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How Randy Wootton Cultivates Fearless Leadership & Builds Impactful Teams

Super Entrepreneurs Podcast

Release Date: 06/11/2025

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Shahid Durrani sits down with Randy Wootton on the Super Entrepreneurs Podcast for a conversation that's packed with real insights. Randy's spent years turning around SaaS companies and building teams that actually work well together, and he credits a lot of that success to lessons he learned in the military.

In this episode, Randy breaks down his approach to fearless leadership and talks about the four key support systems he relies on when business gets tough. He also walks through his go-to 90-day game plan for making real changes happen fast.

You'll hear Randy's take on making decisions when the pressure's on, why having good mentors and coaches matters so much, and how building genuine relationships is what really drives business growth. If you're an entrepreneur or leader looking to step up your game and build something that lasts, this conversation is definitely worth your time.

 

Chapter Stamps:

03:07 Randy's Military Background and Leadership Lessons

08:58 The Importance of Mentorship and Coaching

10:03 Building Effective Peer and Advisory Groups

11:49 Facing Fear and Embracing Change

12:16 The Value of Mentorship and Giving Back

14:25 The Importance of Authentic Relationships

15:50 Finding the Right Mentor or Coach

18:29 Comparing Nutritionists: Different Approaches

19:33 First 90 Days Strategy

20:48 The Four L's Approach

23:06 Quick Wins and Roadmap

25:38 Building Relationships and Trust

26:06 Personality Tests and Team Dynamics

29:26 Meditation and Mindfulness

30:22 The Power of Presence

Pullout Quotes:

“Lead, follow, or get out of the way.”
“In the corporate sector, there’s a lot of fear of failure, but in the military, you learn to step up and say, ‘I got it.’”
“You need a mentor, a coach, a peer group, and a personal advisory board—those four groups will change your life.”
“Software is a people business. If you’re not interested in authentic relationships, people will see that you’re just solving for power or money.”
“My greatest sense of accomplishment is when people I’ve worked with reach out years later and say, ‘You made an impact.’”


Social:


Website: https://ceox.io https://www.maxio.com/authors/randy-wootton

LinkedIn: https://www.linkedin.com/in/randy-wootton-910/

Instagram: https://www.instagram.com/wearemaxio/

 

Disclaimer:


Please be aware that the opinions and perspectives conveyed in this podcast are solely those of our guests and do not necessarily represent the views, ideologies, or principles of Super Entrepreneurs Podcast, its associated entities, or any organizations they represent or are affiliated with. We provide a platform for discussion and exploration, and the content of each episode is understood to be independent expressions from our guests, rather than a reflection of the beliefs held by the podcast or its hosts.


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