Season 2, Ep. 18 | Building What Lasts: A Conversation with Sabrina Parsons

Season 2, Ep. 18 | Building What Lasts: A Conversation with Sabrina Parsons

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…

Season 2, Ep. 17 | For The Greater Good: A Conversation with Don Graves

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…

Season 2, Ep. 16 | Sustainable Thinking: A Conversation with Andrew Watterson

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…

Season 2, Ep. 15 | The Woman in the Arena with Heather Tuason

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…

Season 2, Ep. 14 | Stretch(ing) Grocery Spend in an AI Era

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…