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/.

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 late that some recruits are afraid of ladders or can’t pass drug tests.

Michael’s leadership sharpens through adversity: he reshaped his business model after nearly every early mistake. His approach to staffing centers on deep vetting, video interviews, and second chances for people who own their past mistakes. He’s built a company that sets clear expectations, values honesty, and adapts without lowering standards. This episode is a masterclass in leading imperfect people to create powerful outcomes.

Want to learn more about Michael Cole's work? Check out their website at https://www.nextleveltechnician.com.

Connect with Michael Cole on LinkedIn at https://www.linkedin.com/in/coles-corner/.

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/.

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 price kills service.

Instead, Morris urges business owners to map every customer touchpoint and turn each one into a moment of delight. He explains how even something as small as baking cookies in a dentist’s office or FedExing a proposal can shift your brand from transactional to relational. Whether you’re in retail, B2B, or professional services, Morris shows how intentional design builds brand loyalty, repels price shoppers, and increases profitability.

Want to learn more about Vance Morris's work? Check out their website at https://vancemorris.com.

Connect with Vance Morris on LinkedIn at https://www.linkedin.com/in/vancemorris/.

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/.

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 analyzing ROI on marketing channels to knowing when to hire ahead of growth, he explains how leaders can build confidence through numbers. He also tackles the tension between branding and financial metrics, arguing that long-term value often looks unpredictable in a spreadsheet but is crucial to sustained success.

Leadership, Tom says, is about accountability—not just managing costs but owning outcomes. His insights push leaders to stop hiding from the financials and start using them as tools to scale.

Want to learn more about Tom Dillon's work? Check out their website at https://www.frakfinance.com.

Connect with Tom Dillon on LinkedIn at https://www.linkedin.com/in/tom-dillon-cfa/.

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/.

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 through intentional structure and mindset. He details how ICL pairs students with mentors, designs custom curriculum around passions, and instills the habits of high-performance leadership. Whether training with Novak Djokovic or guiding a student to the French Open, Kirk’s focus stays the same: build people who lead with integrity and impact.

He also addresses equity in education, explaining how ICL delivers personalized, values-driven schooling to students—90% of whom are on scholarship. The model blends traditional respect with forward-thinking tech, ensuring students thrive both online and in the world.

Want to learn more about Kirk Spahn's work? Check out their website at https://www.iclacademy.org.

Connect with Kirk Spahn on LinkedIn at https://www.linkedin.com/in/kirk-spahn-10a913/.

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/.