The Bold Play

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 financia...

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 leade...

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, ho...

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...

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.

In the debut episode of The Bold Play Podcast , host Ryan Prindiville, Partner at Armanino, sits down with John Eck, former President & CEO of Mattress Firm, to explore the bold leadership strategies that drove one of retail’s most significant turnarounds. From navigating post-bankruptcy restructuring and accelerating growth to overseeing a major acquisition, John shares candid stories and har...

The Bold Play  — Where fearless leadership meets real-world results. The Bold Play  dives into the minds of trailblazing executives who dared to bet big, break the mold and build lasting success. In just 30 fast-paced minutes, each episode delivers candid conversations about pivotal business moments, bold decisions and the challenges that shaped transformative outcomes. Every episode spotlights ho...