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.

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.

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.

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.

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.