More Elephant

Former United Nations peacekeeper, leadership coach, mountaineer, and author Urs Koenig has spent his career in environments where leadership is tested under pressure.

From conflict zones in the Balkans and the Middle East to executive coaching and keynote stages, his experiences led him to a simple but often misunderstood idea: humility is not weakness. In this conversation, we explore the philosophy behind his book Radical Humility, why the strongest leaders build trust before crises arrive, and how self-awareness, relationships, and curiosity create more resilient teams.

Urs' path has been anything but conventional. Born in Switzerland, he studied geography before moving to Australia to pursue a PhD, eventually transitioning into management consulting, executive coaching, and leadership development. At age fifty, inspired by his late father and a desire to do meaningful international service, he returned to military service after more than two decades away. His deployments with NATO and the United Nations exposed him to the realities of peacekeeping, where diplomacy, uncertainty, and everyday humility often mattered far more than command and authority. Those experiences became the foundation for the leadership philosophy he teaches today.

Throughout our conversation, Urs challenges the common belief that humble leaders lack confidence, arguing instead that genuine humility requires deep self-awareness, emotional security, and the willingness to ask difficult questions. We discuss psychological safety, the importance of meaningful relationships before a crisis occurs, and why listening has become one of the rarest leadership skills in today's distracted environment. Drawing on stories from military deployments, Urs illustrates how trust built long before an emergency often determines how effectively leaders respond when the stakes are highest.

We also explore the broader challenges facing leadership today, from declining trust in institutions to the rise of strongman leadership and the influence of social media on public discourse. Urs makes the case for critical thinking, curiosity, and the discipline to keep learning. He reflects on personal leadership failures, the importance of embracing a growth mindset, and why leading yourself is often far harder than leading others.

At its core, this conversation reminds us that leadership is not about having all the answers. It is about creating environments where people feel seen, heard, trusted, and empowered to solve difficult problems together.

Key More Elephant Takeaways in this Episode:

• Strong leadership begins long before a crisis. Investing in meaningful relationships creates trust that allows teams to move faster and solve problems together when pressure arrives.
• Humility and confidence are complementary, not competing qualities. The most effective leaders have enough self-awareness to seek feedback, admit mistakes, and continue learning.
• Psychological safety grows when leaders model vulnerability first. Owning your own mistakes makes it easier for others to speak honestly and contribute without fear.
• Listening is a leadership skill that requires deliberate practice. Putting distractions aside and listening beyond words helps leaders understand what people are saying, and what they are reluctant to say.
• Ego often reveals itself when leadership becomes focused on personal recognition instead of collective success. The best leaders consistently shift attention from themselves to the people and mission they serve.
• and more…

Brandy Thompson never set out to become the CEO of a fast-growing health benefits technology company. As CEO of benefitbay, she now leads a platform helping employers and employees rethink how healthcare benefits are delivered, however her path to leadership was anything but traditional.

In this conversation, we explore what happens when someone with an operator’s mindset and a passion for solving real-world problems decides to challenge one of the most complicated systems people interact with every day: healthcare.

Brandy’s career began in accounting and operations, where she developed a reputation for helping organizations improve performance, solve complex problems, and scale sustainably. She joined benefitbay on day one as Vice President of Operations, and just a year later, when the company faced an unexpected leadership transition, she was asked to step into the CEO role.

Our conversation explores the future of healthcare benefits and why Brandy believes employees should have greater control over the healthcare decisions that affect their families. We discuss the rise of ICHRA, a model that shifts decision-making power from employers to individuals, and why she sees it as a transformation similar to the shift from pensions to 401(k)s.

Along the way, we examine human-centered design, customer trust, and the importance of building technology around real human needs rather than forcing people to adapt to systems that no longer serve them. We also spend time discussing leadership, fundraising, and the realities of building a company with limited capital. Brandy explains why benefitbay intentionally hires former teachers and nurses to guide employees through healthcare decisions, and why empathy remains one of the most valuable skills in an increasingly automated world.

As AI continues to reshape industries, Brandy offers a thoughtful perspective on where technology can help and where human judgment, trust, and connection still matter most, where meaningful innovation happens when people are empowered with information, ownership, and the confidence to make decisions for themselves.

Key More Elephant Takeaways in this Episode:

• Unconventional career paths often create stronger operators because overcoming adversity develops resilience, adaptability, and a deeper understanding of how businesses actually function.
• Human-centered design starts by understanding the emotional experience behind a decision. Technology works best when it simplifies complexity while still preserving trust and human connection.
• AI should be used to enhance human judgment, not replace it. In high-stakes decisions involving health, finances, or personal wellbeing, responsible implementation matters as much as innovation.
• Great leaders do not wait for perfect credentials or permission. Growth often begins when people step into opportunities before they feel completely ready.
• and more…

Sabrina Parsons grew up watching entrepreneurship happen in real time inside a cramped Palo Alto home where her father built Palo Alto Software from a tiny bedroom office while introducing his family to bleeding-edge technology long before computers were mainstream. Years later, Sabrina would inherit the company and face a defining choice: evolve or disappear.

In this episode of More Elephant, Sabrina shares her journey from Princeton history major and public school teacher to CEO of Palo Alto Software and creator of LivePlan, a platform helping entrepreneurs build smarter, living business plans. She opens up about leading through massive technology shifts, from the rise of the internet to today’s AI revolution, and why she believed the company had to completely reinvent itself to survive.

Sabrina breaks down the dangerous myth that business planning is only for investors and explains why ongoing forecasting and cash flow management are critical for small business survival. She shares how LivePlan combines decades of planning expertise with AI-powered tools designed to help entrepreneurs think critically, not just generate shortcuts.

We also explores leadership, culture, and autonomy inside Palo Alto Software, including the company philosophy: “We give you the autonomy to be awesome.” Sabrina discusses why trust and accountability matter more than rigid policies, how AI is transforming internal operations, and why she still refuses to replace human customer support with chatbots.

Beyond business, Sabrina reflects candidly on motherhood, leadership, gender bias in entrepreneurship, and raising three sons to understand fairness, responsibility, and empathy. From navigating the realities of being a “Mommy CEO” to mentoring women leaders, she shares a deeply personal perspective on what it means to build a company and a life that aligns with your values.

This episode is a powerful conversation about adaptation, intentional leadership, human-centered technology, and the courage to evolve without losing sight of who you are.

Key More Elephant Takeaways in this Episode:

• Business planning is not a one-time document for funding. It is an ongoing discipline that helps entrepreneurs make smarter decisions and avoid cash flow failure.
• AI can accelerate business creation, but successful founders still need critical thinking, financial understanding, and the ability to defend their strategy to investors and lenders.
• Strong company cultures are built on trust and accountability. Empowering employees with autonomy only works when people act responsibly and “don’t ruin it for the rest of us.”
• Human connection still matters in the AI era. Palo Alto Software continues prioritizing real customer support because entrepreneurship is emotional, stressful, and deeply personal.
• Leadership and parenting share a common principle: listening is not enough. You must truly hear people, understand their realities, and respond with empathy and action.
• and more…

In this episode of the More Elephant podcast, we sit down with Don Graves, former U.S. Deputy Secretary of Commerce and founder of Highland Creek Advisors, to talk about leadership, economic policy, and what it takes to create real impact at scale.

Don’s path into public service was shaped by a deep-rooted commitment to community, influenced by generations of educators and mentors who challenged him to think critically and stay open to new perspectives. From early experiences in law school and civil rights work to advising two U.S. presidents, his career reflects a consistent focus on expanding opportunity and removing barriers.

We explore his role in helping stabilize Detroit during one of its most challenging periods, where listening to communities became the foundation for meaningful change. Don shares how real impact happens when policy aligns with the lived experiences of the people it’s meant to support, and why empowering teams at every level of government is key to execution.

The conversation also dives into the realities of innovation, including the growing influence of AI and its potential to reshape the workforce. Don offers a thoughtful perspective on how technological progress can create opportunity while also increasing inequality in the short term, and what leaders need to consider moving forward.

From workforce investment to global partnerships, Don highlights the importance of building an economy that works for more people. At its core, this episode is about trust, collaboration, and the responsibility leaders carry to create systems that support long-term growth and shared success for all.

Key More Elephant Takeaways in this Episode:

• Effective policy and leadership begin by understanding the needs of communities. Don emphasizes that the most successful initiatives are shaped by those directly affected, not just by top-down decision-making.
• Big ideas only work when the right people are empowered to carry them out.
• Aligning teams, supporting decision-makers, and focusing on implementation are what turn plans into results.
• Advances like AI can drive economic growth, but they can also widen gaps before new opportunities emerge. 
• From government to business to global partnerships, trust shapes outcomes. Without it, collaboration breaks down and progress becomes harder to sustain.
• and more…

In this episode of More Elephant, we sit down with Andrew Watterson, founder of Blue CSR Strategies, an ESG consulting firm dedicated to helping businesses, governments, and nonprofits accelerate their impact on their environmental and sustainability strategies.

Andrew’s journey began with early inspiration from his grandmother and sixth-grade science teacher, both passionate about environmental stewardship and social justice. From there, he led sustainability efforts at KeyBank and GOJO Industries, navigating the unique challenges of driving change within large organizations.

We explore the real-world impact of ESG in business, from the importance of shifting mindsets to the critical role of producer responsibility in tackling plastic waste. Andrew shares insights on how companies can reduce, reuse, and recycle with a closed-loop approach, and how sustainability can drive innovation, attract talent, and strengthen brands.

Despite the current political climate, Andrew remains hopeful, pointing to continued investment in renewable energy, carbon reduction, and innovative solutions by major companies. He reminds us that sustainability is not just about the planet—it’s about our health, our communities, and our future.

We dive deep into the power of business leadership to drive progress, the strategic importance of learning networks and collaboration, and the promise of making sustainability a core part of every organization’s mission.

Key More Elephant Takeaways in this Episode:

• Sustainability is about more than just the environment—it’s also about social impact and strong governance, all of which can drive business value.​
• The most successful ESG programs see sustainability as a strategic advantage, unlocking innovation and differentiation.​
• Producer responsibility is crucial for tackling plastic waste; businesses must focus on reducing, reusing, and recycling in a closed-loop system.​
• Connecting sustainability to health and basic needs helps make these issues more relatable and urgent.
• and more…

Heather Tuason didn't set out to be an entrepreneur—she hustled through a tough childhood in Southern Virginia, working full-time at Domino's Pizza from age 15 to support her family after her parents' divorce, all while raising her younger sister and powering through college.

That grit forged her "doer" mantra, propelling her from bank teller to Capital One exec, where she spotted a glaring gap: 50% of small businesses fail by year five, mostly due to cash flow woes with the vast majority lacking any financial plan. 

Frustrated by corporate red tape blocking her fintech fixes, she launched Arena in 2019—a 2025 Inc 5000 honoree (#409)—pivoting boldly from a failed cashflow platform (Arena Pay) to matchmaking elite fractional CFOs for growing companies needing bookkeeping, payroll, forecasting, and strategic firepower without full-time costs.

This episode dives into Heather's raw resilience against VC bias (like demands for a "male CTO"), her remote team's core values of trust, confidence, and competence, and how rigorous case studies vet only 2.5% of CFO talent to fit real-world needs like construction or tech firms. She shares triumphs, like saving a school IT client through PPP forgiveness, pivots to Zoom-era growth, and now exit prep.

Forward-thinking, we discuss AI's game-changer: automating tactical reports (forecast vs. actuals, KPIs) to free CFOs for high-impact strategy on expansions and scaling. Drawing from Teddy Roosevelt's "Man in the Arena," she aims to slash that 50% failure rate, empowering operators to thrive beyond year five.

A must-listen for the More Elephant podcast—pure tenacity meets actionable finance wisdom.

Key More Elephant Takeaways in this Episode:

• Arena matches fractional CFOs via human "matchmaking" plus case studies, bridging the gap for 6M U.S. employer businesses against just 275K available CFOs.
• 82% of failed businesses blame cash flow; Arena uncovers hidden levers like client collections and capital access to boost longevity past year five.
• Ditch solo hustling—fractional experts deliver 24/7 finance focus, from payroll to performance tracking, unlocking leverage for hires and campaigns.
• AI revolutionizes finance by automating monthly reviews and KPIs, letting CFOs strategize expansions over grunt work.
• Founder resilience shines: Pivot boldly (like killing your own tech), embrace "doer" execution, and own your arena despite biases.
• No VC? No problem—Arena's bootstrapped path proves incremental growth beats dilution, prioritizing family and freedom.
• and more…

In this conversation with Andy Ellwood, founder of Stretch, we explore what happens when childhood frugality, serial entrepreneurship, and AI-powered innovation collide around one persistent problem: how to know you are paying the best price for groceries.

Stretch is building the first true shopping intelligence platform, empowering everyday families to compare full basket prices across nearby stores before they shop—saving families over $1,000 a year amid relentless inflation in early results.

Andy takes us from a Texas homeschool experience where grocery runs taught math and ingenuity, through startups acquired by Facebook, Google, and private equity, to the tragedy of losing a key investor days before funding and COVID shuttering his prior venture Basket.com.

Now a new Dad, he reveals how AI supercharges data from 1 million products, personalizes lists for gluten-free needs, and envisions agentic commerce where AI agents negotiate deals for your family while balancing growth with the demands of nurturing a newborn.

We unpack shocking shopper surveys—17% skipping meals, middle-class families adapting hardest—and Andy's "rule of three": automate any task done three times weekly with AI.

This is a story of curiosity asking "what else is possible?", resilience through loss, and tech flipping grocers' info advantage to families. If you battle weekly grocery math, care about AI's practical edge in business and life, or wonder how founders rebound stronger, this is a must-listen on the More Elephant podcast.

Key More Elephant Takeaways in this Episode:

• Stretch uses AI to deliver real-time basket pricing across thousands of stores, turning mental price comparisons into actionable savings without store-hopping.
• Grocery inflation exposes inequities: low-income families already maxed out trade-offs, while 24% of Americans used buy-now-pay-later for food last year.
• From crowdsourcing prices at Basket.com to AI querying millions of sku’s, Andy's 12-year obsession solves what Expedia did for travel—now for the unchanged grocery world.
• Fatherhood and coaching honed efficiency; AI acts as "smarter interns" for tasks like webpage builds or list tweaks, accelerating Stretch's nationwide rollout.
• Agentic AI promises "agentic commerce": your digital rep shops your profile, unlocking demand-based deals from chains competing for baskets.
• and more…

In this conversation with Dr. Ella Fung and Dr. Nancy Schoenbrunner, co-founders of Rosalind Dx, we explore what happens when scientific rigor, lived experience, and a bold entrepreneurial leap collide around one simple but powerful idea: access.

Rosalind Dx is reimagining prenatal testing by moving it from complex, centralized genome sequencing to a faster, more affordable PCR-based approach. The result? A potential step-change in how non-invasive prenatal testing is delivered, who can access it, and how quickly families receive answers.

Ella takes us from Hong Kong to Cambridge to Oxford and into the deeply personal moment of navigating her own pregnancies, where she experienced firsthand how insurance coverage can determine access to critical information. Nancy shares the origin story that begins not in a boardroom, but with a dream, a whiteboard sketch, and decades of experience working alongside the inventors of PCR at Roche.

We talk about the leap from industry to startup life, the realities of fundraising as female founders, and why decentralizing advanced diagnostics could be one of the most important shifts in global women’s health.

This is a conversation about science, yes. It is also about equity, courage, and the willingness to build something new when the system doesn’t serve everyone equally. If you are interested in and care about the future of healthcare, about designing for access instead of exclusivity, and what it really takes to move from breakthrough idea to commercial reality, this is a must listen.

Key More Elephant Takeaways in this Episode:

• Rosalind Dx is leveraging PCR technology to replace expensive, centralized genome sequencing with a faster, lower-cost, and more scalable approach to non-invasive prenatal testing.
• Access to prenatal diagnostics is not just a medical issue. It is an equity issue. Insurance coverage and geography currently determine who receives the most accurate information during pregnancy.
• Decentralizing testing from a handful of global sequencing hubs to regional labs can dramatically reduce cost, turnaround time, and systemic inefficiency.
• Female-led innovation in women’s health is gaining momentum, particularly in ecosystems that intentionally address historic funding bias.
• and more…

In this second part of the conversation with Anita Ghosh, founder and CEO of Bridjr, we go deeper into what is really missing from most transformation efforts. We talk about why organizations keep failing at digital transformation, why technology alone is not enough, and why human adoption is the real driver of return on investment.

Anita brings a powerful, practical framework that connects strategy, systems, and soul to the work. We discuss how organizations are building compound debt when they ignore the human experience and Anita offers insights from her own journey that provide leaders with a blueprint for what they need to do differently.

We explore how to communicate during change and why the future of business depends on designing for human adoption to deliver compound value. If you are leading change in your organization, this episode is a must listen. It is one of those conversations that forces you to rethink what success really looks like.

Key More Elephant Takeaways in this Episode:

• Anita shares the need to ensure human adoption is at the heart of transformation efforts and very often, most strategy frameworks are missing the customer voice.
• Failure to build human-centered systems creates debt across technical systems, operations, culture, brand, and experience. This debt grows over time and reduces the value of every investment.
• Approaches anchored in strategy, systems and soul will drive business value and help solve for the messy middle of change management.
• and more…

In this episode of More Elephant, I sit down with Anita Ghosh, Founder and CEO of Bridjr, for a deeply human conversation about leadership, listening, and what it really takes to build organizations that work for people, not just systems.

Anita’s work sits at the intersection of empathy, technology, and business transformation. However, this conversation goes further than frameworks and models - so much further that we are holding space over two episodes for the conversation.

We talk about the quiet moments that shape careers, the cost of external validation, and what happens when leaders stop trusting themselves. Deeply personal, Anita shares her path from large organizations to founding Bridjr including the moments that forced her to slow down, listen, and choose bravery without a safety net.

We also unpack why so many organizations struggle with change, how internal transformation thinking and impact often lags behind external ambition, and why human adoption is the real driver of ROI in technology. At its core, this episode is about remembering that progress starts with listening and that being human is not a liability in business. It is the advantage.

Key More Elephant Takeaways in this Episode:

• Anita explains why organizations often struggle when the inside doesn’t change as quickly as the outside, emphasizing that real business value comes from human adoption and continued use, not just implementation.
• We discuss how systems that reward performance over alignment can quietly erode a leader’s inner compass.
• Anita shares how listening opened up new choices for her life and expanded how she saw herself and her purpose.
• We talk through how leaders grow when they give themselves permission to step off the expected route and create their own story.
• and more…