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Rubin held a post-election party at his home in New York in January 1973, attended by [[John Lennon]] and [[Yoko Ono]], after [[Democratic Party (United States)|Democratic]] presidential candidate [[George McGovern]] had lost to [[Republican Party (United States)|Republican]] incumbent [[President of the United States|President]] Richard Nixon at the [[1972 United States presidential election|1972 presidential election]]. Soon after, Rubin retired from politics entirely, becoming an entrepreneur and businessman. He was an early investor in [[Apple Computer]],<ref name="Stanley">Timothy Stanley (May 14, 2008), {{cite web|url=http://www.the-utopian.org/2008/05/000026.html |title=The Long Haired Conservatives: the Children of '68 Reconsidered |access-date=September 26, 2010 |url-status=bot: unknown |archive-url=https://web.archive.org/web/20080820113819/http://www.the-utopian.org/2008/05/000026.html |archive-date=August 20, 2008 }}</ref> and by the end of the 1970s had become a multimillionaire.<ref name="Stanley"/>
In the 1980s, he embarked on a debating tour with [[Abbie Hoffman]] titled "Yippie versus Yuppie". Rubin's argument in the debates was that activism was hard work and that the abuse of drugs, sex, and private property had made the [[counterculture of the 1960s|counterculture]] "a scary society in itself." He maintained that "wealth creation is the real American revolution. What we need is an infusion of capital into the depressed areas of our country." A later political cartoon portrayed Rubin as half-guerrilla and half-businessman.<ref>[http://www.ep.tc/realist/130/ The Realist]</ref>
Rubin's differences with Hoffman were on principle rather than personal. When Hoffman died by suicide in 1989, Rubin attended his funeral.<ref name="Funeral">{{cite news | url=https://www.latimes.com/archives/la-xpm-1989-04-20-mn-2279-story.html
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