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“The first step to developing great habits is to take inventory of your current habits.” with Rohan Gupta

The first step to developing great habits is to take inventory of your current habits, and actively asses which ones are good or bad. It is explicitly a force of will to lean into your good habits and away from the unhelpful ones, but self-awareness and accountability are absolutely necessary in order to do this. […]

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The first step to developing great habits is to take inventory of your current habits, and actively asses which ones are good or bad. It is explicitly a force of will to lean into your good habits and away from the unhelpful ones, but self-awareness and accountability are absolutely necessary in order to do this. I don’t think the 21 days to building a good habit or the cold turkey method of quitting a bad habit really work because it’s too easy to opt in and out. The better solution is just to try and be accountable to yourself. You have to want to improve, and to do that, you must be willing to put in the work.

As a part of our series about “Optimal Performance Before High Pressure Moments”, I had the pleasure of interviewingRohan Gupta, CEO of QuillBot.

Rohan Gupta is the CEO and Co-Founder of QuillBot, a cutting-edge NLP startup with millions of users. He holds a B.S. in Finance and an M.S. in Computer Science from the University of Illinois at Urbana-Champaign. He is passionate about technology, philosophy, and changing the world.

Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I’ve always been very entrepreneurial. Even as a kid, I was constantly coming up with business ideas — for instance, I remember going around my neighborhood selling silk pillow cases that my grandfather had brought back from India. In middle school I began to freelance in graphic design, and I expanded my suite of skills and services in high school to include web design and development. Technology has always fascinated me, and I enjoyed the challenge of learning new things and turning that knowledge into a job.

What or who inspired you to pursue your career as an entrepreneur or business leader? We’d love to hear the story.

My dad is an entrepreneur, and seeing him choose this career path was very influential. Through his endeavors, I saw what it takes to make a business work, and I know that some of those lessons and skills have rubbed off on me. I gained a valuable sense of intuition from seeing my dad succeed as an entrepreneur, and I often think that’s why problem solving in a business context comes so naturally to me. At school, I didn’t enjoy the “one size fits all” approach to learning, and this inspired me to learn independently. My love of tech then transformed into a valuable set of skills that I could leverage for work and personal enrichment.

None of us can achieve success without some help along the way. Was there a particular person who you feel gave you the most help or encouragement to be who you are today? Can you share a story about that?

While I am grateful for the series of short-term mentors I’ve had over the years, I consider the internet to be my life-long and most important mentor. I love that I can look up anything I want to know and find an answer or a pathway to understanding almost instantly. I am also very thankful for those teachers/advisers in high school and college that pushed me to think critically and gave me the latitude to evolve my problem solving skills. Experience has been a great teacher to me as well. Throughout my childhood and my teens, I had a series of entrepreneurial endeavors in sales (e.g. rocks, pillowcases), graphic design, web design, and web development, and these efforts honed my business skills and helped me develop robust risk and failure tolerance.

Can you share the funniest or most interesting mistake that occurred to you in the course of your career? What lesson or take away did you learn from that?

The first time I ever sold anything, I was in preschool. I remember setting up a stall on the playground to sell some nice rocks I’d found for $1 each. I gave one of the popular kids a rock to drive traffic to my ‘store’, and it worked. A girl came up to me and asked to buy a rock, but she said she would have to pay me tomorrow. The next day, she gave me $2, instead of just $1, and I was instantly hooked on business. The story ends in a bit of a heartbreak, though, because soon after this, my grandfather and I were called in to see my teacher. She informed us that the girl I’d sold the rock to had stolen the money she paid me from her sister and needed it back. It was my first experience with a chargeback. There were certainly a lot of business lessons baked into that first selling experience — the cost of doing business, how it all happens, how you learn from the sales process, trusting someone to pay you later, holding to your word, dealing with chargebacks, and the need to plan and be wary of unforeseen roadblocks. I have carried many of these lessons with as I’ve grown as an entrepreneur.

The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?

This is a very loaded question but also important. In business, you need to be failure tolerant, value multidisciplinary approaches, and develop your skills as early as possible because most things you try won’t work — at first. Some ideas may succeed after some iterating, but it’s a whole other skillset to be able to evaluate what will work, what might work, and what will/might work if ‘x’ happens. Entrepreneurs need to be able to repeatedly fail, learn, and iterate without giving up, which takes some serious grit and perseverance. Building your own skills and learning a variety of ways to approach problems empowers you to be able to creatively problem solve and ask better questions, both of which will help you see what went wrong in your failures and give you clues as to how to fix them. I encourage you to be bold and willing to try to do things that others are not willing/able to do or to take chances on, because in the end, you will regret not just giving it a try. After all, what if it works? There is an opportunity cost to everything, and you always have the choice whether to try or to take a safer option.

The path of every entrepreneur is different because of their various life experiences and interests, so no one’s path can truly be emulated. However, there are common traits which often signal entrepreneurial success. These include perseverance, an appetite for risk, cleverness, knowing how to handle feedback, the ability to recognize an opportunity (which is much harder than it sounds) and honestly, a bit of luck.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

In high school and college, I found my philosophy classes to be the most actionable. Thus Spoke Zarathustra by Nietzsche was a favorite that I read because it delved into challenging the status quo and having a growth mindset. I also enjoyed The Stranger by Camus because it was thought-provoking and embodied the nature of reality well in that you have infinite options as a person or a business. Having too many options to pick from, rather than too few, is the limiting factor, and realistically, most of the constraints placed on us and our potential, we set ourselves. I think this idea is very useful because once an entrepreneur comes to terms with it, they can make bigger and better decisions.

Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?

I really enjoy this quote by Voltaire: “Is there anyone so wise as to learn from the experiences of others?” To me, it means that wisdom comes from doing, though wisdom might look different in various contexts. I can know how to do something if someone will tell me the steps, but wisdom is different from knowledge in that it isn’t just information — it’s insight, perspective, and the understanding of what to do with that knowledge. At the end of the day, you have to experiment in order to develop yourself and your business.

What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?

We have so much to be excited for at QuillBot, including new tools, bigger and better goals, and a commitment to advance diversity and inclusion in our technology. We recently launched our Summarizer tool, which uses cutting-edge AI technology to digest articles/papers/etc. and return the key points or a summary. Students, researchers, writers, creatives, and everyone who needs to find and understand new information, including me, can use this tool to keep updated on news, happenings in your industry/field, or anything else they’re interested in. It’s a major time saver, and we’re very proud of how it elevates the lives of our users by increasing their productivity. We are also very excited for our Research Assistant tool, which integrates our existing paraphrasing and summarizing tools into a single automated, end-to-end tool, where AI is sitting with the user during every step of the writing journey. We want to be able to further assist our users with research, argument construction, language refinement, reference management, and more within the Research Assistant AI writing platform. Lastly, we are very interested and excited about making the AI technology we work with more inclusive. This is a large and somewhat nebulous task, but we are making it a priority within our company culture and within our tech.

OK, thank you for all of that. Let’s now shift to the core focus of our interview. As a business leader, you likely often face high stakes situations that involve a lot of pressure. Most of us tend to wither in the face of such pressure and stress. Can you share with our readers 3 or 4 strategies that you use to cope with the burden of stress?

Stress can be inherent to any entrepreneurial journey, so I think it’s really important to find coping strategies that work for you as fast as possible. For me, walking, meditation, talking through issues, and visualization are my go-to strategies for staying cool under pressure. Getting out of my head is really important when I’m feeling stressed. Walking is effective at helping me to clear my mind because I can focus on the activity, give my brain a break, and then, when my mind is less cluttered, I can walk and turn over the details of the situation at hand more objectively. On my walks, I can also use visualization to help me walk through the upcoming stressful situation, which helps me be more prepared for the day, and it also makes me feel more in control. Meditation, especially focusing on my breath, is another way that I get out of my head and back into the present moment. Talking the issues through with cofounders and mentors is very helpful to me as well in terms of getting the support and advice I need to understand where the stress is coming from, from a number of different vantage points. Mentors are incredibly helpful here because they can share their experience and coping mechanisms, while also helping you to see what potential roadblocks you should plan for. Lastly, in the actual moment you have to pitch or speak at an event or whatever the stressful situation is, it is extremely helpful to appreciate the ‘absurdity’ of the situation, which is to say that you have unlimited options for your life and business, so stressing about this one outcome doesn’t really serve you well. Over time, as you encounter more of these high-stakes situations, you will naturally come to this conclusion — that this opportunity is just one of many, and being calm and collected will produce better results than agonizing over the situation. Being able to drop into this mindset makes you calm down, relax, and operate more effectively because you know this isn’t the end, no matter what.

Aside from being able to deal with the burden of stress, can you share with our readers 3 or 4 strategies that you use to optimize your mind for peak performance before high pressure, high stress situations?

Something I’ve been working on lately in my day to day life in order to be ready for high-stress moments is to pay attention to the tone of my voice during conversations, especially difficult ones. I want to make sure I’m level and calm because people can always tell when I’m excited, anxious, frustrated, etc. from my voice. I also have a repertoire of techniques I have been taught specifically for dealing with high-pressure situations, especially if the other party becomes antagonistic. Watching my tone of voice is certainly one of these techniques, but others are more cerebral, such as understanding when to opt of out a conversation if it’s no longer productive or you aren’t in a position where you’re able to respond at that moment. Another technique is de-escalation, where the intent is to calm the other party down in order to have a more productive discussion. Sometimes this can be achieved by asking for permission to respond to an issue they brought up, or merely asking if they are ready to hear your side of the issue. Acknowledging that you have hurt the other party and addressing their concerns by reiterating their points is another way to let them know that they have been heard, which often makes them more willing to hear your side of things.

Do you use any special or particular breathing techniques, meditations or visualizations to help optimize yourself? If you do, we’d love to hear about it.

Breath-focused meditation, box breathing, and visualizing difficult situations all help in preparing for important, stressful moments. I would add writing to this list too because when my thoughts won’t stop buzzing, it helps me to get it all down on paper. If I can articulate what I’m feeling and reiterate to myself that this opportunity is just one of many, then I can clearly see the issues on paper and address them one by one. If I can’t find the right words to express what I’m thinking/feeling, I use our paraphraser tool to help me with articulation.

Do you have a special technique to develop a strong focus, and clear away distractions?

When I’m studying or doing research, I find classical music helps me focus and find a flow state. Lists also help me focus, organize my thoughts, and prioritize my time. I usually have several going at once — some online and others which are physical lists. On my heavier work days, I’ll also isolate myself to focus and minimize distractions because if I’m around friends or family, or even have my phone next to me, then I’m less productive.

We all know the importance of good habits. How have habits played a role in your success? Can you share some success habits that have helped you in your journey?

Habits surrounding growth are huge for a business, as well as for yourself as an entrepreneur. A habit that helps me greatly is to visualize the end point you want, and then work backwards, step by step, so you can make a very actionable path to achieving the goal. For instance, I think about things like: Where do I want the company to be in 3 years? Where do I want to be as an individual in 3 years? Once I have a clear picture of the answers to these types of questions, then I can more easily see what needs to be done in the future and right now, not only to make the roadmap, but also to pace myself and the team.

Focusing on incremental improvements every day is another habit that has definitely played into my success and that of QuillBot. Committing to daily progress toward your personal habits and goals compounds over time, so it really pays to hold yourself accountable. Prioritization, as a habit, is also important because you need to understand what and where the low-hanging fruit is in order to capitalize on it, and the sooner you can do this, the better shape your business will be in, since these early wins similarly compound over time. Additionally, it’s necessary to recognize what actions are going to move the needle fastest — in the right direction — for you and your company. From a leadership perspective, working on my weaknesses has been a very effective habit too. It’s a lot harder to do this than it is to simply focus on mastering your strengths, but taking the time to identify and work on your weaknesses is worth it for the value addition it will bring to your quality of leadership, both personally and professionally.

What is the best way to develop great habits for optimal performance? How can one stop bad habits?

The first step to developing great habits is to take inventory of your current habits, and actively asses which ones are good or bad. It is explicitly a force of will to lean into your good habits and away from the unhelpful ones, but self-awareness and accountability are absolutely necessary in order to do this. I don’t think the 21 days to building a good habit or the cold turkey method of quitting a bad habit really work because it’s too easy to opt in and out. The better solution is just to try and be accountable to yourself. You have to want to improve, and to do that, you must be willing to put in the work.

As a business leader, you likely experience times when you are in a state of Flow. Flow has been described as a pleasurable mental state that occurs when you do something that you are skilled at, that is challenging, and that is meaningful. Can you share some ideas from your experience about how we can achieve a state of Flow more often in our lives?

If you want to spend more time in a flow state, I think it’s very simple: do what you love. Intrinsically, you need to be able to find joy in your work or there’s very little chance you can regularly get into a good flow. It’s also important to understand that flow only happens for activities where you have a certain level of skill because you need to be able to rest in your abilities in order to drop into the passive, almost instinctual, mindset needed for flow.

Ok, we are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Hands down, the movement I think would benefit the world the most is the democratization of education. Giving everyone, everywhere, access to the most robust and diverse educational materials at no cost would level the global playing field in terms of opportunities on a monumental scale. Right now, the caliber of education that an individual receives during their peak growth years is dictated by their location, but imagine if you could remove that barrier! The innovation, advances, and ideas that would arise from a world in which all people have access to quality education would be fantastic.

We are very blessed that 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, whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we both tag them 🙂

I would love to meet Elon Musk because he is someone who embodies the core principles of an entrepreneur in that he reminds me that you really can do whatever you want, build whatever you want, and move the needle on humanity by just trying and doing new things.

How can our readers further follow your work online?

QuillBot is on LinkedIn (https://www.linkedin.com/company/quillbot/), Pinterest (www.pinterest.com/TheQuillBot), Facebook (https://www.facebook.com/thequillbot), Twitter (https://twitter.com/TheQuillBot), and Instagram (https://www.instagram.com/quillbot/). We also are building a library of educational resources on the QuillBot Blog (https://blog.quillbot.com/), hosted on our site, which we are very proud of. Lastly, you can follow me on LinkedIn on my personal account as well (https://www.linkedin.com/in/rohan-gupta-57a8a2134/).

Thank you for these really excellent insights, and we greatly appreciate the time you spent with this. We wish you continued success.

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