Skip to content
The Bold Play podcast artwork

PODCAST · business

The Bold Play

by The Bold Play

The Bold Play is where fearless leadership meets real-world results. Hosted by Armanino’s Ryan Prindiville, this podcast cuts through the noise to spotlight the executives who bet big, broke the mold and built lasting success.

Publisher-supplied feed metadata · PodParley refreshed Feb 4, 2026 · Source feed

Episodes

  1. 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...

  2. 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...

  3. 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…

    more
  4. 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...

  5. 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...

  6. Inside One of Retail's Biggest Comebacks with John Eck, Former President & CEO of Mattress Firm

    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...

  7. The Bold Play Preview

    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…

    more

Type above to search every episode's transcript for a word or phrase. Matches are scoped to this podcast.

Searching…

We're indexing this podcast's transcripts for the first time — this can take a minute or two. We'll show results as soon as they're ready.

No matches for "" in this podcast's transcripts.

Showing of matches

No topics indexed yet for this podcast.

Loading reviews...

ABOUT THIS SHOW

The Bold Play is where fearless leadership meets real-world results. Hosted by Armanino’s Ryan Prindiville, this podcast cuts through the noise to spotlight the executives who bet big, broke the mold and built lasting success.

HOSTED BY

The Bold Play

CATEGORIES

Frequently Asked Questions

How many episodes does The Bold Play have?

The Bold Play currently has 7 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is The Bold Play about?

The Bold Play is where fearless leadership meets real-world results. Hosted by Armanino’s Ryan Prindiville, this podcast cuts through the noise to spotlight the executives who bet big, broke the mold and built lasting success.

How often does The Bold Play release new episodes?

The Bold Play has 7 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to The Bold Play?

You can listen to The Bold Play on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts The Bold Play?

The Bold Play is created and hosted by The Bold Play.
URL copied to clipboard!