Otis McGregor doesn't just teach leadership—he’s lived it. A retired Green Beret Lieutenant Colonel turned entrepreneur, Otis shares hard-earned lessons on how to lead with clarity, trust, and purpose. In this episode, Otis explains why most business leaders fail when they micromanage, avoid accountability, or try to go it alone. He offers a refreshingly direct take on what it means to lead in today’s world—whether that’s in a combat zone, a boardroom, or your own home.

Otis opens up about the grit behind his 38-year marriage, the power of vulnerability, and how true leadership starts with knowing your purpose and building your tribe. His company, Tribe + Purpose, helps business founders develop leaders at every level of their team, enabling them to scale without burning out.

If you're leading a team, growing a business, or struggling with self-doubt, this conversation is a masterclass in resilient leadership.

Want to learn more about Otis McGregor's work? Check out their website at https://www.10xyourteam.net.

Connect with Otis McGregor on LinkedIn at https://www.linkedin.com/in/otismcgregor/.

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/.

Matt Dorman has been building digital platforms since 1995. On this episode of Leaders and Legacies, he shares how his experience coding for major brands like Time, J&J, and Fox News taught him a core truth: without strategy, a website is just decoration. Matt walks listeners through what separates successful sites from failures—and why leadership in tech means understanding both the code and the business behind it.

He discusses the critical elements of strategic planning, including audience segmentation, measuring success across editorial, revenue, and engagement, and how business owners can avoid the trap of “pretty but pointless” websites. Craig and Matt also dig into the current WordPress controversy, cutting through the drama to explain what really matters for business decision-makers.

From shaping narratives after 9/11 to leading Ndevr’s digital innovation today, Matt’s approach to leadership is built on clarity, adaptability, and service to mission.

Want to learn more about Matt Dorman's work? Check out their website at https://www.ndevr.io/.

Connect with Matt Dorman on LinkedIn at https://www.linkedin.com/in/matthewdorman/.

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/.

Brian Massey, founder of Conversion Sciences, joins Craig Andrews to unpack the power of leadership through rigorous experimentation. Known as the "Conversion Scientist," Brian has spent over 15 years transforming how businesses approach their websites—moving from guesswork to data-backed results.

In this conversation, Brian breaks down why most companies treat their websites like static brochures and how that mindset kills performance. He explains his framework for the five types of websites and why identifying your type is the first leadership step in digital strategy.

Brian also dives into A/B testing, revealing why it’s not just about increasing conversions—it’s about creating a culture of learning and humility. He shares costly redesign failures from major brands and why launching a new website without testing is one of the riskiest moves a leader can make.

Finally, Brian reflects on how AI is reshaping marketing and what leaders must do to stay ahead.

Want to learn more about Brian Massey's work? Check out their website at https://conversionsciences.com.

Connect with Brian Massey on LinkedIn at https://linkedin.com/in/bmassey.

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 Szado learned leadership the hard way—dodging lightning strikes and supertankers on commercial fishing boats off Canada’s Pacific coast. Now, he brings that high-stakes clarity to corporate sales. In this episode, Chris shares how his upbringing in a dangerous, consequence-heavy environment shaped his approach to leadership, trust, and accountability.

Craig and Chris dig into the difference between anxiety and fear, persuasion versus convincing, and why emotional readiness trumps facts when delivering hard truths. Chris challenges leaders to stop obsessing over their “why” and instead obsess over their “where”—the clear, repeatable objective that gives teams direction.

They also explore how standards and psychological safety create the conditions for creativity and performance. If you’re leading a sales team, building a business, or wondering why your strategy isn’t sticking, this episode will force you to rethink your approach to leadership and alignment.

Want to learn more about Chris Szado's work? Check out their website at https://www.liftsalesconsultants.com.

Connect with Chris Szado on LinkedIn at https://www.linkedin.com/in/chris-szado-14690a43/.

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/.

Sree Kaluva built his career designing enterprise systems for global Fortune 500s. But what drives him now is helping small business owners thrive with the same kind of technology—without the cost or complexity. In this episode, Sree unpacks how leadership isn't just about people—it's about giving them the tools to succeed.

Drawing from his own journey, including childhood lessons from his father’s pen-and-paper business, Sree explains how the lack of real-time data and automation holds companies back. He shares how My Work Belt—his all-in-one business operating system—removes friction, reveals hidden inefficiencies, and delivers insights that help teams grow without burning out.

From automating invoices and tracking project profitability to empowering frontline staff with transparent data, Sree makes the case that true leadership is removing obstacles. And when employees have clarity and control, they don’t quit—they lean in.

Want to learn more about Sree Kaluva’s work? Check out their website at https://www.myworkbelt.com.

Connect with Sree Kaluva on LinkedIn at https://www.linkedin.com/in/skaluva/.

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/.

Claire Ansell didn’t just build a business—she built a movement. As the founder and CEO of Business Powerhouse, Claire helps entrepreneurs escape overwhelm and lead with strategy, structure, and clarity. In this episode, she breaks down how leadership starts with self-awareness, not hustle.

Claire shares how growing up with high expectations—and overcoming the limits of dyslexia—shaped her ability to create systems that drive results. She explains why most business owners mistake busyness for progress and reveals how her tactical acceleration plan brings instant clarity to chaotic operations.

From identifying the wrong customers to wasting 700 hours a year, Claire exposes the traps small business leaders fall into—and how to get out. Her message is simple: lead with purpose, build with intention, and stop doing work that drains you.

Want to learn more about Claire Ansell’s work? Check out her website at https://www.businesspowerhouse.com.

Connect with Claire Ansell on LinkedIn at https://www.linkedin.com/in/coachclarity/.

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/.

Jack Cohen, CEO of Dark Knight Ventures, joins Craig Andrews to explore the leadership tools that shaped his 40+ year career in commercial real estate and finance. In this episode, Jack breaks down the principles from his book, The Freedom Frameworks, revealing how practical tools—not empty platitudes—help leaders accelerate growth and stay grounded.

Jack shares his philosophy: great leaders acquire skills, accumulate experiences, and develop strong relationships. He unpacks how curiosity fuels those pillars and discusses how “red shirt moments”—unique personal insights—help leaders stand out and build trust.

Jack also speaks candidly about burnout, recovery strategies, and why high-impact leadership demands more than just hustle—it requires deliberate self-renewal. He explains how his aviation hobby and martial arts discipline help him stay sharp and energized. The conversation wraps with actionable frameworks that listeners can immediately use to lead better, think clearer, and create more value.

Want to learn more about Jack Cohen's work? Check out their website at https://darkknightventures.net/.

Connect with Jack Cohen on LinkedIn at https://www.linkedin.com/in/jack-m-cohen-9543269/.

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 Cox doesn’t just talk about leadership—he builds systems that enable it. In this episode, Ken shares how a turbulent upbringing and early tech exposure shaped his leadership style. From hanging around small-town entrepreneurs to diving into the early days of the internet, Ken turned challenges into fuel. He opens up about his dyslexia and how technology gave him a voice, eventually becoming a champion for small businesses and digital empowerment.

Ken explains why he treats AI like employees—and why leadership in the AI era means creating systems that manage, train, and direct those “digital hires.” He urges leaders to stop fearing AI and start leading it. The result? Businesses that run smarter, faster, and leaner.

Whether it’s streamlining customer service or qualifying leads, Ken breaks down how focused AI tools can give business owners time to lead—not just manage chaos.

Want to learn more about Ken Cox's work? Check out his website at https://inlink.com/

Connect with Ken Cox on LinkedIn at https://www.linkedin.com/in/kencox/

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/