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Leaders & Legacies

Leaders & Legacies

By: Craig Andrews
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About this listen

The Leaders & Legacies Podcast celebrates leaders who are making a difference beyond themselves. It was inspired from events in 2021 when the host, Craig Andrews went into a 6-week coma. Even after waking up, his brain was scrambled for another two weeks. When his mind cleared, his wife started telling him how his team stepped up and ran the company without him. Freelancers reached out to his team and offered to do whatever was necessary while he was in the hospital. Craig believes we all make an impact greater than we realize and wants to honor owners and founders as they lead others. Craig Andrews is the founder and Principal Ally at allies4me. He’s been in the marketing space for more than two decades and has driven over a half-billion dollars of revenue. He’s spoken on dozens of podcast as well as conferences including Conversion Conference.Copyright 2025 Craig Andrews Career Success Economics Leadership Management & Leadership
Episodes
  • 209 - From Green Beret to Cybersecurity Leader - Josh Wathen on Business Resilience
    Jul 10 2025

    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/.

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    31 mins
  • 208 - The Three Keys to Success - Philip Portman's Formula for Leading Growth
    Jul 8 2025

    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/.

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    43 mins
  • 207 - Leadership in Action - How Dr. Cristin Dickerson Makes Healthcare Work for Everyone
    Jul 3 2025

    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/.

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    34 mins

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