Q+A: Alex Rappaport, Flocabulary

“There is no learning without joy,” Flocabulary CEO Alex Rappaport told us this fall.

It’s one hell of a mission: and it’s gotten Alex–and his company–very far. Alex and co-founder Blake Harrison started producing SAT prep hip-hop tunes for teens in 2004. What started as two twenty-somethings on a basketball court is now a 60+ person company with a learning platform1,000+ lessons, complete with videos and interactive activities, that serves K-12 students at 20,000 schools in all 50 states. It’s no wonder Alex landed at no. 15 on Fast Company’s Most Creative People in Business in 2018.

Alex Rappaport, Flocabulary
Alex Rappaport, Flocabulary

Flocabulary has been a beloved, important, and impactful member of the Dumbo community since 2008.

Among their greatest local contributions: the company launched one of the Dumbo BID's first Dumbo Test Kitchen Projects, Big Idea Week (think career week meets super friendly and supportive shark-tank) for PS307 kids, voluntarily creating a curriculum and running the program for four years. Flocabulary continues its civic minded work with it's Flocabulary Community Schools program - which benefits PS307 and the Dock Street School today.

When Flocabulary was celebrating ten years in Dumbo  this past year, we sat down with Alex to talk about the company and its mission, the beauty of making ringtones, Flocabulary’s epic growth over the last two decades, why he thinks everyone should try their hand at waiting tables, and, importantly, what comes next. Rather than summarize it, Dumbo, we figured we’d let you in on the conversation. The full interview is below, edited for clarity and length.

The Flocabulary story is one of innovation and intuition. It’s about playing to one’s strengths, and listening to your customers. It’s about leading with your mission, and about that mission having a lot of heart.

And lucky for you, they’re hiring.

The Flocabulary team celebrates the launch of a new video lesson
The Flocabulary team celebrates the launch of a new video lesson

Clara Schuhmacher: I know you’ve told this story a lot, but humor me: what’s the Flocabulary story? Have you honed it, do you tell it differently now than you did five years ago?

Alex Rappaport: I tell it differently every time!

I was a music producer and musician, living in the Bay area after college. I was desperate to find a path in music, trying my hand at any possible music job. I was a recording engineer; I was a music supervisor for low budget films; I was making ringtones for cell phone companies where the ring tones were just ‘beep beep beep’. I’d make like $25 per ringtone–I’d just sit in my studio all day and try to crank out as many ringtones as possible. What was amazing about that was that they’d send me a list of pop songs to turn into ringtones, and I would have to distill these songs into eight parts and play them on this keyboard. It was actually an incredible musical education­–I loved that job!

By night, I waited tables. I was living the dream of pursuing this creative thing. And then I met this other waiter, Blake Harrison, who was doing a similar thing. But, instead of making ringtones, he was writing a novel, and he would be in coffee shops, in the fog with his turtlenecks, writing this novel.

We used to play basketball everyday before our shifts at the restaurant and one day he says: “Do you know what somebody should do? Somebody should make a rap album with SAT words in it. I had that idea in high school and I’ve always thought somebody should do that.”

I looked at him: That should be us!’

Do you know what somebody should do? Somebody should make a rap album with SAT words in it.

CS: I probably would have enjoyed SAT prep way more had it been set to music when I was a kid.

AR: Exactly. As good students, Blake and I had been bored by the traditional learning methods. Studying for the SAT for example, we’d look at flashcards and try to cram [vocabulary words] in our heads, and that’s the worst way to learn. We were both very passionate about this issue. So we went to my studio, which was really my tiny studio-apartment, and my little recording area was like six feet from my bed, nothing glamorous. We made a demo and sent it around to teachers, students, media outlets and publishers – and the next thing we knew, we had a deal with Spark Notes to make two songs. The feedback was immediate, and positive, from all these different sides. We ended up on MTV news and afterwards everyone was like ‘what is this thing?’

The feedback was immediate, and positive, from all these different sides. We ended up on MTV news and afterwards everyone was like ‘what is this thing?’

CS: From waiting tables to MTV! Not a bad trajectory.

AR: We didn’t have a product and we didn’t know how to make money, so we did a thing we sort of knew how to do: we toured. We put together a live show, and went around to schools, mostly on the East Coast. I’m a singer in addition to producing, so I would sing the hooks, and Blake would rap.

It was an incredible experience, and it showed us what the state of education was. We were visiting all sorts of schools, from fancy private schools in New England, to struggling, under-funded public schools, to church basements’ after-school programs, to community centers. We would perform anywhere that would have us.

We never took ourselves too seriously. We were just like “this is a thing we wish we had when we were kids.” We showed our passion, and the kids­–they really got it, got into it.

We used to say the kids would go from skeptical to scintillated in thirty minutes, to use some of our big SAT words.

A member of the Flocabulary team visits students in Standing Rock, ND to lead on a writing workshop
A member of the Flocabulary team visits students in Standing Rock, ND to lead on a writing workshop

In 2005, we did a show in a special needs classroom here in Brooklyn. A kid came up to us and was like ‘I really enjoyed this.’ He was engaged; he used one of the words from our songs in his sentence when he talked to us. He used the word ‘perfunctory’, which is a word I’ve never heard a person use in conversation. We saw that this was about much more than beats and rhymes and having fun. It was about perception, self-esteem. It was about bringing joy to the classroom. Real learning doesn’t happen without joy. That’s been the mission from day one.

We used to say the kids would go from skeptical to scintillated in thirty minutes, to use some of our big SAT words.

CS: That’s beautiful: real learning doesn’t happen without joy.

AR: What started with SAT words on a basketball court is now more than one thousand lessons, with videos, quizzes, interactive activities where kids can write their own songs. We cover everything from math to science to social studies to life skills to financial literacy.

So yeah. That’s one version of the story.

CS: I think it’s interesting how you grew the business as musicians, not as tech entrepreneurs. It’s what you knew. It makes sense–but it’s unexpected.

AR: We were not a tech start-up until 2011. For the first six years of the business, we were printing audio CDs and workbooks and selling those to schools and school districts, through a sales team.

Real learning doesn’t happen without joy. That’s been the mission from day one.

CS: How did the transition from music biz to tech biz happen?

AR: Around 2010, we realized that print was dead. Classrooms were starting to have technology. When we realized we could do subscriptions, we took all the historical content from the books and CDs, put it into categories and digitized everything. That was 2011. From then, the business has completely sky-rocketed.

The thing that has never changed, from when we were two people to now seventy people, is the mission. The mission animates the product; it animates the team. It’s the backbone of everything we do. It just so happens that now more than ever, the education world is valuing what we do in a way that it never has before. The state of education right now is that the whole child matters–social emotional learning is at the core, alongside academic rigor. And Flocabulary happens to be, by nature of harnessing music and culture the way we do, a social emotional product that has academic rigor attached to it.

Brooklyn elementary school students visit the Flocabulary office to meet the team
Brooklyn elementary school students visit the Flocabulary office to meet the team

If you look at the average reading scores for the last twenty years, for fourth graders through eighth graders, they’re flat­–no impact whatsoever from twenty years of policy, legislation and investment, billions of dollars invested in standardized testing, No Child Left Behind. The other thing that is happening from a data standpoint is that while reading scores are flat, student happiness scores are going down. Only 20% of students feel happy in school, and that’s not okay. Students are not connected, they're not having fun, they're not engaged, and therefore they’re not learning.

So if those twenty years of policy investments didn’t work, what do we need to do? Our answer is: you’ve got to think about emotional engagement and cultural relevance. That’s why Flocabulary is so poised right now to enter its next phase of growth.

The state of education right now is that the whole child matters–social emotional learning is at the core, alongside academic rigor. And Flocabulary happens to be, by nature of harnessing music and culture the way we do, a social emotional product that has academic rigor attached to it.

CS: What brought you to New York?

AR: After three-ish years in SF, I visited New York, and, well, New York was giving me this incredible rush of energy. II remember standing in Washington Square Park and looking up Fifth Avenue, seeing that canyon view of a hundred blocks, and thinking, this is the scale that I want. And it just so happened, that from a Flocabulary standpoint, being in New York gave us access to artists and the media in a way that the Bay area didn’t. Immediately we were tapped into an amazing underground hip-hop scene.

Our first office in New York was an office that we could only access at night-time, on East 23rd Street, across from Madison Square Park. We could only work there from 6pm to 6am. Then we got our own place between 38th and 9th, and we could work during the day. Imagine that. Adulting.

Flocabulary's office in 55 Washington
Flocabulary's office in 55 Washington

CS: How did you end up in Dumbo?

AR: We were getting tired of Manhattan  and we saw a Craigslist an ad for a space in DUMBO, in 25 Washington. We were like ‘What’s DUMBO?’ This was the summer of 2008. We checked it out­–the space looked right out onto the Manhattan Bridge, and we knew: we’re moving in. We left Manhattan, and never looked back.

After 25 Washington, we moved to 55 Washington. Then 20 Jay. Then back to 55. The amazing thing about Two Trees is that they will let you move as you grow, within your lease structure. It’s been a great  experience, as a growing company, to say ‘we’re outgrowing this space, can you find us something else?’ And it happens.

DUMBO has been in many ways a constant character in the story. The core of Dumbo hasn’t changed. I see the same people on the street that I saw ten years ago. It’s a little creative village and it has remained somewhat constant, even as everything about the company has changed. DUMBO is this great backdrop, and I really value that because in a start-up that’s growing as fast as we have, it’s really nice to have some constancy. DUMBO has been our anchor.

DUMBO has been in many ways a constant character in the story.

CS: What was the journey from two employees, to seventy employees like?

AR: It was pretty organic from about two to thirty. Not much had to change. Around twenty-five, thirty people, there was an inflection point where our band of merry individuals became a band of tribes. That’s where management and process and meetings started to become a thing. It seems corporate, but you have to put these things in place to actually foster good culture and creativity. Otherwise, you have breakdowns in communication, and chaos.

For me the hardest part of running this company is the scale of the operation. Not the product, not the market, not the sales, not the fundraising–it’s what happens day to day in the office that is really challenging. There’s a joke around here that’s like “In your prior jobs how did this work?” and everyone looks at us like “oh yeah, you guys were waiters, yeah, never mind.”

CS: Waiting tables requires multi-tasking and management of people and personalities, though. Seems like good practice for being CEO. Everything is related.

AR: Yes, and it requires empathy and communication. I’m in that camp that says everyone should be a waiter at some point. I think it’s a great exercise in humility, it’s a great exercise in hard work, and it’s a great exercise in communication.

We are very much focused on this problem of student happiness – which equals engagement, learning, success. We’re taking it to the next level. We are leveraging technology to support student creativity, amplify the student voice.

CS: Being a sound engineer in a recording session is similar. You have to be able to read a room, keep people motivated to create. So what’s the next phase of growth look like?

AR: We are very much focused on this problem of student happiness – which equals engagement, learning, success. We’re taking it to the next level. It’s not enough anymore to just have kids watch our videos. We’re turning the tables, and we are having students writing their own songs in the product. We’re planning to launch a recording function embedded in the product, and potentially add a way for kids to make their own videos as well. Kids these days are digital natives who expect far more out of their learning experience. We are leveraging technology to support  student creativity, amplify the student voice.

An artist records a track in Flocabulary's in-office recording studio
An artist records a track in Flocabulary's in-office recording studio

CS: Must be fun to have a recording studio right here in the office.

AR: Yes! It has been a game changer. We used to record outside of the office, around the neighborhood – in the basement of 68 Jay, in 10 Jay for a long time, really in what were the the dungeons of DUMBO, which was great in its own way. Now, we can record on our schedule. And it’s great for our team, for press. This is not just a boring tech office: we have a studio. It’s also our cool factor when students come to the office for a visit.

CA: Ok, last question. I always have to ask: what is your favorite place in DUMBO?

AR: Hm. I do have an affinity for the pile of rocks to the left of the beach, where it says “Don’t Sit on the Rocks.” Blake and I used to sit there and figure stuff out in the very early days.

But really, Superfine is my favorite, if I have to give you an answer. That’s where we used to do all of our celebration lunches, our holiday party. Superfine is very much everything that I could ever want.