As part of my series about prominent entrepreneurs and executives that overcame adversity to achieve great success, I had the pleasure of interviewing…

As CFO of Chegg, Andy’s goal is to drive the financial performance of the company. Andy has over 25 years of experience in the financial sector, over 10 of which he’s spent as CFO of three public companies: Palm, Legato Systems and ADPT Corporation. Andy’s proven ability to help build organizations, impressive track record in high growth environments, and significant experience in the consumer technology space make him the right leader to ensure Chegg’s continued growth.

Jason Crowley: Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to this specific career path?

Andy Brown: Since earning my B.S. in Accounting, I’ve spent my entire career in finances. Prior to joining Chegg, I was actually semi-retired and was compelled by the CEO’s vision to transform Chegg from a textbook rental company to one that makes the entire student experience — from learning to earning — easier with a 24/7 digital subscription platform. It’s Chegg’s student-first mission and the passionate people I work with that have kept me here for more than seven years

Crowley: Can you share your story of when you were on the brink of failure? First, take us back to what it was like during the darkest days.

Brown: Shortly after Chegg went public in 2013, Amazon entered the textbook rental market to compete with us. As you would expect, it was an immensely difficult time. Amazon’s move contributed to a steep fall in the company’s stock prices. We had to reinvent ourselves and transform our business model in the public markets right after our IPO. Since then, we have successfully evolved our business and are now a market leader with incredibly strong financial performance. It’s a great turnaround story.

Crowley: What was your mindset during such a challenging time? Where did you get the drive to keep going when things were so hard?

Brown: Whenever you are evolving a company, investors and employees get nervous. It’s an expected and natural response due to uncertainty on many fronts. What kept me going was our incredibly passionate team and our common determination to help students be more successful and make education more accessible. The people at Chegg are committed to our mission and are willing to do what it takes to succeed, which inspires me to come back every day.

Crowley: Tell us how you were able to overcome such adversity and achieve massive success? What did the next chapter look like?

Brown: We never lost sight of our vision and mission. We streamlined our textbook business and doubled down on our goal to become the must-have digital learning service that addressed the unmet needs of students. We made the decision to not make the financials the priority, and instead focused on building our customer base so we could have a strong platform to build on top of.

Crowley: Based on your experience, can you share a 3 actionable pieces of advice about how to develop the mindset needed to persevere through adversity? (Please share a story or example for each.)


  1. Have a clear long-term vision and mission and never lose sight of that core. Every day, every decision we make at Chegg is about bringing learning directly to today’s students who don’t have the time, money or ability to conform to the rigid and outdated university model because they’re earning while they’re learning. I’ve received countless gratitude on social media and recognition from students explaining how Chegg has helped them understand their homework, pass a class, and go on to graduate and be successful in life. Staying true to that student-first mission and knowing we’re making a difference has helped power me through adversity.
  2. Remain relentlessly focused on your audience and their needs. With Chegg, we changed the playing field and focused on the modern student’s needs rather than textbook rental. Students need to know how to get into college, understand their homework, pass classes and get internships and jobs. When we stay laser-focused on delivering the solutions that address those needs, we are more nimble, more efficient, and ultimately, we believe, more successful.
  3. Bet on yourself. Recognize that you may fail more often than you succeed, but it’s confidence in yourself that will enable you to get back up, learn from your failures and keep working toward your goal.

Crowley: None of us are able to achieve success without some help along the way. Is there a particular person who helped get you to where you are? Can you share a story about that?

Brown: You can’t have success on your own because it’s not about one person. It’s about a team that wants to work together. I often remind people that the success of Chegg and myself should really be attributed to the people who work for me. I just happen to be the mentor, the “coach.”

There was one individual in my career that embodied leadership. In my early thirties, this individual really believed that I should be an executive and having him believe in me fundamentally changed the way I believed in myself. A big part of leadership is taking on the coach role and this individual did that, helping me with how I think about my team today. I would say that being a coach and mentoring your team is very pervasive in the leadership culture at Chegg. All of my colleagues recognize the potential of their teams, allowing them to make their own decisions and succeed.

Crowley: Are you working on any exciting new projects now? How do you think that will help people?

Brown: Our goal is to help students speed their path from learning to earning. We’re working with students and employers to streamline the pathways to help make this journey more successful. We do this by continuing to invest in creating rich content and continuing to invest in technology to make our digital platform smarter and faster.

Crowley: You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Brown: Being at Chegg has helped me understand the power of positively impacting people early in their lives. I’m a big believer in helping students develop in their formative years of life because what you instill in them early on gets to their core. For instance, I’m on the board for a nonprofit called Teen Challenge, they help kids who have drug addiction problems. I know that if you can get those kids out of drugs early, then they become better citizens for our country.

I see a movement in our society where we can be more helpful towards people in their formative years by having the best teachers. Income disparity in this country is a real problem. We need to properly fund our educators because they’re the ones helping and supporting these students. Our society is truly missing an opportunity to build something amazing here and to guarantee a better future by giving all students an equal opportunity to succeed.

Crowley: Any parting words of wisdom that you would like to share?

Brown: Work with people you want to work with. If you have the ability to create an environment at work where people are happy to be there, do it. I think we’ve really done that here at Chegg. And not just because we have a great company culture. Everyone here is truly mission-based and is excited to be supporting students.

Bet on yourself and bet on the team you’re playing with. I’m an unapologetic, team-driven guy. I love being a part of a team where everyone has each other’s backs. Never let a teammate fail. If someone’s failing, the team is failing, so never let them fail.

Crowley: How can our readers follow you on social media?



Crowley: Thank you so much for joining us. This was very inspirational.