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This episode continues the financial planning of the entrepreneur as Jim and Matthew pick up in Stage 3 of their four-part process: Shaping Your Story.

WIth Jim fresh off an Alice Cooper/Judas Priest concert and Matthew a Vermont fall-foliage wedding, the guys explore how clarity meets action when entrepreneurs begin planning what’s next — their Life 3.0. They challenge the old idea of “What’s your number?” and instead walk through a more nuanced, risk-aware way to structure your assets using their money barrels framework: Now, Soon, Later, and Never.

If you’ve ever wondered, “Do I really have enough?” — whether you’re sitting on a couple million or a couple hundred million — this conversation will help you see life after the exit as a strategy. It's not an end point but the next chapter of your whole wealth story.

In this episode, you’ll learn:

• Why gratitude, curiosity, and “firsts” in your 50s (and beyond) matter when planning what’s next
• How Stage 3: Shaping Your Story fits into the Whole Wealth Journey process
• The difference between defining your story and actually building Life 3.0
• Why the old “What’s your number?” commercials and the classic 4% rule can create a false sense of arrival
• How entrepreneurs’ vision of “retirement” differs from traditional work-and-stop models
• The money barrels approach: separating your wealth into Now, Soon, Later, and Never buckets
• Why Jim and Matthew are passionate risk-managers, not just asset managers — and why cash is an asset class
• How to align your investments with when you’ll actually need the money, not just how much you have

Chapter Summaries

(00:00) Gratitude and Family Celebrations
Managing risk through cash reserves, gratitude for a heavy metal concert, and family connections in Vermont.
(07:06) Shaping Your Financial Story
Integrating personal and financial planning, gaining clarity on desired lifestyle, guiding clients towards fulfilling Life 3.0.
(17:15) Retirement Planning and Life 3.0
ING's memorable commercial featuring a tangible retirement "number" sparks discussion on oversimplification, personalized planning, and varied perspectives.
(31:25) Planning for Future Wealth Success
Financial planning is like managing "money barrels" for risk and growth, adjusting for timeframes and aligning with personal goals.

Learn more about The Whole Wealth Journey and get periodic updates or helpful content by getting on our email list HERE. Entrepreneurs, exit strategies and personal financial planning before the sale are topics you can count on every episode. You can follow us on Instagram @thewholewealthjourney.