[citation needed] While at University of Chicago, Simon attended Universidad Catolica in Santiago, Chile, for one trimester.

USLaw was financed with $15 million led by UBS Capital, and the website USLaw.com quickly became the leader for consumers and small businesses researching their legal issues.

In late 2001, in the midst of the bursting of the tech bubble, USLaw was sold to Grand Central Holdings in New York City.

[12] As part of the transaction, Bronfman Rothschild moved its headquarters to Rockville, Maryland, and Simon was hired as chief executive officer.

In 2015, Simon appeared on the cover of Charles Schwab’s Portraits of Independence, a collection of success stories in investment management.

[15] In July 2016, Bronfman Rothschild was recognized by Financial Advisor Magazine as the second-fastest growing investment advisory in the country.

[16] In August 2017, Simon hired Michael LaMena as president and COO, creating a new position in the company's leadership team.

[20][21][22][citation needed] On February 6, 2018, Simon declared his candidacy to represent the state of Maryland in the U.S. Senate as an independent.

[23][24] Three weeks after the campaign launch, Unite America, a grassroots political organization that advocates for the statewide election of independent candidates, announced their formal endorsement of Simon,[25] Governor Bill Walker (I-AK), Greg Orman, Terry Hayes, and Craig O'Dear.

[27][28] On July 19, 2018, Simon submitted over 12,000 signatures to complete Maryland's state requirement for nomination by petition so he could be included on the ballot.

[34] On Sunday, October 7, Simon participated in a debate against Senator Ben Cardin and Republican candidate Tony Campbell.

Contract to Unite America makes a compelling case for reforms that were dear to John: not only campaign finance reform and bipartisan administrations, but also enriched civics education and expanded national service.” CNN and Sirius XM politics host Michael Smerconish wrote in his review, "Whenever I speak about the dysfunction in our politics, which is often, I am asked for solutions.

"[39] The book also received praise from Frank Luntz, Michael E. Porter, Jason Altmire, Glenn Nye, Nancy Jacobson, and Evan McMullin.

Simon supports same-sex marriage, maintaining the legality of abortion, and universal background checks for gun purchases.

[46] In February 2019, in an op-ed co-authored with Greg Orman in The Wall Street Journal, Simon defended Howard Schultz's right to run as an independent in the 2020 presidential race.

[47] In February 2020, in The Bulwark, Simon called for Mitt Romney to launch an independent bid for president along with a Democratic vice presidential candidate.

[48] In March 2019, Unite America announced that Simon had joined their board of directors to help scale the democracy reform movement.