Gary Leland Podcast Hall of Fame InducteeJaime Jay welcomes Gary Leland to today’s podcast. Gary was one of the first 100 podcasters in the world and was recently inducted into the Podcast Hall of Fame in Chicago at Podcast Movement 2016.

The Gary Leland Show

The latest endeavor Gary is working on is his new self-entitled show called the Gary Leland Show.  It’s going to start out as a once a week show, but he wants to take it to five days a week.  There are a lot of shows where people have listeners send in their questions and the host answers the questions when they record the show.  Gary is going to have a live show where guests will come on the show and ask questions.  The show is going to be a question and discussion show, not a question and answer show.

Gary’s Background

Gary LelandGary arrived in Texas in 1978 with a grand total of $6.00 in his pocket.  Being broke, he was forced to get a job.  He started a small business on the side and within six months, his side business was making more than his day job.  He quit his full time job and went into business by himself and never looked back.

In 1996, his podcast website was in Time Magazine as one of the 50 coolest websites on the planet.  In 1996, he started a wallpaper website.  People told him he was crazy for trying to sell something on the internet.  He didn’t listen to the naysayers and became very successful.

The move into the podcast genre of softball proved to be one of the best moves Gary ever made.  He is one of the most well-known faces, and voices, in the world for girls fast-pitch softball.

Achieving Dreams Through Podcasting

The Gary Leland ShowWhen asked how he became so successful with podcasting, Gary was quick to say that he uses the medium as his marketing arm.  Most of his shows are about girls fastpitch softball.  At one point, Gary was spending about $10,000 per month on Google adwords.  When Google raised their advertising, podcasting is what he turned to.  Gary creates his own shows so that he can save on advertising and be in total control of his platform.

“One of the reasons I do podcasting is because I can advertise on my podcast.  I don’t want to give money to someone else for advertising.” – Gary Leland

Tweet this episode for Gary

With so much experience, he’s gotten pretty good at podcasting.  Where it used to take him several hours to edit his show and write his show notes, he has learned all the short cuts.  Now he has an assistant to help him.  When asked what does he do with all his free time, Gary said “I don’t have free time.  I’ve found other things to take up my time”.

The ultimate “because of my podcast” story, Gary was invited to the Olympics.  Softball was awarded to be an official sport in Japan for the 2020 Olympics.  This means, Gary will be the first podcaster to get press pass credentials for the Olympics.  Pretty dang exciting.

How Does Gary Leland Monetize His Podcast?

This is Gary’s sweet spot.  He is much different than the average person when it comes to monetizing his shows.  If you want to learn how Gary Leland does it, then make sure to listen to this episode.  You can also check out his links below to learn more about him.  He welcomes all questions, comments, and inquiries! Don’t forget to mention you heard about Gary on Stop Riding the Pine:-)

Gary Leland and Jaime JayThe Gary Leland Show
Gary Leland on LinkedIn
Tweet Gary
The Fast Pitch Softball YouTube Channel

Here are the highlights of my conversation with Gary Leland if you are in a hurry:

  • Who is Gary Leland? (4:50 Mark)
  • How does Gary monetize his podcast? (13:20 Mark)
  • What can you podcast about? (20:10 Mark)
  • Gary can help you edit your podcast. (25:30 Mark)
  • What is the Gary Leland Show about? (28:13 Mark)
  • Gary’s breakaway moment (35:00 Mark)

Special Mentions:
(iTunes Shout Out) The Toy Box Studio with Lij Shaw

Thank you to Alexis Ayala, for providing the incredible editing for this episode. If you need to find an audio editor, send Alexis an email at

Interview ValetThank you to our awesome sponsor, Interview Valet, A professional concierge guest booking podcast service for hosts and guests – You be the Guest, We do the Rest! Check out their new website at

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