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Listen to the audio version of episode #010
Watch the video version of episode #010

Episode Summary

To lead you must learn to follow and to lead well you must learn to ask a lot of questions while communicating in an effective manner. Joining us today is Jordan Montgomery, owner and founder of Montgomery Companies a company focused on helping you reach new levels in your public speaking and leadership goals.

In this episode, Jordan Montgomery shares his journey that led him to be a successful entrepreneur and business owner. Jordan also offers his take on leadership, how to establish and maintain connections, and how you can start to improve your own public speaking and leadership skills!  

In this episode we discuss...

  • Show Introduction [0:01]
  • Introducing Our Guest [0:17]
  • Jordan’s Journey to CEO [1:20]
  • What is Montgomery Companies? [3:05]
  • The Concept of Being a Good Leader [4:43]
  • The Fear that Plays in Asking Questions [7:42]
  • How to Establish and Maintain Connections [9:29]
  • Coaching Leadership Skills [11:12]
  • The Importance of Receiving Feedback [13:03]
  • You Must Learn to Follow Before You Can Lead [15:39]
  • Public Speaking Fears and How to Overcome [17:50]
  • Nerves Before Going on Stage [20:34]
  • Advice on How to be a Better Speaker [22:01]
  • Best Way to Prepare for That Big Speech [24:38]
  • What is Your Truth? [27:18]
  • Advice on How to Start Your Journey [30:32]
  • Connect with Jordan [32:17]
  • Closing Thoughts [32:54]
  • Outro [33:20]

Resources Mentioned

Guest Details

Jordan Montgomery, Speaker + Performance Coach  

Want to connect with Jordan? 

Episode Notes

In today’s episode, we are joined by Jordan Montgomery, the founder and CEO of Montgomery Companies. The episode consists of discussions around leadership and public speaking. We talk about how Jordan was able to refine his public speaking craft and how he helps others in his leadership coaching and consulting.

Jordan Montgomery graduated from the University of Iowa and 2010. He knew he wanted to be an entrepreneur and have his own business one day but there were two problems standing in his way. He had no experience and no money. Jordan took a financial planning opportunity where he worked for several years.

This opportunity allowed him to make a lot of connections and he admits, taught him most of what he knows today about professional growth and development as well as topics around leadership. During this time, Jordan developed a love for leadership, coaching, and developing others and this is where most of his efforts are focused today.

Montgomery Companies is a combination of things. From coaching work on an individual and group level to public and keynote speaking. Montgomery Companies also offers consulting work where he helps companies on their journey to success. Jordan’s team also is constantly creating consistent content on social media.

When it comes to being a great leader, Jordan believes that in all of the people and things you are leading the most difficult task is leading yourself. Working on yourself and leading self is critically important and allows you to grow in confidence. Jordan continues that it’s incredibly important to ask a lot of question and he challenges new emerging leaders to break the record in their firm or organization for questions asked. To be a great leader, Jordan says you must focus on leading yourself first, ask a lot of questions, and absorb as much content as you possibly can.

When Jordan looks at some of the people, he has coached over the years the people who really grasped the concepts of leadership and flourished had two things. A commitment to continuous improvement and the idea that we never stop evolving and growing over time. To Jordan, a leader is one who has the desire to grow and get better. The greatest leaders also seem to be the most self-aware. If you are constantly aware of how you are communicating, showing up, and being received you will be a better leader.

Jordan finished the episode by offering advice to college students based on his own experience and path. Jordan shares to fail fast. Try new things and fail, put yourself out there and be willing to look like you don’t have it all together. It’s the quickest way to get onto the path that you should be on and the best way to figure out where you want to be. People often are afraid to fail but the quicker you can find out what you don’t want to do the quicker you can move to the things that give you energy!


Ryan has been heavily involved in the world of Information Technology and entrepreneurship since the early 2000s. From small business consulting to Fortune 500 IT leadership, Ryan has a wide array of tech industry knowledge. Ryan has his BBA and MBA from the University of Iowa. Connect with Ryan on Twitter or Instagram.

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