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50: How Resilience and Relentless Drive Built an 8-Figure Business | Rick Jordan

Release Date:听

April 15, 2025

Release Date: Aug 22

How can you lead and grow a business while keeping your culture intact? On this episode of 鈥淭he Learn-It-All Podcast,鈥 Damon Lembi sits down with Rick Jordan, founder and CEO of ReachOut Technology, a managed service provider specializing in cybersecurity.

Rick鈥檚 journey is nothing short of remarkable. Starting from scratch, he grew his company to eight figures before taking it public, all while staying true to his values and leadership style.

In this conversation, Rick shares how the lessons he learned from baseball have shaped his leadership approach, emphasizing the importance of resilience, teamwork, and continuous learning. Rick also explains how his ability to self-reflect and kill his ego has been crucial in overcoming challenges, and why he believes that patience and curiosity are key to driving success in both business and life.

Whether you鈥檙e a leader looking to scale your business, or someone interested in the mindset behind successful entrepreneurship, this episode is packed with actionable insights and real-world wisdom.

In This Episode:

  • Leadership Lessons from Baseball - Rick shares how the principles of teamwork, consistency, and learning from failures in baseball have shaped his leadership style.
  • The CEO鈥檚 Role in Cultivating Culture - Rick delves into the CEO鈥檚 crucial responsibility in establishing and sustaining a strong company culture, especially during periods of rapid growth and acquisition.
  • Self-Awareness as a Leadership Imperative - Rick highlights the importance of self-reflection and humility in leadership, emphasizing the need to confront and address personal and professional weaknesses.
  • Navigating the Journey to Going Public - Drawing from his experience, Rick discusses the critical role of due diligence and strategic planning in successfully taking a company public.
  • The Power of Resilience - Rick closes with a compelling message on the importance of resilience in business, underscoring how it distinguishes successful leaders from the rest.
  • The Dummy Tax - Understanding the cost of experience and how to use past mistakes to accelerate future successes.
  • Due Diligence in Business - Lessons learned from acquisitions and going public, and why thorough due diligence is crucial.
  • Delegating with Confidence - How recognizing your weaknesses and empowering your team can drive organizational success.
  • Embracing Curiosity - The importance of asking "why" and allowing curiosity to fuel innovation and problem-solving in leadership.

About Our Guest:

Rick Jordan is the Founder and CEO of ReachOut Technology, a leading managed service provider in cybersecurity, which he built from the ground up and grew to eight figures before going public. A nationally recognized voice on cybersecurity, business ethics, and entrepreneurship, he is the best-selling author of Situational Ethics and the host of the popular podcast "All in with Rick Jordan." Rick is known for his strong emphasis on organizational culture, self-awareness in leadership, and resilience.

Resources:

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