Monica Gray

DreamWakers, Cofounder
Monica Gray

Monica Gray is an entrepreneur and innovator who has been featured in the New York Times, Washington Post, People and Newsweek for her pioneering nonprofit, DreamWakers. In just two years, DreamWakers has virtually connected high-need public school classrooms across 30 states to diverse and dynamic professional role models, serving thousands of students from coast to coast.

As a young professional in Washington, D.C., Monica couldn’t find the time to fulfill volunteer opportunities in public schools while maintaining a full-time job. Her friend and fellow UVA alum, Annie Medaglia, had the same frustration. Both women were passionate about finding solutions for education inequality, so they teamed up to create DreamWakers.

Having grown up in Staunton, Virginia and attended UVA for both undergraduate and graduate school, Charlottesville was the logical choice to launch Dreamwakers. Monica and Annie took their idea to the Batten Institute’s iLab in 2014. It was there that they fleshed out their business model and have since had speakers from Apple, CNN, Makerbot 3D Printing, The White House and JetBlue, inspiring and mentoring students from all over the country — with a focus on serving schools in high-need urban and rural communities.

A long-time education advocate, Monica also contributes to Huffington Post Education, where she writes on topics related to social justice, entrepreneurship, and education innovation. Her goals for the next year: triple the amount of students DreamWakers’ serves, expand to schools in all 50 states, and turn her organization into a self-sustaining nonprofit through DreamWakers’ new Corporate Partnership Program. With the rate in which she’s succeeded, it’s a likely bet.


DreamWakers is a nonprofit that believes students can’t be what they can’t dream—and they can’t dream what they can’t see. We aim to close the growing gap between classroom and career by leveraging free video chat technology to bring diverse and dynamic professionals into public schools. Our focus is on 4th – 12th grade teachers working in schools where at least 50% of the student population is enrolled in free or reduced lunch. We connect their classrooms with vetted, professional role models from a variety of public and private sector industries. Each 45-minute virtual session, called a “flashchat,” exposes students to a career path that’s relevant to what they are learning in the classroom, and is intended to inspire students to not only stay in school, but also explore career aspirations earlier and dream big about their personal and professional futures beyond graduation day.


The question we are trying to answer with DreamWakers is this: if young, underprivileged students aren’t exposed to the range of diverse and exciting career possibilities available to them, how can they adequately prepare?

Public school students in low-income school districts have far fewer opportunities than their wealthier peers to engage with professionals from various career occupations, and more than two-thirds of U.S. employers have admitted that they currently have little to no interaction with children in our public schools.

On top of that, 65% of today’s students will be employed in career fields that don’t yet exist. If students aren’t even exposed to exceptional leaders shaping the industries of today, how can they be inspired to create the careers of tomorrow?

In addition to facilitating these connections between in-school learning and real world opportunities, we also felt that DreamWakers could help to redefine traditional volunteerism. By harnessing the power of free and existing video chat services, we wanted to help democratize public service for the next generation. In the amount of time it takes to have a lunch break, DreamWakers empowers professionals at all stages of their career to have positive, meaningful public service experiences without ever leaving their desk. By using basic technologies that one can access on a smartphone, tablet or laptop, we’ve created a fun and efficient portal for professionals from all walks of life to volunteer “in schools,” and 100% of our speakers report having a positive experience because of it.


Seeking advice from peers and mentors has been key for us in so many ways. When “starting up” a key question we asked was how could we best test our program in classrooms across the Commonwealth, and how could we do so right away? There are a few individuals from those early days in Charlottesville that really stand out. Our mentor at the iLab was MJ Toms. She provided moral support, crucial brainstorm sessions and early introductions which led us to key leaders and professors within the UVA community — such as Pace Lochte and Professor Victor Luftig — both of whom graciously agreed to meet with us. Both Pace and Victor are involved in various education and business growth initiatives in southwest Virginia. Their generosity in connecting us to community and education leaders is what led Annie and me to being invited on a tour of Southwest VA in our “startup summer” of 2014. We ended up taking an epic road trip all over the state, meeting with teachers, principals, and superintendents who then became DreamWakers’ first and most loyal users. What’s more, MJ, Pace, and Victor still reach out and help us to this day. They are among the dozens of people who have gone above and beyond to help us since the very start; we are deeply appreciative for our “Dream Team” of supporters.

Defining Moments of Success

The most gratifying moments are when a student really lights up and connects with a speaker during a flashchat. You can almost see the lightbulb flicker and they instantly want to learn more. Those are the times when I feel most successful.

This year we took the important step of creating a DreamWakers team and office in New York City. Having incredibly bright minds working with us to help achieve our goals–and a space that is truly ours–has been a turning point in our ability to serve even more students more effectively. We hired our first employee and created a DreamWakers Advisory Council made up of exceptional young professional representatives from places ranging from Google and HP to and Citi and the White House. We also brought on two awesome interns — one of whom is Amanda Coombs, a full-time UVA student I met at the Youth Summit at the Tom Tom Founders Festival!

Our definition of success changes every day, but it always revolves around the positive impact we want to have on our next generation of thinkers and doers.


Any entrepreneur will tell you that, sometimes, everything feels like a setback. And for us, that first year was really difficult. When funding was extremely tight and there seemed to be an unending list of reasons why this idea of ours wouldn’t work, it was a challenge to keep my sights set on the ultimate goal. DreamWakers encountered a lot of push back in the beginning from critics who doubted that an organization built to “inspire students” and “expose real-world career opportunities” would be able to thrive in an education system that so often values test scores above all else. How would we know whether the flashchats made a lasting impression on students? But all of the skepticism made me more committed to take a leap of faith and push to not only grow DreamWakers, but to track as much data as possible so that we had numbers to back the incredible testimonials we continued to receive from teachers, speakers and students alike. For background, approximately 70 percent of our schools have more than 50 percent of their students on free and reduced lunch, with most coming from rural and urban communities across the country. And only 16 percent of our partner classrooms were exposed to a speaker outside of their city limits before engaging with DreamWakers. What’s more, we’ve seen time and time again that our flashchats don’t end at 45 minutes when the speaker exits the virtual discussion: Nearly all — 93 percent — of classrooms continue to discuss the topics and lessons learned in the flashchat in the days following. Now, two years later, there are still setbacks, but my belief in what we are doing and my resolve to bring DreamWakers to more children nationwide only continues to grow, as does our list of teachers and speakers who wish to participate in the DreamWakers program.

Biggest Impact

Last fall, a fifth grade Teach for America Social Studies teacher in Newark, NJ, Mr. Ojeikere (aka “Mr. O”), submitted a request on our website for a speaker to give his kids some personal and professional encouragement. “My students are from a Latin-American and African-American community,” he said. “They love to learn and they love opportunities, but at the same time I feel like they are missing some inspiration that I am not able to currently give.” School budgets were tight, he explained, and bringing guest speakers into the classroom — mentors the children would relate to and click with — was a challenge.

DreamWakers immediately set to work. We virtually connected Mr. O’s students with African American leaders at the U.S. Department and with White House Political Director David Simas. A son of Portuguese-immigrant factory workers, Simas described his experience speaking to those students as “one of the best things” he’s done during his time at the White House. He even extended an invitation for the entire class to visit 1600 Pennsylvania Avenue. And visit the White House they did. At the end of the semester, Mr. O’s students, fellow teachers, and our NYC-based DreamWakers team loaded onto a bus in Newark at 6 a.m and headed through rain and traffic to our nation’s capital. It was a trip unlike any other and stands out as an example of the positive ripple effect of our work.

Ultimately we hope that the virtual classroom to career connections we facilitate at DreamWakers will continue to serve as a springboard for further learning, exploration and innovation. We can’t wait to see where DreamWakers leads our students, and us.

Thriving as an Entrepreneur

I believe everyone finds their own formula. But for me, I’ve found the most fulfillment when I remind myself constantly that my ultimate goal is simply to serve students. Being intentional about keeping this at the forefront of my mind helps fuel the daily grind. It can feel simultaneously exhilarating and daunting to think that the organization’s future and impact is dependent on my ability to keep pushing us forward. Deadlines don’t exist unless I make them. Projects don’t get managed unless I assign someone to them. Literally, the wheels of the operation don’t run unless an entrepreneur sets them in motion. Nobody else is going to do it for you. It’s therefore invaluable to surround yourself with a supportive team of action-oriented people who truly care about your organization’s ultimate mission; I feel especially grateful to have the support, encouragement and counsel of my co-founder, Annie. As we say at DreamWakers, “teamwork makes the dream work.” It truly takes a “Dream Team,” and I am so lucky to have discovered mine.


I grew up in Staunton, and went to undergraduate and graduate school at UVA. When I made that trip back down to Charlottesville (in a rented car from Enterprise that was packed full of my belongings as I moved from Washington, D.C.) in 2014 to participate in the iLab and launch DreamWakers, it felt like coming home.

Our roots are in Charlottesville; it’s the place where DreamWakers transformed from idea into reality. My brilliant and fabulous co-founder Annie Medaglia and I founded DreamWakers at the iLab—Darden’s business incubator—in 2014, and have since worked within a number of local Virginia schools here in Charlottesville as well as in places such as Abingdon, Gate City, Jonesville, Hillsville, Nickelsville, Norton, Norfolk and Staunton. We’ve connected these classrooms with public and private sector professions across the country working at places such as: Amazon, Apple, Facebook, Twitter, Boston Consulting Group, Time Magazine, Slate, The Baltimore Sun, NFL, the U.S. Department of State and The White House. Since those first days at the University of Virginia, DreamWakers has served thousands of students across 30 states, and we hope to be in all 50 by the end of the year. The Charlottesville community served as an ideal launch pad and catalyst, propelling DreamWakers onto a national stage. We feel incredibly fortunate and proud to be a Cville-founded organization.

Also, the iLab specifically was such a powerful home base as an entrepreneur. The built-in support system of mentors and fellow entrepreneurs, many of whom were weathering the ups and downs, the hopes and failures, the late-night pitch preps right there with you. And I would be remiss if I didn’t also admit that Charlottesville is a great place for entrepreneurs who need a good meal on a budget. It’s amazing how far 20 bucks can go when living on Bodo’s bagels and Christian’s pizza!

I recently saw that Charlottesville was rated one of the top U.S. cities for entrepreneurs, and I couldn’t agree more. The entire town is the perfect mix of academia and real-world initiative. For example, I remember sitting in lectures that delved into the minute details of design thinking one day, and the next day putting those very same ideas to the test while piloting our program at the Boys & Girls Club on Cherry Avenue. Charlottesville gave me the unique opportunity to pivot between academic theory and real-life application, and I learned priceless lessons in the process.

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