Get automatic updates delivered straight to your inbox.

Connect with Steve Sipress


Advice From A Rich Entrepreneur

Steve Sipress & John Rich

Country music star John Rich was the winner of Donald Trump’s Celebrity Apprentice show last season.

He’s written over 2000 songs spanning a 20-year career, but until last Thursday, he had never been asked to speak onstage at an event.

I was fortunate enough to be in the audience for his first-ever public speaking engagement, at the world’s #1 annual event for direct response marketers: the Glazer-Kennedy Insider’s Circle SuperConference in Dallas, Texas.

You may have been to a business conference with a celebrity speaker, so you can imagine that the audience didn’t expect much from Rich in the way of meaningful, actionable content. And we didn’t expect him to be a true entrepreneur.

We were wrong.

Rich instantly connected with the crowd of about 1,000 entrepreneurs, small business owners and sales professionals by declaring, “The greatest thing you could be is an entrepreneur in America.” He then shot a big, fat grin and said, “I hope some of those evil one-percenters come out of this room!”

He went on to establish an even deeper connection by sharing his “rags-to-riches” success story full of ups and downs – something every entrepreneur can relate to.

Rich grew up in a trailer park home, and set out to chase his dream when he was 18. As he put it, “20 years ago, I was one guy, with one guitar and one piece of paper.”

He explained that he lost three record deals early in his career, repeatedly failing to achieve success in his first attempts. He wrote 500 songs, in fact, before one stuck.

As an entrepreneur, can you relate? How many times have you felt like giving up? As Rich encouraged, “You have to be a relentless maniac about your business. If you want to win, you figure out a way to win – to do better for yourself, your family and your country.”

He also had something to say to those small business owners who start to experience success, then become satisfied and stop pushing: “When you get the ball rolling, don’t ever just watch it roll. Get up there and kick it forward, and then hire people to kick it even more.”

That’s advice I wish I had heard – and followed – decades earlier. I had built my first multi-million dollar business from scratch to the largest in its industry; but then I lost my drive. I failed to re-set my goals higher, and “put my feet up.” Sure enough, the business started to stagnate. Then it declined, and finally disappeared, taking everything I had with it. I had let my ball stop rolling.

Rich showed us his blue alligator boots, relating them to what are called “hooks” in music writing: “doing something so memorable that people remember you.” He knows that the worst thing to be seen as in business is just another ______________. Every small business owner must provide something unique – something I wrote about in this space two weeks ago.

After his talk, some of the event VIP’s got to line up for a photo opportunity with the superstar entertainer and entrepreneur. When I reached the front of the line wearing my outrageous, big, obnoxious red cowboy hat, Rich cracked up and congratulated me for following his advice, telling me, “I’m never gonna forget that big, red hat!”

How about you? Are you following the advice of successful entrepreneurs who have come before you? Are you setting big goals that motivate you to do whatever it takes to persevere and succeed, and surrounding yourself with successful people who can help you get things done?

As John Rich says, “the best way to serve your country is to build a successful business and hire people. Generosity breeds success: successful people helping people, instead of the government.”

Oh, and one last bit of advice from a true-blue, down-to-earth, 100% real American entrepreneur success story: “Don’t forget to have fun and celebrate.”


3 Responses to Advice From A Rich Entrepreneur

  1. Donna G. Reply

    April 25, 2012 at 8:49 am

    It’s teriffic the business world is discovering what John Rich fans knew all along. He is a multi-facated, super initelligent, talented, true person, wh
    o works hard and loves his country.

  2. Robin WC Reply

    April 27, 2012 at 2:20 pm

    Hey Steve,

    Great Photo …..Who would have guessed that U TOO would be a country fan??

    I only realized it was You in the photo after I read the article!

    Nice photo and article,

  3. Steve Sipress Reply

    April 28, 2012 at 5:02 pm

    Thanks, Robin!

    I’m a fan of all true-blue, hard-charging, forward-thinking, aggressive entrepreneurs!

Leave a Reply

Your email address will not be published. Required fields are marked *