The Bold Play

Building for the Fortune Five Million with René Lacerte, CEO & Founder of BILL

In this episode of The Bold Play, Ryan Prindiville sits down with René Lacerte, CEO & Founder of BILL, for a wide-ranging conversation on leadership, technology, and building companies that stand the test of time. René shares his perspective on how AI is leveling the playing field for small and mid-sized businesses - what he calls the “Fortune 5 Million” - by putting enterprise-grade financial capabilities into the hands of entrepreneurs. Drawing from nearly two decades of building BILL, he reflects on the evolution from founder to CEO, why the role must be earned every day, and the importance of humility, patience, and trust in long-term leadership. Throughout the conversation, René discusses why AI should be viewed as an enabler rather than a replacement, howleaders can unlock creativity within their teams, and why understanding the work deeply is essential before adopting new technology. He also shares lessons on navigating growth, maintaining culture at scale, and leading with convictionin an era of rapid change. Whether you’re a founder, executive, or advisor helping businesses grow, this episode offers thoughtful insight onleadership, innovation, and building organizations designed to endure.

Leadership, Scale and the Future of Women-Owned Businesses with Jean Freeman

In this episode of The Bold Play, Ryan Prindiville sits down with Jean Freeman, Principal & CEO of Zambezi, to explore what it takes to build, scale, and sustain a business through constant change. Jean shares lessons from nearly twodecades of leading one of the largest female-owned creative agencies in the country from surviving early-stage volatility and economic downturns to evolving leadership styles, expanding services, and navigating industry disruption driven by technology, media fragmentation, and AI. Throughout the conversation, Jean discusses the importance of adaptability, knowing when to shift from founder tocoach, building resilient teams, and creating organizations that can scale without losing their culture. She also reflects on supporting the next generation of women leaders and what it truly means to build a business that lasts. Whether you’re scaling a founder-led company, navigating change in a fast-moving industry, or rethinking how you lead as your organization grows, this episode offers grounded perspective on sustainable leadership in an era defined by constant evolution.

Leading Through the AI Inflection Point with Aaron Harris of Sage

In this episode of The Bold Play, Ryan Prindiville sits down with Aaron Harris, Global CTO at Sage, to explore how AI is reshaping the foundations of modern business from the rise of agentic AI to the shifting relationship between humans, machines, and the software that powers today’s enterprises. Aaron shares deep insight into why AI agents will soon become primary users of business software, how SaaS business models must evolve, and what leaders can do to stay ahead as technology cycles compress faster than ever before. He also discusses the growing importance of digital trust, assurance, and building organizations capable of navigatingconstant disruption. Whether you’re leading a high-growth business, rethinking your digital strategy, or preparing your teams for thenext era of innovation, this conversation offers a compelling look at what it takes to thrive in a world undergoing historic transformation.

Operating at AI Speed with Ivan Makarov of Andreessen Horowitz

In this episode of The Bold Play Podcast, Ryan Prindiville sits down with Ivan Makarov, Partner at Andreessen Horowitz, to explore how AI is transforming the pace of innovation,the structure of modern startups, and the role of today’s finance leaders. Ivan shares firsthand insights from working with the world’s most cutting-edge founders, from building lean, compute-first companies to why today’s CFO is becoming the “Chief Architect Officer.” He breaks down what it takes to lead in an era where competition moves weekly, decisions must be made quickly, and the foundations of finance and operations are being rebuilt through AI. Whether you're scaling a startup, advising high-growth teams, or navigating accelerating change, this conversation is a masterclass in modern leadership.

Scaling Globally and Leading Through AI with Mark Orttung, CEO of Projectworks

In this episode of The Bold Play Podcast, Ryan Prindiville sits down with Mark Orttung, CEO of Projectworks, to discuss scaling a SaaS startup across five countries, embedding AI into every part of the business and leading with courage through uncertainty. Mark shares practical lessons on growth,innovation and why every bold move starts with a thousand little things.