Kessler has worked for about 20 years as a research analyst, investment banker, venture capitalist, and hedge fund manager.

[2] Raised in Bridgewater Township, New Jersey,[3] Kessler attended Bridgewater-Raritan High School East.

From January to March 2003, Kessler wrote and successfully self-published a book, Wall Street Meat: My Narrow Escape From the Stock Market Grinder, about working with Jack Grubman, Frank Quattrone, and Mary Meeker, after hearing that traditional publishing houses would take over a year to publish it.

I’ve watched my 15-year-old son and his friends take turns editing the page for the animated film 'Land Before Time,' flipping the gender of the character Littlefoot from he to she and back.

"[6] In March 2023, Kessler suggested in The Wall Street Journal that the Silicon Valley Bank "may have been distracted by diversity demands" in the lead up to its collapse.