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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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🚀 Settling for "average"? Let’s be real—that mentality doesn’t serve you or anyone else. It's about breaking limits and defining success on your own terms. From 40-foot RV road trips and sunsets over the Grand Canyon to diving into entrepreneurial drive, personal growth, and real estate strategies—this episode isn’t your typical self-help spiel. It’s a reminder that life isn’t about fitting in; it’s about pushing the boundaries of what’s possible. This convo lays it out, no BS.
📌 Key Takeaways:
✅ Finding "average" isn’t about settling; it’s about redefining success for yourself and challenging societal norms.
✅ Real estate investment isn't just a path to wealth—it's a method for long-term stability and freedom, when approached strategically.
✅ Achieving financial freedom requires intentional planning, especially if you want time to enjoy life, family, and personal milestones along the way.
✅ Generational wealth isn’t just a goal; it’s a way to break cycles, influence the future, and build a legacy.
✅ Environment matters. The people around you shape your ambition, outlook, and how far you’re willing to go.
🔉 Sound Bites:
➤ "What’s average, anyway? It’s a sliding scale. You set it."
➤ "You’re the sum of who you surround yourself with."
➤ "It’s not about working harder; it’s about creating freedom to live life on your terms."
➤ "Money mentioned in the Bible more than anything else? There’s a reason for that."
00:00 The Journey Begins: Road Trip Reflections
03:10 The Value of Experience: Family and Work Life
06:02 Understanding Average: Perspectives on Life
08:57 Desire for More: The Entrepreneurial Mindset
12:05 Financial Freedom: Rethinking Retirement
14:46 Real Estate Strategies: Building Wealth
18:07 Challenging the Average: Personal Growth and Society
21:05 The Power of Environment: Influences on Success
23:55 Breaking Generational Cycles: Wealth and Mindset
26:48 The Nature of Desire: Want vs. Need
29:55 Finding Your Average: Personal Happiness and Fulfillment
32:47 Final Thoughts: Embracing Life's Vastness
48 episodes
