Jermaine Gassaway grew up in Washington, DC, at a time when his zip code decided which school he could attend. He did not accept that quietly. As a teenager, he wrote to the Board of Education asking to transfer out of an underperforming school. The answer was no. So he found another way out: a scholarship to The Piney Woods School, a boarding school in Jackson, Mississippi, more than eight hundred miles from home.
That decision at fourteen set the direction for everything after it. Jermaine became the first person in his family to go to college, graduating from Johnson C. Smith University in Charlotte with a degree in business administration. In 2010, he joined Teach For America as a corps member in Detroit, teaching third through eighth grade. Most of his students scored proficient or advanced on the state assessment, a result that pointed him toward school leadership rather than away from the classroom.
Years later, he turned that experience into something lasting. His book, Unopened Books: Multiplying the 2%, looks at how few Black men work in American classrooms and why that gap matters for students. He followed it with When You Arrive: A Children’s Book About Racism, written for kids who are already asking questions adults sometimes avoid.
Jermaine still reads constantly, still runs most mornings, and still believes a student’s zip code should never be the ceiling on their future.
What is your typical day, and how do you make it productive?
I read before most people are awake, usually thirty to forty minutes with coffee and no phone nearby. That quiet stretch sets the tone. The rest of the day fills up with meetings and writing, but I try to protect that first hour because it is the only part of the day nobody else can claim.
How do you bring ideas to life?
I write things down the moment they show up, even half-formed. Both of my books started as notes I kept adding to over months. I do not wait for an idea to feel finished before I start shaping it. I just keep returning to it until it is.
What’s one trend that excites you?
I like seeing more schools treat independent reading as real instructional time instead of a filler activity. Giving kids books they actually choose, not just the ones on a list, changes how they talk about reading.
What is one habit that helps you be productive?
Running. I started it as a way to clear my head and it turned into the thing that actually organizes my thinking. Some of my best sentences have come to me three miles into a run with no notebook in sight.
What advice would you give your younger self?
Ask for help sooner. At fourteen, I thought leaving home for boarding school was something I had to figure out entirely on my own. I did not need to carry that alone, and neither does anyone else staring down a hard decision.
Tell us something you believe almost nobody agrees with you on?
Summer reading lists often do more harm than good. When reading feels like an assignment handed out in June, kids treat it like homework they are dreading instead of something they chose. I would rather a student finish ten comic books by August than start one assigned novel and never open it again.
What is the one thing you repeatedly do and recommend everyone else do?
Ask kids what they are reading right now, not what they read last. It is a small question that tells you a lot, and it tells the kid you actually want to know.
When you feel overwhelmed or unfocused, what do you do?
I close the laptop and go run. It is not complicated. I come back to the problem afterward and it almost always looks smaller than it did an hour before.
What is one strategy that has helped you grow your business or advance in your career?
Writing down specific numbers instead of general impressions. When I started tracking exact reading and math growth for my students instead of just a feeling that things were improving, I could see which strategies were actually working and which ones just felt good.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
My first year teaching in Detroit, I underestimated how much structure young students needed before any lesson could land. I spent too much energy on content and not enough on routines. I rebuilt my classroom management from scratch that winter, and by spring, the difference in how much students could actually absorb was obvious. I learned that structure is not separate from learning. It is what makes learning possible.
What is one business idea you’re willing to give away to our readers?
A subscription box that pairs a children’s book about a hard topic, like race or grief, with a short discussion guide for parents who do not know where to start the conversation. The book does the opening. The guide does the rest.
What is one piece of software that helps you be productive? How do you use it?
I keep most of my writing in Google Docs because it is simple and lets me draft from anywhere, including my phone when an idea hits on a run.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
Between the World and Me by Ta-Nehisi Coates. It is written as a letter from a father to a son, and it shaped how I think about writing honestly to young readers about race instead of softening everything for comfort.
What’s a movie or series you recently enjoyed and why?
Abbott Elementary. It gets the exhaustion and the small victories of working in a school right, and it does it without making teachers into either saints or punchlines.
Key learnings
- A single early decision, like leaving home for a scholarship at fourteen, can reroute an entire life if someone is willing to act on it.
- Treating independent reading as a choice rather than an assignment can change how young people relate to books.
- Tracking specific, measurable outcomes reveals which teaching strategies work better than general impressions do.
- Classroom structure and routines are a precondition for learning, not a separate concern from it.
- Writing for children about difficult topics, like race, works best when it opens a conversation rather than trying to resolve it.