Jamie Rosenberg Of ClassWallet: “If you’re not failing, you’re failing”

If you’re not failing, you’re failing: Stretching yourself beyond your comfort zone gets you where you need to be. As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Jamie Rosenberg, The CEO of ClassWallet. Jamie Rosenberg, the founder, and CEO of ClassWallet […]

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If you’re not failing, you’re failing: Stretching yourself beyond your comfort zone gets you where you need to be.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Jamie Rosenberg, The CEO of ClassWallet.

Jamie Rosenberg, the founder, and CEO of ClassWallet is no stranger to the education sector, having launched two successful technology companies in the space, ClassWallet, and AdoptAClassroom.org. His journey from mergers and acquisitions lawyer to social entrepreneur is a living example of how one person can change the world.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I wanted to give back to the world outside my law firm environment. I started mentoring a student at a nearby school for mentally and physically delayed children. During my time in the classroom, I was shocked to see how few resources the teacher had to work with and how often she would bring in materials that she had purchased with money out of her own pocket.

Meanwhile, at work, I was exposed to billions of dollars flowing through corporate America, and thought, “Why isn’t there a program that funnels some of these corporate dollars into classrooms where it’s needed most?” Then, driving to work one day, I saw a sign for “Adopt A Highway” and it hit me: If we can adopt roads to make them better, we can certainly adopt classrooms to give teachers the resources they need to better educate our children. After that, my first venture, AdoptAClassroom.org, was born.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

ClassWallet has enabled federal, state, and local government funds for education to reach students and teachers in a way that’s never been done before. Everything was done by paper and it took a lot longer for money to reach teachers and students, compared to how money moves on platforms like PayPal and Venmo. Prior to our TeacherWallet platform, no such technology existed for money to quickly go from administrators to teachers and students with complete transparency and accountability. We took the disruption possibilities of the fintech world and directly applied them to education.

Can you share a story about a mistake you made when you were first starting? Can you tell us what lesson you learned from that?

For my very first investor meeting, I brought an entire investment banking team. The feedback I received was that this was overkill and that I would have been a much more formidable candidate had I done the presentation by myself. It was a key lesson learned; that I, as the main individual leading the organization, was the best suited to present my overall vision, passion, and experience.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Bill Gutman“, one of my earliest investors and current Board Chair,” is my mentor. The experience he’s had, his confidence, etc. His confidence in me has contributed to building my own self-confidence as I pursue this entrepreneurial journey. As my mentor, he’s helped me think about the things I am not thinking about as well as providing the foresight for the larger tools and direction ClassWallet and I need to be successful.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

ClassWallet, under my leadership, is disruptive in the sense that we are empowering teachers to be as successful as possible. We want to help to create a more positive workplace for teachers. However, in education, not all disruption is necessarily good. Too much reliance on technology platforms and self-driven learning deteriorate the important connections between teachers and students. We don’t ever want to lose sight of the connection between students and teachers.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

If you’re not failing, you’re failing: Stretching yourself beyond your comfort zone gets you where you need to be.

90 percent of life is showing up: ClassWallet was incorporated in 2009, 12 years ago. We are still here and still showing up each and every day to make a difference for teachers, parents, and students.

The harder you work, the luckier you get: Simply put — hard work = success

We are sure you aren’t done. How are you going to shake things up next?

We are taking the same seamless fund distribution model for our original TeacherWallet solution and applying it to FamilyWallet, which helps deliver available grants to families for tuition and educational technology needs.

In addition, our MaintenanceWallet solution helps in the distribution of funds to schools’ maintenance and custodial staff, so they can purchase the materials they need on a day-to-day basis to keep their buildings safe and clean. The idea of both of these offerings is to have a better impact on these dollars; to be more impactful overall.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

The Surrender Experiment: by Michael Singer. It’s a great education on universal intelligence and the importance of being centered and balanced by “letting go” and through practices such as meditation. The book taught me to be clear, more in touch, and ready for the opportunity each and every day. Also committing to intelligence and spirituality. I would highly recommend reading The Surrender Experiment. It’s made a significant change in my life and in the way I approach work and my life as a whole.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite quote is from Michael Jordan: “I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over again in my life. That is why I succeed.”

I love this quote because it talks about how you learn from failure. If you get knocked down or fail at something you need to get back up and try again. I live by this quote and so does ClassWallet. This is one of the reasons we have been so successful.

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. 🙂

Teachers are with our children 8 hours a day, 5 days a week, 8 months a year. No one is more important in our schools and communities. If I could create a movement, it would be to ultimately put teachers at the top of the education pyramid. The care, passion, and devotion that teachers put into their jobs are so inspiring. Today, many of the best teachers are leaving the field. We need to turn this around and attract the most talented people to this profession. My mission has been to support this effort by helping to create a culture where teachers feel not only appreciated but empowered and entrusted to do their jobs to the best of their abilities.

This was very inspiring. Thank you so much for joining us!

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