97: Self-Motivation Through the Tough Times with Joe Calloway

We have the great pleasure of speaking to Joe Calloway today! Joe is a multi-faceted character who has had a remarkable career as a speaker! Since retiring from the speaking industry, he has involved himself in many different ventures.

Whenever Joe speaks, there is always something to learn! In this episode, he tells his fascinating story and shares some valuable nuggets from his vast experience. He talks about preparing for keynotes, his way of selling, and entrepreneurship. He also explains how he motivates himself to keep going when times get tough, discusses what he has learned from his involvement in the wholesale Kentucky bourbon business, and talks about the happy process of figuring out life after retiring.

We hope you learn something new today and enjoy listening to our captivating conversation with Joe Calloway!

Joe Calloway’s bio

Joe Calloway is an investor and entrepreneur who lives in Nashville, Tennessee, with his wife Annette. They have two daughters, Cate and Jessica.

A former business consultant and speaker, Joe worked with companies ranging from Coca-Cola and Verizon to Delta Air Lines and American Express. Joe also worked as an advisor with small to mid-sized businesses, as well as professional services groups, non-profits, and government organizations.

Joe has presented workshops at leadership events in countries around the world including Italy, Sweden, South Africa, England, Swaziland, Canada, Mexico, and throughout the Caribbean.

He is a member of the Speakers Hall of Fame.

Joe is a Principal in The Disruption Lab and has served as Executive In Residence at Belmont University’s Center For Entrepreneurship.

He is a partner in Barrel Stock Trading Company, a company in the wholesale Kentucky bourbon business.

Joe is the author of eight published business books, including Becoming A Category of One: How Extraordinary Companies Transcend Commodity And Defy Comparison, which received rave reviews from The New York Times, Retailing Today, Publishers Weekly, and many others.

His other books include Be The Best At What Matters Most, Magnetic: The Art Of Attracting Business, Keep It Simple, and his latest book, The Leadership Mindset.

Joe is an investor in and active advisor to two successful start-up companies, Gilson Boards, a snowboard and ski manufacturer, and EVAmore, an online event and booking company. He is a partner in several real estate developments throughout the mid-South.

Joe Calloway’s story

Joe started his career traveling from city to city as a subcontractor, doing full-day pre-packaged training program workshops geared mostly for business managers. After that, he started doing workshops of his own. That later evolved into keynote speaking, which Joe continued doing for more than thirty years.

Changing his content regularly

Joe has a low threshold for boredom, so he found it fun to regularly change his topics and content because that kept his interest level high.

Many irons in the fire

Joe has “been there and done that”, and he wanted to do something new. So, three years ago, he went from doing keynotes to doing about a year of small group workshops with senior leadership teams for mid-sized companies. He also did some executive coaching and real estate projects, and got involved in the manufacture of snowboards and skis and the wholesale Kentucky bourbon business.

Preparing for keynotes

When preparing for a keynote, Joe always personalized what he would say. He had a lot of material which he put together differently each time he spoke.


Many speakers spend most of their time marketing and selling. Joe did not do that because bureaus were his pipeline, and they did the selling. Joe knew that if he did a good job, then word of mouth, referrals, and repeats would take care of the selling. So, he kept working on his upcoming speeches to make them as good as possible.


Over time, doing speeches became less and less exciting for Joe. Eventually, he did not want to do them at all, so he emailed every bureau that represented him, saying that he would no longer be doing keynotes and asking them to remove him from their websites.

Conversational presentations

Over time, Joe developed a preference for doing more conversational presentations.


Joe points out that entrepreneurship is not for everyone, and the journey of most entrepreneurs is a hard one.

The trap entrepreneurs can fall into

People can fall into a trap when they get an idea and fall in love with it. When they put their idea out into the marketplace, they may discover it is not marketable.

Helping college seniors

Several years ago, Joe was the entrepreneur in residence for Belmont University’s Center for Entrepreneurship. He helped college seniors who were starting companies navigate their way.

Gathering information

The early stages of entrepreneurship are about gathering information and getting your business off the ground.


As an entrepreneur, you need to be clear about what you want and love to do. The beauty of entrepreneurship is that you can run your business in any way you want to.

Things could go wrong

When Joe gets a good idea, he thinks about all the reasons why it might not work. He also considers that there will be downturns in the economy and understands that other problems could arise.

Motivation to keep going

A long time ago, Joe learned that when something goes wrong, it is probably normal- even if it is awful. Knowing that, and adopting a constructive approach to any situation, helps him get through tough times. He has also developed a network of other speakers over the years who support one another when times are hard.


Getting involved in the wholesale Kentucky bourbon business has been a catalyst for Joe to learn a whole lot more about the fascinating bourbon industry!


Since retiring, Joe has been trying to figure out how to live without the day-to-day engagement he is used to having with his various businesses.

Connect with Joe Calloway

On LinkedIn

Books mentioned:

Buy Then Build by Walker Deibel

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Eric Rozenberg

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