Jon Morris built Rise Interactive from a solo operation to one of the largest independent digital marketing agencies in the world, scaling it to nearly $40 million in revenue over 16 years. He started with prize money from the University of Chicago's New Venture Challenge in 2004 and rode the wave of digital advertising's explosive growth.

Today, Jon is the founder and CEO of The Fiscal Advocate, where he serves as a fractional CFO for professional service firms. In this episode, Jon shares his "double wind" framework - the idea that success comes from having wind at your back in both your service offerings and your client selection. He explains why picking high-growth industries and rapidly growing clients matters more than raw talent, discusses the future of AI in financial planning, and reveals why structured data is the key to unlocking AI's potential. Jon also opens up about the challenges creative agency owners face when forced to become entrepreneurs and why getting into the financial weeds separates great CEOs from the rest.

Want to learn more about Jon Morris's work? Check out their website at https://www.fiscaladvocate.com/.

Connect with Jon Morris on LinkedIn at https://www.linkedin.com/in/jonmorrisramsayinnovations/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

Pietro Canestrelli is a tax attorney and former IRS attorney who helps business owners and taxpayers protect their hard-earned money. As the founder of the Law Office of Pietro Canestrelli and author of America's Tax Defender, he focuses on getting the IRS out of your life as fast as possible.

In this episode, Pietro breaks down the three areas of tax work: compliance, proactive planning, and tax defense. He explains why being audited is actually a "badge of success," why CPAs don't do proactive tax planning, and shares underutilized strategies like R&D tax credits and cost segregation that could save business owners tens or hundreds of thousands of dollars.

Want to learn more about Pietro's work? Check out his website at https://ietaxattorney.com/.

Connect with Pietro on LinkedIn at https://www.linkedin.com/in/pietro-canestrelli-18032a21.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.

In this episode of Leaders and Legacies, Craig Andrews sits down with Bernie DeSantis, CEO of Insignia Training Partners, to explore how leaders can transform virtual training from a dull obligation into a powerful leadership tool. Drawing on more than 20 years of experience in corporate learning and development, Bernie shares how organizations can deliver high-impact virtual experiences that engage people and drive real results.

Bernie explains why many virtual events fail: leaders treat them like in-person presentations and simply “turn on the camera.” But virtual environments demand a different approach. Leaders must intentionally create interaction, structure engagement, and guide participants through meaningful learning moments.

The conversation also covers the psychology of audience engagement, why attention spans are shrinking, and how simple tools like polling, chat prompts, and structured interaction can dramatically improve participation. Bernie also highlights common mistakes leaders make—such as overwhelming audiences with too much information and failing to provide a clear call to action.

Ultimately, great virtual experiences come down to intentional leadership. When leaders design training and events that prioritize engagement and clarity, they build stronger relationships, deeper trust, and better business outcomes.

Want to learn more about Bernie DeSantis's work? Check out their website at https://insigniatraining.com/.

Connect with Bernie DeSantis on LinkedIn at https://www.linkedin.com/in/badiii/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.