Reynolds' blog got started as a class project in August 2001, when he was teaching a class on Internet law. Much of Instapundit's content consists of links to other sites, often with brief comments.
Between early 2006 and early 2010, Reynolds began to host podcasts of "The Glenn & Helen Show", along with his wife, Dr. Helen Smith.
In 2007 network theory researchers who studied blogs as a test case found that Instapundit was the #1 blog for "quickly know[ing] about important stories that propagate over the blogosphere".
In the past, Reynolds has called for the assassination of Iranian scientists and clerics, and advocated the use of nuclear weapons against North Korea "if they start anything."
In 2016, on his Twitter account, Reynolds suggested running over protesters objecting to the fatal shooting of Keith Lamont Scott in Charlotte, North Carolina. In his tweet he wrote, "run them down" next to a link to a news story about the protests. Twitter suspended Reynolds' account, but restored it shortly after and told him to delete the tweet in order to be allowed to use Twitter again. The University of Tennessee released a statement that it was investigating Reynolds as it does not condone language that encourages violence. On September 27, 2016, the law school's Dean Melanie Wilson issued a statement to announce that the University had ended its short-lived investigation with a recommendation that no disciplinary action be taken. Dean Wilson wrote that Reynolds' tweet "...was an exercise of his First Amendment rights. Nevertheless, the tweet offended many members of our community and beyond, and I understand the hurt and frustration they feel." USA Today said that Reynolds had violated the newspaper’s standards and suspended his column for one month. Reynolds issued an apology at the request of USA Today saying:
Wednesday night one of my 580,000 tweets blew up. I didn’t live up to my own standards, and I didn’t meet USA TODAY’s standards. For that I apologize, to USA TODAY readers and to my followers on social media. ... Those words can easily be taken to advocate drivers going out of their way to run down protesters. I meant no such thing, and I'm sorry it seemed I did. What I meant is that drivers who feel their lives are in danger from a violent mob should not stop their vehicles. I remember Reginald Denny, a truck driver who was beaten nearly to death by a mob during the 1992 Los Angeles riots.
As a law professor, Reynolds has written for the Columbia Law Review, the Virginia Law Review, the University of Pennsylvania Law Review, the Wisconsin Law Review, the Northwestern University Law Review, the Harvard Journal of Law and Technology, Law and Policy in International Business, Jurimetrics, and the High technology law journal, among others.
Reynolds also writes articles for various publications (generally under his full name, Glenn Harlan Reynolds): Popular Mechanics, Forbes, The New York Post, The New York Times, The Atlantic Monthly, The Washington Post, The Washington Times, The Los Angeles Times, USA Today, and The Wall Street Journal. He has written for the TCS Daily, Fox News, and MSNBC websites as well.
Reynolds is often described as conservative, but holds "liberal" views on some social issues such as abortion, the War on Drugs and gay marriage. He describes himself as a libertarian and more specifically a libertarian transhumanist. He customarily illustrates his combination of views by stating: "I’d like to live in a world in which happily married gay people have closets full of assault weapons to protect their pot."
Reynolds is a former member of the Libertarian Party.
He delivered the keynote speech at a September 2011 conference at the Harvard Law School to discuss a possible Second Constitution of the United States and concluded that the movement for a constitutional convention was a result of having "the worst political class in our country's history".
Reynolds grew up a Methodist but is now a Presbyterian. He is married to Dr. Helen Smith, a forensic psychologist.
Reynolds also once ran his own music label WonderDog Records, for which he also served as a record producer. Reynolds has also worked as an indie music artist. One of his albums reached the number one album chart spot on the website service MP3.com for several weeks.
Reynolds is of Scots-Irish ancestry.Outer Space: Problems of Law and Policy (1989), ISBN 0-8133-7622-X (with Robert P. Merges); 2nd ed. (1997), ISBN 0-8133-1802-5
The Appearance of Impropriety: How the Ethics Wars Have Undermined American Government, Business, and Society (1997), ISBN 0-684-82764-6 (with Peter W. Morgan)
An Army of Davids: How Markets and Technology Empower Ordinary People to Beat Big Media, Big Government, and Other Goliaths (2006), ISBN 1-59555-054-2
"An Army of Davids: How Markets and Technology Empower Ordinary People to Beat Big Media, Big Government, and Other Goliaths" looks at modern American society through the lens of individuals versus social institutions, and Reynolds concludes that technological change has allowed more freedom of action for people, in contrast to the "big" establishment organizations that used to function as gatekeepers. Thus, he argues that the balance of power between individuals and institutions is "flatting out", which involves numerous decentralized networks rising up.
The Higher Education Bubble (2012), ISBN 9781594036651
About the rising price of higher education, causing students to take on excessive debt, even as they face an uncertain job market. Higher education spending fueled by cheap credit resembles an economic bubble
, and higher education bubble
has become a common term to describe this phenomenon.
The K-12 Implosion, Encounter Broadsides No. 31, (2013) ISBN 9781594036880
"The K-12 Implosion" provides a description of what's wrong with America's K-12 education system, and where the solutions are likely to come from, along with advice for parents, educators, and taxpayers. He argues that America has been putting ever-growing amounts of money into the existing public education system, while getting increasingly worse results. He suggests that while parents are losing hope in public schools, new alternatives are appearing, and change is inevitable.