Alex Rappaport



Alex Rappaport, 36, wants to get kids really excited about learning. He cofounded education startup Flocabulary more than 10 years ago, which uses hip hop to teach kids about things like dividing fractions or the history of ancient Egypt.


He also founded Big Idea Week, which pairs New York City students with mentors to teach them about entrepreneurship and collaboration. Now in its fourth year, Big Idea Week has grown from one Brooklyn middle school to 1,500 students in 18 schools in Brooklyn, Queens and Manhattan.


The week starts with presentations from people at companies like Facebook, Etsy and MakerBot. Then the kids are unleased to create their own business ideas that solve a problem in the world. Past ideas have included everything from a kid-safe Instagram to a smartwatch for people with diabetes. This Friday, they’ll present their ideas back to the judges.

What about your job most excites you?

The uncertainty of it. I once read that conditions of uncertainty are what distinguish a startup from a small business. Flocabulary has been around since 2004, but we’re still very much a startup. Every day is an adventure, and that’s what gets me out of bed in the morning and/or keeps me up at night.

I also love the impact we’re having with Flocabulary. You can see that in formal data, but you also see it in emails, Facebook messages and tweets. Here’s a tweet we just saw recently. It sums it all up for me.


How many hours do you sleep?

I work hard to get more than 7 hours sleep. I feel unstoppable on 8 hours, I function on 7 and I’m a waste with 6. My wife and I have a rule: in bed before 10:30, lights out by 11. We break that rule about 90% of the time. Another rule we break all the time is no screens in bed. It’s well known that screens trick our brains into thinking it’s daytime and make it hard to sleep. And yet we can’t resist watching Game of Thrones. My daughter wakes up between 6:00 and 6:30, so that 11 o’clock cutoff is key if I want to get my 7+.


What do you eat for breakfast?

My standard breakfast is a fried egg on a piece of whole wheat toast with a half a grapefruit on the side. It’s like a breakfast from the 1950s. But it’s the only thing that gives me enough energy to bike to work and not have to eat breakfast again at 9:30. My daughter loves it too. We eat together every morning.


If you could pitch to one person, who would it be?

Dave Eggers. First of all, I love his writing. A Heartbreaking Work of Staggering Genius, What is the What and Zeitoun made a huge impression on me. But he’s also done such incredible work in education. His tutoring centers in disguise are brilliant. Combining education with something kids genuinely love is at the core of Flocabulary as well. The difference is that we choose to use rap instead of pirates and superheroes.

As for the pitch, I created a program called Big Idea Week that brings mentors from tech companies into elementary schools for a week of creativity and problem solving. I have a hard time wrapping my head around how to scale it up while maintaining its integrity as a community program that prizes face-to-face contact above all else. I’m pretty sure Dave Eggers could help.


What’s on your home screen?

My homescreen, like my Instagram, is dominated by my daughter.


How often do you exercise?

I have been reduced to using my commute for exercise, but that can be pretty good in NYC. If it’s nice, I ride my bike to DUMBO. It’s 6 miles each way and pretty hilly. Prospect Park feels like Mt. Everest in the morning. But I get to work awake. If I take the subway, I always make a point of taking the stairs. If I’m lucky, I get out for a run on the weekend, generally behind a jogging stroller.


What app can’t you live without?

The New York Times. I look at the top stories every morning and night. I’m one of those boring people who always says, “Did you see that Times article about…”


What's your favorite city and why?

New York has its claws in me. It has an energy I’ve never found in any other city. I remember visiting in 2004, just as we were starting Flocabulary out in San Francisco. I was standing in Washington Square Park, looking up 5th Avenue. It felt like I could see for a hundred miles, looking up through what seemed like a canyon between the buildings. And the bustle of people and creativity, mashed up with the history of the place, just sort of carried me away.

At that moment, I decided that we needed to move the business to New York if we were going to make it. We needed to ride that wave of energy. It makes you fight and it makes you hustle.

I’ve also had the privilege to see another side of New York through my work with Big Idea Week, particularly how much New Yorkers care about giving back. Like so many other cities, New York is suffering from growing income inequality and segregation, so it’s inspiring and hopeful to see members of the business community carving out time to make an impact.

Students touring Etsy as a part of Big Idea Week


What’s the most important company we’ve never heard of?

There’s a DUMBO-based company called Biolite that’s doing amazing things. They designed a line of stoves that converts burning wood into storable energy that can charge a cell phone or power LED lights. They sell one version to campers in the consumer market and then distribute a lower-cost version to families in the developing world. The stoves help people generate power and stay connected, but they also cut down on wood smoke from cook fires, which is ultimately helping with public health.

Biolite has provided mentors for Big Idea Week for the last 4 years, and they’re always a big hit with the kids. Part of this is because they’re solving a major social issue and students naturally gravitate to products that help people. But it’s also because they get to light stuff on fire in a lab. Really cool.

Biolite Director of Design Anton Ljunggren presenting as a part of Big Idea Week.


Are there any social platforms you refuse to participate in?

Not on principle. It’s just a matter of not having time. I try to stay on top of everything even if I don’t use it. It’s very easy to start losing touch with all kinds of culture when you’re a parent -- music, technology, fashion, food. I’m desperately hanging on and probably kidding myself.


What are you reading right now?

The book I read most recently was Between the World and Me by Ta-Nehisi Coates. As Toni Morrison said, it should be required reading for every American. I’m amazed at how little we reveal about our history of slavery and white supremacy in social studies textbooks. These are the stains and scars in our past, and I think we all need to be talking about them before we can really move forward as a society. Flocabulary pulls no punches when dealing with difficult topics in history, and we’re proud to be starting important conversations in classrooms.


Do you think there’s a tech bubble?

Yes. Companies with unproven business models are getting outsized valuations on speculation and hype. Entrepreneurs are seduced into taking moonshots with the most disruptive products in the largest possible markets. They raise big rounds at high valuations and think that’s the definition of “making it,” but some of the VCs making the investments are making nine other gambles and expecting that most of their deals won’t work out. This creates a misalignment of expectations.

You can blame the VCs for hyping the market, or you can blame the entrepreneurs for being cavalier. But I also blame the broader startup culture.

Success should not be defined by how much you raise. It should be defined by whether you can build a product or service that people want to buy and use in a sustainable way. It’s easy to raise money. It’s much harder to execute on a product and build a sustainable business. Flocabulary bootstrapped our way to significant scale, and I think a lot of companies would be better off doing the same.


Best piece of advice you've been given?

You have to show up. My mother used to say this when I was too nervous to go to school dances. I interpreted it literally and metaphorically. You have to be physically present if you want to make something happen, and you have to show up with your best self. You may not know what the outcome will be, but you can be sure nothing will happen if you sit things out.


What keeps you up at night?

Ask my wife. I have a very active brain at night. I talk and walk in my sleep. I think I’m working things out in a semi-conscious state. Once I got up and took all of the pictures off the wall and stacked them on a couch. The worst part is this didn’t even happen at my house; I was staying with someone I didn’t know very well. The source of the stress tends to be work, generally the sudden demise of the business. These fears are really amplified at 3 a.m.


If you could tell your 18-year-old self one thing, what would it be?

Do the reading.

Photo Credits: Alex Rappaport, Shutterstock, Tory Williams, Rowa Lee.