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/.

Trust is often treated as a vague leadership ideal, but Kim Bohr argues it’s one of the most measurable and practical drivers of performance inside organizations.

As President and CEO of SparkEffect, Kim works with executive teams navigating disruption without breaking trust. In this conversation, she explains how leadership failures rarely come from malicious intent. Instead, they stem from blind spots—small behaviors, missed signals, and unexamined habits that slowly erode trust within teams.

Kim shares how leaders can recognize these “micro-moments” that shape trust every day. Whether it’s acknowledging mistakes quickly, demonstrating transparency during difficult decisions, or showing curiosity instead of judgment, leaders have constant opportunities to strengthen relationships.

She also highlights why organizations often overlook leadership development at the frontline level, where trust issues frequently begin. Without the right skills and emotional intelligence, leaders unintentionally damage the culture they’re responsible for building.

Ultimately, Kim’s message is clear: trust is not abstract. It can be measured, strengthened, repaired, and intentionally built into how organizations operate.

Want to learn more about Kim Bohr's work? Check out their website at https://sparkeffect.com/.

Connect with Kim Bohr on LinkedIn at https://www.linkedin.com/in/kimbohr/.

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 Jeremy Fennema, founder of Fennema.io and a fractional CIO/CTO who helps growth-stage companies bring order to chaotic technology environments.

Jeremy explains why most companies struggle with technology—not because of poor tools, but because they lack strategy. Leaders often buy solutions to solve isolated problems, creating a patchwork of systems that don’t work together. Jeremy’s role is to step in, align technology decisions with business goals, and build a clear roadmap for execution.

He also breaks down the difference between tactical IT support and true technology leadership. Instead of simply fixing problems when systems fail, strategic leaders design environments where those problems rarely happen in the first place.

Jeremy also tackles one of today’s biggest leadership challenges: AI adoption. Too many companies start with the question, “How can we use AI?” when the real question should be, “What problem are we trying to solve?” Technology should follow strategy—not drive it.

Through stories from international business expansion and years of technology leadership, Jeremy shows how leaders can build systems that scale, reduce chaos, and support long-term growth.

Want to learn more about Jeremy Fennema's work? Check out their website at https://fennema.io.

Connect with Jeremy Fennema on LinkedIn at https://linkedin.com/in/fennema.

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/.

Leadership often hinges on decisions made with incomplete information. In this episode of Leaders and Legacies, John C. Scott explains why strong leaders build financial clarity into their organizations rather than relying on intuition or a bank balance.

John, a CPA and partner at Anders, specializes in helping law firms understand the business side of their practice. Many attorneys excel in legal reasoning but never receive training in finance or firm management. That gap often leads to poor cash planning, uneven partner distributions, and missed opportunities to reinvest in growth.

John explains how law firms can shift from reactive accounting to proactive financial leadership. Instead of looking backward at reports, leaders should forecast cash flow, set operating cash targets, and plan distributions strategically. This forward-looking discipline helps firms avoid cash crunches and operate with confidence.

The conversation also explores leadership culture inside professional services firms. John emphasizes the importance of hiring smart people, building flexible work environments, and creating a culture where employees choose to stay. Leaders who treat their people well build organizations that thrive beyond themselves.

For law firm leaders—and any professional services owner—this episode highlights how financial discipline, thoughtful leadership, and strong culture combine to create long-term success.

Want to learn more about John C. Scott's work? Check out their website at https://anderscpa.com/virtual-cfo-legal/.

Connect with John C. Scott on LinkedIn at https://www.linkedin.com/in/john-c-scott-cpa/.

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/.

Nick Jain, co-founder of Eagle Rock CFO, believes leadership in the AI era comes down to leverage. The best leaders won’t be replaced by AI—they’ll use it to multiply their impact.

Nick explains how AI and smart automation are eliminating low-value work like data cleanup, financial modeling, and report creation. That shift frees leaders to focus on judgment, relationships, and strategic decisions. Instead of spending weeks analyzing spreadsheets, leaders can now generate insights in hours—and act faster than competitors.

He shares how AI can compress consulting-level analysis into a fraction of the time and cost, making elite financial insight accessible to small and mid-sized businesses. From predicting cash flow risks to uncovering hidden cost savings, technology now surfaces what most humans would miss.

Nick also challenges leaders to rethink roles. Coders become architects. Analysts become decision-makers. Owners become system designers. The future belongs to leaders who adapt quickly, expand their capabilities, and use AI as a force multiplier.

Want to learn more about Nick Jain's work? Check out their website at https://eaglerockcfo.com.

Connect with Nick Jain on LinkedIn at https://www.linkedin.com/in/nickmjain/.

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/.

Sriram Mangudi believes leadership reveals itself in moments of pressure. In this episode, he shares hard-earned lessons from global HR leadership, M&A integrations, and navigating COVID while running essential pharmaceutical operations.

He explains why most leaders fail during transformation: they push agendas instead of listening. In one high-stakes acquisition, Sriram walked into a room filled with suspicion. Instead of forcing integration plans, he listened. That shift built trust, preserved value, and turned a tense acquisition into a long-term success.

Sriram breaks down what separates reactive managers from strategic leaders. Strong leaders create space for dialogue. They protect autonomy. They focus on root causes instead of surface symptoms. During COVID, while others reacted daily to chaos, his team focused on preventive health and long-term workforce stability. That decision preserved operations and saved lives.

He also challenges private equity’s habit of replacing executives too quickly. Sustainable performance requires governance, alignment, and transparent communication—not constant leadership churn.

Leadership is not about control. It’s about clarity, calm, and disciplined execution when the ground shifts beneath you.

Want to learn more about Sriram Mangudi's work? Check out their website at https://consultmsg.com/.

Connect with Sriram Mangudi on LinkedIn at https://www.linkedin.com/in/srirammangudi/.

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/.