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Choosing Leadership with Sumit Gupta
Sumit Gupta
279 episodes
16 hours 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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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 (20/279)
Choosing Leadership with Sumit Gupta
Leadership Journeys [241] - Zach Smith - "Connection through new cultures or places can spark powerful inner growth."

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 soulful episode of Choosing Leadership, Zach Smith, founder and CEO of Anywhere, shares how a chance meeting in Costa Rica sparked a global movement rooted in meaningful travel and authentic connection.

Together with host Sumit Gupta, they unpack how travel—when done with intention—can catalyze profound personal growth and cultural understanding.

Zach opens up about leading through crisis, staying true to his values during the pandemic, and redefining success beyond transactions.

This conversation is a must-listen for any leader who feels the tension between scaling a business and staying aligned with their deeper purpose.

If you're craving a leadership journey that nourishes your soul as much as your goals, this episode will leave you inspired and reconnected.


You can find Zach Smith at the below links

  • https://www.linkedin.com/in/anywhereincceo/
  • https://www.anywhere.com/


In the interview, Zach shares

  • “Connection—especially through new cultures and places—can spark powerful inner growth.” 
  • “We’re not just building a travel company. We’re curating soulful experiences that change people.” 
  • “Leadership is choosing purpose and connection over comfort and convenience.” 
  • “Our story started with a chance encounter in Costa Rica. What followed was a decades-long journey of intentional creation.” 
  • “Even when borders closed during the pandemic, our commitment to values kept us open—open to adapt, grow, and serve.” 
  • “We’re not here to sell travel. We’re here to change the way people experience the world.” 
  • “True leadership isn’t about shouting louder—it’s about embodying your values when it matters most.” 
  • “The future of travel is not about ticking boxes. It’s about meaningful moments that connect us to something greater.”
  • “Trust, authenticity, and intention—those are the currencies that matter in business and in life.”
  • “This episode is a reminder that choosing leadership means making bold choices that align with your soul—not just your strategy.”
Show more...
16 hours ago
33 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [240] - Jonne Välilä - "Most things—whether in life or business—just aren't worth the stress."

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 drives someone to keep building after 14 years of wins and failures?

In this candid conversation, serial entrepreneur Jonne Välilä shares how he went from selling skateboards in Finland to running 20+ brands and a hedge fund in Dubai—all while staying grounded, honest, and ambitious.

You'll hear his take on stress, cultural adaptation, and the mindset shifts that help leaders thrive in uncertain terrain.

If you're wrestling with pressure, imposter syndrome, or the constant chase for “more,” this episode will feel like a deep exhale.

Tune in for a refreshingly real take on leadership, risk, and what it truly means to play the long game.


You can find Jonne Välilä at the below links

  • https://www.linkedin.com/in/jonne-valila/
  • https://www.wealthrone.com/


In the interview, Jonne shares

  • "Entrepreneurship is a cycle—start, stumble, learn, grow, repeat."
  • "In Finland, I studied entrepreneurship; in Dubai, I lived it."
  • "Most things in business—and life—aren’t worth the stress we give them."
  • "I’d rather be painfully honest than politely misunderstood."
  • "It’s not just about success—it’s about the feeling of becoming successful."
  • "Failures don’t define your story—they sharpen your strategy."
  • "Dubai pushes you forward without pushing you down."
  • "Risk is essential—as long as it’s you taking it, not your clients or investors."
  • "Transparency builds trust. And trust builds everything else."
  • "Leadership is a choice. So is the courage to keep choosing it every day."
Show more...
1 week ago
32 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [239] - Steven Meersman - " You can never achieve balance because then you're standing still and you die"

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 in the climate tech space—beyond the buzzwords and boardrooms?

In this candid conversation, Steven Meersman, co-founder of Zenobi Energy, shares how he went from resisting entrepreneurship to leading a company that's transforming energy infrastructure across 11 countries.

You’ll hear hard-won lessons on scaling with purpose, building a culture of ownership, and navigating the messy middle of leadership.

Steven’s insights on balancing innovation with financial viability are gold for any leader trying to do work that actually matters.

If you’re building something bold and want to stay grounded while growing fast, this episode is for you.


You can find Steven Meersman at the below links

  • https://www.linkedin.com/in/stevencgmeersman/
  • https://www.zenobe.com/


In the interview, Steven shares

  • “Leadership is a pendulum—you don’t want perfect balance, you want movement. Knowing when to push back is key.” 
  • “We don’t just hire startup veterans—we hire passionate people who care deeply about our mission. Ownership can be taught.” 
  • “If sustainability isn’t financially viable, it won’t scale. Our job is to make green solutions make business sense.” 
  • “My journey into entrepreneurship was reluctant at first, but purpose pulled me in—climate tech gave me a reason to build.” 
  • “Lessons from oil and gas—like managing risk and optimizing cost—are surprisingly useful when scaling clean tech.” 
  • “I don’t make decisions based on labels. I look at the opportunity, the timing, and the impact we can make.” 
  • “A good leader supports without micromanaging and communicates without creating silos.” 
  • “We’re solving the first mile, the last mile, and everything in between to make renewable energy work at scale.” 
  • “We’ve repurposed EV batteries to replace diesel generators—real innovation happens where the grid doesn’t reach.” 
  • “Culture isn’t just values on a wall—it’s what people do when no one’s looking. That’s what drives innovation.”
Show more...
2 weeks ago
1 minute

Choosing Leadership with Sumit Gupta
Leadership Journeys [238] - Saasha Celestial-One - "Every dollar that you spend is a vote for the world that you wanna live in"

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 mean to lead with purpose in a world that’s constantly pulling us toward profit and performance?

In this inspiring conversation, Saasha Celestial-One—co-founder and COO of Olio—shares how she’s tackling food waste while staying grounded in mission, sustainability, and conscious leadership.

From building a globally recognized app to not buying new clothes for over a decade, Saasha’s choices challenge the status quo and invite us to rethink our own.

We explore how vulnerability, emotional energy, and authentic partnerships shape bold leadership.

If you're navigating growth while trying to stay true to your values, this episode is a must-listen.


You can find Saasha Celestial-One at the below links

  • https://www.linkedin.com/in/saasha-celestial-one-929390/
  • https://olioapp.com/en/


In the interview, Saasha shares

  • "Leadership is a choice—and I choose to lead with purpose, not just profit."
  • "Every transaction is a vote for the kind of world we want to live in."
  • "Starting Olio wasn’t just about food waste—it was about reimagining our relationship with the planet."
  • "The highs and lows of entrepreneurship are real—but so is the power of resilience."
  • "I haven’t bought new clothes in 13 years. Sustainability starts with small, personal decisions."
  • "Building a startup is like a marriage—you need shared values, mutual respect, and a whole lot of patience."
  • "Creativity without structure is chaos; structure without creativity is lifeless. You need both to lead."
  • "Vulnerability and authenticity aren't weaknesses—they're leadership superpowers."
  • "Scaling globally means working with—not against—regulations, and seeing them as tools for impact."
  • "We all have the power to create change. Start with what’s on your plate—and what you choose to waste."
Show more...
3 weeks ago
5 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [237] - Anant Agarwal - " Sales is vanity. Profit is sanity, and cash is reality. "

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 a stable global career and build something from the ground up?

In this episode, Anant Agarwal, CEO of Skill Mine, shares the raw emotional journey of choosing leadership and stepping into entrepreneurship with courage and conviction.

From growing up surrounded by business conversations to building a tech company that aims to serve the world, Anant’s story is packed with insight and inspiration.

He talks about the weight of starting over, the power of frugality, and how he nurtures leadership within his team.

Tune in for an honest, energizing conversation that will challenge you to dream bigger and lead with intention.


You can find Anant Agarwal at the below links

  • https://www.linkedin.com/in/agrawalanant/
  • https://skill-mine.com/


In the interview, Anant shares

  • "Choosing leadership is not a role—it's a decision, driven by dreams too big to ignore."
  • "Leaving a secure global career wasn’t easy, but I realized—if not now, then when?" – Anant Agarwal
  • "Business wasn’t just a subject in school—it was dinner table conversation in my family."
  • "You can’t build something new while clinging to the comforts of the old."
  • "Frugality is not about scarcity—it’s about intelligent resourcefulness."
  • "When you lead with purpose, your team stops being employees and starts becoming ambassadors."
  • "We’re not just building for India—we’re building in India, for the world."
  • "The hardest part of entrepreneurship? Leaving behind people who only knew the professional version of me."
  • "Innovation happens when failure isn’t punished—it’s studied and celebrated."
  • "Choosing leadership is a daily act—it’s not about titles, it’s about responsibility and courage."
Show more...
4 weeks ago
36 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [236] - Jason Foster - "People do their best work when they feel safe to disagree."

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, Jason Foster, CEO of ORI Biotech, shares how he's reshaping the future of healthcare by leading with purpose, not just profit.

From Capitol Hill to health tech, his journey is packed with lessons on building culture, navigating chaos, and staying grounded in a mission that truly matters.

We explore why autonomy without alignment can derail a startup, and how fairness and psychological safety drive innovation more than perks ever could.

If you're a leader trying to build something that lasts—especially in a fast-moving industry—this conversation will challenge how you think about compensation, culture, and impact.

Tune in for real talk, bold ideas, and leadership wisdom you won’t find in a textbook.


You can find Jason Foster at the below links

  • https://www.linkedin.com/in/jasoncfoster/
  • https://oribiotech.com/connect


In the interview, Jason shares

  • "Culture eats structure for breakfast—if you don’t build it intentionally, it builds itself by accident."
  • "We don’t use carrot-and-stick compensation. We aim for fairness, transparency, and intrinsic motivation."
  • "Innovation doesn’t happen in chaos. You need clarity, rhythm, and alignment—even in a startup."
  • "Autonomy is powerful, but without shared purpose and regular check-ins, it becomes a recipe for misalignment."
  • "We’re not here just to build a company—we're here to change how people access lifesaving therapies around the world."
  • "Leadership is less about control and more about removing obstacles so your team can do their best work."
  • "Healthcare today is reactive. What we need is a proactive, tech-enabled system that serves people before they get sick."
  • "Bringing business thinking into public policy could be the key to fixing broken healthcare systems globally."
  • "You can’t scale a mission like ours without scaling trust, transparency, and psychological safety."
  • "I’m here to mentor, support, and build the next wave of health tech leaders—let’s connect."
Show more...
1 month ago
37 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [235] - Jonathan Brun - "Anything valuable and lasting takes time to build."

This is the Leadership Journey series on the Choosing Leadership Podcast.

In this episode, Jonathan Brun—Founder and CEO of mnemonic—shares what it really takes to build a company that lasts.

Far from the glamorized startup hustle, Jonathan’s journey is a masterclass in patience, consistency, and values-driven leadership.

He opens up about competing with giants as a bootstrapped founder, navigating compliance in a changing world, and why true impact means thinking beyond profits.

Whether you’re scaling a business or leading a team, this conversation will challenge you to rethink your definition of success.

Tune in to discover why playing the long game might just be your greatest leadership advantage.


You can find Jonathan Brun at the below links

  • https://www.linkedin.com/in/jonathanbrun/
  • https://nimonik.com/contact-us/usa/


In the interview, Jonathan shares

  • "Success isn’t always fast or flashy—sometimes, it’s about quietly showing up for years and playing the long game."
  • "We didn’t start mnemonic with a grand plan for compliance—it grew out of curiosity, grit, and a willingness to learn."
  • "Real growth comes from consistency. Like Arctic explorers, we set goals every two months and march forward, no matter the weather."
  • "Being bootstrapped means being bold—we’ve built a business that competes with giants, one smart decision at a time."
  • "Leadership isn’t about ego or titles—it’s about serving something bigger than yourself, even when no one’s watching."
  • "I’m more inspired by Gandhi than billionaires. Building something meaningful matters more than building wealth."
  • "AI may be the future, but values, process, and human insight will always be part of smart compliance."
  • "We turned an old consulting database into a thriving B2B SaaS company. Not magic—just patience, mistakes, and iteration."
  • "Business is a long game. If you want to create impact, build like you’ll be around for 50 years."
  • "Compliance may sound boring—but done right, it saves lives, prevents disasters, and protects what matters."
Show more...
1 month ago
31 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [234] - Siddhi Joshi - "Being a CEO & the only female employee was adventurous"

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 lead in an industry that tells you you don’t belong?

In this powerful conversation, Siddhi Joshi, CEO of Emos UAE, shares how she broke barriers, built the region’s top relocation company, and created space for women to lead boldly.

From emotional intelligence to Gen Z leadership hacks, she drops real-world insights you can apply today—whether you're managing a team or building one from scratch.

We also dive into how she scales culture with intentional themes like “License to Question” and why she believes human connection is the ultimate leadership edge.

If you’re ready to rethink what’s possible in your leadership, this episode is your permission slip.


You can find Siddhi Joshi at the below links

  • https://www.linkedin.com/in/siddhijoshiemovers/
  • https://emoversuae.com/


In the interview, Siddhi shares

  • "Leadership is not about serving content—it's about shifting the context."
  • "I was told logistics wasn't a space for women. So I built a team of all-female packers instead." – Siddhi Joshi
  • "You don’t need industry experience to lead—you need vision, courage, and emotional intelligence."
  • "My father led without boundaries. I’ve made that philosophy my legacy too." – Siddhi Joshi
  • "Micromanagement is out. Clear goals and empowered teams are the future."
  • "Gen Z doesn’t want a boss—they want a partner in growth. Adapt or get left behind."
  • "Leadership isn’t about knowing it all. It’s about creating the space for others to shine."
  • "We introduced a company theme: 'License to Question.' Because culture changes when conversations change."
  • "Emotional intelligence isn’t soft. It’s the hardest, most human edge in leadership today."
  • "If you want to lead, get personal. Understand your people beyond their job titles."
Show more...
1 month ago
37 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [233] - Bidhan Baruah - " I spend 70% of my time in one-on-ones with my teams"

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 grow a company from a basement startup to a 400-person powerhouse?

In this episode, Bidhan Baruah, co-founder and COO of Taazaa Inc., shares how he chose leadership not as a position, but as a mindset—grounded in empathy, accountability, and bold vision.

We dive into how he spends 70% of his time in one-on-ones, why balancing psychological safety with performance matters, and how he’s future-proofing his business through AI.

If you're a leader feeling stuck or navigating change, this conversation is a practical and inspiring nudge forward.

Tune in to be reminded that you can lead with heart, and still build something extraordinary.


You can find Bidhan Baruah at the below links

  • https://www.linkedin.com/in/bidhanbaruah/
  • https://www.taazaa.com/


In the interview, Bidhan shares

  • “Leadership is a choice—and Bidhan Baruah chose courage over comfort when he left the safety of a stable job to build a company from a basement.”
  • “Empathy isn't a buzzword for Bidhan—it’s a strategy. He spends 70% of his time in 1:1s to build trust, reduce attrition, and create loyalty.”
  • “Leadership isn’t about having all the answers—it’s about being willing to ask the hard questions while making people feel safe to do the same.”
  • “In a world rushing toward AI, Bidhan is not just adapting—he’s educating. Because future-proofing means teaching before transforming.”
  • “Culture isn’t created by accident. It’s built moment by moment—in how you listen, how you lead, and how you show up for your team.”
  • “From off-roading to running a 400-person tech company, Bidhan thrives at the edge of risk and precision. That’s where real growth lives.”
  • “True leadership is being willing to step into the unknown—with empathy in one hand and accountability in the other.”
  • “If you want to build something that lasts, start by understanding your people—not just their skills, but their stories.”
  • “AI might be the future, but leadership remains deeply human. That’s Bidhan’s secret: embracing both.”
  • “Choosing leadership isn’t about titles—it’s about taking ownership, staying curious, and committing to continuous reinvention.”
Show more...
1 month ago
27 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [232] - Craig Dunham - " You can be direct and transparent without being mean."

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 both courage and clarity in today’s chaotic business world?

In this episode, Craig Dunham, CEO of Voltron Data, shares raw and practical lessons from the trenches—from making tough career pivots to leading teams through high-stakes acquisitions.

He talks about the power of directness, why transparency beats politeness, and how routine and self-care fuel high-performance leadership.

If you’ve ever struggled with balancing empathy and honesty, or felt overwhelmed by shifting priorities, this conversation is your compass.

Tune in to discover how choosing leadership—again and again—isn’t about perfection, but about presence, priorities, and purpose.


You can find Craig Dunham at the below links

  • https://www.linkedin.com/in/craigadunham/
  • https://voltrondata.com/


In the interview, Craig shares

  • "Leadership is a conscious choice—it’s about stepping into discomfort, not away from it." 
  • "You can be direct and transparent without being harsh. Honesty builds trust when it's delivered with empathy." 
  • "The most transformative growth often follows the most difficult decisions." 
  • "Being a repeat CEO doesn’t make the job easier—it just sharpens your ability to prioritize and stay even-tempered." 
  • "I’ve learned that switching contexts rapidly—without losing focus—is a leadership muscle you have to build over time."
  • "Taking care of your body and mind isn't optional. It’s the foundation of sustainable leadership." 
  • "In a noisy market, clarity of mission and message is what makes a company stand out." 
  • "As your company grows, your leadership must evolve. What got you here won’t get you there." 
  • "Leadership is less about knowing all the answers, and more about being willing to navigate uncertainty with integrity."
Show more...
2 months ago
29 minutes

Choosing Leadership with Sumit Gupta
Leadership Journeys [231] - Crafting a Meaningful Legacy: KK Gupta's Leap into Entrepreneurship

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 a 30-year global banking career and start over — completely from scratch?

In this powerful episode, KK Gupta shares his courageous leap into entrepreneurship, revealing what most leaders don’t talk about: the fear, the loneliness, and the deep desire to build something that actually matters.

If you're feeling stuck in a successful-but-unfulfilling role, this conversation will challenge you to rethink what legacy and leadership really mean.

KK doesn’t just talk strategy — he opens up about identity, discipline, culture, and how introverts can lead with quiet strength.

Tune in to hear how doing one thing well (and saying “no” to everything else) might be the boldest move you make as a leader.


You can find KK Gupta at the below links

  • https://www.linkedin.com/in/kkgupta/


In the interview, KK shares

  • "I wanted to create something, craft something, and solve a problem deeply — not just clock in and clock out."
  • "Leaving behind the security of a 30-year career wasn’t easy — but staying would’ve meant ignoring a calling I couldn’t unhear."
  • "When you go from leading thousands to a team of one, the silence can be deafening — but also clarifying."
  • "Factum isn’t just a business — it’s a culture experiment in kindness, clarity, and doing one thing exceptionally well."
  • "Saying no is a leadership skill. Focus is how we honor what truly matters."
  • "You don’t have to be loud to lead. Introverts can lead just as powerfully — through intention, empathy, and presence."
  • "Covid didn’t just change the world — it gave me the courage to change mine."
  • "We’re not just solving problems. We’re building a place where people feel seen, supported, and challenged to grow."
  • "Authentic leadership is less about charisma — and more about the willingness to keep learning, listening, and leading with care."
  • "Legacy isn’t built in boardrooms. It’s built in the moments where you choose courage over comfort."
Show more...
2 months ago
29 minutes

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...
2 months 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...
2 months 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...
3 months 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 months 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...
3 months 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...
3 months 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...
3 months 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...
4 months 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...
4 months ago
27 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?