From “Medium” | An Interview With Chad Silverstein | Published September 23,
2024
Positivity — Having a good attitude is infectious. An optimistic outlook is inspiring to others and helps foster a supportive environment.
In today’s competitive business landscape, the race for profits often takes center stage. However, there are some
leaders who also prioritize a mission-driven purpose. They use their business to make a positive social impact
and recognize that success isn’t only about making money. In this interview series, we are talking with some of
these distinct leaders and I had the pleasure of Jamie Rosenberg, ClassWallet.
Bio: Jamie Rosenberg is the founder and CEO of ClassWallet, a Hollywood, Florida-based financial technology
company that has been used by state and local agencies across 34 states to maximize the impact of more than $4
billion in public funds. Prior to founding ClassWallet, Rosenberg launched the pioneering crowd-funding
platform, AdoptAClassroom.org, which provided funding for teachers in 30% of schools and improved the learning
environment of more than 3.5 million children. A graduate of Vanderbilt University and the University of Miami
School of Law, Rosenberg lives in Miami with his wife Lisa, his three children Ivy, Reid and Nica, and their
dog, Lola.
Other supporting materials:
- https://classwallet.com/videos/
- https://youtube.com/shorts/85JciJvJPJU?feature=share
- https://youtube.com/shorts/vU8nDR-LixU?feature=share
Thank you so much for doing this with us! Our readers would love to get to know you a bit better. Can
you tell us your "Origin Story"? Can you tell us the story of how you grew up?
I started my career as a corporate attorney, and in my free time mentored at a local school for disabled,
pre-kindergarten students. The experiences I had while mentoring that student changed my life. I wanted my career
and journey to be connected to the energy I felt in that classroom — much more positive energy than I felt in my
law firm office. So I quit my job as a lawyer and started my first business, AdoptAClassroom.org, an organization
that made it easier for individuals and organizations to donate directly to classroom teachers to purchase
educational supplies and resources for their students.
Over the next 12-14 years, AdoptAClassroom.org became one of the largest education philanthropy platforms in America.
By the time I left, we had raised and distributed donations to teachers in 30% of U.S. public schools and impacted
the lives of 3.5 million children. This was done by developing a fully automated technology platform that made it
easy for teachers to access and utilize the funds and it provided full visibility to donors to the impact their
donations had made. While the platform and technology have evolved since then, this is the same approach I took for
my current business, ClassWallet.
ClassWallet’s mission is to help our clients maximize the positive impact for the people they serve. We give public
sector agencies best-in-class technology, within the most secure architecture, to ensure their funds have maximum
positive impact toward their organizational goals and objectives. With ClassWallet, clients are able to give the
people they serve the easiest experience to access public benefits they have qualified for, with the least amount of
bureaucracy. We also provide clients with J.D. Power award-winning customer support, plus expansive spending
flexibility that is coupled with helpful information, to make use of funds in a way that has the most positive
impact on their lives.
Can you share the most interesting story that happened to you since you began leading your company or
organization?
I remember one spring a couple of years after starting ClassWallet. I was certain we were not going to make it. My
stress level was so high, my partner literally made me leave the office and go away for a week. That’s what I did.
In the depth of my despair, I received a phone call, out of the blue, from a large state agency leader asking if our
technology could be used to solve a problem he had. The state agency went on to become our largest client and opened
the door to an entire vertical in which we have become the market leader.
I’ve come to learn that when it’s low, I know the rebound will always be higher than where we started.
We often learn the most from our mistakes. Can you share one that you made that turned out to be one
of the most valuable lessons you’ve learned?
My mantra is "if you’re not failing, you’re failing." The valuable mistake I’ve learned from is the mistake
I made thinking mistakes were a bad thing. It took me a few years, but I eventually came to realize that each
mistake is actually a win, a lesson learned about an assumption, and how to incorporate the data from that lesson
into the next step through the journey. This lesson has been invaluable not only for corporate success, but also
personal fulfillment.
As a successful leader, it’s clear that you uphold strong core values. I’m curious what are the most
important principles you firmly stand by and refuse to compromise on. Can you share a few of them and explain
why they hold such significance for you in your work and life?
The one principle I firmly stand by is gratitude. Gratitude humanizes our existence at home, in life and at work. It
bonds us as people, and as fellow employees, and it bonds us with our clients and users. It levels the organization
horizontally and reminds us about the priorities in life. This value organically translates into a supportive work
environment, attracts the highest caliber of people, and produces the best outcomes that have enabled us to
consistently meet our company goals, year after year after year.
What inspired you to start a purpose-driven business rather than a traditional for-profit enterprise?
Can you share a personal story or experience that led you to prioritize social impact in your business?
To be clear, ClassWallet is a for-profit business that has a purpose. Who doesn’t want to go to work everyday with a
sense of purpose? Both of the businesses I started, AdoptAClassroom.org and ClassWallet, are a manifestation of that
life aspiration. I view the entrepreneurial journey very much as a reflection of a journey toward personal
fulfillment. Building industry-defining financial technology, being the market leader in multiple verticals,
experiencing triple-digit growth for multiple successive years, and enjoying the time we spend together is
energizing, invigorating and rewarding. But that we can accomplish all that, AND make such a positive impact in so
many people’s lives, is fulfilling.
Can you help articulate a few of the benefits of leading a purpose-driven business rather than a
standard "plain vanilla" business?
A purpose-driven business creates a platform that enables people within the business to realize their true purpose.
Build a company that maximizes that mission, and the purpose of the company and product out in the world will be
realized beyond one’s wildest imagination. That’s what we have created at ClassWallet, and that’s why we have been
able to help our clients maximize the positive impact for so many millions of people they serve.
How has your company’s mission or purpose affected its overall success? Can you explain the methods
or metrics you use to evaluate the impact of this purpose-driven strategy on your organization?
Our mission is to help clients maximize the intended positive impact of funding for the people they serve. We do this
by 1) Enabling them to give their constituents the easiest experience to utilize funds with the least amount of
bureaucracy and the best customer support; 2) Give them expansive spending flexibility coupled with helpful
information to use funds in a way that makes the most positive impact on their lives; and 3) Give clients
best-in-class tools, within the most secure architecture, to ensure their funds have maximize positive impact toward
their organizational goals and objectives.
We track each of these value propositions with data that fuel our focus on perpetual innovation and delivering on our
mission. What is amazing to me is that even though end users of our product are forced to use it by government
agencies (school districts, state agencies, etc.), we actually have a customer loyalty higher than Target, Google,
and Apple. Based on over 20,000 responses to our most recent customer satisfaction survey, more than 92% of users
say ClassWallet makes it easy to access funds and over 96% of clients say ClassWallet has helped them accomplish
their organizational goals and objectives.
What technology platform have we been forced to use by a public agency that we would rate the experience better than
the experience we get from a company like Apple? ClassWallet is changing the game and creating a whole new paradigm
on how public benefits are accessed and maximized.
Can you share a pivotal moment when you realized that leading your purpose-driven company was
actually making a significant impact? Can you share a specific example or story that deeply resonated with you
personally?
I remember when I started AdoptAClassroom.org in 1998, I used to fulfill teacher orders by hand, and manually deliver
boxes of supplies to the classroom. During one of the first, early deliveries, I recall watching the children open
the boxes of supplies as if it was Christmas. The joy and positive energy in the room was palpable. I remember
grouping the kids together for a photo, and the sheer happiness they emanated as I looked through the lens,
literally made it feel as if time stood still. While this sounds like a corny cliche, this is the truth. For a few
days after, life was a bit off balance. Something happened that day, at that moment, and the best I can describe it
is my soul was indeed truly touched.
Have you ever faced a situation where your commitment to your purpose and creating a positive social
impact clashed with the profitability in your business? Have you ever been challenged by anyone on your team or
have to make a tough decision that had a significant impact on finances? If so, how did you address and
reconcile this conflict?
There was an instance when ClassWallet was subject to sustained nefarious activity by a competitor vying to win an
account away from us. Throughout the entire episode, our core values were truly stress tested. But we remained true
to our authentic, positive selves and the outcome was not only positive, but it strengthened the fabric of the
company that accelerated our success.
What advice would you give to budding entrepreneurs who wish to start a purpose-driven business?
Your business has to serve a purpose for yourself that extends beyond making money. Its mission should resonate
personally with you and impact the broader community. While generating revenue is important, if the sole focus of a
company is financial gain, you’ll face significant challenges, even if it is contributing positively to social good.
The true essence of a successful business lies in its ability to create a meaningful culture that benefits all
stakeholders, fostering a sense of shared purpose beyond everyday business goals. By integrating personal values
with organizational goals, leading with transparency and showing vulnerability, you can create a winning formula.
This approach not only enhances your own self-fulfillment but also helps you craft business focus areas that make a
genuine difference in the world.
What are your “5 Things You Need To Create A Highly Successful Purpose-Driven Business." If you
can, please share a story or example for each.
To have a successful purpose-driven business, leaders should embody the following values:
- Authenticity – Be genuine in everything you do. Let your values guide your decisions. The market can
sense when a social impact company is not coming from a place of authenticity. You should truly believe in the
mission and demonstrate that confidently to others. - Holding Yourself to a High Standard – Everyone, including and most importantly, yourself, must give 100%
effort all the time. Ensure that your actions align with this purpose and inspire others to do the same. - Humility – Leadership is not about having all the answers but about learning and growing. Acknowledge
your mistakes and be willing to learn from others. - Curiosity – Never stop learning and growing. Stay open to new ideas and be willing to adapt and evolve.
- Positivity – Having a good attitude is infectious. An optimistic outlook is inspiring to others and helps
foster a supportive environment.
I’m interested in how you instill a strong sense of connection with your team. How do you nurture a
culture where everyone feels connected to your mission? Could you share an example or story that showcases how
your purpose has positively influenced or motivated people on your team to contribute?
Every week, on Fridays at 9:30, I host a weekly, company-wide, 60-minute "Win / Gratitude" meeting.
Everyone, no matter the role in the company, has an opportunity to share personal wins and stories. We hear about
celebrations, tragedies and frequent reminders about the little things in life that matter the most. These
interactions propel our mission of leading with transparency and humanity, which naturally compound a shared sense
of purpose.
Imagine we’re sitting down together two years from now, looking back at your company’s last 24
months. What specific accomplishments would have to happen for you to be happy with your progress?
Our digital wallet will be viewed as the industry standard through which any funding intended to have a positive
impact will be managed. We will have catapulted from all of market leadership in the K12 education space into other
markets such as early childcare, career and workforce development, emergency funding, housing and other agencies who
strive to make a positive impact in people’s lives and will have the advantage of using our platform to maximize the
success of their goals.
You are a person of enormous 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.
There is a huge lack of understanding and appreciation among teenagers about the power and lessons of failure. I
believe this is a significant contributor to the mental health crisis within that age demographic, and what is
contributing toward factors that undermine employers’ ability to find talent. So, many kids simply are not being
prepared for the real world.
I aspire to teach, develop and scale a curriculum on failure. When you think about it, no one is teaching failure.
While students can encounter failure such as in tryouts, there is no curriculum that I have seen that actually puts
the value of failure into a lesson plan that gives them tools for success. I don’t think I’ll have a challenge
attracting students to a class that markets "the more you fail, the better grade you’ll get "!
How can our readers further follow your work or your company online?
Readers can follow ClassWallet on our website. Our blog has lots of resources about digital
wallets, education trends and information about public funding. We’re also on LinkedIn and X, @ClassWallet.
Original article on Medium.com can be viewed here
The post Purpose Before Profit: Jamie Rosenberg Of ClassWallet On The Benefits Of Running A Purpose-Driven Business appeared first on ClassWallet.