NGPF Podcast: Tim Talks To Chegg President and CEO Dan Rosensweig

Feb 01, 2019
Podcasts, Paying for College, Entrepreneurship

From PC Magazine to CNET to Yahoo to Guitar Hero to Chegg, Dan Rosensweig has had a fascinating front-row seat in seeing (and sometimes driving) the paradigm shifts in tech as it has evolved from the PC to the Internet to the cloud. In this wide-ranging and fast-paced conversation, Dan shares his thinking behind leaving Guitar Hero to join a then simple textbook rental company (Saying ‘hey I am the CEO of guitar hero’ then going to say ‘i rent textbooks’... you can imagine how that went in the ‘coolness’ category). He also describes how he has completely transformed and expanded Chegg's digital offerings to, in his words, "realign the education system" to meet the needs of the students they serve. Enjoy!  


  • 0:00~1:39 Introduction
  • 1:39~2:30 Who is Dan?
  • 2:30~10:39 Early job experience
  • 10:39~15:38 Working at Yahoo and his meeting with a young entrepreneur with a social media site
  • 15:38~18:26 Passion for music and Guitar Hero
  • 18:26~27:08 Pathway to Chegg
  • 27:08~27:39 Word from NGPF
  • 27:39~32:40 Dan's innovations at Chegg
  • 32:40~37:10 The modern college student and money
  • 37:10~40:59 The future of online learning
  • 40:59~49:01 Changes in higher education
  • 49:01~50:30 Conclusion

Resource mentioned:


  • “Saying ‘hey I am the CEO of guitar hero’ then going to say ‘i rent textbooks’... you can imagine how that went in the ‘coolness’ category.”
  • “I think we are seeing curriculum evolve but we aren’t seeing unit economics evolve yet in colleges but I think we are going to in the next 5 to 10 years.”
  • “What we are trying to do at Chegg is to realign the education system faster with the needs of who it's supposed to serve, which is the student.”
  • “We encourage every school to look at the question: how does your curriculum relate to the jobs of the future in your communities?”


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About the Authors

Tim Ranzetta

Tim's saving habits started at seven when a neighbor with a broken hip gave him a dog walking job. Her recovery, which took almost a year, resulted in Tim getting to know the bank tellers quite well (and accumulating a savings account balance of over $300!). His recent entrepreneurial adventures have included driving a shredding truck, analyzing executive compensation packages for Fortune 500 companies and helping families make better college financing decisions. After volunteering in 2010 to create and teach a personal finance program at Eastside College Prep in East Palo Alto, Tim saw firsthand the impact of an engaging and activity-based curriculum, which inspired him to start a new non-profit, Next Gen Personal Finance.

Ren Makino

Ren has been working part-time at NGPF since 2014, interning through high school and college. With his knowledge growing alongside NGPF, after graduating from college in 2020, he joined the team to work full time with a focus on teacher onboarding. He is also the editor of the NGPF podcast and makes sure it is accessible to teachers on iTunes, Stitcher, and Google Play Music. During his free time, he likes to try out coffees from different roasters across the world and try out new brewing methods, even though personal finance gurus tend to caution against buying a cup of joe.