Jay’s 2020 EntreLeadership Summit Experience

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EntreLeadership Summit

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It’s often said that it’s lonely at the top. Entrepreneurs, business owners, and leaders of all types feel this. There’s something isolating about the reality that the final decision rests with you. When no one else can decide, you have to. That can be an overwhelming feeling.

But it doesn’t have to be that way. As a business leader, you don’t have to walk through business growth alone. It took me too long to realize that, but one of the biggest things that has had an impact on me over the years is an organization that comes from Dave Ramsey called EntreLeadership.

Nearly a decade ago, I picked up a book by Dave that didn’t look like his other finance books. It was focused on small businesses. The subtitle was “20 Years of Practical Business Wisdom from the Trenches.” Little did I know that this book and this organization would play a huge part in helping me to get to 20 years of business growth myself.

Attending EntreLeadership Conferences

Image of car trunk open full of books with quote: Don't despise humble beginnings
Over the years, I’ve attended multiple EntreLeadership live events, including the EntreLeadership Master Series (basically like getting a practical application MBA in a week), EntreLeadership 1 Day, and EntreLeadership Summit. Master Series focuses on teaching the core EntreLeadership curriculum and is taught by Dave and his team. The 1 Day event is just an abbreviated version, usually focused on the entire team and not just the top leaders or owners. And Summit… well, that’s something really special. Summit is a leadership conference that comes around once a year and tends to be a showcase of inspiration, encouragement, and education. It comes from Dave and his team, plus some of the absolute best speakers and teachers anywhere in the world. Every speaker at Summit could be a headline keynote speaker at any other event.

They’ve had speakers like George W. Bush (former US President), Alan Malary (former Ford CEO), Dan Cathy (Chick-fil-a CEO), Simon Sinek (NYT best-selling author of Start with Why and many more), Pat Lencioni (best-selling author of The Ideal Team Player and many more), Lou Holtz (football coach and then football analyst for ESPN), Sarah Blakely (CEO of Spanx), and so many other talented people.

The EntreLeadership Summit 2020

Dave Ramsey standing on stage speaking with EntreLeadership Summit on big screen behind him

The 2020 event, originally scheduled for May, was moved to July. Then it was moved from Orlando, FL to Franklin, TN due to issues with Marriott and COVID-19 restrictions.

Despite all of the changes, the event went off without a hitch (from a participant’s perspective).

The event was held at the brand-new Ramsey Solutions headquarters in Franklin, TN, decked out with the theme of Work that Matters.

Summit 2020 included an incredible array of top-notch business speakers including Lou Holtz, Benjamin Zander, Daymon John, Craig Groceal, Ian Cron, Mike Rowe, Chris Hogan, Ken Coleman, Christy Wright, and of course, Dave and much of his leadership team.

Day 1

Dave taught on lies business owners believe; Ken Coleman talked about the idea of the leadership edge; Craig Groeschel helped us learn to change how we think.

The day was concluded by a powerful talk from one of the greatest college football coaches of all time, Lou Holtz.

Lou mentioned that he had buried his wife of 49 years just the week before. Many people asked if he still planned to come to the event and he said, “Of course. She would have told me, ‘If you can help them, you should go. So here I am.’”

Day 2

Dave focused on the six drivers of business and how to stop the chaos; Ian Cron shared how the Enneagram could help us lead our teams better; Mike Rowe told incredible stories of growth from Dirt Johns and more, and the day was finished out with one of the most creative, inspirational talks I’ve ever seen, which was conducted by Benjamin Zander.

At 83 years old, he hopped around on the stage more spryly than most kids would. His energy, enthusiasm, and spirit for life was incredible and his teaching on the art of possibility required us all to step back and ask what was really possible, regardless of the circumstances. If that’s not relevant, I don’t know what is.

Day 3

The final day of the event rounded out with Christy Wright reminding us to not lose ourselves in business. This was followed by a powerful conversation on diversity and inclusion from some of the Ramsey leadership team. Daymon John did a talk highlighting his rise to Shark Tank status and then answered Q&As from the world-class interviewer, Ken Coleman.

The day was wrapped up by Chris Hogan who brought his booming deep voice and big heart to show us how to get connected and get real.

Any of these speakers could have been headliners at any other event — the EntreLeadership Summit brings nothing by A-class talent to the stage every year.

While the speakers are all amazing, the real magic of summit is the time between. It’s the lunch breaks, it’s the coffee breaks, it’s the dinner times where other entrepreneurs and leaders are gathered together. It’s the times we’re reminded that we’re not alone in this, that the struggles we’re facing are not unique, and there is support — support to make it through, but also support to thrive in all types of economies and circumstances.

A Unique Experience

Jay Owen standing with Dave and Sharon Ramsey

One unique experience I had the privilege of being a part of was having dinner at Dave Ramsey’s house one evening. He and his wife Sharon were incredibly gracious to open up their home to a group of us EntreLeaders. We were able to spend time with Dave and his leadership team, talking, laughing, and fellowshipping together (and by fellowship, I mean cigars and bourbon).

The impact this event and other EntreLeadership events have had on me over the years cannot be overstated. I started my podcast and started writing my book after leaving Summit one year. Next year’s event will be back in Nashville, and I’ll be there, along with several members of our team at Design Extensions. I’d love to see you there, too!

Want More? Attend My Business Growth Event in March!

Jay Owen smiling as he plans his March 2021 business growth event

I believe these types of events are important to entrepreneurs, leaders, and business owners. So important, in fact, that I’ll be hosting my very own business growth event March 29-30, 2021!

Held at the Treasury on the Plaza in sunny, historic downtown St. Augustine, Business Builders Live will be a live, two-day event. Over two days in our nation’s oldest city, I’ll be sharing my 21 years of business growth strategy to help you get a clear plan for 2021 and beyond. What got us here isn’t going to get us there, and you always need to be thinking ahead.

Limited to 150 people, this event is on a first-come, first-serve basis. So if you want to be there, ask me about it NOW! Seats are going to fill fast. 

Don’t go at business alone — get in community! Come to Business Builders Live in March and then join me as an attendee at EntreLeadership in May. I can’t wait to see you!

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