Leaders & Legacies

Donovan Pyle pulls back the curtain on an industry most business leaders misunderstand: employer-sponsored health care. In this episode, Donovan explains how companies are overpaying by as much as 25%—often without realizing it—and why the current broker model keeps them trapped. Drawing on his own experience inside a major insurance company and later as a broker, Donovan saw firsthand how incentives are misaligned and how brokers ...

William Bissett, founder of Portus Wealth Advisors, joins Craig Andrews to unpack what it really takes to lead a company that survives and thrives beyond its founder. William shares how watching his father struggle in solo practice shaped his commitment to team building. His insight is simple but powerful: don’t just hire talent—hire people who fill your gaps, not mirror them.

The episode cuts through leadership myths and focuses on...

Brian McRae walked away from a comfortable W-2 job to chase something more fulfilling—control, freedom, and impact. What followed was a leadership journey rooted in service. In this episode, Brian shares how he transitioned from the mortgage world to building a coaching and mastermind business that thrives on authentic relationships.

He didn’t advertise. He didn’t pitch. Instead, he launched a free monthly event focused on giving aw...

Kyle Schwarz brings clarity to what leadership really looks like. A U.S. Naval Academy graduate and surface warfare officer, Kyle shares how a blunt rejection from his blue and gold officer nearly derailed his academy ambitions—but ultimately became a catalyst for transformation. He didn't quit. He trained, returned, and earned one of the strongest recommendations in years.

Now with 17 years of leadership experience, including more ...

Alan Gregerman nearly lost everything after a stroke robbed him of his ability to speak and see. But instead of giving in, he turned that moment into one of his greatest leadership lessons. In this episode, Alan shares how navigating life without communication forced him to rethink how leaders engage, innovate, and lead. Through his recovery, he uncovered deeper truths about humility, clarity, and the need to constantly evolve.

Alan...

Emily Erstad joins Craig Andrews for a candid conversation about the real heart of leadership—emotional intelligence. A former speech-language pathologist turned hospice leader, Emily shares how leading in high-stakes environments taught her the power of trust, vulnerability, and consistency.

She explains why leadership isn’t about commanding—it’s about partnering. Whether guiding patients through recovery or teams through chaos, Em...

Lee Pepper brings battlefield-tested leadership into the boardroom. In this episode, Lee breaks down how military strategies—some dating back to the Romans—can drive success in today’s marketing and business landscape. Drawing from his Army background, time at Fort Knox, and career in behavioral healthcare marketing, Lee explains how setting clear intent and empowering teams to execute leads to superior outcomes.

He makes the case f...

Stan Sukhinin knows what it’s like to rebuild from scratch. After a meteoric rise in Eastern Europe’s finance world—managing a $450M mezzanine loan portfolio—he moved to New York to launch a hedge fund. It didn’t survive the pandemic. What did survive? His ability to spot financial blind spots and fix them fast.

Now, as founder of The Sorso, Stan serves as a fractional CFO for outpatient clinics across the U.S. He combines deep fina...

Hark Herold brings three decades of military precision to the entrepreneurial world. As a retired U.S. Air Force colonel turned EOS implementer, Hark shares how his leadership experience in high-stakes environments—from serving in Desert Storm to overseeing base recovery during rocket attacks in Iraq—shaped his approach to business.

Now, he empowers small and medium-sized businesses to build clarity, cohesion, and execution with the...

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...