Leaders & Legacies

Hillary Gale didn’t just pivot careers—she rewrote the script entirely. A former college writing teacher, she stepped away from academia, launched a one-woman marketing firm, and then discovered she was pregnant—all within days. With nine months on the clock, she had to lead fast, build smart, and carve out space for maternity leave while launching Moneta Copy.

In this episode, Hillary breaks down how strong writing skills are found...

Donovan Ryckis is leading a healthcare revolution—one grounded in leadership, accountability, and total transparency. As CEO of Ethos Benefits, he exposes the broken incentives in traditional benefits brokerage, where rising premiums often pad broker commissions. His fiduciary approach flips the model: no backdoor deals, no hidden fees, and no vague renewals. Just clear numbers and bold decisions.

In this episode, Donovan walks thro...

Alex Sanfilippo shares how a childhood marked by dyslexia and self-doubt evolved into a leadership platform spanning podcasting, public speaking, and entrepreneurship. As the founder of PodMatch, Alex has enabled thousands of leaders to get their voices heard, but his path started with personal healing and self-expression.

In this episode, Alex details how podcasting became his tool for leadership—helping him own his voice, refine h...

Chris Hurn, CEO of Community Bankshares, joined the show to talk straight about entrepreneurial leadership in high-stakes environments. He traces his roots to watching his single mother run a chocolate business out of their basement, an early masterclass in grit, marketing, and operations. That foundation shaped his view of what it means to lead—not just manage.

Now a leader in small business financing, Chris outlines the crucial di...

Allison De Paoli joins Craig Andrews to break down how employers can lead through one of the most neglected aspects of their business—health insurance. Drawing from decades of experience and her family’s entrepreneurial legacy, Allison shows how leaders can stop hemorrhaging money on bloated health plans and start using benefits as a tool for retention, loyalty, and long-term cost control.

She argues the system isn’t broken—it’s rig...

Everett O’Keefe shares the origin story of Ignite Press, from a chance reconnection to a publishing powerhouse. His leadership was tested early when co-founder John tragically passed away, forcing Everett to carry the vision forward alone. Instead of folding, he doubled down. That decision sparked the launch of nearly 200 bestselling books and reshaped how thought leaders share their message.

In this episode, Everett unpacks the pow...

Mike Jesowshek, founder of TaxElm, delivers a masterclass on leadership by eliminating one of the biggest pain points for entrepreneurs: tax confusion. His leadership style centers on simplifying complexity and empowering clients and employees through clear strategy and execution. On the Leaders and Legacies podcast, Mike breaks down how he uses transparency, consistency, and responsiveness to lead both a growing team and a nationa...

Michael Cole, President of Next Level Technician, shares how he turned a failed Subway franchise and a few unlikely training classes into a thriving staffing and training company in the low-voltage trades. In a field plagued by high turnover and unpredictability, Cole stands out by building systems that value integrity and grit over credentials. His leadership journey is rooted in real-world trial and error—like discovering too lat...

Vance Morris doesn’t just deliver services—he designs unforgettable experiences. In this episode, he shares how Disney’s obsession with systems shaped his philosophy for building customer loyalty and price elasticity. Morris breaks down his transition from security guard at a birth control factory to Disney executive, then to bankrupt entrepreneur, and finally to the founder of Deliver Service Now. His key insight? Competing on pri...

Tom Dillon, founder of Frak Finance, joins Craig Andrews to break down how smart financial leadership unlocks business growth. As a fractional CFO, Tom helps companies escape the trap of gut-based decisions and start leading with data. He exposes the cost of common blind spots—like selling at a loss, underestimating hiring costs, or ignoring traction metrics.

Tom shows how predictable revenue isn’t a myth—it’s a method. From analyzi...

Kirk Spahn brings leadership to life at ICL Academy, a school built for students who aim higher—on the court, on the stage, or in their communities. In this conversation, Kirk breaks down what it takes to lead with purpose. He shares how ICL moves beyond academics to develop discipline, resilience, and character. The goal? To build champions for life.

Kirk reveals how elite athletes and performers grow not just through hard work but...

Michelle Griffin joins Craig Andrews to deliver a sharp message for leaders flying under the radar—visibility is not vanity, it's your responsibility. As founder of Brand Leaders and creator of the “Own Your Lane” framework, Michelle helps professionals become the go-to voice in their space. In this episode, she breaks down the four key steps of her method: Launch Your Vision, Articulate Your Difference, Navigate Your Brand, and El...

David Forster joins Craig Andrews to dismantle one of the most persistent myths in business: that people are the problem. With eight businesses under his belt, Forster explains why 94% of business issues stem from broken or missing processes—not bad hires. He shares how simplifying systems, building checklists, and offloading mental bandwidth into clear SOPs empowers teams to thrive.

Craig and David dive into leadership lessons lear...

Josh Wathen, COO of Triad InfoSec and former Green Beret, joins Craig Andrews to sound the alarm on a growing leadership challenge: cyber resilience. In a world where ransomware is a billion-dollar business and hackers operate in full-fledged corporate teams, Josh breaks down why small businesses are soft targets—and how leadership complacency can be fatal.

He shares hard-earned insights into the psychology of cyber threats, the hig...

Philip Portman, founder of Textdrip and author of Three Keys to Success, shares his raw journey through entrepreneurship and leadership. At his lowest point—deep in debt, grieving the loss of his dog, and questioning his choices—Philip made a commitment: he would never work for anyone else again. That moment became his turning point.

In this episode, he explains how personal hardship catalyzed business growth, ultimately scaling his...

Dr. Cristin Dickerson isn’t waiting for the healthcare system to fix itself—she’s leading the charge. As founder of Green Imaging, Dr. Dickerson cuts through red tape and bloated bureaucracy to deliver affordable, high-quality imaging. In this episode, she walks through how leadership rooted in ethics, transparency, and accountability can change the industry from the inside out.

She breaks down the rising costs of care, how private ...

Ken LaCroix, Chief Insight Officer at Insightful Partners, brings a sharp leadership lens to financial strategy. In this episode, he explains why a good CFO doesn’t just report history—they help leaders forecast and shape the future. Ken shares stories from the trenches, including uncovering a private jet buried in company expenses, and warns how these tactics might slash a company's valuation.

He breaks down common leadership misst...

Jeff Peterson didn’t start with investors, privilege, or a fallback plan. At 17, he jumped into business and never looked back. On this episode of Leaders and Legacies, Jeff breaks down the leadership lessons behind building a $150 million real estate project from the ground up. What started as a cash-flowing trailer park evolved into a 316-unit, mixed-use development—thanks to years of patience, calculated risk, and grit.

Jeff reve...

Dr. Kushagra Verma doesn’t just run a spine care practice—he leads it with intention, integrity, and data. In this episode, Dr. Verma lays out a clear blueprint for what leadership looks like in medicine. He shares how rejecting volume-based care in favor of concierge-level attention has allowed him to maintain high standards and build lasting trust with patients.

Craig Andrews explores Dr. Verma’s early pivot from engineering to su...