PH014: Josh Wilson of Bet the Jockey and Orlando Entrepreneurs

Josh Wilson is a serial podcast host, but on today’s episode, we focus on two of his shows. These podcasts are Bet the Jockey and Orlando Entrepreneurs. Bet the Jockey is the podcast that promotes Josh’s personal brand and has recently undergone a major content pivot. Orlando Entrepreneurs is dedicated to showcasing the awesomeness that is Orlando and the unique business opportunities.

[click_to_tweet tweet=”When the recording stops, that’s when a really great conversation happens.” quote=”When the recording stops, that’s when a really great conversation happens.”]

Until recently, Josh’s show, Bet the Jockey was the typical success story business podcast. However, after a personal financial crisis, Josh found himself with nothing. This gave him the idea to format the show to discuss the mistakes he made to help others who were also struggling. This decision has caused some anxiety for him, but Josh believes his audience expects and wants authenticity from him.

We discuss the importance of showing both sides of the entrepreneur’s journey to present an honest and complete portrait of the experience.

Today’s highlights:

• The origins of Josh’s brand name “Bet the Jockey.”
• Josh’s sudden misfortune and how it changed his show.
• The types of guests that appear on Bet the Jockey.
• Why it is important to show your failures as well as your successes.
• Josh’s fear of changing his content.
• Presenting an authentic picture to your audience.
• How Josh interacts with his audience.
• Using your gut to make content decisions.
• Lessons Josh has learned during his time as a podcaster.
• Orlando Entrepreneurs’ mission and focus.

[click_to_tweet tweet=”I think it’s going to be more important for people to feel connected by listening to stories… so I think there will be a greater connection of people via social platforms and podcasting.” quote=”I think it’s going to be more important for people to feel connected by listening to stories… so I think there will be a greater connection of people via social platforms and podcasting.”]

Resources:

Bet the Jockey

Orlando Entrepreneurs

Josh Wilson on LinkedIn

Thank you for joining me for today’s Podcast Hackers episode! Tune in next time as we continue to have in-depth conversations with experts who can help make your podcast the best it can be!