Choosing Leadership with Sumit Gupta

Sumit Gupta
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As a leader, you are always making choices. Even when you think you have no choice. And if you are unable to make a decision, you are choosing to stay in a state of indecision. The only question is - are your choices taking you where you want to go? I am Sumit Gupta, and this is "Choosing Leadership" - a podcast for high performers with big dreams - who know deep inside that there is more. This is a podcast for people who know they are more powerful than the level they are currently playing. I have spent a long time feeling powerless, and that is why I see where you are powerful even when you cannot. I dare to say what most people would not. I dare to speak to the "tremendous power" which you already have rather than what you believe are your strengths and limitations. This podcast is called "choosing leadership" - because that is what leadership is - a choice. The choice to step into the unknown. The choice to see fear as a friend. The choice to take courageous action rather than waiting for readiness. Join Sumit in exploring this question when it comes to your leadership. In each moment of life, are you Deploying Yourself or not? In each moment of life, are you Choosing Leadership or not?

  1. Leadership Journeys [275] - Janardan Dalmia - "Success has many fathers and failure is an orphan"

    2D AGO

    Leadership Journeys [275] - Janardan Dalmia - "Success has many fathers and failure is an orphan"

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. What does it really take to walk away from certainty and choose leadership in the unknown? In this episode of Choosing Leadership, host Sumit Gupta sits down with Janardan Dalmia to unpack his journey from Wall Street banking to building Trukkin in one of the world’s most complex logistics markets. JD shares the unglamorous truths of entrepreneurship—unlearning old mindsets, navigating uncertainty, and building resilience when the playbook no longer exists. This conversation is a powerful reminder that leadership isn’t about linear growth or perfect balance, but about endurance, self-awareness, and choosing courage over comfort. If you’re a leader facing big decisions, internal resistance, or the fear of starting over, this episode will challenge you to raise your bar and play a longer, bolder game. You can find Janardan Dalmia at the links below https://www.linkedin.com/in/jdalmia/ jd@trukkin.com. In the interview, Janardan shares “Leadership isn’t a title you earn once — it’s a choice you make every day.”“Leaving Wall Street didn’t make me brave — staying uncomfortable did.”“Entrepreneurship isn’t a straight line. It’s a messy, non-linear journey, and that’s the point.”“You don’t rise in business by avoiding failure — you rise by learning to recover faster.”“Success is temporary. So is failure. What lasts is who you become through both.”“Unlearning the banker mindset was harder than learning how to build a startup.”“Real leadership is about endurance — staying in the game when the excitement wears off.”“You can’t professionalise chaos without first learning to operate inside it.”“Work-life balance isn’t about equal hours — it’s about protecting your energy.”“Growth isn’t about doing more. It’s about becoming more.”

    25 min
  2. Leadership Journeys [274] - Christopher Graham - “Transformation starts when the founder steps back and the team steps up.”

    FEB 23

    Leadership Journeys [274] - Christopher Graham - “Transformation starts when the founder steps back and the team steps up.”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. This episode is a masterclass in what happens when a leader stops reacting and starts thinking. Christopher Graham shares how stepping back from daily chaos unlocked scale, clarity, and a completely new way of leading at Crown Capital. You’ll hear why micromanagement feels productive but quietly kills growth—and what to do instead. The conversation dives into curiosity, mental space, and building businesses that don’t depend on the founder for every decision. If you’re tired of being the bottleneck in your own leadership, this episode will challenge how you run your company and yourself. You can find Christopher Graham at the links below https://www.linkedin.com/in/christophertgraham25/https://crown-inv.com/In the interview, Christopher shares “Leadership changed for me the moment I stopped reacting to daily problems and started blocking time to actually think.”“Growth didn’t come from working harder—it came from creating mental space to see what was possible.”“My move into private equity wasn’t planned; it emerged by saying yes to opportunities my clients put in front of me.”“Ego convinces founders they need to touch everything. Scale demands the opposite.”“Real leadership begins when the business can operate and grow without the founder being in every decision.”“Micromanagement feels productive, but it quietly suffocates innovation and limits scale.”“Mapping a business forces clarity—it exposes inefficiencies you can’t see when you’re too close to the work.”“When leadership teams are involved in diagnosing problems, change stops being forced and starts becoming owned.”“Curiosity is a competitive advantage—it keeps leaders adaptable in environments that won’t slow down for them.”“The future belongs to leaders who can step back, challenge tradition, and build systems that outlive them.”

    29 min
  3. Leadership Journeys [273] - Liza Roeser - “Panic means I’ve lost the bigger picture. Faith brings it back.”

    FEB 16

    Leadership Journeys [273] - Liza Roeser - “Panic means I’ve lost the bigger picture. Faith brings it back.”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. In this episode of Choosing Leadership, Liza Roeser, founder and CEO of 50Flowers, opens up about what it really takes to lead when fear, ego, and uncertainty show up uninvited. She shares raw lessons from nearly three decades of entrepreneurship—moments where faith mattered more than strategy and pausing was more powerful than reacting. This conversation challenges leaders to rethink success, shift from control to trust, and build businesses that don’t depend on their constant presence. Liza’s honesty about letting go, saying no, and leading with vulnerability offers practical insight for anyone feeling stretched, stuck, or overly responsible. If you’re ready to lead with more courage, clarity, and calm, this episode will meet you exactly where you are. You can find Liza Roeser at the links below https://www.linkedin.com/in/liza-roeser/https://fiftyflowers.com/In the interview, Liza shares “Leadership isn’t about position; it’s about the choices you make when fear shows up.”“For nearly three decades, I didn’t lead without fear—I learned how to face it and keep going anyway.”“Entrepreneurship wasn’t a plan; it became a path to freedom, impact, and empowering women around the world.”“When something goes wrong, panic is optional. You can pause, respond, and fall back on what you know to be true.”“Faith has been my rock—not because challenges disappear, but because perspective returns.”“Success isn’t about what you build; it’s about how people feel when they work with you and leave your presence.”“The business truly scaled when I separated my ego from my role and trusted my team to lead.”“Implementing EOS didn’t just free up my time—it forced me to let go and become a better leader.”“If it’s not a hell yes, it’s a no. Focus is saying no to good things so you can say yes to what matters.”“You don’t lead others well until you learn how to lead yourself—especially in moments of fear and vulnerability.”

    29 min
  4. Leadership Journeys [272] - Jason Stone - “My faith and family come first”

    FEB 10

    Leadership Journeys [272] - Jason Stone - “My faith and family come first”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. Most leaders say they value relationships—then build systems that quietly destroy them. In this episode of Choosing Leadership, Jason Stone, President and CEO of Frontline Selling, challenges the obsession with automation and reminds us why human connection still wins in leadership and sales. He shares the hard lessons of stepping into the CEO role, navigating patience-demanding change, and leading with integrity when shortcuts are tempting. This is a grounded, honest conversation about trust, transparency, faith, and what it really takes to scale without losing your soul. If you’re leading people, selling ideas, or building something that actually matters, this episode will hit close to home. You can find Jason Stone at the links below https://www.linkedin.com/in/jasonstonefrontline/ jStone@frontlineselling.com.https://frontlineselling.com/ In the interview, Jason shares “We’re not in the business of rushing to leads. We’re in the business of creating real human conversations.”“Automation can scale activity, but it can’t replace trust. People still buy from people.”“Sales isn’t about pushing a product—it’s about offering a solution that actually serves the person in front of you.”“Becoming CEO taught me patience in a way nothing else could. Real change takes time, alignment, and humility.”“That eight-month CRM overhaul wasn’t a tech project—it was a leadership lesson in listening and involving everyone.”“Integrity isn’t a value you put on the wall. It’s what you choose when the easy shortcut is right there.”“If a deal doesn’t feel right, we don’t do it. Long-term trust always beats short-term wins.”“Faith and family keep me grounded. Doing the right thing has a way of working out—even when it’s uncomfortable.”“Scaling fast is easy. Scaling without losing who you are—that’s the real challenge.”“Great salespeople don’t come from one background. Hospitality, sports, service—those worlds understand humans.”

    35 min
  5. Leadership Journeys [271] - Fredrik Meurling - “Great leaders know when to turn it on and when to let go.”

    FEB 2

    Leadership Journeys [271] - Fredrik Meurling - “Great leaders know when to turn it on and when to let go.”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. In this episode of Choosing Leadership, Fredrik Meurling—CEO of Yazen Health—shares what it really takes to lead a fast-growing healthcare startup without losing your soul (or your sanity). We talk about the tension between passion and metrics, why sustainable results matter more than vanity numbers, and what happens when leadership shifts from “doing everything” to building leaders around you. Fredrik offers an honest look at scaling in a heavily regulated industry, navigating uncertainty, and staying mission-driven when the pressure is on. If you’re a founder or leader wrestling with growth, energy, and impact, this conversation will feel uncomfortably familiar—in the best way. You can find Fredrik Meurling at the links below https://www.linkedin.com/in/fredrik-meurling-2477421/https://www.yazen.com/In the interview, Fredrik shares “I’ve always been drawn to early- and mid-stage companies—the energy, the uncertainty, and the challenge of finding real product–market fit.”“What hooked me about startups wasn’t the title or the metrics; it was the adrenaline of building something that didn’t exist yet.”“Healthcare isn’t just another industry—you’re dealing with regulation, culture, and real human lives, all at the same time.”“At Yazen, we don’t see obesity as a simple calorie problem; it’s a complex disease that requires a holistic solution.”“Medication alone isn’t the answer—sustainable weight loss only happens when lifestyle change and coaching are part of the journey.”“Our North Star metric is sustained weight loss, because if we get that right, the revenue follows.”“Leadership, especially as a CEO, is a constant exercise in knowing when to lean in and when to let go.”“As the company grows, my job shifts from doing the work to creating the conditions where others can lead.”“Scaling across Europe forces you to balance speed with responsibility—especially in a regulated healthcare environment.”“Great leadership isn’t about being ‘on’ all the time; it’s about managing your energy so you don’t burn out while building something meaningful.”

    30 min
  6. Leadership Journeys [270] - Prashant Issar - “Integrity is simple: if I give my word, I keep it - especially when it’s hardest.”

    JAN 26

    Leadership Journeys [270] - Prashant Issar - “Integrity is simple: if I give my word, I keep it - especially when it’s hardest.”

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. This episode pulls back the curtain on what it really takes to lead with integrity in a world obsessed with shortcuts. Prashant Issar shares how purpose, grit, and an almost stubborn commitment to his values helped him build businesses that actually change lives—not just balance sheets. If you're wrestling with culture, scaling, or staying true to your word when the pressure is suffocating, this conversation will feel like a breath of fresh air. You’ll hear how inclusivity, long-term thinking, and courageous leadership can become your unfair advantage. Tune in and walk away with the kind of clarity that makes you rethink what you’re building—and why it matters. You can find Prashant Issar at the links below https://www.linkedin.com/in/prashantissar/mallika@aimil.comIn the interview, Prashant shares “Leadership isn’t a title—it’s a choice to step into courage and vision every single day.”“Integrity isn’t negotiable. When everything is falling apart, your word is the only anchor that keeps your team together.”“Purpose-driven leadership outlasts profits, trends, and even the leaders themselves.”“Inclusivity isn’t charity—it’s good leadership. When you bet on people, they bet on you.”“If your business doesn’t stand for something bigger, it won’t stand for long.”“Scaling a company is easy. Scaling culture is where most leaders fall asleep at the wheel.”“Hire people who believe in your mission—not people looking for the next shiny thing.”“Challenges are temporary. Human connection, experience, and dignity are forever.”“Legacy isn’t built in boardrooms. It’s built through the lives you elevate along the way.”“Comfort is the enemy of greatness. Mediocrity is a choice—and so is excellence.”

    37 min

  7. JAN 22

    Leadership Journeys [269] - Mark Rampolla - "Your calendar tells the truth your mind refuses to admit."

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. In this episode, Mark Rampolla pulls back the curtain on what it really takes to leave the comfort of corporate life and build a business—and a life—on your own terms. He shares the unfiltered truth about dancing with bankruptcy, rediscovering purpose, and learning that freedom isn’t a future milestone but a present-moment choice. Together, we explore how self-awareness, curiosity, and intentional living can transform not just your work, but your entire relationship with leadership. Mark’s journey from Zico Coconut Water to becoming an investor reveals the mindset shifts that separate leaders who feel trapped from those who feel truly liberated. If you’re ready to rethink success and design a life you don’t need an escape from, this conversation is exactly what you’ve been needing. You can find Mark Rampolla at the links below https://www.linkedin.com/in/marksrampolla/https://www.markrampolla.co/In the interview, Mark shares “Freedom doesn’t show up after the exit—it begins the moment you choose differently.”“Leaving corporate wasn’t a leap of logic for me; it was a leap of self-respect.”“Entrepreneurship isn’t about a perfect idea—it’s about a relentless desire for autonomy.”“Everything changed when I stopped filling my calendar and started aligning it with who I wanted to become.”“Success without self-awareness is just another form of imprisonment.”“You don’t build freedom in the future—you build it in the choices you make right now.”“Corporate life taught me efficiency; entrepreneurship taught me who I really am.”“If you’re not curious, you’re not growing—and if you’re not growing, you’re not free.”“The biggest risk I took wasn’t leaving my job—it was learning to trust myself.”“Leadership is simply choosing—again and again—to live aligned with your values, not your fears.”

    42 min
  8. Leadership Journeys [268] - Hanim Dogan Jain - "Self-confidence comes from outside but self-worth is from the inside"

    JAN 19

    Leadership Journeys [268] - Hanim Dogan Jain - "Self-confidence comes from outside but self-worth is from the inside"

    This is the Leadership Journey series on the Choosing Leadership Podcast. I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name. In this episode, Hanim Dogan Jain takes you on a journey from humble beginnings across two cultures to building a multimillion-dollar company grounded in purpose, grit, and heart. She breaks down the difference between self-confidence and self-worth—and why most leaders mix the two up at their own expense. You’ll hear how embracing her roots, trusting her inner voice, and leading with authenticity reshaped not just her career, but her entire identity. Hanim also opens up about blending spirituality with business, and why inner peace might just be your most underrated leadership advantage. If you’ve ever questioned your value, your path, or what leadership really demands, this conversation will recharge you and challenge you in all the right ways. You can find Hanim Dogan Jain at the links below https://www.linkedin.com/in/hanim-doganjain/https://pa-capitalpartners.com/In the interview, Hanim shares “Self-confidence comes from what you achieve; self-worth comes from who you already are.”“Leadership isn’t a title—it’s the courage to show up as your truest self.”“Growing up between two cultures didn’t divide me; it expanded my empathy and strengthened my identity.”“Education is the one asset no one can take from you—my father called it a ‘golden bracelet,’ and he was right.”“Entrepreneurship, at its best, isn’t about money—it’s about uplifting communities and contributing to something bigger.”“Authenticity and vulnerability aren’t weaknesses; they are the real engines of power in leadership.”“I didn’t build a multimillion-dollar company because I had everything—only because I believed I could create something meaningful.”“Balancing spirituality and business isn’t a contradiction; it’s the key to leading from a place of inner peace.”“Female founders don’t need permission—they need equitable opportunities and a system that finally sees them.”“True leadership begins the moment you stop waiting for external validation and start trusting your inner worth.”

    26 min
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About

As a leader, you are always making choices. Even when you think you have no choice. And if you are unable to make a decision, you are choosing to stay in a state of indecision. The only question is - are your choices taking you where you want to go? I am Sumit Gupta, and this is "Choosing Leadership" - a podcast for high performers with big dreams - who know deep inside that there is more. This is a podcast for people who know they are more powerful than the level they are currently playing. I have spent a long time feeling powerless, and that is why I see where you are powerful even when you cannot. I dare to say what most people would not. I dare to speak to the "tremendous power" which you already have rather than what you believe are your strengths and limitations. This podcast is called "choosing leadership" - because that is what leadership is - a choice. The choice to step into the unknown. The choice to see fear as a friend. The choice to take courageous action rather than waiting for readiness. Join Sumit in exploring this question when it comes to your leadership. In each moment of life, are you Deploying Yourself or not? In each moment of life, are you Choosing Leadership or not?

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