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1340 – Choosing Leadership with Deploy Yourself’s Sumit Gupta
7th October 2022 • The Thoughtful Entrepreneur • Josh Elledge of
00:00:00 00:18:04

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In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder and Leadership Coach of Deploy Yourself School of Leadership, Sumit Gupta.

Sumit helps business owners organize themselves to the next level of success by connecting what they want to achieve to how they get there. Sumit explains many leaders are stuck with small problems or hidden desires they might not see that is standing in the way of their growth. Business owners struggle to reach out for leadership help because they don’t know when to ask for it. Sumit explains individuals with big visions or individuals that know they are stuck should talk to a coach or advisor to help get to the next step. Many business owners surround themselves with people who tell them what they want to hear and not what they need to hear. This can be a disadvantage as criticism or feedback is where growth and new ideas form. Sumit explains that reframing the criticism from negative to helpful can aid individuals in accepting this type of feedback.

Sumit explains that individuals often make it too hard on themselves and simply stepping into the entrepreneurial space is winning for oneself. The achievements or failures are stepping stones on a larger journey that many people will never go on. Sumit explains that rumination is often done over things that cannot be changed and actually take an individual away from their responsibilities. While the worst case may happen, it is important to remember it is possible to come back from that and plan the next steps after it. Sumit explains his coaching consists mostly of long-term coaching that could be one leader or an entire leadership team.

Key Points from the Episode:

  • Sumit’s work and impact in the world
  • Where leaders struggle
  • When leaders should seek out coaching
  • How to overcome shielding oneself from feedback
  • Fear manifesting into courage
  • Perfectionism
  • Rumination
  • Engagement Sumit has with clients

About Sumit Gupta:

Sumit Gupta was born and grew up in New Delhi, India, and is now based in Amsterdam, Netherlands. Over the years, he has lived in multiple cities in India. In addition, he has traveled, worked along, and photographed people from all over the world.

One of his superpowers is to create safety and trust so that people do not have to wear a mask in front of him. He started as a techie in 2005 and fit the typical geek profile – good at computers but introverted when it came to working with people. In a way, he had learned to hide behind computers and not be visible.

He has worked in companies like InfoEdge ( (2005-2008), Yahoo (2010-2011), 91Mobiles (2013), and Booking (2014-2020). In addition, he also incorporated two startups – SaleRaja (from 2007-2010) and CricketRadius (in 2012) and co-founded a non-profit Pick A Fight (2011-12).

He started leading a team at 24 years of age. At that time, he had no idea what leadership was all about. To make it worse, he wasn’t even aware that people management and other so-called soft skills could be learned.

In 2012, he lost my mom to cancer. This event shook his world in ways he is still realizing. In a way, the old him died and a new Sumit was born that day – however, it took him a long time to realize that. In 2021, he reprioritized his life in the pursuit of Deploying Myself.

Earlier, he thought the unpredictability of human beings was a bug and it used to piss him off badly. However, now he sees it as a feature. He is left in awe and wonder as he supports people in finding and shining their own unique light upon the world.

People come to him feeling frustrated, low on energy, and stuck in achieving something that matters to them. They come confused and with their lights dim and leave with their lights shining many times brighter.

They leave feeling empowered, confident, relaxed, and ready to produce expanded results and relationships – for themselves as well as their teams. Today, he is good at helping people see their light because he has spent so much of his life hiding his own.

Tweetable Moments:

3:02 "It's easy to surround yourself with people who will say what you want to hear, not necessarily what you need to hear."

4:32 "Once I understood my fear, my fear was telling me what was meaningful for me. I was able to build the courage to go through that."

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 Links Mentioned in this Episode:

Want to learn more? Check out the Deploy Yourself School of Leadership website at

Check out Deploy Yourself School of Leadership on LinkedIn at

Check out Sumit Gupta on LinkedIn at

Check out Sumit Gupta on Facebook at

Check out Sumit Gupta on Twitter at

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