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 high failure rate of insurance claims, and why reactive security costs 10x more than prevention. Josh outlines a leadership approach rooted in responsibility, training, and smart risk transfer. His advice? Stop assuming you're safe. Get real, get proactive, and lead by example.

Want to learn more about Josh Wathen's work? Check out their website at https://triadinfosec.io.

Connect with Josh Wathen on LinkedIn at https://www.linkedin.com/in/joshua-wathen/.

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/.

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 startup across six states. Philip lays out the three pillars of his leadership philosophy: written goals, healthy habits, and what he calls “arrogant confidence”—a mindset just bold enough to fuel breakthrough action.

He also digs into the power of SMS marketing, explaining why it delivers stronger engagement than email and how to use it without annoying your audience. His insights on human connection, especially in a world saturated with AI-generated content, emphasize authenticity as a core leadership trait.

Want to learn more about Philip Portman's work? Check out their website at https://philportman.com.

Connect with Philip Portman on LinkedIn at https://www.linkedin.com/in/philportman/.

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/.

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 equity is warping priorities, and why independent physicians matter now more than ever. Dr. Dickerson also dives into her strategic decisions, including how she scaled a national imaging network without selling out to private investors. Along the way, she shares a powerful story about seeking affordable care for her son—and why empathy drives every business choice she makes.

This episode is a crash course in practical leadership in a broken system. Dr. Dickerson’s story proves that real leaders don’t follow trends—they set new standards.

Want to learn more about Dr. Cristin Dickerson's work? Check out her website at http://www.greenimaging.net.

Connect with Dr. Cristin Dickerson on LinkedIn at https://www.linkedin.com/in/cristin-dickerson-md-a1a1b013/.

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/.

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 missteps: over-reliance on a single client, underinvesting in marketing, and clinging too tightly to founder control. Ken pushes leaders to hand off responsibility, plan for exits—even if they never intend to sell—and value their businesses like an outside investor would. Whether you’re preparing for an acquisition or planning to pass the torch to the next generation, Ken's insights are direct, actionable, and critical for any serious business leader.

Want to learn more about Ken LaCroix's work? Check out their website at https://insightfulpartners.com.

Connect with Ken LaCroix on LinkedIn at https://www.linkedin.com/in/kenlacroix/.

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/.

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 reveals how starting small taught him discipline. From driving a school bus in high school to running his family’s upholstery shop without knowing the craft, every challenge refined his resilience. He also shares a sharp strategy: always charge your own business market rent. If it can’t afford that, it doesn’t belong there.

Leadership, to Jeff, is about vision, but also survival. He teaches why speculative investing is dangerous for beginners and why long-term thinking always wins. This episode is a masterclass in entrepreneurial endurance, strategic property ownership, and staying grounded while scaling big.

Want to learn more about Jeff Peterson's work? Check out their website at https://petersonproperties.co.

Connect with Jeff Peterson on LinkedIn at https://www.linkedin.com/in/jeff-peterson-b4a4534/.

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/.

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 surgery, his work in global outreach, and the leadership lessons learned while operating under extreme constraints. Dr. Verma explains how creating an evidence-based practice means blending data, experience, and patient preferences—never defaulting to one-size-fits-all decisions.

From his surgical philosophy to the way he builds patient relationships, Dr. Verma demonstrates that leadership in healthcare is about discipline, education, and consistency. This episode is a masterclass in doing hard things the right way.

Want to learn more about Dr. Kushagra Verma's work? Check out their website at https://www.advancedspinecare.com.

Connect with Dr. Kushagra Verma on LinkedIn at https://www.linkedin.com/in/kushagra-verma-99595714.

You can also follow him on Instagram at @asc.md.

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/.

Aurora Winter joins Craig Andrews to explore how leaders can use books to amplify authority, build trust, and accelerate business growth. As the founder of Same Page Publishing, Aurora reveals her spoken author method—a system that turns interviews into books, saving time and maximizing impact. She shares how one hour of recorded content generated $250,000 in new business, proving that books aren't just products—they're strategic lead magnets.

Aurora dispels the myth that people must be avid readers to benefit from publishing. Instead, she positions books as trust builders and authority badges, especially effective for high-ticket offers and speaking gigs. She and Craig dive deep into common pitfalls—like launching without a plan or failing to tailor content for a specific reader. Aurora stresses the importance of vulnerability, personal storytelling, and knowing your ideal audience.

This episode is a blueprint for leaders who want to scale their message without spending years writing a manuscript. Whether you're a seasoned entrepreneur or just getting started, Aurora’s insights offer a compelling case for using your story as your strongest leadership tool.

Want to learn more about Aurora Winter's work? Check out her website at https://www.aurorawinter.com.

Connect with Aurora Winter on LinkedIn at https://linkedin.com/in/AuroraWinter.

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/.

Peter Culver doesn’t just save clients money—he helps them rewrite their financial future. In this episode, Peter breaks down how tax strategy, not tax filing, is the critical leadership tool most business owners ignore. As co-founder of Wealthrive, he combines legal insight and financial acumen to reveal how affluent families protect and grow wealth across generations. Peter challenges the reactive mindset common with CPAs and presents tax planning as a proactive lever for leadership. He shares the hidden value of strategies like the Augusta Rule and “paying your kids,” while contrasting the limits of compliance with the opportunities of strategy.

Whether it’s avoiding capital gains on a $10 million sale or designing structures that maximize multi-generational impact, Peter emphasizes intent and clarity as pillars of wealth leadership. His approach reframes tax from an obligation into an opportunity—and leadership from status into stewardship.

Want to learn more about Peter Culver's work? Check out their website at https://www.wealthrive.com.

Connect with Peter Culver on LinkedIn at https://www.linkedin.com/in/pculver/.

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/.