[3] Simchowitz believes that conversations on social media hold a degree of influence over the artworld comparable to other canonical forums for artistic discussion and legitimization, including art reviews written by critics for key publications.

A number of them, including, but not limited to Sterling Ruby, Oscar Murillo, Paa Joe, Lucien Smith, Petra Cortright, Zachary Armstrong, Kour Pour, Jon Rafman, and Marc Horowitz have all been advised by Stefan Simchowitz.

[citation needed] Simchowitz gained attention when a 2014 Bloomberg article about speculation in the contemporary art market reported on his purchase on-the-cheap of 34 paintings by the Colombian artist Oscar Murillo[7] near the beginning of his career in the early 2000s, paying as low as US$1,500 for some canvases.

[11][16] Simchowitz is a popular target for critics who claim that his particular penchant for promoting young, undiscovered artists through bulk acquisitions of their work to later flip for profit, destabilizes established workings of the art world[17] — age-old, value-determining systems composed of a long-standing and tight network of critics, publications, universities, museums and galleries that collectively define the nature of 'good' art.

He subverts the establishment by selling his curated acquisitions directly to a diverse network of wealthy clients who trust his taste implicitly.

Art Review's entry on Simchowitz states that "if the artworld needed its Howard Stern, its Ari Gold, its Donald Trump, it got 'Simcho': a brash, publicity-hungry yet highly intelligent collector-adviser-dealer...".

[5] Andrew M. Goldstein of Artspace argued that "his approach to collecting and nurturing artists systematically abrogates—annihilates—a whole series of beliefs that lie at the foundation of the art world's critical, institutional, and commercial structures.

"[19] Simchowitz's trademark transparent and honest attitude leads some to believe that he is simply lifting the veil off of previously hidden activities already prevalent in the artworld.

Marc Spiegler, director of Art Basel, attributes Simchowitz's success to the fact that he does exactly what the galleries do, except at a significantly faster clip, and that "he has taken a market that was built on opacity and been much more transparent.

"[20] Spiegler characterizes Simchowitz's practice as similar in function to galleries of past, in that he holds exclusive access to his collector base.