Boomer Summer continues with an attempted 4:30 p.m. dinner, an upcoming Austin/New Orleans trip, disappointing Hollywood movies, and a eulogy for the phone number Apple finally killed after 24 years.

Then I answer a question I’ve learned the hard way: should you quit your job to follow your dream? Maybe, I think you should do THIS first...

0:00 Intro
1:43 Austin and New Orleans Road Trip
5:51 Hollywood Keeps Making Mediocre Movies
10:43 RIP My 24-Year-Old Phone Number
13:05 Should You Quit Your Job to Follow Your Dream?
18:42 How to Protect the Dream From Income Pressure
22:05 Biggest Lesson from the Tough Times

In this episode of The Brandon Beeyard Show, Boomer Summer continues with a jellyfish wrapping its tentacles around me, the challenges of dating in Pensacola, and Apple finally destroying the phone number I’ve had my entire life.

Topics:

0:00 Intro
 1:53 Attacked by a Jellyfish
 6:24 Dating in Pensacola
 9:05 Apple Destroyed My Phone Number

In this episode of The Brandon Beeyard Show, Boomer Summer continues with brittle parents, radioactive Keurig water, Antiques Roadshow, and my third straight week trapped in Apple jail.

Then I get into the AI automation project that was supposed to save me time but instead burned through my OpenAI limits, wasted most of my week, and left me no closer to my business goals. That experience led me to Ray Dalio’s personality test, where I learned that I’m a “shaper”—someone who naturally focuses on vision but can get stuck trying to implement everything alone.

Finally, I talk about the quieter pressure that builds when you’re running out of time, falling behind on your goals, and unconsciously expecting every new effort to fix your life. The real challenge is learning to welcome small wins, fail quickly, and make the work playful again.

Topics:

0:00 Intro & Boomer Summer Continues...
6:21 Three Weeks in Apple Jail
9:10 My AI Automation Disaster
15:24 My Billionaire Personality Type
21:37 Sneaky Pressure
24:58 Making the Work Fun Again

In this episode, I talk honestly about moving back home at 43, running out of financial runway, and realizing I had been putting the thing I cared about most on the back burner. I also explain why I’m choosing freedom over stability, going all in on building a media business, and designing the life I actually want instead of continuing to delay it.

Topics:

0:00 Intro: Boomer Summer Continues
 6:37 Moving Back Home at 43
 10:50 Choosing Freedom Over Fear
 14:44 Going All In on a Media Business
 17:12 Reverse Maslow's Hierarchy
 20:14 Calculating Your Freedom Number
 27:47 Game: Spin the Globe
 31:31 Conclusion

In this episode of the Brandon Beeyard Show, Brandon discusses the absurdity of societal contradictions, particularly regarding crocodile attacks and lack of sympathy for extreme sport injuries. Brandon also questions the conventional wisdom of being "responsible." Would it actually be more responsible to do what you want? 

TOPICS

0:00 Dodging snowmageddon travel nightmare

4:50 Crocodiles and COVID in Australia

7:49 Why no sympathy for skydiver injuries?

13:22 The responsibility paradox 

In this episode of the Brandon Beeyard Show, Brandon talks about the patterns we get into and how to break free from them. He looks at the invisible rules of our society and examines whether we can start to break free from them. He also shares his personal struggles with money, entrepreneurship, and identity. 

TOPICS:

0:00 Brandon's biggest limiting belief

10:00 Brandon's struggle with starting a business

16:29 The Matrix and breaking free of society's invisible rules

24:22 Falling for the entrepreneur identity trap

28:11 Snowpocalypse: Can AI tell me if I should cancel my trip?

In this episode of the Brandon Beard Show, Brandon talks about the heartbreak of fleeing New Orleans during the pandemic, the end of the reign of terror by Mayor Latoya the Destroya, and what he's gonna do now that she's gone. He also recounts his return to stand-up comedy after a nine-month hiatus, possibly buying a plane so he can more easily visit family and friends, and more!

Topics:

00:00 Intro

04:19 Goodbye, mayor from hell

10:57 The heartbreak of leaving New Orleans and moving to Austin

18:00 Travel modes for lifestyle design

23:15 Brandon's return to stand-up comedy this week

29:51 Name that movie plot

In this episode of the Brandon Beeyard Show, Brandon discusses the importance of setting goals, taking breaks for perspective, and the role of accountability in achieving success. Brandon also explores how AI can assist in business growth and emphasizes the need for honest self-assessment and planning to avoid burnout. He concludes with encouragement for listeners to pursue their goals and the necessity of travel for gaining perspective.

The Brandon Beeyard Show is your guide to fast-tracking creative independence and making your big dream actually happen. 

In this episode, Brandon caps of a semi-sweet 2025 and shares some hard-fought lessons so you can have a successful new year:

Topics:

• The annual airing of grievances and lamenting of failures
• Standup comedy and dropping neediness 
• Skydiving accomplishments
• Resistance is the way, not the obstacle
• You are exactly where you're supposed to be
• Silencing mental chatter
• Will I keep doing this show? 
• A BONUS Christmas surprise to end the show!

The Brandon Beeyard Show is your guide to fast-tracking creative independence and making your big dream actually happen

In this episode, Brandon recounts his adventures from Thanksgiving week including: deer hunting, spending Thanksgiving alone, the art of permissive sobriety, finding happiness by avoiding political news, and the false dichotomy between your dream pursuit and income.