Eric Schmidt reveals that this issue of Playboy is the reason Larry Page and Sergey Brin never do interviews

Alphabet executive chairman Eric Schmidt gave a talk at a Stanford computer science class recently and told a story that reveals why Google founders Larry Page and Sergey Brin haven't talked to the press in more than 11 years.

They had a bad experience after giving an interview to Playboy, apparently, which risked derailing their IPO, according to a transcript of the class.

Schmidt was asked:

Q: How did the relationship with Larry and Sergey develop?

I knew that it was Larry and Sergey's company, and I acted that way. For example, I never did any press. Right before the IPO, Larry and Sergey did an interview with Playboy - no pictures. It turns out that the interview was at the wrong time in the quiet period, and it put the IPO in jeopardy. But the even more correct answer is no problem, we'll fix this. From that moment on, they've never given an interview. That was 12 years ago.

When they wanted to do interviews, they did them. Once they didn't want to do it anymore, I did them.
It's their company.

You can read the September 2004 Playboy interview here (don't worry - it's safe for work). The interview was controversial at the time because it revealed that the true state of Google had changed since the information it filed in its S-1 IPO filing, according to CNET:

For instance, Google said that it now has more than 2,000 employees, not the 1,000 cited in the article, and that its Gmail service no longer has the significant advantage in storage space that it had over rival free e-mail services earlier this year.