Our Q&A with the Insight team continues this week with Ajit Jain, the Co-owner and Co-CEO of Insight Education! Celebrating our 18th Anniversary, Ajit looks back on his fondest memories. 

Where did you go to college?

I attended the University of Toronto in Toronto, Canada where I grew up. I studied Civil Engineering with a focus on structural engineering and construction management.

What is your favorite memory from your college days?

My engineering program was quite brutal so the happy memories are few and far between in all honesty. But I do remember an all-nighter in my second year for an environmental engineering class. We had to write code for the processes related to a water treatment facility and there was a bug we couldn’t find. Our group of four was going nuts trying to crack the problem and finally my friend, who is still my friend today, figured it out. We were filled with emotions that I had never before felt for schoolwork. It was likely a combination of relief, joy, and exhaustion all rolled into one and it drove us to dance around the computer lab like lunatics.

What inspired you to become a college admissions counselor?

My path to Insight wasn’t an obvious one. Purvi Mody and I met at the Stanford Graduate School of Business, pursuing our MBAs. Her lifelong focus had been education and I was looking for a change career-wise. After spending my summer at McKinsey & Co on two separate strategy consulting projects, influenced by the entrepreneurial spirit at the Stanford GSB, I was inspired to think of going out on my own after graduation. Although I interviewed and got offers from traditional corporations for full-time post-MBA work, nothing really got me excited. Serendipitously, while in Boston for an interview, an education company in Cupertino posted about selling their client list. Since I had no background whatsoever in education or college admissions, other than applying for undergrad and grad schools, Purvi Mody and I teamed up to make a bid for the client list and start Insight Education. Early on, I was motivated more by the entrepreneurial opportunity that Insight presented but as I slid into the counseling role I realized how valuable a role we play in the lives of each individual student and their families. And that continues to motivate me today.

What is the best thing about being a college admissions counselor?

There are two things that I enjoy most. The first is the moment, as a counselor, when you realize that an essay has finally made it to the finish line. There is no scientific method that tells us when an essay is final. Rather, it is a feeling you get that crescendos as you read the essay and ends with fireworks. The second is results season. As kids hear back from the colleges they’ve applied to and get their offers of admission, our office is filled with both nervous tension and pure joy. The way a student chooses to share the news and the words they use is just as exciting as the result itself! At this point in their lives, barely young adults, seeing and feeling that sense of accomplishment that they’re overcome with, with never gets old.

What is the most challenging thing about being a college admissions counselor?

One of our responsibilities as college counselors is serving as mediators between the student and his/her parents. This requires a skilled diplomacy and a great deal of patience. Especially when managing expectations in terms of a student’s preferred list of colleges to apply to and a parent’s preferred list.

Reflecting on the fact that Insight is now 18, what is your best memory from this time?

My fondest memory is hearing back from my first student to have been accepted to Stanford University. It was my first year working as a college admissions counselor at Insight and I was learning and doing as I went along. Seeing his email, which I believe said, “Yippee!” was a special Insight moment for me.

Looking forward to the next 18 years, where do you see Insight Education? What has changed, and what hasn’t changed? 

I hope that the company can continue to grow while honoring our mission and values. Many companies struggle to stay true to their identity as they grow and in our case, working with high school students, it is imperative that we don’t allow that to happen. 

Tell us about your favorite restaurant in the Bay Area

I have a nostalgic place in my heart for Celia’s Mexican Restaurant in Palo Alto because that was where I had my first meal after moving here. It was also where I celebrated my first Bay Area birthday and where my oldest son had his first birthday party!

Who is your favorite sports team?

Since I am obsessed with sports (along with my 7 year-old son), this is a challenging question! As a native Torontonian, I would have to say that I love the Maple Leafs, Blue Jays, and Raptors. The Leafs and Blue Jays were around when I was a kid so there is a lot tied to my childhood that those teams remind me of. I will never forget the Blue Jays winning two World Series, back-to-back, in 1992-1993. Celebrating on the streets of Toronto was amazing! The Raptors came along when I was in college so it was a huge deal in Toronto that Canada was finally part of the NBA. Locally I do love the San Francisco 49ers and they are by far my favorite NFL team.

What do you like to do in your spare time?

I wish I had a more exciting answer. But my spare time is spent with my family/two boys. I am especially busy with my older son as I zip him around from his guitar lessons to baseball and football practice. Life is busy but fun!

If you could pick any 3 people in the world to invite to a dinner party, who would they be and why?

I would invite Wayne Gretzky, Bill Clinton, and Bono from U2. Wayne Gretzky is my idol and in my opinion the greatest athlete of all time across all sports. I grew up watching him and idolizing him. I think that Bill Clinton and Bono are very similar individuals in spite of their very different paths. They can captivate a stadium filled with people or they can connect with a person one-on-one. Their charm, wit and concern for social issues is compelling and would make for an unforgettable dinner party.

If you had to pick a motto to live by, what would it be?

Don’t be afraid.

What is your favorite weather season and why?

As a Canadian living in California I always say that summer is every day. While it may get a bit chilly here and there in the Bay Area “winter” it doesn’t fluctuate enough for me to really sense a difference. Growing up I preferred Spring and early Fall because the weather was nice but less humid than a Toronto summer.

If you weren’t a college admissions counselor, what would your dream job be?

I would play centre ice for a professional hockey team and for the Canadian National Hockey team in the Olympics.

Where in the world would you love to travel?

I would appreciate the chance to drive across Canada one day with no calendar or schedule rushing me along. In spite of having grown up there, I know much more of the United States than I do Canada. Further out I’d love to visit Brazil, Argentina and possibly Kenya.

Any parting words of wisdom or advice to students?

You miss 100% of the shots you don’t take. Similarly, you will not attend 100% of the college you don’t apply to.

Welcome to a new Insight Series: Q&A with your Counselors. We’re starting off with our Insight Counselor Zach Pava, who works with us out of his hometown in Boston. Get to know Zach and a little more about why he loves being a College Admissions Counselor!

Tell us about Insight Education Newton?

We offer a comprehensive yet personalized approach to college admissions counseling. Counselors work one-on-one with students, in conjunction with their families, and schedule recurring meetings to aid in academic support, course selection, setting goals, staying organized, test prep and decisions. We also cover extracurricular activity building, help with applications and inquiries for volunteering, summer internships and jobs, interview prep, major selection, college research, essay development, application review, and more!

Where did you go to college? What is your favorite memory from your college days?

I graduated from Trinity College in Hartford, Connecticut with a degree in psychology. Trinity is a small liberal arts college located between Boston and New York, and combines a beautiful, green college campus with the resources of a small city. I built life-long friendships with terrific roommates and enjoyed playing intramural sports on the quad. My favorite classes included Mass Media & Pop Culture, Creative Writing, & Social Psychology.

How long have you been with Insight Education? 

I started working with Insight Education in May, 2013 and am now entering my 5th full season as a college admissions counselor. I look forward to many more as we continue to grow this terrific company.

What inspired you to become a college admissions counselor?  

I have worked with students of all ages ever since graduating college. As my students have grown older over time, so has the need to build services for older students as they’ve matured from 5-year-olds to middle schoolers to teenagers on their way to applying to and selecting the “right” college for them. It’s truly a privilege to witness their growth and progress over a period of years and I have had the rare opportunity to build long standing relationships with families across the country.

What is the best thing about being a college admissions counselor?

My favorite part about my job is being able to help students grow socially, to become their own people, to maximize their potential and find their voices, and ultimately, to be happy with their choices. I want them to head to college with the confidence and ability to make decisions that will positively influence their futures.

What is the most challenging thing about being a college admissions counselor?

We work long hours during the application season, which runs from about July to December each year.  I casually refer to it as our “tax season.” I think sometimes finding the appropriate balance between work and family is challenging, particularly when students rely on you so heavily for support.

Tell us about your favorite restaurant in the Newton area

Mandarin Cuisine has been a personal favorite of mine since I was young. I originally went there on Sunday evenings with my family and continued regular lunch visits with my best friend during high school and beyond. They are always very friendly and deliver great food with incredible speed. The scallion pancakes are a must!

Who is your favorite sports team?

The Boston Celtics have been the team I’ve followed most passionately since I was young. The Red Sox are a close second though and I try to get to a few games a year at the TD Garden & Fenway Park. Seeing both play in the Bay area against the Warriors and Giants was exciting.  It’s fun to root for your teams as a visitor and you learn to appreciate the passion of fans in other areas as well. There is a healthy respect between Boston and San Francisco.

What do you like to do in your spare time?

I enjoy doing fun activities with my family. My wife, Tarah, and I have two young children, a 3-year-old boy named Benjamin, and a baby girl, Emily, who joined the family just this May.  We recently returned home from Maine, where we spent time playing on the beach, took trolley rides around town, and enjoyed the freshest lobster in the world.

If you could pick any 3 people in the world to invite to a dinner party, who would they be and why?

I’d pick Barack Obama because he is the best public speaker I’ve ever heard. I’d pick Patriots coach Bill Belichick because he is the worst public speaker I’ve ever heard. And I’d pick comedian Larry David to see how quickly he could make each of them retreat from the table.

If you had to pick a motto to live by, what would it be?

“Hope is a good thing, maybe the best of things…” No wait I’m sorry, that’s from The Shawshank Redemption 🙂 Seriously though, I would tell students in particular to “Try new things, as many as you can. The older you get, the fewer opportunities there are to explore your passions and find time for hobbies.”

What is your favorite weather season and why?

My favorite season by far is the fall. The leaves changes color, the summer heat disappears, my kids enjoy Halloween, and football returns. My favorite weather exists in October, when I can walk down the street comfortably in blue jeans and a t-shirt, a mellow breeze accompanying my stroll.

What is your favorite holiday to celebrate and why?

My favorite holiday is Thanksgiving, a time of family gathering, great food, and (usually) no snow on the ground yet.

If you weren’t a college admissions counselor, what would your dream job be?

I would either be a full-time screenwriter creating a new film comedy every 18 months or a professional poker player in Las Vegas, one of my favorite hobbies during my free time.

Where in the world would you love to travel?

I would love to visit Barcelona, Australia, and Italy, none of which I have been to.

Any parting words of wisdom or advice to students?

Be yourself and stay true to who you are. There will always be people in your life who want you to travel a specific path, either directly or indirectly. Find what you truly love and do whatever you can to pursue it.