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…