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Choosing Leadership with Sumit Gupta
Sumit Gupta
268 episodes
1 day ago
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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Business
Education,
Self-Improvement
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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?
Show more...
Business
Education,
Self-Improvement
Episodes (20/268)
Choosing Leadership with Sumit Gupta
Leadership Journeys [230] - Puneet Shivam - "Every critical choice is the beginning of an action set."

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 success and start over—again and again?

In this powerful conversation, Puneet Shivam shares how he’s made bold choices at every turn, trading comfort for challenge in pursuit of deeper growth and impact.

From the chaos of New York City to the cutting edge of AI, Puneet reveals the mindset shifts that have shaped his leadership journey.

If you’ve ever felt stuck at the edge of a big decision, this episode will inspire you to choose courage over certainty.

Tune in to hear how letting go might just be the most powerful leadership move you can make.


You can find Puneet Shivam at the below links

  • https://www.linkedin.com/in/puneetshivam/
  • https://www.rightskale.ai/


In the interview, Puneet shares

  • “Leadership isn’t a title—it’s a choice you make every time you step into discomfort and say yes to growth.” 
  • “I didn’t plan to become an entrepreneur—it happened when I followed the itch to solve problems and build something better.”
  • “Leaving a successful company wasn’t easy, but I knew I had to let go of comfort to chase what was truly calling me.”
  • “Your choices paint the picture of who you are. Every decision, especially the tough ones, becomes part of your identity.” 
  • “New York challenges you like no other city—it demands your best and constantly reminds you of your potential.” 
  • “Entrepreneurship is more than business—it's about unlocking human potential and moving society forward." “Financial freedom isn’t a luxury—it’s a mindset. And we must educate ourselves and others to claim it.” 
  • “The real courage lies in choosing to grow, even when it means walking away from what’s already working.” 
  • “At its core, leadership is about trusted partnerships—relationships built on integrity, resilience, and shared purpose.” 
  • “If we can help people believe in themselves again, we’ll witness a tidal wave of innovation, compassion, and impact.”
Show more...
3 days ago
36 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [229] - Akhil Shahani - "Your mind wants to be challenged"

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, Akhil Shahani—Managing Director of the Shahani Group—reveals how he transformed personal setbacks into a bold vision to revolutionize education across Asia.

From navigating the weight of a century-old family legacy to building an education-to-employment ecosystem, Akhil shares real talk on leadership, resilience, and reinventing outdated systems.

You’ll walk away with fresh insight on bridging the gap between theory and practice—and why empathy, adaptability, and critical thinking are the true markers of future-ready leaders.

If you're a leader tired of playing by broken rules, this conversation is your permission to reimagine what’s possible.


You can find Dr. Akhil Shahani at the below links

  • https://www.linkedin.com/in/akhilshahani/  
  • https://shahanigroup.com/


In the interview, Dr. Akhil shares

  • "Legacy can be a gift or a burden. The challenge is in choosing to build upon it rather than be confined by it."
  •  "I had an MBA from Kellogg, but still failed in business. That’s when I realized traditional education was missing something vital."
  •  "We need to move beyond textbooks and teach life skills like critical thinking, resilience, and adaptability."
  •  "We’re building Asia’s largest education-to-employment ecosystem—where students aren’t just educated, they’re employable."
  •  "Success isn’t just about academic scores. It’s about how well you communicate, adapt, and collaborate."
  •  "Being part of a legacy business means honoring the past while boldly reinventing the future."
  •  "You need both the visionary and the operator in a leadership team. One without the other is a recipe for chaos."
  •  "Think of life as a game—when you focus on the process instead of the outcome, stress becomes a teacher, not a threat."
  •  "Leadership isn’t about control. It’s about empathy, understanding your team’s dreams, and helping them get there."
  •  "We’re not just educating students. We’re equipping them to thrive in the real world—no matter where they start from."
Show more...
1 week ago
30 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [228] - James Jackson - " Our culture is being humble and not having egos."

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 candid conversation, James Jackson, CEO and co-founder of Bumper, shares the behind-the-scenes of building a high-growth fintech—while staying humble, hiring intentionally, and protecting company culture across borders.

From fixing tractors on his farm to navigating billion-dollar payments, James proves that great leadership isn’t about titles—it’s about ownership, balance, and grit.

If you’re leading a team through rapid change or wrestling with how to grow without losing your soul, this episode is your playbook.

Tune in to discover how humility, vision, and discipline come together to create lasting impact.


You can find James Jackson at the below links

  • https://www.linkedin.com/in/james-jackson-103ba412/    


In the interview, James shares

  • "Our culture is rooted in humility—no egos, just people making things happen together." 
  • "Leadership means being willing to do the dirty work and the strategy—sometimes in the same hour."
  • "We built Bumper by seeing a financial gap no one was solving for—and then obsessively solving it."
  • "Hypergrowth doesn't happen by accident. It takes bold moves, strong talent, and a culture of ownership."
  • "Hiring the right people isn’t about speed—it’s about patience and finding those who truly fit."
  • "Leadership is about creating a place where people want to take ownership, not where they’re told to."
  • "We’ve evolved from a buy-now-pay-later tool into a full payment orchestration platform. That’s scale with intention."
  • "Farming keeps me grounded. Fixing a tractor gives me clarity a boardroom sometimes can’t."
  • "Daily high-intensity workouts are my mental reset—they make me a sharper leader."
  • "Great leadership isn’t about being in charge. It’s about being in service—to your team, your customers, and your mission." 
Show more...
2 weeks ago
29 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [227] - MJ - " Today's leaders must think beyond their companies for larger community impact."

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 happens when you walk away from corporate security to chase a vision only you can see?

In this candid conversation, MJ—Managing Director of UHP Technologies and a serial entrepreneur—shares the raw truth behind 17 years of entrepreneurial grit, resilience, and reinvention.

From navigating early failures to building partnerships rooted in trust, MJ reveals what it really takes to lead with courage and empathy.

If you're a leader facing uncertainty, struggling with setbacks, or seeking a deeper sense of purpose—this episode is your permission slip to keep going.

Tune in to rediscover why leadership is less about control, and more about choosing to lead with heart.

You can find MJ at the below links

https://www.linkedin.com/in/mj-manjunath-jyothinagara-6174451/

In the interview, MJ shares

  • "I left corporate comfort not for certainty, but to discover who I could become without a safety net."
  • "Entrepreneurship tested me more than any boardroom ever did—and I wouldn’t have it any other way."
  • "Persistence isn’t a tactic. It’s the bridge between vision and reality."
  • "When failure came knocking, I answered with resilience—and kept going."
  • "Support from my wife wasn’t just emotional—it was the fuel that reignited my dream when I almost gave up."
  • "Empathy isn’t soft—it’s strategic. It’s how you build leaders, not just businesses."
  • "Entrepreneurship in India needs more collaboration, not competition. Let’s grow together."
  • "My mornings with family are non-negotiable. That’s where I center myself before taking on the world."
  • "Credibility isn’t built through perfection—it’s built through transparency, trust, and time."
  • "Leadership isn’t about titles or balance sheets. It’s about choosing to show up—with heart, every single day."
Show more...
3 weeks ago
36 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [226] - Tessa Clarke - "The current system is profoundly and fundamentally broken"

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 if your next leadership breakthrough came from a snowy day and a bag of leftover food?

In this episode, Tessa Clarke, co-founder and CEO of Olio, shares how she turned a moment of frustration into a global movement against food waste.

You'll hear raw insights about leaving a corporate career, building something from scratch, and leading with values in a world that often rewards short-term thinking.

This isn’t just a story about sustainability—it’s a masterclass in courage, clarity, and solving real problems with bold leadership.

Tune in if you're ready to challenge the status quo and lead with purpose, even when the path isn’t clear.

You can find Tessa Clarke at the below links

https://www.linkedin.com/in/tessaclarkeolio/
https://www.linkedin.com/company/olio-share-more-waste-less/

In the interview, Tessa shares

  • "A snowy day and a bag of unwanted food sparked the idea that would become Olio. Innovation often begins with frustration."
  • "Don't obsess over ideas—focus on the problems that truly matter. That’s where real innovation lives." 
  • "Every entrepreneur starts small. Baby steps can lead to massive change if you're consistent." 
  • "You don’t need to have all the answers—just the courage to take the first step and the resilience to keep going." 
  • "Values aren’t just words on a wall. At Olio, they guide our decisions, fuel our culture, and shape our impact." 
  • "Sustainability isn’t a trend—it’s a necessity. Even when the market wavers, our mission stays clear." 
  • "Building a community and a business at the same time isn’t easy—but it’s where the magic happens." 
  • "The future belongs to those willing to act—not just talk—on the big issues facing our world." 
Show more...
1 month ago
31 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [225] - Lamar J Romero - " The entrepreneurial journey is about leaving some kind of a mark on the world"

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 comfort and step into the unknown as a leader?

In this episode, Lamar J Romero, founder and CEO of Hire Dragons, shares the gritty truth behind building a business from the ground up—Uber rides, failed experiments, and all.

He opens up about the internal battles every leader faces, especially the constant tug-of-war between comfort and greatness.

If you’ve ever wrestled with self-doubt, growing pains, or the pressure to scale without losing your soul, this conversation will hit home.

Tune in for a refreshingly honest take on leadership, resilience, and choosing impact over ego—every single day.

You can find Lamar J Romero at the below links

https://www.linkedin.com/in/lamarromero/
https://www.linkedin.com/company/hiredragons/

In the interview, Lamar shares

  • “true leadership isn’t given; it’s chosen every single day.”
  • “i quit my comfy dell gig to promote tequila—because leaving a mark beats playing it safe.”
  • “when your bank account says no, your determination says go—uber, lyft, bootstrapping: that’s the grind.”
  • “mix tech with hustle—that pivot is what took hire dragons from idea to impact.”
  • “covid didn’t break us; it made us adapt faster and lead more authentically.”
  • “the real battle in leadership is comfort versus greatness—i pick greatness.”
  • “leaving a monument isn’t about billions; it’s about building teammates up to win.”
  • “in our culture, mistakes aren’t failures—they’re experiments to level up.”
  • “after 12 years, i’m not slowing down; i’m doubling down on service through investing and advising.”
  • “choice is the cornerstone of entrepreneurship—decide to lead, decide to leave a legacy.”
Show more...
1 month ago
37 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [224] - Viktor Pryshlyak - " If you don't know how to sell, you probably won't succeed"

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 if your biggest leadership breakthrough came from breaking the rules of how things have always been done?

In this powerful conversation, Viktor Pryshlyak, CEO and co-founder of United Software, reveals how he walked away from traditional outsourcing models to build a global, trust-first tech company.

We explore what most founders miss about sales, why trust is non-negotiable, and how real leadership often means leaning into discomfort.

Whether you're scaling a startup or leading a team through uncertainty, Viktor’s story is packed with real, relatable lessons on courage, clarity, and conviction.

Tune in to challenge your leadership assumptions—and walk away with practical tools to lead with more heart and impact.

You can find Viktor Pryshlyak at the below links

LinkedIn
 victor@usoftware.co.

In the interview, Viktor shares

  • “Leadership isn’t about content—it’s about context and courageous choices in the face of discomfort.”
  • “We saw a broken model in outsourcing—so we built one rooted in trust, transparency, and shared success.”
  • “Entrepreneurship begins when you’re willing to leave your comfort zone—timing and courage make all the difference.”
  • “Sales isn’t just for business—it’s a leadership skill, and it’s deeply personal.”
  • “Founders from technical backgrounds often avoid sales, but it’s the first battlefield of real entrepreneurship.”
  • “Trust isn’t a soft skill—it’s the foundation of scaling a business across 19 countries.”
  • “We run quarterly reviews and keep Calendly open for tough conversations—because transparency builds long-term loyalty.”
  • “Wars and recessions are out of our control—but how clearly we communicate our value? That’s on us.”
  • “Fatherhood and leadership aren’t separate—personal experiences shape the leader you become.”
  • “Success or failure isn’t the point—it’s what you learn when you dare to act.”
Show more...
1 month ago
33 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [223] - Kevin Kilty - " In six months of a startup, I learned more than 10 years in investment banking"

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 lead with purpose in a fast-moving, high-stakes world?

In this episode, Kevin Kilty, CEO of Hub Pay, shares his bold journey from London’s finance world to launching a FinTech startup in Dubai—with zero startup experience and a lot of heart.

He opens up about the gritty realities of leadership, building culture across continents, and staying grounded when the pressure never lets up.

If you're a leader navigating uncertainty, scaling a business, or simply craving more meaning in your work, this conversation delivers raw insight and practical inspiration.

Tune in to discover how impact and innovation can go hand in hand—without losing your sanity.

You can find Kevin Kilty at the below links

https://www.linkedin.com/in/kevinkilty/
https://www.linkedin.com/company/hubpay/

In the interview, Kevin shares

  • "In six months of building a startup, I learned more than I did in over a decade of investment banking."
  • "You don’t need to have all the answers. Just start. The clarity comes from doing."
  • "FinTech isn’t just about technology — it’s about unlocking financial inclusion and societal progress." 
  • "Leadership is about defining your values early and then living by them—especially when things get tough." 
  • "The startup grind is relentless, but regular workouts are my meditation — they keep me centered." 
  • "We built Hub Pay on the belief that business can be both profitable and deeply purposeful." 
  • "The team you build is more important than any business plan. Culture trumps strategy every time." 
  • "True leadership means grounding big visions in practical, revenue-generating actions." 
  • "Startups are built on grit, not glamour. You grow by facing uncertainty, not avoiding it."
  • "Inspired by impact pioneers like Professor Yunus, I saw FinTech as a bridge to a better world."
Show more...
1 month ago
29 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [222] - Heather Udo - " I was taught to work hard for what I want at an early age"

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 take to turn obstacles into opportunities and build a thriving business from the ground up?

In this episode of Choosing Leadership, Heather Udo, founder and CEO of Shoppable, shares how she went from growing up on a farm to leading a game-changing e-commerce company.

She reveals the mindset shifts that helped her land Fortune 500 clients, scale her business, and empower her team to operate independently.

If you're a leader navigating challenges, wondering how to build a resilient team, or looking for fresh insights on adaptive leadership in a remote world, this conversation is packed with practical wisdom.

Tune in to discover how choosing leadership—every single day—can transform your career, business, and impact.

You can find Heather Udo at the below links

https://www.instagram.com/heatherudo1/
https://www.heatherudo.com/

In the interview, Heather shares

  • "Entrepreneurs don’t wait for opportunities; they create them." 
  • "Setbacks aren’t roadblocks—they’re stepping stones to innovation." 
  • "A great leader doesn’t just build a business; they empower a team to run it without them." 
  • "Success isn’t about avoiding failure—it’s about learning from it and moving forward with confidence." 
  • "The best way to scale a company is to make yourself replaceable." 
  • "Authenticity in entrepreneurship is more valuable than the illusion of overnight success." 
  • "If you want something badly enough, there is always a way to make it happen." 
  • "Leadership is a daily choice—one that requires courage, resilience, and vision." 
  • "Growth happens when you push beyond conventional limitations and challenge the status quo." 
  • "Your mindset determines your trajectory—choose one that turns challenges into opportunities." 
Show more...
2 months ago
27 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [221] - James Kellett - " It makes more sense investing and then founding rather than the other way round."

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, Anders Jones, CEO of Facet, shares the hard-won lessons of scaling a disruptive FinTech company while navigating the challenges of modern leadership.

In this episode, James Kellett, founder and CEO of Spot Ship, shares how his journey from hedge funds to entrepreneurship shaped his approach to leadership, innovation, and resilience.

He reveals why investors make great founders, how AI is transforming the $500 billion maritime industry, and the leadership principles that drive his team’s success.

James also opens up about the relentless, high-stakes world of startups—where being ‘unkillable’ is the key to survival.

Whether you're scaling a business or navigating tough leadership decisions, this conversation offers powerful insights on strategic thinking, autonomy, and adapting to market forces.

Tune in for an unfiltered look at what it takes to build a game-changing company in a rapidly evolving industry!

You can find James Kellett at the below links

https://www.linkedin.com/in/jameskellett/
https://www.linkedin.com/company/spot-ship/

In the interview, James shares

  • "Entrepreneurship is the natural next step after investing. If you know how to allocate capital, why not build something yourself?" 
  • "The best entrepreneurs make pivotal decisions with the same strategic mindset as top investors."
  • "We set out to be the 'Bloomberg for ship brokers,' but innovation led us to a much bigger vision."
  • "AI and data are revolutionizing the $500 billion maritime industry—those who leverage them will lead the future."
  • "A great leadership culture grants autonomy, demands agility, and fosters transparency—this is how we operate at Spot Ship."
  • "Startups are an adrenaline rush—relentless, stressful, but incredibly meaningful."
  • "If you want to survive in entrepreneurship, you have to be 'unkillable'—resilient, adaptable, and driven."
  • "Success isn’t just about the idea—it’s about the culture, execution, and the people who believe in the mission."
  • "Leadership isn’t a position; it’s a choice. Every day, we decide whether to step up or step back."
  • "In business and in life, the bold choices define us—choose leadership, embrace risk, and create impact."
Show more...
2 months ago
39 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [220] - Rupesh Sanghavi - " There are no set rules for life other than what you have set for yourself."

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, we dive into the extraordinary journey of Rupesh Sanghavi—from selling brass gifts in college to building a multibillion-dollar e-commerce company.

He shares how calculated risks, empowering leadership, and bold decision-making shaped his success, offering invaluable lessons for anyone looking to scale their impact.

Rupesh’s story challenges the notion that leadership is about control—instead, it’s about trust, autonomy, and creating opportunities for others to thrive.

If you’ve ever felt stuck in your career or business, his insights will shift your perspective on what’s truly possible.

Tune in for a conversation that will inspire you to think bigger, lead bolder, and create lasting change.

You can find Rupesh Sanghavi at the below links

https://www.linkedin.com/in/rupeshsanghavi/
https://www.linkedin.com/company/ergodecorporate/

In the interview, Rupesh shares

  • "The seeds of entrepreneurship often lie dormant until the right opportunity presents itself."
  • "Leadership isn’t about control—it’s about empowering others to act as CEOs of their own domains."  
  • "Success is built on calculated risks, not blind leaps."  
  • "The right mentors can change the trajectory of your life—surround yourself with those who challenge and inspire you."  
  • "There are no set rules for life—only the ones we create for ourselves." 
  • "True leadership is trusting your team enough to let them lead." 
  • "Travel broadens not just the mind, but also the possibilities we dare to imagine."
  • "Building a business is not just about revenue—it’s about creating opportunities that transform lives."  
  • "Your past does not define your future—your choices do."
  • "Choosing leadership means stepping into the unknown with courage, again and again."
Show more...
2 months ago
31 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [219] - Anders Jones - "‍ What got you here is not going to get you to the next level"

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, Anders Jones, CEO of Facet, shares the hard-won lessons of scaling a disruptive FinTech company while navigating the challenges of modern leadership.

From overcoming imposter syndrome to building a high-performing remote team, Anders reveals why the strategies that got you here won’t take you to the next level.

He opens up about breaking outdated industry norms, fostering innovation, and the personal routines that keep him sharp.

Whether you're a founder, executive, or aspiring leader, this conversation will challenge you to rethink growth, resilience, and success.

Tune in for actionable insights that will help you lead with clarity, adaptability, and impact.

You can find Anders Jones at the below links

https://www.linkedin.com/in/anders-jones/
jones.anders@gmail.com

In the interview, Anders shares

  • "What got you here might not take you to the next level. Growth requires reinvention." — Anders Jones
  • "Entrepreneurship is often about recognizing gaps in the market—Facet was born from the need for transparency in financial advisory."
  • "In leadership, imposter syndrome is real. The key is embracing humility and learning from those around you."
  • "Resumes don’t tell the whole story—real-world skills and adaptability are what truly matter in a fast-paced tech environment."
  • "A fully remote company brings unique challenges, but intentional connection and culture-building make all the difference."
  • "Success in leadership isn’t just about strategy—it’s about personal discipline, reflection, and the ability to adapt."
  • "A strong morning routine isn’t a luxury—it’s an investment in sustained energy and clarity as a leader."
  • "Innovation isn’t just about new ideas; it’s about continuously questioning outdated norms and building something better."
  • "Every stage of growth demands a new way of thinking—what worked yesterday may not work tomorrow."
  • "Leadership is about making choices that reflect innovation, empathy, and resilience—not just chasing success."
Show more...
3 months ago
29 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [218] - Kjetil Kriken - "‍ My strength is finding strengths in other people"

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, we dive into the unconventional leadership journey of Kjetil Kriken—founder and CEO of Paldo—who went from organizing festivals to building an AI-powered competitive intelligence company.

Kjetil shares how embracing uncertainty, tackling tough questions early, and staying adaptable have been key to his success.

We explore the role of sports in developing resilience, why leaders must anticipate market shifts instead of reacting to them, and how startups can avoid being blindsided by change.

If you’ve ever faced the challenge of navigating unpredictability as a leader, this conversation will give you practical insights and inspiration to stay ahead.

Tune in and discover how choosing leadership—every single day—can transform your business and your life.

You can find Kjetil Kriken at the below links

https://www.linkedin.com/in/kjetilkriken/
kjetil@kriken.no

In the interview, Kjetil shares

  • "Leadership isn’t a title—it’s a choice. Kjetil Kriken’s journey shows how embracing uncertainty can unlock unexpected opportunities."
  • "From festival organizing to leading an AI-driven intelligence company—Kjetil Kriken proves leadership paths are rarely linear."
  • "True leadership is about adapting, innovating, and never being blindsided by change. That’s the vision behind Paldo."
  • "Sports teach discipline, resilience, and strategy—qualities that shape strong leaders like Kjetil Kriken."
  • "Startup success isn’t just about the idea—it’s about tackling hard questions early, embracing change, and building with purpose."
  • "Great leaders see potential where others see uncertainty. Kjetil Kriken’s story is a testament to that mindset."
  • "What if Mondays weren’t dreaded but anticipated? Leadership has the power to transform workplace culture."
  • "The best leaders don’t just react to market shifts—they anticipate and navigate them strategically."
  • "Innovation isn’t about avoiding risk—it’s about embracing the unknown with clarity and confidence."
  • "Every leadership journey is unique, but one thing remains constant: the courage to step up and make an impact."
Show more...
3 months ago
29 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [217] - James O Sullivan - "‍ I pride myself on communication"

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, James O'Sullivan, CEO of Project One Consulting, shares hard-won insights on navigating complex transformations with authenticity and resilience.

He challenges the traditional pursuit of profit, advocating instead for meaningful, sustainable change that truly serves clients.

James opens up about the dual layers of leadership—balancing project execution with company-wide vision—and how transparency builds lasting trust.

If you've ever struggled with leading through uncertainty or questioned how to scale without losing your core values, this conversation is for you.

Tune in to discover how seasoned leaders cut through complexity, embrace their individuality, and drive real impact.

You can find James O'Sullivan at the below links

https://www.linkedin.com/in/james-o-sullivan-3a2596/
james.osullivan@projectone.com

In the interview, James shares

  • "Leadership isn't just about managing projects—it's about shaping a culture where people thrive, not just survive."
  • "True transformation isn’t about chasing profit; it’s about delivering meaningful, sustainable change."
  • "Authenticity in leadership isn’t optional—it’s the foundation of trust and long-term success."
  • "Mature leadership turns chaos into clarity, helping teams embrace change instead of fearing it."
  • "Great leaders prioritize real conversations over rehearsed sales pitches—trust is built through transparency."
  • "Leadership isn’t about being the loudest in the room; it’s about knowing when to listen and when to lead."
  • "Navigating complexity requires more than strategy—it demands a deep commitment to people and purpose."
  • "Growth isn’t just about scaling a business; it’s about staying true to your mission while making an impact."
  • "Stepping outside your comfort zone isn’t about changing who you are—it’s about expanding what you’re capable of."
  • "Choosing leadership means aligning with your values, leading with integrity, and embracing the challenges that come with it."
Show more...
3 months ago
35 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [216] - Kaushik Burman - " Pick up the phone—hearing a voice builds empathy and resolves conflicts better than any message ever could."

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, I sit down with Kaushik Burman, CEO of Spiro, to explore his extraordinary journey from engineer to global leader.

Kaushik shares powerful insights on building resilience, making tough choices, and leading with integrity in an ever-changing world.

We discuss how to foster innovation from the ground up, embrace distributed leadership, and align personal values with professional impact.

If you're navigating leadership challenges or striving to inspire your team, this conversation is packed with actionable wisdom to help you thrive.

Tune in to discover how to lead with purpose and create meaningful change—no matter where your journey begins.

You can find Kaushik Burman at the below links

https://www.linkedin.com/in/kaushikburman/
kaushik.burman@gmail.com

In the interview, Kaushik Burman shares

  • "Leadership is not about titles or positions. It's about making choices that often aren't easy." 
  • "Resilience is a muscle that grows stronger with each challenge we face."
  • "Leadership is no longer top-down; it's dynamic and requires nurturing at every level."
  • "Our values, choices, and identity shape how we lead, even in the face of uncomfortable decisions."
  • "Innovation must be frugal and pragmatic—empowering individuals at every level to contribute."
  • "Hearing a voice, connecting face-to-face—even virtually—builds empathy and resolves conflicts better than written messages."
  • "Distributed leadership fosters innovation by allowing leaders to emerge across all levels of an organization."
  • "A leader's higher purpose is not just professional success but transforming lives and building a better future."
  • "Creating space for reflection and personal growth is essential to lead effectively without getting lost in chaos."
  • "Leadership is a lifelong journey of learning, teaching, and mentoring to inspire the next generation."
Show more...
3 months ago
29 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [215] - Grant Ballard-Tremeer - "A different opinion doesn't mean they're wrong and I'm right."

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 inspiring episode of the *Choosing Leadership* podcast, I sit down with Grant Ballard-Tremeer, founder of Eco, to uncover the transformative power of empathy in leadership.

Drawing wisdom from his personal encounter with Nelson Mandela, Grant shares how embracing multiple truths and diverse perspectives can drive collaboration and innovation.

We dive into the challenges leaders face when transitioning from hands-on control to empowering their teams and staying aligned with purpose.

Grant also reveals his secrets to intentional living, slow productivity, and leading with balance in a world driven by busyness.

If you’re looking for actionable insights to elevate your leadership and create meaningful impact, this conversation is one you can’t afford to miss!

You can find Grant Ballard-Tremeer at the below links

https://www.linkedin.com/in/grantballardtremeer/
https://ecoltdgroup.com/

In the interview, Grant Ballard-Tremeer shares

  • "Leadership is about empathy—seeing the world through others' eyes and acknowledging that two truths can exist simultaneously."
  • "Meeting Nelson Mandela taught me the power of embracing multiple truths and using empathy to bridge differences."
  • "Great leadership requires balancing vision with letting go—empowering your team to flourish while staying aligned with shared goals."
  • "To lead effectively, keep your 'nose in but fingers out'—guide the mission without micromanaging the details."
  • "Understanding that others' priorities may differ from your own is the first step toward moving from confrontation to collaboration."
  • "Empathy is a 'super skill' that transforms not only leadership but also relationships with clients, teams, and communities."
  • "Life isn't just about productivity; it’s about living intentionally, being present, and prioritizing purpose over output."
  • "Setting boundaries—like blocking email access and creating time for deep work—helps leaders stay proactive rather than reactive."
  • "Leadership is a journey of continual learning—embracing new perspectives and growing through curiosity and innovation."
  • "By choosing to lead with empathy and an open mind, we create ripples of impact that extend far beyond ourselves."
Show more...
4 months ago
33 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [214] - Sanne Wolters-Verstegen - "Do your best with what you can control, and let go of what you can't."

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 inspiring episode, former Dutch middle-distance runner turned corporate leader, Sanne Wolters-Verstegen, shares her incredible journey from the track to the boardroom.

She reveals how the lessons of resilience, focus, and adaptability from her athletic career shaped her approach to leadership in high-pressure environments.

Discover how teamwork, passion, and embracing what you can control can transform your leadership challenges into opportunities for growth.

Sanne also highlights the power of having mentors and finding joy in the journey to fuel both personal and professional success.

Tune in for actionable insights and a fresh perspective on what it takes to lead with purpose and drive!

You can find Sanne Wolters-Verstegen at the below links

https://www.linkedin.com/in/sanne-wolters-verstegen-3427212/

In the interview, Sanne shares

  • "Commitment and adaptability can bridge the gap between success in sports and leadership in the corporate world." 
  • "Do your best with what you can control and learn to let go of what you can't. It's a philosophy that transforms challenges into opportunities."
  • "High-pressure environments teach us to focus on clear goals and ignore distractions beyond our control."
  • "Success is rarely a solo journey – a strong support network is vital, whether in sports or corporate life."
  • "Teamwork and collaboration empower individuals to achieve more than they ever could alone."
  • "Passion turns challenges into joy and transforms routine into an adventure worth pursuing."
  • "Mentors and coaches aren’t just for athletes – they’re essential in driving motivation and clarity in corporate leadership."
  • "Finding joy in the journey is as important as reaching the destination – embrace the process wholeheartedly."
  • "Leadership is like a race: it demands resilience, dedication, and a supportive team to reach the finish line."
  • "Choose leadership in your life – strive for excellence, embrace growth, and make your journey meaningful."
Show more...
4 months ago
32 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [213] - Srikant Chellappa - " Every CEO has a boss"

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, I sit down with Srikant Chellappa, CEO of Engagedly and author of *Into The Blue: Implementing the Ikigai Philosophy to Create a Meaningful Workplace*.

Together, we explore the transformative power of the "blue zone"—the sweet spot where passion, skills, and organizational needs align.

Srikant shares actionable insights for tackling disengagement, reigniting team passion, and creating workplaces that empower individuals to thrive.

From balancing corporate demands with personal purpose to leading with courage during times of failure, this conversation is packed with strategies to elevate your leadership.

Tune in to discover how to design meaningful work environments that inspire growth, fulfillment, and lasting impact.

You can find Srikant Chellappa at the below links

https://www.linkedin.com/in/srikantchellappa/
https://engagedly.com/

In the interview, Srikant Chellappa shares

  • "The blue zone is where passion, skills, and organizational needs converge—a space of true alignment and fulfillment in the workplace."
  • "Misalignments in the workplace often lead to disengagement and burnout. Leaders must act boldly to realign roles and reignite passion."
  • "Recognize when employees have outgrown their roles. Position them in work that sparks joy and unlocks their potential."
  • "Courageous leadership means making tough talent mobility decisions—even if it means letting go of great talent to help them grow."
  • "A healthy workplace thrives on open conversations, trust-building practices, and a culture of continuous learning."
  • "Reigniting team passion requires regular check-ins, honest feedback loops, and opportunities for skill development."
  • "Fulfillment is measurable: well-designed surveys can uncover trends linking employee happiness to business outcomes."
  • "Failure is a part of leadership. Respond with empathy, transparency, and a focus on root cause analysis to build trust and resilience."
  • "A healthcare success story proves that investing in employee development and coaching leads to empowerment and continuous improvement."
  • "Choose leadership daily. Lead with joy, meaning, and pride—not just for yourself, but to inspire those around you."
Show more...
4 months ago
31 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [212] - Ritu Mohanka - " Leadership is about the constant thing between power and love, push and pull, hard and human, and grit and grace"

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," I sit down with Ritu Mohanka, the inspiring CEO of VONQ, to uncover how intentional choices and authentic leadership can transform careers and lives.

From navigating cultural shifts across continents to embedding trust and innovation in her organization, Ritu shares powerful lessons on resilience, empathy, and servant leadership.

She opens up about balancing family and professional values, leveraging feedback for growth, and the pivotal role of AI in reshaping talent attraction.

Whether you're a leader striving to empower your team or seeking fresh insights to elevate your leadership style, Ritu’s journey will leave you inspired and ready to take action.

Tune in for an engaging conversation filled with real-world strategies and heartfelt wisdom!

You can find Ritu Mohanka at the below links

https://www.linkedin.com/in/ritu-mohanka-1337031/
https://www.vonq.com/

In the interview, Ritu shares

  • "Intentional choices reshape our paths and motives, paving the way to significant achievements." 
  • "Leadership begins with service. Servant leadership is the cornerstone of organizational success."
  • "Feedback isn't criticism; it's a catalyst for growth and a lifelong commitment to learning." 
  • "Children keep me grounded, offering unfiltered honesty that shapes my leadership style."
  • "Trust and innovation are at the heart of my vision as a CEO. Empowering leaders and embedding AI responsibly will define the future of work." 
  • "Resilience and empathy are essential strengths in leadership, enabling us to foster environments of psychological safety." 
  • "Balance may be elusive, but intentional presence allows us to manage energy and priorities effectively."
  • "The leadership journey isn’t linear or easy—it’s a constant process of learning and adaptation." 
  • "Great leaders empower others to take ownership, celebrating openness and accountability as pathways to success." 
  • "Designing a life infused with joy, meaning, and dedication starts with authentic conversations about what truly matters."
Show more...
4 months ago
32 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [211] - Georgios Syntellis - " Intuition comes with experience. Experience means I've messed it up 300 times."

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, we dive into the remarkable journey of Georgios Syntellis, who left the structured world of investment banking to lead a thriving FinTech startup in Greece.

Georgios shares how curiosity and adaptability have shaped his leadership style, offering practical insights for navigating change and embracing growth.

He reveals the secret to building a company culture rooted in trust, integrity, and collaboration—one that empowers teams to thrive.

With parallels between sailing and decision-making, Georgios unpacks the balance between intuition and strategy when leading through uncertainty.

Tune in to discover how you can lead with resilience, foster innovation, and create a legacy of meaningful impact.


You can find Georgios Syntellis at the below links

https://www.linkedin.com/in/georgiossyntelis/
https://www.everypay.gr/

In the interview, Georgios shares

  • "Curiosity is the compass that led Georgios Syntellis from investment banking in London to leading a FinTech startup in Athens."
  • "Leadership thrives at the intersection of trust, integrity, and a commitment to continuous learning."
  • "Life's greatest opportunities often come disguised as abrupt changes—embrace them with courage and curiosity."
  • "Building a strong company culture isn’t just about today; it’s about creating values that resonate far into the future."
  • "Leadership is like sailing—decisions are made with incomplete data, guided by intuition, experience, and strategy."
  • "Georgios sees every challenge as a building block toward becoming a more resourceful and humble leader."
  • "Innovation and cultural evolution must go hand in hand to create workplaces where everyone can thrive."
  • "Failures and successes teach us what spreadsheets cannot—intuition is born from experience."
  • "Georgios reminds us that as leaders, we occupy a small but significant place in shaping the world around us."
  • "Choosing leadership is a daily decision—make it with resilience, humility, and a commitment to growth."
Show more...
5 months ago
32 minutes

Choosing Leadership with Sumit Gupta
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?