10 Things You Didn’t Know about Chegg CEO Dan Rosensweig

Dan Rosensweig is both the president and the CEO of Chegg, which started out in online textbook rentals but has since branched out to a considerable extent. Rosensweig brings plenty of expertise and experience to his position, seeing as how he has spent a lot of time as an executive with a lot of roles.

Here are 10 things that you may or may not have known about Dan Rosensweig:

His First Job Was Selling Word Processors

After he graduated from college, Rosensweig’s first job was selling word processors as a door-to-door saleman operating in Manhattan. Given that this was in the 1980s, said word processors were not the programs called by that name but rather the machines called by that name, which served much the same functions.

He Got Fired in 3 Hours

Unfortunately, Rosensweig got fired within 3 hours of starting out as a door-to-door salesman of word processors. This was not his fault. Instead, what happened was that his employer at the time, Pitney Bowes Dictaphone had to fire close to 1,000 people, which happened to include his entire division.

Continued On As a Salesman

Following Pitney Bowes Dictaphone, Rosensweig went on to work for the Ziff Davis Publishing Company. Once more, he became a salesman. However, this time he was a cold caller who specialized in selling magazines to computer stores rather than someone who went around knocking on doors.

Rose Through the Ranks

At the Ziff Davis Publishing Company, Rosensweig started rising through the ranks. He started out cold-calling computer stores, but in time, he switched over to classified ads and then front-of-book ads. Eventually, Rosensweig went on to become the publisher of PC Magazine, which went on to become the number one magazine of its kind as measured by not just reach but also revenue under his leadership.

Became an Executive

By 1999, Rosensweig was both the President and the CEO of ZiffNet, which was an online service offered by the Ziff Davis Publishing Company. Some people might be familiar with ZiffNet under its current name of ZDNet, which was its name when it was sold to CNET. Unsurprisingly, Rosensweig had a critical role in ensuring that the merger was a smooth and uninterrupted process. After which, he went on to have a critical role in promoting new ways of marketing on the Internet, which was perhaps unsurprising in light of his background in advertising.

Headed Guitar Hero

After CNET, Rosensweig went on to serve in a number of other executive positions with other companies. One example is how he was the person in charge of the game series called Guitar Hero. In fact, it was under Rosensweig’s leadership that Guitar Hero branched out by launching not just Band Hero but also DJ Hero.

Respects Starbucks

When he was asked in an interview about what companies he respected, Rosensweig brought up Starbucks as one example. In main, his respect for the corporation seems to be based on how it managed to create a thriving culture centered around its powerful brand, which is something that it had to build from the ground up. However, it is interesting to note that Rosensweig also sees Starbuck as a force for positive change in the world as well.

Respects Adobe

Speaking of which, Rosensweig has also expressed his respect for Adobe. In that particular case, his respect seems to be based on their corporate culture, which provides their people with the resources needed to provide outstanding performance. Furthermore, Rosensweig made mention of Adobe’s long-term thinking as well as its interesting ability to handle CEO transitions with an unusual grace.

Believes In the Importance of Getting Back Up

Rosensweig had encouraged other people to follow their dreams. He acknowledged that there was a serious chance of failure whenever people make that particular choice, but he also pointed out that it is alright for people to fail because what matters most is that they get back up again afterwards.

Believes in Being Authentic

When asked about the best advice that he has ever been given, Rosensweig stated that it was, “Being authentic.” In short, Rosensweig respects a lot of people as well as a lot of companies out there. However, he is not one of those people but rather himself and no one but himself, meaning that being true to himself is the choice that makes the most sense.


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