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“I started a movement to solve the Entitlement Epidemic” With Neha Gupta

“Wash, Rinse, Repeat. While having a lofty vision can be sexy, the truth is, all you need to do is find one paying customer who is not…


“Wash, Rinse, Repeat. While having a lofty vision can be sexy, the truth is, all you need to do is find one paying customer who is not your friend, not your mom not your dad, not your sympathetic sister. This one paying customer will help you to learn what your business solves and why it matters. I started my company, years ago with $500 dollars, an ugly logo, and an immigrant hustle. I put an ad in my college newspaper seeing if any family in the neighborhood wanted to hire me. I put myself out there. And, I will tell you it all started with one customer…Once we had a solid system down, it was wash, rinse, repeat. But you should know, that to get to this point, it requires an insane amount of execution. It required blood, sweat, and tears before I finally figured the system out over time. And the sad part is, so many entrepreneurs quit before they hit this part.”


I had the pleasure to interview Neha Gupta. Neha is changing the way teenagers grow up. Her company College Shortcuts is helping thousands of students across the globe to find their passion.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

NEHA: I was fifteen years old and my school had a program where we volunteered at a lower income school to tutor elementary students. I remember going to the school and tutoring students in dance and art and realizing how much I enjoyed it. While the focus primarily was to help the students, I felt like I was receiving so much in return. Years later, I decided as a part-time job in college to start tutoring, and it all started with one student. I ended up working with her on time management, motivation, finding her passion, and ultimately being a mentor. I couldn’t believe I was getting paid to do this, because it was so much fun and I was creating an impact. It definitely didn’t follow the doctor, lawyer, engineer formula most South Asian females are force-fed. From there, College Shortcuts was born and over the last 12 years, it has turned into a global educational firm that now pairs mentors and consultants with teenagers all over the world.

Can you share the most interesting story that happened to you since you began leading your company?

NEHA: I would say that one of the most interesting stories is that through entrepreneurship I have learned more about myself than ever sitting in a cubicle. I started my personal development journey over the last eight years, and have discovered more about myself. At one point, I was at a small private Business Mastery group with Tony Robbins in Fiji, and I remember asking him a simple question one-on one, “Tony, we have the exact same DISC profile. How do you deal with frustration with others when you have such a high D? (D is for decisiveness)” Tony laughed and kissed me on the forehead and said, “Neha, you can’t kill a rabbit with a cannonball. You will obliterate it.” While this sounds like an odd response, it was exactly what I needed to hear. At the time, I was struggling with truly building relationships with my team members, getting frustrated with them when they didn’t do what they needed to do, and I slowly realized that relationships are everything in business.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

NEHA: I actually don’t have a funny mistake. Most of my mistakes I take pretty seriously — and I am constantly trying to improve how we do what we do every single day.

What do you think makes your company stand out? Can you share a story?

NEHA: I believe that what makes us truly stand out is that we are the one of the only female run companies of our size that focuses on the importance of mentorship of teenagers in a world where they are truly struggling more than ever before. I remember a young boy one of my consultants was working with — and reading through his essay. It was about losing his father to cancer and how challenging it was for him, but yet, all the things he learned in the process. After losing my father when I was 18 in a car accident, I was crying as I read his essay. A lot of what happens in the admissions essay process is that we are helping students heal and transform, and the work we do is extremely powerful.

Are you working on any exciting new projects now? How do you think that will help people?

NEHA: Yes, right now we are working on creating a reality TV show around getting students into their dream college. I think it will help parents to understand that mentors can be extremely powerful for their teenager — and uncover the reality of what really happens between parents and teens behind closed doors.

What advice would you give to other female leaders to help their team to thrive?

NEHA: The number one way to be helpful to your team is trust and delegation. Instead of being the bottleneck to every project or task, allow your team to make mistakes and grow. I have learned to delegate so many things — and I am still learning. When you first start a company, it is easier to be a control freak and do everything yourself. The truth is, if you want to scale, you better be ready to let go of the control.

What advice would you give to other female leaders about the best way to manage a large team?

NEHA: I manage a large team by setting up rock star players as managers. By having incredible managers — it makes it easier to disseminate information quickly between team members. Also, I recommend hiring people that are better than you in that area, and outsource to agencies for expertise on the areas of your business you are NOT known for.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

NEHA: My mother. My mom moved here with less than $20 in her pocket with my dad, and they built a multi-million dollar company within 10 years. I remember distinctly when I first started my company and said to her, “mom I think just four coaches on my team is good enough.” She looked at me and said, “what about 40? Why not? Our company had 40 people just in the accounting department — you can definitely have more team members and do this at a bigger size than four people.” and it was from there, that I started scaling faster and faster. Growing up in a culture where women were expected to be in the kitchen and stay at home, my mom was the exception to the rule. I grew up in a house where both of my parents discussed business every single day 24/7. I am extremely grateful to have that expertise in my back pocket as mentors in my life.

How have you used your success to bring goodness to the world?

NEHA: Yes, and it is actually what I am most proud of. Not only are we helping teenagers get into their dream colleges, just in the last year, I recently built a school in Africa with Village Impact in Nicaru, Kenya. I traveled to Africa in August this year and it was life changing. I now have the vision of taking teenagers and getting them involved in contribution at a deeper level and building over 100 schools in the next 10 years.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

NEHA: Five Lessons:

FIRST: Bring Your Demons To The Party

As women we feel the need to prove ourselves, and in order to right, to be seen, and to be heard, we must backup everything with evidence so we can earn a seat at the table. Women need to feel qualified to feel legitimate — getting degree after degree and seeking the stamp of external approval to feel qualified — but the truth is you will never feel that way from external success.

And our male counterparts who have fewer degrees/experience or less credentials are succeeding ten fold but what is the difference? They just do it anyways. And so today, I invite you to bring all your demons to the party.

Bring you terrified little girl self and her PhD, bring your angry mean bully, bring the person that tells you, you are a fraud or imposter, bring them all. Because no matter how many degrees, certificates, endorsements you get, these demons are always right there.

It is all about how you entertain these demons at the party. Have them carry your bags, they are not the star of the show — and you get to decide who shows up for you — but don’t expect them to disappear as a matter of fact, as you stand on the threshold of a big success, they will be standing right beside you.

You decide who shows up for you. You want to change the world, ignore them and do you.

SECOND: Clarity is bullshit

I’m so tired of people writing 10 year business plans. You can find out on day one that your ten year business plan won’t work. And the worst part, is that many people try to stick to their plan and miss the opportunities right in front of them. For most people when they don’t have clarity they see this as justification to not move forward. People use clarity as an excuse not to take action. If you don’t know, you don’t go.

And for women, we love to have all of our ducks in a row — to be perfect. In the book El Doctor, there’s a quote that defines entrepreneurship, it’s like driving a car at night and you can only see the end of your headlights but you know you will make the whole trip that way. The only clarity that is required is the decision to move forward, and the practice to believe that you will have what you need when you need it. Even when you don’t know what you were doing, know that you will get the end result and adapt and fine-tune as you go.

Entrepreneurship is messy. There is no pathway, you are forging your own path and making a way there that works for you on a moment to moment basis.

THIRD: Wash, Rinse, Repeat.

While having a lofty vision can be sexy, the truth is, all you need to do is find one paying customer who is not your friend, not your mom not your dad, not your sympathetic sister. This one paying customer will help you to learn what your business solves and why it matters. I started my company, years ago with $500 dollars, an ugly logo, and an immigrant hustle. I put an ad in my college newspaper seeing if any family in the neighborhood wanted to hire me. I put myself out there. And, I will tell you it all started with one customer. Kimberly, a second grader, was excited to have me tutor her. I walked into their house in a full suit and my two page resume — and her mother was just looking at me, but I was ready to rumble. Kimberly showed me how much fun I was having while tutoring her, getting paid, and decades later, I saw the impacts we made on her life and why I exist. Back then, I was a one woman show. I was the secretary booking appointments, I was the service provider, I was the accountant, I was the web developer and marketer. Eventually we went from 1 to 100 to 1000 to 10,000, but this would have never happened if I didn’t have solid systems and teams in place.

As women — we can’t do it all — it is important to lean and delegate.

From this one customer, I learned exactly what the market needed for education for children. I hired team members that were smarter than me, and I began to build systems so that we could impact millions.

I knew I had to grow from a one woman show to a company — and the only way to do that — was to get out of the way. My dream for myself, became a shared dream that involved many.

Once we had a solid system down, it was wash, rinse, repeat. But you should know, that to get to this point, it requires an insane amount of execution. It required blood, sweat, and tears before I finally figured the system out over time. And the sad part is, so many entrepreneurs quit before they hit this part. There was no problem we couldn’t solve, and our team made the dream work so that we could get to a place where we could live our lives fully — to go from starting a start up to a well-oiled machine.

FOURTH: Entrepreneurship is a marathon not a sprint

Early on in my entrepreneurship journey, all I did was sleep, eat, breathe my company — and yes, there are still times I do this even today. I have realized that entrepreneurship is a marathon not a sprint. It is much more powerful if you ENJOY yourself during this journey and realize that you will learn as you go.

FIFTH: Remember daily why you became an entrepreneur

It is easy to lose site of why you became an entrepreneur. I focus heavily on this on a daily basis: I grew up up with two entrepreneurs that worked all the time. And, I do believe it is EASY to get stuck in the workaholic trap of entrepreneurship because no one is there to tell you to stop working, especially if you work from home. Instead, I have learned to set boundaries with myself, because one of my main reasons was to enjoy life more and have a flexible schedule. And so, it is so pertinent for me to take a moment and enjoy. I recently wrote about this in my TEDx talk, “Is Achievement Killing Us?” that launches in December.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

NEHA: My movement would be from Entitlement To Empowerment. Entitlement is the #1 success killer for teenagers in America. I want to solve the Entitlement Epidemic, and it is a book I am currently working on that will tie into the TV show.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

NEHA: “If you do what you have always done, you will get what you have always gotten.” –Tony Robbins

This quote is highly relevant every time I am dissatisfied in any area of my life. I start to look closely and see what are the patterns, who do I need to get involved to help me take it to the next level. I always believe I am 2 millimeters off from my goal, and if that is the case, I have to change my behavior to get the success I want in any area of my life — and many times, it involves a coach.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

NEHA: This is an easy question for me. I grew up watching Oprah my entire life. I never thought I would end up creating a school in Africa, and following in her footsteps so closely. I would say that if I could meet her, it would be revolutionary — as I do want to help as many teenagers in the world. I do believe that if we helped children at this level, we would see less problems that we are currently seeing in adulthood, politics, violence, and more if we helped create better role models and mentors at a younger age for children. Of course, it wouldn’t hurt to be connected with someone who believes in female entrepreneurs as a celebrity endorsement or from a funding perspective as well or helping us launch our TV show. We are all open ears at College Shortcuts.

Originally published at medium.com

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