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Have you ever wondered what it truly means to leave a legacy in business? Today’s guest, Richard Ryan, is a powerhouse entrepreneur whose journey spans building businesses, pioneering media strategies, and living a life anchored in intention.

Throughout our conversation, Richard and I explore the importance of curiosity, adaptability, and strategic thinking in achieving success.

We dive into everything from rally cars and starting from scratch to building a coffee empire and redefining success after an IPO.

This episode is packed with lessons about legacy, grit, and why how you show up matters more than what you achieve.

Click play to hear all of this and:

(00:05:00) How digital marketing’s evolution has changed the game for creators and businesses alike.

(00:06:19) Why being a subject matter enthusiast is the secret weapon for positioning yourself as an expert.

(00:07:19) The intersection of luck, passion, and preparation—and how it creates opportunity.

(00:08:34) Why follow-through matters more than ideas and how building the right team can make all the difference.

(00:09:01) A peek behind the curtain of Richard’s joint venture with Verizon Media and Hearst Publications.

(00:10:00) How to tailor content to a specific demographic to create a fiercely loyal audience.

(00:15:48) The exact media strategy blueprint that turned Black Rifle Coffee into a household name.

(00:20:12) Lessons from the Wild West of analytics and early YouTube—how Richard stayed ahead of the curve.

(00:24:02) How to use current events to inspire a brand’s visibility and market position.

(00:24:51) How to manage your time and focus while juggling multiple projects.

(00:25:59) The importance of building a bingeable content library to educate, entertain, and emotionally connect with your audience.

(00:30:22) How storytelling creates an emotional bond with your audience.

(00:33:23) Richard’s life post-IPO and what it means to transition to a publicly traded company.

(00:34:20) Making bold moves, from early Bitcoin investments to financial freedom.

(00:35:28) The importance of living modestly despite major success.

(00:44:50) The importance of enjoying the process, not just chasing the end result.

Listen to Related Episodes:

Connect With Richard Ryan:

https://x.com/RichardRyan

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9:15 AM ET: Economy rose much faster than expected in Q1