In this episode, Jay and I reflect on how our vision for life and business has evolved—and how we intentionally build a real estate business that fuels our freedom, not just our finances. We unpack how thinking creatively about resources, like boat or airplane clubs, shifted our mindset away from ownership and toward lifestyle design.

This conversation dives into why your calendar should reflect your values, how to move closer to your ideal life using “waypoints,” and why waiting for retirement isn’t the answer. We also talk candidly about creating multiple streams of income and real-life examples from our community of how people are aligning their goals with their daily choices.

Episode Timeline:

[0:01] – Why time—not money—is the most valuable asset

[0:42] – How our vision work turned dreams into actual calendar items

[1:59] – The boat ownership mindset shift and what we learned from boat clubs

[3:07] – Why we started exploring airplane clubs instead of private plane ownership

[5:27] – What this all has to do with designing a life that fits you—not the other way around

[8:02] – Our “Florida test run” and using waypoints to validate vision

[11:04] – Case study: laundromats, seller financing, and building cash flow creatively

[13:35] – Setting health goals with measurable steps and long-term focus

[15:28] – Short-term rental strategy targeting travel nurses

[18:44] – Why we prefer paying interest to individuals over banks

[25:01] – A discussion on hedge funds, portfolio debt, and what we’re seeing in the market

[33:59] – Comparing your income to others—and the real definition of success

[36:39] – Building multiple businesses and staying focused on your version of wealth

[43:48] – How a camping trip in Hawaii became a lesson in resourcefulness

[45:21] – Final encouragement: calendar your vision, write it like it’s already happened

5 Key Takeaways:

1. Design your business to serve your life—not the other way around.

2. Waypoints help you test your big dreams before going all in.

3. You don’t have to own everything—use clubs, rentals, and partnerships to live your vision now.

4. Creative cash-flowing assets (like laundromats or STRs) can support long-term freedom.

5. Writing your vision as if it already happened helps it become real.

If this episode helped you reframe how you think about time, income, and lifestyle design—please rate and review The Real Estate Ride, and don’t forget to share it with someone who’s ready to start building freedom today.