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Deep Leadership
Deep Leadership
Author: Jon S. Rennie
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© Jon S. Rennie
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“Leadership is a People Business.” That's the philosophy of this leadership podcast from Jon Rennie. It's real-world, actionable advice from Jon as well as his expert guests. As a former Cold War Submarine Officer who spent 22 years leading businesses in Corporate America before starting his own manufacturing business, he knows that leadership matters!
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What happens when your identity is built on achievement, and then everything you’ve achieved disappears?
In this episode of the Deep Leadership podcast, I talk with Steve "Moby" Leitch, Amazon bestselling author, endurance athlete, leadership coach, and one of only a small number of people to complete the Ocean Seven. Steve shares his remarkable journey from success to losing his business, marriage, health, and sense of identity, and how he rebuilt his life through faith, discipline, purpose, and self-leadership.
We discuss why leadership starts long before you lead anyone else, the danger of tying your identity to your job or accomplishments, and why the work you do on yourself ultimately determines the kind of leader you become.
Steve also shares the daily disciplines he uses to strengthen his spiritual, physical, relational, and professional life, and what swimming some of the world's most difficult open-water channels has taught him about resilience, perseverance, and purpose.
If you want to become a stronger, more resilient leader, this conversation is a powerful reminder: lead yourself first.
What You'll Learn:• Why leadership begins with self-leadership• The danger of building your identity around achievement• How failure can expose what needs to change• Why discipline matters more than motivation• How to strengthen the areas of your life people don't see• What extreme endurance teaches us about resilience• Why purpose can keep you moving when you want to quit
Connect with Steve “Moby” Leitch:
Against the Current Book: https://amzn.to/4izuNCP
Instagram: https://www.instagram.com/stevemobyleitch/?hl=en
Website: https://stevemobyleitch.net/
Subscribe to Deep Leadership:
If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader.
Sponsors:
Cadre of Men
Farrow Skin Care
Salty Sailor Coffee Company
Leader Connect
The Qualified Leadership Series
____
Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE
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Strategy is not planning. And being busy doesn’t necessarily mean you’re being strategic.
In this episode of the Deep Leadership podcast, I’m joined by Charlie Curson, founder of Mandarin and author of the international bestselling book Be More Strategic. Charlie has spent more than 25 years helping leaders around the world develop their ability to think strategically and make better decisions in complex environments.
We discuss why so many leaders confuse strategy with planning, why operationally strong leaders can struggle when they move into strategic roles, and how strategic thinking is a capability that can be deliberately developed and practiced.
Charlie also explains why strategy requires making difficult choices, how pressure causes leaders to fall back into operational habits, and why listening, self-awareness, curiosity, and comfort with uncertainty are essential skills for strategic leaders.
In this episode, we discuss:
• The difference between strategy and planning• Why strategy must come before planning and execution• Why leaders become trapped in operational thinking• How to develop strategic thinking as a leadership capability• Why strategy requires deciding what not to do• How short-term pressure can pull leaders away from strategy• The importance of self-awareness and open-mindedness• Why better listening leads to better strategic decisions• How leaders can balance execution with long-term thinking• Simple practices you can use to become more strategic
Charlie reminds us that strategic thinking isn’t something reserved for CEOs, consultants, or annual planning sessions. It is a leadership capability that can be learned, practiced, and strengthened over time.
If you find yourself constantly reacting, solving the problem in front of you, and struggling to find time to think about where you’re actually going, this conversation is for you.
Connect with Charlie Curson:
Be More Strategic Book: https://amzn.to/4iW0x5p
LinkedIn: https://www.linkedin.com/in/charliecurson/
Website: https://www.teammandarin.com/
Subscribe to Deep Leadership:
If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader.
Sponsors:
Cadre of Men
Farrow Skin Care
Salty Sailor Coffee Company
Leader Connect
The Qualified Leadership Series
____
Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE
Learn more about your ad choices. Visit megaphone.fm/adchoices
What if one of the best signs of leadership is that your business runs better when you’re not there?
In this episode, I sit down with Joe Sandin, founder and CEO of Onsharp, a software company he started from his college dorm room more than 26 years ago. Joe built the company without outside investment, choosing to grow at his own pace while focusing on relationships, culture, and building a business designed to last.
We talk about the difficult transition every entrepreneur eventually faces: moving from doing the work yourself to trusting other people to lead. Joe shares why founders have to learn to let go, allow people to make mistakes, stay focused, and sometimes simply get out of the way.
We also explore how AI is changing the opportunities available to small businesses and why Joe believes technology should elevate people rather than replace them.
In this episode, we discuss:
• Why Joe chose to build his company without outside investors• The transition from doing everything yourself to developing leaders• Why delegation requires trust, patience, and allowing mistakes• How a founder can become the bottleneck in their own business• Why focus is critical as a company grows• The danger of constantly chasing new opportunities• How AI is changing software development and small business• Why patience may be one of the most important traits for entrepreneurs• What 26 years in business taught Joe about leadership and success
If you’re an entrepreneur, business owner, or leader trying to build an organization that doesn’t depend on you for every decision, this conversation will give you plenty to think about.
Listen in and learn why sometimes the best thing a leader can do is get out of the way.
Connect with Joe Sandin:
Website: https://www.onsharp.com/
Podcast: https://www.businessblueprintshow.com/
Instagram: https://www.instagram.com/mjcollectiondotcom/?hl=en
Subscribe to Deep Leadership:
If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader.
Sponsors:
Cadre of Men
Farrow Skin Care
Salty Sailor Coffee Company
Leader Connect
The Qualified Leadership Series
____
Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE
Learn more about your ad choices. Visit megaphone.fm/adchoices
Hope is not a strategy.
In this episode of Deep Leadership, I sit down with Alan Porter, a retired U.S. Army Blackhawk instructor pilot, financial fiduciary, author, and founder of Strategic Wealth Strategies.
Alan spent more than 21 years in the Army, where he learned that when the pressure is highest, you don’t rise to the occasion. You fall back on your preparation. Today, he applies that same philosophy to financial stewardship, risk management, and helping leaders prepare for the unexpected.
We discuss:
• What military aviation teaches us about leadership and preparation• Why leaders need to think about risk before a crisis occurs• The dangers of focusing on growth while ignoring protection• Why financial stewardship is a leadership responsibility• How unexpected life events can change everything• Why preparation, redundancy, and risk management matter in business and life• The importance of protecting your family, your business, and your legacy• Why “hope is not a strategy”
Alan’s message is simple: Life rarely goes exactly as planned. Strong leaders prepare for what could go wrong before it does.
If you’re a business owner, entrepreneur, or leader responsible for others, this conversation will challenge you to think differently about risk, preparation, and financial stewardship.
Listen in and learn why the best time to prepare for the unexpected is before it happens.
Connect with Alan Porter:
Website: https://www.strategicwealthstrategies.com/
YouTube: https://www.youtube.com/@StrategicWealthStrategies
Subscribe to Deep Leadership:
If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader.
Sponsors:
Cadre of Men
Farrow Skin Care
Salty Sailor Coffee Company
Leader Connect
The Qualified Leadership Series
____
Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE
Learn more about your ad choices. Visit megaphone.fm/adchoices
What if some of the best answers to today’s leadership challenges were written thousands of years ago?
In this episode of the Deep Leadership podcast, I’m joined by Dr. Josh Herring, Director of the Logres Institute for Classical Liberal Studies, Curriculum Program Manager for the Rafiki Foundation, and author of Sons of Adam, Daughters of Eve: C.S. Lewis’s Images of Gender.
Josh makes the case that modern education has increasingly emphasized skills and credentials while losing touch with the deeper intellectual traditions that once shaped leaders and critical thinkers. We discuss what leaders can learn from classical education, why studying history and literature matters, and how thinkers like Plutarch, Shakespeare, and Machiavelli can help us better understand leadership and human nature.
We also explore why leaders need to explain the “why” behind their decisions, the importance of practicing leadership before the stakes are high, and why timeless truths may be more useful than chasing the latest leadership trends.
If you want to think more deeply, make wiser decisions, and become a better leader, this conversation will challenge you to look backward in order to move forward.
What You’ll Learn:• Why classical education matters for modern leaders• How ancient wisdom can improve leadership decision-making• Why knowledge, logic, and critical thinking still matter• What Plutarch, Shakespeare, and Machiavelli can teach us about leadership• Why leaders must clearly communicate the “why” behind their decisions• How timeless truths can help leaders navigate a rapidly changing world
Listen now and discover why modern leaders may need ancient wisdom more than ever.
Connect with Dr. Josh Herring :
Website: https://www.logresinstitute.org/
Book: https://amzn.to/467eOVd
LinkedIn: https://www.linkedin.com/in/joshua-herring-ph-d-1943a7119/
Twitter: https://x.com/TheOptimisticC3
Subscribe to Deep Leadership:
If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader.
Sponsors:
Cadre of Men
Farrow Skin Care
Salty Sailor Coffee Company
Leader Connect
The Qualified Leadership Series
____
Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE
Learn more about your ad choices. Visit megaphone.fm/adchoices



