Ray Dass: From Aspiring Rapper to Rockstar Educator

Young girl with freckles.

“Could I write this interview for Our City in two days?”

Ray asked over Bluetooth. His six-year-old son, Luke, sat behind him in the car.

“Okay,” I said.

“Em!” he said. “Thank you!”

Other past students of Ray’s would do the same—more than for other teachers. No one likes to let down Ray Dass.

From the backseat, Ray’s son started a conversation that helped me clarify why. The conversation was this: One time, Luke ordered chicken nuggets and fries. But the takeout bag came with triple the food.

“It wasn’t magic,” Luke said.

“What do you mean?” Ray said, laughing.

“It was too much. No one could eat all of that,” Luke said. Ray paused a minute.

“You’re right,” he said. “That’s true.”

He listened to Luke thoughtfully, and I realized why it still matters to me what Ray thinks. Twelve years ago, I was seventeen with a belly-button ring, and chronically annoyed, and Ray took me seriously. He listened to what I said.

That is to say that long before his “Know You Can” tagline, Ray convinced students he knew what they could do. He said other kids’ success wasn’t genetics or destiny—if you wanted something, you just had to push. You (I) wanted that to be true. We didn’t want to let down Ray.

He walked through the high school hallways with celebrity-level fanfare, as an SAT instructor. He built the #1 National Merit Program among private schools in the nation, producing hundreds of National Merit finalists and semi–finalists. No one else did that.

That actually does seem a little like magic.

EB: Ray, what drew you to education?

RD: Before I started school, my mom and I had so much fun playing together. I realized when I was older than our games were educational. She made learning fun and was way ahead of her time. She got her Master’s in computer science in the early ‘80s, before most people even thought about owning computers. I was like a little assistant in her lab, helping grad students print their papers on these computers that no one understood yet. I was learning and teaching before I really even knew what I was doing.

EB: How did you get into test prep?

RD: I always wondered what I was capable of. We didn’t have a lot of money growing up and I didn’t feel like I was a genius, so I wanted to know what was possible for my future. If I could help a friend with a seemingly unsolvable problem, it made me feel like maybe there was hope for me, too.

I know how this sounds but by the time I was in college, I was certain I was going to be a rapper. I was in the studio every night and was going to classes and tutoring during the day.

The thing is, I kept getting drawn into what was happening with every student I worked with. I couldn’t stand the thought of any student thinking they were anything less than capable.

I wanted every student to see the genius within themselves, so they could become great learners and thinkers, and not be dependent on me, or any tutor. I kept taking on more tutoring because I felt like I couldn’t leave these people—who were often family friends—to be dumped into the “test prep world” filled with so many people just looking to make some quick cash.

These students’ futures and how they felt about themselves was too important for that.

Then genius struck me, and I thought, “I can actually help these people, and whatever money I make can fund my rap career.”

EB: Seriously?

RD: Yes! Originally, I didn’t even name the company after myself! I wanted to fade into the background and make music. But anytime anyone called, they were asking, “Is this the Ray Dass program?” So I had to change the name, even though it completely ruined any chance of my having any street credibility.

EB: I’m sure a lot of parents will be reading this interview. What would you say to them?

RD: Don’t let your kids listen to rap music.

I’m joking.

First, come out to the RAY DASS PARENT NIGHT! That’s where I can get into a lot more detail than I can here! If you can’t make it to the event, check out the RAY DASS EXPERT TIPS page we created for this magazine, and then contact us so we can speak with you!

Beyond that, the most important lesson I’ve learned working with so many kids is that most of us are capable of so much more than we realize.

Incredible achievements aren’t usually so much about innate talent, as they are about believing in ourselves and putting in the work!

EB: That’s always been your message, more or less. I wasn’t sure if it was just an angle you used to get us to work harder at first. But it seems like something you live by.

RD: To start this company, I had to believe. I didn’t have money or business experience. I had to believe and literally banked my future on a bunch of credit card accounts. This isn’t just a message to drive students to do their best, it’s what I’ve had to live by.

EB: I haven’t asked you yet about SARA. What was your vision for the app?

RD: I wanted a book that was alive: I wanted to be able to touch a question, and have it come to life, to teach me—in a high quality, well-produced video—and then I’d want to be able to practice until I understood. That didn’t exist, so we created it. It feels like destiny that it was named after my mom, who was a visionary in computer science and gave me my love for learning.

EB: Last question: Do you think you’ll rap again?

RD: I am rapping! I’ve been rapping!

I haven’t stopped!

EB: That’s a wrap!

RD: Em. Stop.

To learn more about Ray Dass’ award-winning prep, with the best results in the nation visit www.raydass.com.