Episode 165: Shaping Your Financial Story. Preparing for Life After the Exit.

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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.

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