Bolelli was born in Milan, Italy, in a family of writers. His father, Franco Bolelli, is one of the most influential modern Italian philosophers. His mother, Gloria Mattioni, is the author of four books and a freelance journalist. After high school, Bolelli moved to Los Angeles, where he began attending Santa Monica College. He later graduated from UCLA with a B.A. in Anthropology, and continued his graduate work at UCLA (in American Indian Studies), CSULB (History) and Cardiff University (History). He currently lives in the Los Angeles area.
When he was 20 years old, Bolelli co-authored his first book Mitologie Felici, which was published in Italy. He later co-authored two more books in Italy Starship, and Frontiere. His first solo book, La Tenera Arte del Guerriero, was published when Bolelli was 22 years old. This work, which is a philosophical exploration of the martial arts, became popular in Italy even outside the confines of martial arts circles and it has been used as a textbook in several universities in the United States, Canada and Italy. Bolelli later translated it into English and added three additional chapters; the end result was published in the United States in 2003 under the title On the Warrior's Path. Two new chapters were later added for a second edition published in 2008. A Russian edition of On the Warrior's Path was published in 2011, and an updated Italian edition was released in 2013.
He next wrote a book on comparative religions, which was published in Italy in 2011 under the title iGod: Istruzioni per l'Uso di una Religione Fai da Te, and in the United States in 2013 as Create Your Own Religion: a how-to book without instructions.
Bolelli's third book, 50 Things You're Not Supposed To Know: Religion, was published in the United States in December 2011. It was well received, scoring 4.1 stars (out of a possible 5) from Goodreads.
Bolelli's fourth book, "Not Afraid: On Fear, Heartbreak, Raising a Baby Girl, and Cage Fighting" was published in 2015. It's an autobiographical tale on the theme of facing fear which discusses Bolelli's experiences in martial arts, the death of his wife, and his raising his daughter as a single parent.
He says that the most influential thinkers to have affected his world view include Tom Robbins, Friedrich Nietzsche, Ikkyu Sojun, Thomas Paine, Henry David Thoreau, Lao Tzu, and Heraclitus.
Bolelli regularly teaches at several colleges and universities in Southern California. Unlike most scholars who tend to specialize in one particular field of knowledge, Bolelli adopts a "renaissance" man-approach to teaching that has led him to lecture for diverse departments including History, Social Sciences, American Indian Studies, Asian American Studies, and World Arts and Cultures. The range of subjects he teaches include American Indian history and philosophy, history of the United States, world religions, history of ancient Rome, history and philosophy of martial arts, the ethnic experience in the United States, world history, and several courses on the relationship between cinema and history. Student feedback shows that Bolelli is very popular; students appreciate his lecturing style that combines discussions of complex, deep subjects with humor and "street lingo". For this reason, he has been described as "half stand up comedian and half Zen master."
Bolelli has trained in several styles of martial arts including kung fu san soo, taijiquan, baguazhang, xingyiquan, shuai jiao, submission wrestling, Brazilian jiujitsu, boxing, and judo. He holds a fifth degree black belt in kung fu san soo – a style that he has taught for several years at UCLA's John Wooden Center. Bolelli also coached and fought professionally in mixed martial arts (MMA). His MMA role models are Uberreem, Genki Sudo, Evan Tanner, Rumina Sato and Kazushi Sakuraba.
Bolelli was featured in I Am Bruce Lee which broke Spike TV's rating record for documentaries. He has appeared as a guest on popular podcasts such as Adam Carolla's, Joe Rogan's, Duncan Trussell's and Skepticality, the official podcast of the Skeptic Society. On Jan. 24, 2012 an interview with Daniele Bolelli about his new book 50 Things You’re Not Supposed to Know: Religion was published in Wired magazine.
In October 2012, Bolelli began his own podcast named The Drunken Taoist Podcast. A little over a month after its debut, The Drunken Taoist Podcast was ranked number 1 in the world in the Philosophy section of iTunes.. Bolelli explained the naming of the podcast in his interview with Taoism Network: Taoism forms the philosophical roots of his worldview. The 'drunken' part links to a type of consciousness that emphasises on instinct, a celebratory and egalitarian attitude, and his hero Ikkyu Sojun .
In 2014, Bolelli released a sixteen-part lecture series about Taoist philosophy.
In 2015, Bolelli joined his friend, pro-skateboarder and musician Mike Vallely as co-host of Vallely's podcast The Mike V Show.
In 2015, Bolelli also released the first episodes of a new historical podcast called History on Fire, which was included in iTunes' list for 'Best of 2015' podcasts in the "Recent Debut" category.