Lifelong Lessons From Teachers That Edtech CEOs Still Live By

Teaching and Learning

Lifelong Lessons From Teachers That Edtech CEOs Still Live By

By Tony Wan     May 7, 2019

Lifelong Lessons From Teachers That Edtech CEOs Still Live By

It can often take until adulthood before one finally understands the wisdom imparted by our classroom teachers. Sometimes, it’s not until we lead and guide others that we appreciate what educators do every day.

Starting and running an education company isn’t for the faint of heart. In celebration of Teacher Appreciation Week, we asked industry leaders to recall one teacher whose advice has guided them through the ups and downs, twists and turns of the entrepreneurial journey.

Some of the most memorable lessons didn’t make much sense as a kid. Others start off as small gestures—like a hug or a handshake. Sometimes, those special moments meant staying after school to help—or staying in touch long after one has graduated. Whenever and however they happen, these experiences make an indelible mark beyond the classroom.

To every educator laying the groundwork for the future, Happy Teacher Appreciation Week.

Lifelong Homework Lessons

Larry Berger, CEO, Amplify

Larry Berger, CEO of Amplify

Ms. W was my 10th grade English teacher. She was quiet and prim and seemingly from a more formal era than the noisy Reagan decade we were navigating. She gave us ambitious, intellectual things to do with literature and helped us choose hard things to read.

But most vivid for me were a few times when I worked especially hard on an essay, and thought I’d had a literary epiphany, only to see my efforts doused in red ink. “Your thesis is banal. No great author is didactic or moralistic” sent me to the dictionary for all three adjectives.

At first I was indignant that the principle of A-for-effort no longer applied. But over time I realized I was being welcomed into the world of serious thinking about literature and life, where not all one’s ideas are good, and where all insights exist in a tradition of great thinkers who have grappled with the same questions.

I wanted to know what she knew, to have read what she had read. Most of all I wanted to make something she might acknowledge as an original contribution to the field. While other teachers were patting me on the back, she was pushing me toward the fire. I put in the extra time and visited her after class and began to see another side of Ms. W. She was entirely authoritative in class, but it turned out she was also a 28-year-old, a few years out of grad school, trying to sort out if she was meant for this job. I just googled her and it seems she left teaching soon after.

Jess Gartner, CEO, Allovue

Jess Gartner, CEO of Allovue

My 10th grade English teacher, Mrs. Santoro, was the best writing teacher I ever had. She gave me a B- on my first writing assignment, which felt like an F to me. The whole paper was covered in red ink. I was devastated at first, but she encouraged me to rise to the challenge. I learned so much from her that school year that I jumped at the chance to take an elective course with her my senior year and still keep in touch with her today.

Eli Luberoff, CEO, Desmos

Eli Luberoff, CEO of Desmos

I had the privilege of having Liliana Klass as my 5th grade teacher. She was 4'10" of joyful, patient, resilient teaching. When we weren’t paying attention, she’d count down, “3… 2… 4” and we’d all giggle and immediately focus. She led us through month-long projects, like when we measured the circumference of the Earth as Eratosthenes did using shadows and geometry.

I remember a 1-page paper that I turned in, a paragraph short of the target. She gently chastised me and, in a huff, I adjusted the margins, increased the font a bit, and said, “Here you go. A page.” I don’t remember her exact words but it was something to the effect of: “When I push you for more, it’s for your sake, not mine. If you’re proud to turn this in, I’ll take it.” I went back to work and have carried that conversation with me for 20 years.

Megan O’Connor, CEO, Clark

Megan O'Connor, CEO of Clark

In 3rd grade, my teacher Mrs. Overstreet asked me to start coming in after school to practice my spelling and reading. At first I didn’t think anything of it, but in time it became clear that she believed I had dyslexia.

Because Mrs. Overstreet took extra time to work with me, she identified an issue that had gone unnoticed up until that point. Without her, I wouldn’t have gotten special reading comprehension therapy that allowed me to become a straight-A student.

I still have to work hard to overcome my brain’s inclination to read right to left, but what I've learned from this is that persistence always wins. Putting in the hours, training and never giving up produces outcomes. Now as a CEO, I would say endurance is my superpower.

Speak Up, Be Heard

Waine Tam, CEO, Selected

Waine Tam, CEO of Selected

Mrs. Rich was a teacher who supported extracurricular programs, such as the school- and district-wide speech and spelling bee competitions, at my elementary school. She worked tirelessly for hours after school with 4th to 6th grade students preparing for those competitions. She taught us how to consistently prepare and refine our practice, remain calm under pressure, and manage adversity when it inevitably strikes. To this day, I still recall her tips whenever I prepare for a public speaking engagement or pitch!

Tony Weaver, CEO, Weird Enough Productions

Tony Weaver, CEO of Weird Enough Productions

Being an entrepreneur means believing in yourself and your ideas. My 8th grade English teacher Mrs. Craft taught me that first hand. When I had trouble speaking up in class, she told me to never be afraid to make myself heard. She taught me that my voice mattered, and now, I use comics to let students around the country know their voice matters too.

Always in Touch

Chip Paucek, CEO, 2U

Chip Paucek, CEO of 2U

Education fundamentally transformed my life. Without it, I would not be who I am or where I am today. Many teachers impacted me throughout the years but one, while I was an undergraduate at George Washington University, taught me lessons that still impact how I communicate, think and lead today.

Professor Jerry Manheim was the department chair when I was a political communications major at George Washington University. He taught me how to write, think critically and authentically articulate my point of view. I also learned quickly in his class that the word media is plural, a seemingly small but meaningful truth. Above all, Professor Manheim showed up for me—both while at GW and still today, with his wife, at every 2U annual meeting.

Teachers don’t only teach; they guide and shape human beings and leaders. Thank you to every teacher who showed up for me over the years. I am eternally grateful.

Joanna Smith, CEO, AllHere

Joanna Smith, CEO of AllHere

I remember the last time Ms. Valentine and I talked. It was a particularly rough day, and I was sitting outside our office space, wondering if I had made the right choice to go into edtech. Building a team was hard. Figuring out messaging was harder. It felt like I was spinning my wheels—too slow, too young, too uninformed, too black to make a difference. And I felt like griping.

Ms. Valentine was always a thoughtful listener, and that day, in her own way, she told me to stick with it. As long as the “why” was pure, she said, God would work the rest out. She was proud. She encouraged me to stay committed.

I’d first had her as a kindergarten teacher 20 odd years earlier. She was, then, a fiery Puerto Rican woman who ran her class with the precision of a drill sergeant and the love of your favorite abuela. At once you could feel the depth of her support and strength of her challenge to not take our surroundings—shared books, worn buildings, and busing twice a week to access advanced curricula—as an assessment of our capabilities. She always said we needed to believe we could fly, and I believed her.

She passed away two years ago, just a few months after that last talk. But, to that fiery Puerto Rican woman who decided to teach a class of kindergarteners in the Liberty City section of Miami—encouraging them to dream, set high standards, never take “I can’t” for an answer, embody persistence, and model humility—who created a learning environment full of risk-taking and love, empathy and joy, I thank her. Her lessons and advice took me from the first days of school to the earliest stages of starting a growing company. I owe my career in edtech to her.

Ms. Valentine: You helped this little girl truly believe she could fly, and in so doing continuously inspire me to follow your example and dedicate myself to ensuring every child has the opportunity to get an excellent education. Happy Teachers Appreciation Week to you and all the teachers who construct our future’s foundation, every day.

The Humanity of Education

Michelle Ching, CEO, Literator

Michelle Ching, CEO of Literator

Mrs. Beach was my first grade teacher. Everyday, before any other morning routines and rituals, she would have each one of us come to her desk for a hug. When I led a classroom of my own, I knew immediately that I’d put the same practice in place. (I adjusted it a bit to include high-fives and handshake options too.) I did it because I wanted to make sure my students knew I loved them—just like Mrs. Beach had. It was a small gesture but it set the tone: you belong, you are safe, you are loved.

I think often about how we might practically create a more loving, kind, and just world and I go back to this: teachers are doing that work every single day. Their work also happens to be extraordinarily challenging. The work I do now with Literator is rooted in deep empathy for the challenges teachers face and great respect for their relentless commitment to their students. On the most difficult days I am humbled by the bigger cause at hand: to be in service of teachers.

For Mrs. Beach, who made it look effortless to be generous and patient, and who labored long before and after those morning hugs, to create a classroom that helped me become who I am today.

Mike Teng, CEO, Swing Education

Mike Teng, CEO of Swing Education

Behind facts and narratives of history, there are always real people and humanity. That was the lesson my 10th grade U.S. History teacher Mr. Tate ingrained in me. He turned historical figures into real people with flaws and weird idiosyncrasies and personal motivations.

In that same vein, as an organization that works with schools, it’s incumbent on Swing to always remember that we’re in the business of people. We succeed when we improve the day-to-day lives of students, administrators, and educators. Not everything always boils down to numbers and figures, and that’s the best part about being in the education business.

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