Meet a Dad: Aron Boxer, Founder & CEO of Diversified Education Services - Greenwich Moms

Where are you originally from and how long have you lived in town?

I was born in New York City, and after my mom’s divorce, she moved us to Greenwich on March 1, 1978 — the day of one of the most epic snowstorms in Greenwich history. I was a toddler, so I do not remember it, but I have seen the pictures of the chaos that day.

I live in the North Mianus section of Cos Cob now. I have lived all over Greenwich — Byram, Riverside, and  Old Greenwich. Even though I moved around in my 20s, I always maintained my residency. Basically, Greenwich has pretty much always been home.

Tell us about your family.

My wife’s name is Janette, and I have two stepsons, Carter, who is 13, and Dylan, who is 16. We also have two dogs: Brody, our 11-year-old cockapoo, and Lola, our 5-year-old cavapoo.

You grew up in Greenwich. What was your childhood like here, and how has the community changed since then?

I grew up in the Brookside Drive apartments across from Town Hall. My mom chose that building because money was tight after her divorce, but she got us a three-bedroom apartment because she never had her own room growing up and did not want that for my sister and me. It was $300 a month for a three-bedroom apartment, which is almost impossible to imagine now.

I went to the Family Centers nursery school, Julian Curtiss for elementary school, and then Brunswick for middle and high school. When I started at Brunswick, my mother and stepfather bought a house on Lawrence Street, so I really grew up in the center of town.

I have lived in many places in Greenwich, and one thing that has remained consistent is the town’s beauty, safety, and friendliness. People outside Greenwich sometimes think it is unfriendly or stuck-up because of its affluence, but I have never experienced it that way. To me, Greenwich has always been a warm, beautiful place, and that is why I have called it home for almost 50 years.

What do you love most about being part of the Greenwich community?

I love that Greenwich has a small-town feel, although it’s anything but tiny. There are incredible families, teachers, coaches, small business owners, and people who quietly do a lot of good without needing attention for it.

There is also something special about raising a family and running a business in the same town where I grew up. I just opened a South Florida location for Diversified Education Services in Boca Raton, but Greenwich is home. There is no place like it.

You began your career in financial services before transitioning into education. What inspired that career change?

If you asked the teenage version of me whether I would become an executive function coach and special educator, I probably would have said, “What is an executive function coach?” I originally went into finance because my sister and I used to joke that we were the poorest family in the richest town in America, and I wanted my piece of the pie.

I worked in financial services, including major asset management firms, but I eventually realized it was not who I was. I felt empty because my greatest strengths were not being used.

After being laid off during the 2008 financial crisis, I volunteered in kids’ martial arts classes and realized I had a real affinity for working with children who were distracted, impulsive, or struggling to manage themselves. Many of them had ADHD, just like me. That experience, combined with having a mother who was a learning specialist and special education teacher, helped me put the pieces together.

Education gave me a sense of purpose that finance never did. Working with kids, families, and adults who are struggling gives me a level of satisfaction that makes me feel whole.

What led you to start Diversified Education Services, and what gap did you see that you wanted to fill for students and families?

Diversified Education Services started in 2009, although I did not officially incorporate until 2012. It began as homework help and academic tutoring, then grew into reading support, Orton-Gillingham work, and DES ultimately became a Greenwich hub for executive function coaching and broader academic support.

I saw a clear gap. Many bright students were not failing because they were incapable. They were struggling because they did not know how to plan, organize, manage time, start tasks, study effectively, or follow through.

I have always believed executive function should be taught directly in schools, especially in elementary and middle school. We expect kids to manage themselves, but very often no one has explicitly taught them how.

For parents who may not be familiar with executive function coaching, how do you explain it in simple terms?

Executive functioning is the foundation of how we manage ourselves. In simple terms, I describe it as sequencing: how do you start a task, what are the steps, how do you stay with it, and how do you finish?

That sounds simple, but for many students and adults, it is not. If simply telling someone the steps worked, there would be no need for executive function coaches. My team and I help students build those skills through direct instruction, structure, repetition, and accountability.

What are some of the most common challenges you see students struggling with today?

Technology is an obvious one. It has had a serious impact on children’s ability to focus, sustain attention, and tolerate boredom. Most kids would probably admit that technology makes it harder to focus.

The other major challenge is executive dysfunction. We work with many brilliant students, including students with very high IQs, but executive functioning does not care how smart you are. It is the great equalizer.

Give me a student with average intelligence and strong executive function skills next to a genius with executive dysfunction, and I would put my money on the student with stronger executive functioning. Intelligence matters, but the ability to manage yourself often matters more.

Parents often worry that their child is “lazy” or unmotivated. What do you wish more families understood about executive functioning challenges?

“Lazy” is a four-letter word in my field. I think it is often a shortcut people use when they do not understand what is really going on.

Lazy is not wanting to go to the grocery store on a rainy Sunday afternoon. Having a mountain of assignments, feeling overwhelmed, and then doom-scrolling instead of starting is usually not laziness. It is a problem with initiation, planning, anxiety, avoidance, or learned helplessness.

As a step-parent to two children with disabilities, this is not just professional for me — it is personal. One of my stepsons has ADHD and learning differences, and Dylan has profound autism. Living inside that reality has changed the way I understand behavior, frustration, communication, and what families carry every day.

There is always a reason for behavior. That does not mean every behavior is acceptable, but it does mean we need to understand what is underneath it before we label a child as lazy, defiant, or unmotivated.

As Dylan gets closer to adulthood and gets physically bigger, experiencing his anxiety and self-injurious behaviors breaks my wife’s heart. In recent years, I have stepped in more to insulate her from a reality that is hard to ignore.

He does not mean to hurt himself, but with limited language capability, he cannot fully express himself, and that frustration can become overwhelming. Although his situation is more extreme, I feel so strongly that behavior needs to be understood before it is judged.

How early can parents start helping children build executive functioning skills at home?

Very early. Even a five-year-old can learn to put a plate in the sink, clean up toys, make a bed, or follow a simple routine.

I think chores are one of the most underrated executive function tools. They teach sequencing, responsibility, frustration tolerance, and follow-through. Posting routines in a visible place also helps because most kids need to see expectations clearly.

The biggest trap is permissive parenting. Kids need warmth, but they also need limits. A little structure is not cruel — it helps children feel safe and teaches them that frustration is something they can survive.

What is one mistake well-intentioned parents often make when trying to help their children stay organized or succeed academically?

They often do too much too fast, or they jump in and rescue too quickly. I understand why, because no parent wants to watch their child struggle, but struggle is part of learning.

The key is scaffolding. It is like teaching a child to ride a bike: first you show them, then you use training wheels, then you hold the seat, and eventually you let go. Parents need to build skills gradually, not just take over the task.

Also, yelling and shaming do not help. Kids need instruction, patience, and practice.

What is the most rewarding part of what you do?

For me, it is not always about grades. Many of our students are already high-achieving, but the way they get there creates chaos at home.

When a parent tells me they are no longer playing homework police, or that Sunday night homework battles have calmed down, that means everything. If my team and I can help a student become more independent and help a family have more peace, that is the reward.

Relationships matter. A student’s relationship with their parents, with school, and with themselves can change when they start to feel more capable.

Can you share a success story that has stayed with you over the years?

There are so many, but one that has stayed with me was a boy from Westchester I began working with during his freshman year of high school, right in the middle of COVID. He was hearing impaired, but the bigger issue was confidence. He would not do homework, had learned helplessness, and truly believed he was not smart.

During freshman year, he dropped from geometry to Algebra 1 because he thought he was terrible at math. But over time, I came to see that his reasoning ability was exceptional. It took a while for him to believe it himself.

By junior year, he found his stride. This was a student who had barely been holding a 2.0 GPA, and now he is a mechanical engineering major at a technical institute. He also earned a paid internship at his university, which is offered to only a handful of students.

We recently started working together again, and I do not see that as a failure at all. Executive functioning skills sometimes need reinforcement, especially when life gets more demanding. His growth has been incredible.

What advice would you give to a parent whose child is struggling with organization, time management, or school-related stress?

Other than “call me,” I would say sometimes you need to surrender to win. That does not mean giving up. It means recognizing that your child may need support from someone other than their parent.

As kids get older, their natural desire for independence often conflicts with a parent’s desire to help. The more a parent squeezes for control, the more that control can slip through their fingers.

You are not alone. Whether your child has ADHD, another diagnosis, or no diagnosis at all, executive functioning struggles are common and very real.

What are some simple habits or routines every family can implement to help children become more independent?

Post routines where kids can actually see them, perhaps on a dry-erase board, the refrigerator, the mudroom, or the bedroom. Visual reminders matter.

Also, invite them into the process. Give them a say, offer choices for rewards and incentives. A good plan without a reinforcer will ultimately fail.

Give children one responsibility at a time. If they handle it, give them more. Do not assume that just because a child wants independence, they are ready for all of it at once.

And above all, protect the relationship. You can have the best routine system in the world, but if the relationship with your child is broken, the system will not work.

That’s why parents hire us to offload executive functioning instruction. Dynamics matter.

We love to support local businesses. What are your favorite places when you are in Greenwich?

There are so many. I love LPQ on Greenwich Avenue, and my family and we have been dedicated members of the Greenwich Water Club. I also love Greenwich staples like Louie’s in Cos Cob.

For haircuts, I go to Jafar Tazi Salon on Greenwich Avenue. Javier gives the best men’s haircut in Greenwich, and I do not think you could find a more qualified colorist than Lea Arpell.

Grab coffee or tea?

Coffee for Good, because they employ young people with disabilities.

Workout?

Greenwich Water Club.

Have fun as a family?

Greenwich Water Club again. We especially love Ambrose, and Peggy, who runs yoga there, is one of the best human beings you could ever meet.

Favorite local restaurant for a date night?

L’escale — hands down.

Favorite local restaurant to go out to dinner as a family?

We love Louie’s, a Cos Cob staple, and The Ginger Man is always great. Some of our newer spots are Lotus East and La Taqueria, both on the Ave.

Get your hair done?

Jaafar Tazi Salon on Greenwich Avenue. Javier gives a great men’s haircut, and Lea Arpell is one of the best colorists in the region.

Podcast or book you would recommend?

The Anxious Generation by Jonathan Haidt.

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