Leaders & Legacies

David Solomon built and ran a $100 million toy manufacturing company in the 1990s with 840,000 square feet of facilities in Montreal and Plattsburgh, New York, successfully competing against China at a time when conventional wisdom said it couldn't be done. Today, as founder of SERO Growth, he helps manufacturers expand into international markets and supports international organizations entering North America.

In this episode, David...

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 ...

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 audit...

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.

Be...

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 signa...

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...

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 trainin...

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...

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 forci...

Erik Brenner doesn’t lead from theory. He leads from structure.

As President and CEO of Hilltop Wealth & Tax Solutions, Erik built a firm that integrates advanced tax strategy with wealth management. He saw what others missed: reactive advice was failing clients. CPAs focused on last year. Advisors focused on investments. No one owned the full picture.

So he changed it.

Erik shares how a defining client case exposed the cost of di...

Leadership isn’t just vision. It’s responsibility. In this episode, Catrina M. Craft challenges business owners to rethink what leadership really means when it comes to money, decisions, and long-term impact.

Catrina explains why most entrepreneurs unknowingly overpay the IRS—not because the law requires it, but because they were never taught how the system actually works. She draws a sharp line between compliance and strategy, argu...

In this episode of Leaders and Legacies, Craig Andrews speaks with Brett Swarts, founder of Capital Gains Tax Solutions, about what leadership looks like when business owners think beyond today.

Brett makes the case that strong leaders plan for exits long before they happen. Most owners focus on growth, customers, and operations, but fail to prepare for the financial reality of selling. That lack of foresight can cost 20–50% of thei...

Most leadership failures don’t start with people. They start with poor visibility into the business. In this episode, Heidi DeCoux explains why leaders who don’t understand their numbers end up working longer hours while making less money.

Heidi breaks down the leadership trap of chasing top-line revenue without understanding profitability. She explains why many founders scale chaos instead of results and how unclear financial data ...

Leadership today demands more than vision and execution. It requires the ability to protect people, data, and trust in an increasingly hostile digital environment.

In this episode, Craig Andrews sits down with Robert Siciliano, a leading authority on identity theft, cybersecurity, and personal risk management. Robert breaks down why security is no longer an IT issue—it’s a leadership responsibility. He explains how leaders who ignor...

Adam House doesn’t believe in waiting for the right moment—he builds momentum. In this episode of Leaders and Legacies, Adam shares how his “Why Not?” mindset propelled him from serial entrepreneur to professional basketball player at 32—and later, to becoming CEO and co-owner of the very team he joined.

Craig Andrews explores Adam’s leadership journey through seven ventures, including a healthcare analytics platform that went publi...

Jennifer Bookspan knows that leadership isn’t about filling seats—it’s about shaping the future of an organization. In this episode, she joins Craig Andrews to discuss how her firm, Bookspan Search Partners, goes beyond typical executive recruiting to help companies build intentional, aligned leadership teams.

Jennifer shares why the best leaders are usually the best listeners, and how humility, clarity, and vision all factor into s...

Greg Giniel, Professional EOS Implementer, joins Craig Andrews to break down the mindset shift every business owner must make: stop being the easy button for your team. In this candid conversation, Greg explains how the EOS framework builds leaders at every level, freeing business owners from the daily grind while increasing performance across the organization.

He shares personal stories, including how his team kept his business thr...

Chris Brown, CTO of Wow Remote Teams, shares how Latin America became his go-to talent solution—and why more U.S. businesses should follow. After running a booming medical e-commerce operation during the pandemic, Chris needed scalable, affordable, and reliable help. His wife Julie, originally from Bogotá and now CEO of Wow Remote Teams, helped him build a nearshore workforce that outperformed U.S.-based teams at a fraction of the ...

David Kreeger traded legal briefs for business breakthroughs. In this episode, the founder of GoPedal shares his journey from practicing law at WilmerHale and IBM to owning a painting franchise and now leading strategic transformations for companies that feel stuck.

David reveals what drew him away from the legal grind—a desire to make decisions, improve quality of life, and be present for his family. His pivot into entrepreneurship...