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After the events of September 11, Winn began a research project with colleague Ken Power to "uncover the roots of terrorism". They visited 120 countries and interviewed members of al-Qaeda, Hamas, Islamic Jihad, Fatah, Al-Aqsa Martyrs' Brigades, Force 17, the Palestinian Authority, the Knesset, IDF, and US generals, as well as Israeli secret service agents in the Mossad and Shin Bet. The two published their findings in the novel Tea With Terrorists.
Winn has made numerous appearances in the media around the United States, including 1500 radio interviews by his own count.  Some of the shows are made available on his website. Winn has been interviewed by Business Week.BW Talk: The Spy Who Came In From...
Prior to becoming an author, Winn was a businessman who founded the now defunct ValueAmerica.com.
In 2010 Winn repudiated the letters of St Paul, in his online book Questioning Paul.
Business career 
In 1977 Winn joined his father's company, Winn Co., after graduating from the University of Southern California with business degrees in marketing and finance. There he worked as a manufacturer's representative.
In 1986, he founded and built a lighting company called Dynasty which he brought public in 1990; it went bankrupt in 1993.
In 1996, he became a Dot.com entrepreneur when he founded Value America, an early sort of electronic mall that was briefly second only to Amazon.com. The company raised investments from Paul Allen and Frederick W. Smith, among others.
Valueamerica.com had a successful IPO in April 1999, starting at $23 per share, reaching up to $74.25 at its highest point. Winn's share of Value America was, on paper, worth over $1 billion after the company's IPO. By December 1999, Winn had resigned from the board after disagreeing with all but one of the rest of the board regarding restructuring. Value America filed for bankruptcy in August 2000, less than a year after its IPO. It was one of the first large dotcoms to fail.
Winn's book In the Company of Good and Evil: A True Story of Seduction and Betrayal is about his experience with Value America. Winn stated, "I, along with a small but great team of people, built a large and innovative retail company. But the founders turned the firm over to 'professionals' after taking it public in harmony with prevailing wisdom. They promptly ran it into the ground while lining their pockets. To cover their crime, they blamed it on me."
Published works 
Winn's books are self-published. His first book is titled Tea With Terrorists, co-written with Ken Power. This is a novel that purports to document an investigation of the motives of terrorists. Winn has also authored Prophet of Doom, which is a survey of Muhammad's life as derived from the Qur'an and Hadith. Other works of his are In The Company of Good & Evil (also written with Ken Power), Future History and Yada Yahweh.
Analysis of Islam 
According to Prophet of Doom and Tea With Terrorists, Islamic terrorists are inspired by the actions of Muhammad and the verses in the Qu'ran. Winn quotes extensively from the Qur'an and Hadith throughout his books.
He publishes a rendition of the verses of the Qur'an in Chronological order which was compiled by analyzing the material of Hadith. Winn worked with his team of researchers to compile a time line of Islamic terrorism.
|“||The critics of this work will claim that Prophet of Doom is offensive, racist, hatemongering, intolerant, and unnecessarily violent. I agree - but I didn't write those parts. They came directly from Islam’s scriptures. If you don't like what Muhammad and Allah said, don't blame me. I'm just the messenger. . .
One last thought before you head down this perilous path. I pray that when you have reached the journey’s end, you will share my heart for the plight of Muslims. I want nothing more than to free them from Islam, and in so doing, free us from the terror their doctrine inspires.
—Winn, in a letter to the readers on the Prophet of Doom website
Muslim response 
Winn claims to have documented attempts of "Muslims filing complaints with the domain registrar to release private information" regarding his location and their repeated attempts to hijack the site . Daniel Pipes claims that this anti democratic and violent response to Winn's books raises important concerns regarding freedom of speech and the press.
- Yada Yahweh: A Conversation with God, Cricketsong Books (? 2007)
- Prophet Of Doom: Islam's Terrorist Dogma In Muhammad's Own Words, Faithworks (April 2004)
- Tea With Terrorists: Who They Are, Why They Kill, What Will Stop Them Faithworks (October 2002)
- In the Company of Good and Evil: A True Story of Seduction and Betrayal Cricketsong Books (January 2002)
- Questioning Paul
- Chapter 0 Yada Yahweh
- Tea With Terrorists: Interview with the Authors
- Crazy Craig's C-Commerce
- Questioning Paul
- "Craig Winn, Netrepreneur," Businessweek 2000 article
- Craig Winn, Netrepreneur
- Value America Declares Bankruptcy: CHARLOTTESVILLE, VA, Aug. 11, 2000
- dot.bomb: My Days and Nights at an Internet Goliath. J. David Kuo, 2001
- "A Short Time Ago," Fortune, July 25, 2005
- Prophet of Doom: Questions and Answers
- Craig Winn,Ken Power. "In the Company of Good and Evil". Retrieved 2006-12-31.
- Ken Power. "Future History". Retrieved 2006-12-31.
- Craig Winn. "Yada Yahweh". Retrieved 2006-12-31.
- Description of Tea with Terrorists
- American Muslim Perspective: The News Sentinel – May 4, 2006. Anti-Islamic ravings are shameful By Sultan Muhammad
- Daniel Pipes: Censor Anti-Islamic Books? November 22, 2004
Winn's On-line Books
Audio and Video of Winn
- Radio Interviews
- Audio debate between Craig Winn and Muslim Jalal Abualrub
- Craig Winn Radio Interview (The Edge, Daniel Ott)