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 coordinating air operations 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 Entrepreneurial Operating System (EOS). In this episode, Hark explains why leadership alignment is non-negotiable, how ego can cripple growth, and what it means to have the “right people in the right seats.” He also highlights resources available for veteran-owned businesses and shares why coaching is essential, even when all the tools are already at your fingertips.

Want to learn more about Hark Herold's work? Check out their website at https://www.eosworldwide.com/hark-herold.

Connect with Hark Herold on LinkedIn at https://www.linkedin.com/in/joeharkherold/.

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/.

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 foundational to leadership. She challenges the myth that good writing must follow rigid rules, arguing instead for authenticity, emotion, and real connection. Craig and Hillary dig into what makes content persuasive, how AI is changing the writing landscape, and why personal voice still matters.

Her story is a lesson in resilience and resourcefulness. She didn’t wait for permission to lead—she made the deadline non-negotiable. If you’re a business owner relying on stale content and ChatGPT shortcuts, this conversation will remind you that powerful words—and clear leadership—still win.

Want to learn more about Hillary Gale's work? Check out her website at https://monetacopy.com.

Connect with Hillary Gale on LinkedIn at https://www.linkedin.com/in/hillary-meehan/.

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/.

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 through how he saved a client from a 37% rate hike—without cutting coverage. He explains how ERISA laws make employers responsible for plan decisions, even if they don't understand them. He also breaks down how healthcare lawsuits are forcing CEOs, CFOs, and HR leaders to take their fiduciary duties seriously—or face legal consequences.

Donovan doesn’t talk about leadership in theory—he practices it by telling hard truths, navigating complex data, and challenging a system rigged for opacity. This episode is a must-listen for any leader responsible for a company’s healthcare decisions.

Want to learn more about Donovan Ryckis' work? Check out his website at https://www.EthosBenefits.com.

Connect with Donovan Ryckis on LinkedIn at https://www.linkedin.com/in/donovanryckis.

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/.

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 his message, and grow his confidence. He makes the case for why CEOs and founders shouldn’t delegate guest appearances or hosting duties. Alex argues that being the voice of your company is irreplaceable when building connection and trust.

He also explains why podcasting isn’t just a marketing tool—it’s an engine for clarity, learning, and growth. Whether it’s guesting to articulate your message or hosting to expand your network, Alex views podcasting as one of the most strategic moves a leader can make.

Want to learn more about Alex Sanfilippo's work? Check out their website at https://podmatch.com/.

Connect with Alex Sanfilippo on LinkedIn at https://www.linkedin.com/in/alexsanfilippo/.

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/.

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 difference between being an entrepreneur and becoming a CEO. He explains how leaders must eventually move beyond scrappiness and take calculated risks with debt to scale their companies. But he’s quick to note that optimism must be balanced with pragmatism. Cash flow—not charisma—is what gets a loan approved.

Chris also unpacks the coming wave of business acquisitions driven by baby boomer retirements, sharing insights on what industries are hot and where private equity is warping the landscape. His message is clear: real leadership is about seeing around corners and backing up vision with execution.

Want to learn more about Chris Hurn’s work? Check out their website at https://www.phxbusiness.com.

Connect with Chris Hurn on LinkedIn at https://www.linkedin.com/in/chrishurn/.

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/.

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 rigged. But with the right strategy, employers can bypass middlemen, reclaim fiduciary control, and offer high-quality care without budget blowouts. Allison walks through real-world examples of employers who’ve turned skyrocketing premiums into savings—without shifting the cost burden onto employees.

If you lead a team and think better healthcare is out of reach, this episode will challenge that belief—and give you a roadmap to lead differently.

Want to learn more about Allison De Paoli's work? Check out their website at https://www.altiqe.com.

Connect with Allison De Paoli on LinkedIn at https://www.linkedin.com/in/allison-de-paoli/.

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/.

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 power of books as a leadership tool—helping entrepreneurs build credibility, refine their message, and amplify their impact. He also offers a practical roadmap through the complex publishing landscape, covering ghostwriting, hybrid models, and the importance of editorial integrity.

His message is clear: authorship is leadership. A book is more than a marketing tool—it’s a durable asset that outlives trends, outlasts platforms, and outperforms expectations. For Everett, real leadership means using your voice to unlock someone else’s potential.

Want to learn more about Everett O’Keefe's work? Check out their website at https://IgnitePress.us.

Connect with Everett O’Keefe on LinkedIn at https://www.linkedin.com/in/everettokeefe/.

Get a complimentary copy of The Power of the Published: https://mypodcastperk.com/.

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/.

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 national client base.

Mike shares how most accountants are overworked or hesitant to charge for high-value advice, leaving business owners in the dark. His leadership challenge was to change that. By launching TaxElm and building a proactive software tool backed by expert support, he created a system that doesn’t just educate—it equips.

He explains how he built trust through consistent communication, set clear expectations with his team, and scaled impact with tech and systems. His leadership isn’t about doing more—it’s about doing the right things and making those repeatable.

Want to learn more about Mike Jesowshek’s work? Check out their website at https://www.TaxElm.com.

Connect with Mike Jesowshek on LinkedIn at https://www.linkedin.com/in/mikejesowshek/.

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/.