggest stars, collectively known as the Sway Boys. This encounter occurred on Clayborne’s birthday.

Three members of the Sway Boys—18-year-old Josh Richards, along with 21-year-olds Bryce Hall and Griffin Johnson—expressed their interest in venturing into the world of venture capitalism, seeking ownership stakes in promising startups. Clayborne pondered whether to allow them to invest in his company.

Rather than resorting to traditional fundraising methods, Clayborne opted for a different approach. He collaborated with the Sway Boys on TikTok content and socialized with celebrities like the Chainsmokers, all within the lavish confines of the Sway House. Despite the allure of the extravagant setting, Clayborne harbored doubts about the Sway Boys, fearing they might be dismissed as mere “air-headed TikTok e-Boys.”

Nonetheless, Clayborne permitted them to acquire a small share of his company. To his surprise, their involvement proved beneficial, leading to an increase in customers for his product, which aids financially strained individuals in accessing funds to maximize their company’s 401K match. Notably, their appeal extended beyond college students to include suburban mothers.

Richards, Hall, and Johnson have since made investments in several other startups, with founders expressing satisfaction with the partnership. However, the Sway Boys’ foray into venture capitalism has not been without controversy, typical of young celebrities aged 18 to 21. Critics often view them as mere party enthusiasts with superficial interest in venture capital, lacking sophistication.

Business Insider engaged with the Sway Boys, their manager, startup founders, and critics to gain insights into this burgeoning narrative.