FORTUNE — Dan Rosensweig believes in the American Dream. After earning a bachelor’s degree in political science from Hobart and William Smith Colleges, he worked his way up from a job selling computer magazines to becoming a major player in the Internet boom. (How’s this for a résumé: He has been the president of CNET Networks, the chief operating officer of Yahoo, and the chief executive of Guitar Hero.)
Along the way, Rosensweig noticed that there was a market begging to be disrupted: Education — specifically around the escalating cost of student textbooks. Which is why in 2010 he joined Chegg, an online textbook rental service and student resource hub.
Rosensweig, 52, spoke with Fortune.
1. Who in technology do you admire most? Why?
I’m going to give you two answers. First of all, there is a whole host of people that I admire. I admire [Marc] Andreessen and [Mark] Zuckerberg and all of these people; they’re amazing. But right now I admire [Brian] Chesky and Joe Gebbia — they’re two of the founders of Airbnb — because they had no engineering background or technology background. They went to a liberal arts design school, and they had an idea that they discovered by accident, and they’re building it into one of the most disruptive companies in any industry. They have no fear. They have great values. They’re just admirable young people, exactly what you want to see coming out of this country.
2. Which companies do you admire? Why?
I admire Starbucks (SBUX), because here’s a company that had an idea, then turned it into a brand, then turned into a culture. And it’s a culture for good and a positive force for change.
I admire Adobe (ADBE), not just because I’m on the board, but [because] this is a company that has handled the transition of CEOs remarkably well over the years, and their co-founders are still on the board because they value long-term thinking and long-term investment, and they want to provide the capabilities and the tools so that other people can do great things. They have an unbelievable culture around their people, and they’re one of the most admired companies.
I admire Airbnb and Facebook (FB) and so many other companies, too. But what they all have in common is that they all have people who had their own courage and conviction, took a much longer view, took lumps along the way, but didn’t waver from the desire to build a great business while doing great things for people. It’s an admirable position to be in.
3. What advice would you give to someone who wants to do what you do?
Don’t wait as long as I did to do it. If you’re going to bet on somebody, bet on yourself. I don’t mean you should be arrogant. You have to do it with humility and recognize that you’re going to fail more often than you succeed, but at least you’re going to do it with your own convictions if you do fail. The beauty of America is not in failing; it’s in getting up. Every one of those people that we admire — that I admire — are all people who have failed prior to success. But they had a belief. If you think you have something you want to do, go do it. Don’t worry about the naysayers. Do it with everything you have.
4. What is the best advice you ever received?
I’ve been given it many ways by many people, by my grandfather, by my wife, by my daughters, by my friends like John Donahoe, which is: “Be authentic.” I am not going to be able to be Steve Jobs or Mark Zuckerberg or Sheryl Sandberg, and the truth is, I don’t have to be. I have to be Dan, and I have to be authentic with who Dan is. I have to learn to overcome the things that are hard for me to do, and I have to go with the strength of my conviction of who I am.
5. What challenges are facing your business right now?
The challenges facing our business are not unusual to anybody that’s building a new category, which is the unknown, the uncertainty. There are a lot of players, a lot of entrenched constituents, who would prefer things don’t change. As I say when I give speeches: “How many of you wish you were three years away from retirement so this was someone else’s problem?” Every industry that’s been disrupted has had a lot of people who prefer that it not be. With education in particular, the skills you need are fluid, but institutions are not fluid. The whole system has been designed around supporting the institution and not supporting the student. So there are a lot of obstacles, but they’re the same obstacles that anyone who’s taken on these things has faced, and we know they can be overcome.
6. What was the most important thing you learned in school?
The importance of learning the right way to ask a question. It’s as important to know how to get the right answer as it is to have the right answer. I can give you the exact example of my epiphany in college. I was in world politics, and this was when there was still the Cold War. There had been no Gorbachev yet. And the professor walked into the room and said, “All of you are the president of the United States, and I am the secretary of state. I walk in, and I say, “Mr. or Madame President, the missiles have launched; what would you like me to do?” And most students said, “Let’s get you to the bunker.” Some said, “Launch back.” And what had really happened was that we had launched test missiles, and he just wanted to let the president know. The right answer would have been to ask, “What missiles, launched at whom?” It was about learning to ask the right question as opposed to having the right answer. So half the class started a nuclear war.
7. What is one goal — either personal or professional — that you would like to accomplish during your lifetime?
Most of the goals that I had set for myself I set in high school. They were to become financially independent, to get married and stay married, to have children who seek a value in life and purpose, and to meet Bruce Springsteen and see as many of his shows as possible.
At this point in my life, my wife’s goals and my goals are as much for the hope and happiness of our children as they are for ourselves, so the things that we focus on outside of work are to make sure they have the right support system to follow whatever their passions may be. I don’t know what they’re going to be yet, but I hope they will have the strength and passion to go after it. I feel very confident they will, because their mom has done a phenomenal job with them. For me personally, what they do is more interesting to me at this point than what I do. I just hope that whatever I do is creating value in people’s lives.
8. What was the last book you read?
The last book that I read was Lean In. Sheryl Sandberg sent it to me on a Sunday and told me that I had to read it that day and give my comments, and when Sheryl says to do something, you do it.
But the real reason I read it is, I think it’s required reading for a CEO, and I think it’s required reading for a father with daughters. It’s extremely powerful. Fifty-plus percent of the population and the people who go to college are women. It’s time that everybody understands the full perspective. I applaud her courageousness. I thought it was great, and I didn’t realize there would be all this backlash. Her courage to write it, her courage to stick with it, her courage to communicate it is extraordinary. And it had a powerful and meaningful impact on me personally and the decisions I make.
9. What is one piece of technology you can’t live without?
I’m a big fan that the greatest invention of my time is air conditioning. I cannot live without it. I grew up in an apartment that didn’t have air conditioning, and when we got it, it was like, “Oh my god, I love whoever invented this.”
But also the Internet itself, what it does, which is give me untethered access to anything that I might need. I can live without a specific app, but not without the ability to be connected and do the things that I want to do.
10. What is one unique or quirky habit that you have?
My passion for Springsteen shows. It’s probably a little unusual for a CEO to see somebody perform live 65 times with another five planned for this tour. Some people probably consider that a little odd.
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