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/.