The Whole Wealth Journey

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Reflecting back to a certain Christmas Eve five years ago, a journey began that reshaped the approach to finances by aligning them with life's true purpose. That pivotal moment, intertwined with unexpected connections and encounters, taught us the value of authenticity and vulnerability, transparency and truth. With stories rich in serendipity and meaningful coincidences, we celebrate the unpredictability of life and the profound impact of embracing it with gratitude.

As we continue to navigate the aftermath of global events, effects from the pandemic like supply chain disruptions and the memorable toilet paper shortages, we've unearthed profound lessons in gratitude and resilience. These challenges have been catalysts for personal growth and have altered societal relationships, pushing us towards self-reliance and away from codependency. Our discussions mirror a hero's journey, emphasizing the strength developed through trials and the determination to face future uncertainties with confidence, amidst political and economic anxieties.

Finally, we close with a festive reimagining of a reading by Matthew of his interpretation of "Twas the Night Before Christmas," reflecting the Gebhardt Group's unique approach to to your whole wealth journey. As we embrace the joy and gratitude of the holiday season, let's celebrate the power of partnership and our shared mission to help you achieve your dreams and leave you with a greeting for a very merry Christmas holiday and the happiest of healthy and prosperous new years. 

Chapter Highlights

(00:00) The Whole Wealth Journey
Gratitude for connections made on our financial journey, reflections on health challenges, and embracing life's unpredictability.

(14:40) Lessons of Gratitude and Resilience
Past global events have shaped behaviors and relationships, fostering personal growth and resilience amidst uncertainties.

(26:51) The Wealth Journey Festive Celebration
How about that night before Christmas?

(33:36) Investment Advice Disclaimer

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. 

We would love to hear what you have to say about this episode. Please send us a text.

In this episode the guys, Jim and Matthew, put a bow on their financial planning framework and talk about what really happens once the plan is “done” and you’re launched into Life 3.0 — the season where you finally get to live your why.

They explore what most people actually do the moment they exit a business or retire (hint: it usually starts with a passport), why the first 10 “go-go” years can be the most expensive years of your life, and how that clashes with the industry myth that you’ll only need 70–80% of your working income in retirement.

Through real client stories, hear how the best-laid blueprints often change: from restoring a historic Victorian to suddenly moving across the country, or from corporate burnout to a fully expressed creative life. You’ll hear how a thoughtful plan gives you permission to pivot without panic.

Most importantly, they unpack the real value of an advisor once the portfolio is built and the wealth gap is closed. It’s not about chasing returns—it’s about having a “family CFO” who walks with you through best times or your worst or final hour.

If you’ve created significant wealth and are now asking “What’s next?” this conversation will help you reframe the question you ask your advisor from “How much can you make me?” to “How will you be there for me and my family when it matters most?”

Chapter Summaries:

(00:00) 

Importance of building a supportive team and focusing on "who, not how" in navigating life's challenges with trusted professionals and individuals.

(09:37) Launching Into Life 3.0
Retirees transition into new phase of life, living their "why" with higher spending and difficulty making office visits.

(16:55) Living Your Why
Retirees like Hank and Jill often live vibrant lives, embracing their unique abilities and finding fulfillment in creative pursuits.

(29:23) Navigating Life's Financial Challenges
Having a trusted financial advisor is crucial for navigating life's challenges, similar to the security provided by insurance.

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. 

We would love to hear what you have to say about this episode. Please send us a text.

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. 

We would love to hear what you have to say about this episode. Please send us a text.

This episode, your hosts, Jim Gebhardt and Matthew Grishman explore the intertwining of financial planning with personal growth, emphasizing the impactful role gratitude plays in their process. They'll discuss the efficiency of the clarity compass, their approach to client financial and personal planning, and share their personal experiences and philosophies on balancing life and work. They also highlight the importance of saying 'no' and how it contributes to a richer, more focused life. Join the guys as they unpack and define both personal and financial stories to help entrepreneurs navigate their wealth own personal journey.

00:00 Introduction to The Whole Wealth Journey
00:52 The Importance of Gratitude
05:02 The Ryder Cup Experience
07:57 Blending Financial and Personal Planning
16:24 Defining Your Future
20:15 The Essence of St. Francis
20:27 A Quick Quack Encounter
21:11 The Importance of Being Interested
21:49 Personal Planning and Assessments
22:30 The Clarity Compass: Secret Sauce
25:22 Memory Dividends and Die With Zero
28:02 The Power of Saying No
36:43 Upcoming Episodes and Conclusion

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. 

We would love to hear what you have to say about this episode. Please send us a text.

Hear what happens when host, Jim Gebhardt invites his daughter to comment on her perception of the content of the show, some of her lived experiences as a family member during some very challenging financial times, what her outlook is as the daughter of a holistic financial specialist, and what it would look like to feel financially secure at 22 years old. 

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. 

We would love to hear what you have to say about this episode. Please send us a text.

This episode, hosts Jim Gebhardt and Matthew Grishman dive into the concept of work-life balance and reflect on their own journeys towards financial confidence. They discuss the importance of gratitude, building meaningful relationships, and finding clarity in financial decisions. The guys elaborate on their experiences with financial confidence, the significance of understanding clients' personal values, and how intentionality with money can lead to greater fulfillment and empowerment in financial decision-making one faces as an entrepreneur.

Chapter Breaks
00:00 Introduction to Work-Life Balance
00:34 Meet the Hosts: Jim and Matthew
00:50 Gratitude Moments
02:35 Special Guest: Daughter Grace in the Studio
04:54 Deep Dive: Financial Conversations
14:29 Understanding Financial Confidence
21:51 The Importance of Intentionality with Money
22:22 Managing Joint and Separate Bank Accounts
23:50 The Power of Visualization in Financial Planning
24:59 Overcoming Financial Anxiety
26:15 The Journey from Scarcity to Abundance
26:36 The Role of Debt in Financial Confidence
28:29 Finding Purpose Beyond Financial Success
31:09 The Importance of Authenticity in Personal and Professional Life
37:14 Defining Financial Confidence and Personal Investment
40:43 Conclusion and Final Thoughts

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. 

We would love to hear what you have to say about this episode. Please send us a text.

What if the relentless pursuit of wealth is actually keeping you from enjoying it? Join, us, Matthew Grishman and and Jim Gebhardt as we navigate the delicate art of balancing financial success with life’s simple pleasures. We'll explore the transformative concept of "investing in fun" and how it can act as a catalyst for not just joy, but also as a new form of wealth in your life. We open the floor to the emotional journey of becoming empty nesters, which brings newfound financial freedom and the chance to redefine life's goals. 

On a more poignant note, we share the heartfelt story of Stevie's unexpected passing, Jim's brother, which served as a stark reminder of life’s fragile nature and the importance of reevaluating priorities. From the shocking late-night call to honoring Stevie's last wishes, this narrative is both raw and revealing. We also take a moment to challenge the work-centric mindset many of us grew up with—illustrated by my a family’s alarm code—and advocate for a balanced approach where fun is a vital ingredient in building experiential wealth. We'll explain our structured process to examine your own money stories and embark on a path toward a future filled not just with financial prosperity, but also well-being and happiness. In so many cases, as we've learned from experience, money is not necessarily what brings one joy. Our F-O-R-M journey we'll take you on, explains it all. 

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. 

We would love to hear what you have to say about this episode. Please send us a text.

This episode, your hosts, Jim Gebhardt and Matthew Grishman really get their arms around the entrepreneur's journey as they wrap up the series for entrepreneur's personal planning. This is perfect for that time when the business gets sold or there's an exit and the next steps become mandatory as to what to do. They'll dive into the intersection of personal and financial planning for entrepreneurs teeing up the next steps post exit as well as the next series of episodes. They recap the recent series by by discussing the importance of time management and resistance in daily routines. The episode reflects on the core aspects of personal planning, including health, relationships, values, and experiences. Jim and Matthew emphasize the need for a holistic approach that integrates financial, personal, and business planning to achieve long-term success and fulfillment. They also summarize their four-part financial planning process: unpacking your story, defining your story, shaping your story, and ultimately living your 'why.' With a segment from Guy Raz's "How I Built This", Don Vultaggio from Arizona Iced Tea shares the concerns he has about next steps as he shares what he was told by the owners of Snapple when they sold their business. Poor personal preparation post business sale or exit, is not a healthy process. Practical advice and real-life examples make this episode a comprehensive guide for entrepreneurs looking to balance wealth and well-being as they enter into the next chapter of their lives.

Jim mentioned the book, "The Untethered Soul" by Michael Singer. You can find it on Amazon HERE. 

00:00 Introduction to The Whole Wealth Journey Podcast
00:46 Gratitude for Resistance
03:45 Health Coaching and Personal Progress
06:39 Recap of Personal Planning Episodes
08:20 The Importance of Personal Planning in Business Transitions
20:38 The Who, Not How Concept
25:06 The Power of the Who, Not How Mindset
26:06 Clarity, Confidence, and Capability
28:32 The Importance of Personal Planning Teams
33:38 Understanding Whole Wealth
34:17 The Seven Asset Classes
45:32 The Financial Planning Process
50:34 Conclusion and Next Steps

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. 

We would love to hear what you have to say about this episode. Please send us a text.

This episode, the guys dive deep into the concept of 'Life 3.0,' an era post-business exit where entrepreneurs can create meaningful, fulfilling lives into what some may call retirement. They discuss the importance of personal planning alongside business and financial planning, offering a comprehensive roadmap to better wealth and well-being. Key topics include the importance of time as a finite resource, the concept of 'who not how,' forming a robust personal planning team, and practical steps for life optimization through various asset classes such as health, relationships, superpowers, and values. The episode also underscores the significance of experiences and provides actionable steps to kickstart the journey towards a fulfilling life post liquidation event or sale of the company.

To learn more about some of the programs recommend for self assessment, here are the various links. "Print" can only be performed through certified professionals. 

Clifton Strengths

KOLBE Index

Working Genius

Chapter Timestamps

00:00 Introduction: The Finite Nature of Time
00:36 Welcome to the Wealth Journey Podcast
01:01 Gratitude and the Concept of 'Who, Not How'
01:22 The Exit Planning Conference Experience
02:25 Collaborating with Cultivate
04:56 The Importance of Small Steps
07:46 The Personal Planning Process
09:24 Building Your Personal Planning Team
13:34 Understanding Yourself Through Assessments
31:24 Exploring Natural Strengths and Working Genius
33:13 The Power of the Clarity Compass
34:41 Identifying and Leveraging Your Superpower
39:14 Optimizing Time and Health Assets
42:34 Building and Auditing Your Health Team
46:38 Enhancing Relationship and Values Assets
53:44 Experience Asset Planning
56:40 Integrating Money and Whole Wealth
58:47 Immediate Action Steps for Life 3.0
01:01:46 Conclusion and Final Thoughts

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. 

We would love to hear what you have to say about this episode. Please send us a text.

Emphasizing a departure from the traditional concept of retirement, Jim Gebhardt and Matthew Grishman dive into the paradox of entrepreneurs' disdain for conventional retirement and the need for holistic personal planning. They highlight the importance of clarity, confidence, and capability in preparing for life after selling a business. They share personal anecdotes, insights from their experiences, and actionable advice for business owners to envision a future rich in meaning and impact, beyond just financial wealth.

To get the book mentioned in the program, "The Majesty of Calmness", you can find it on Amazon HERE.

Key segements

00:00 Introduction to Retirement Concepts

00:53 Introducing the Wealth Journey Podcast

01:18 Gratitude and Family Moments

05:24 Personal Planning and Health

09:04 The Three-Legged Stool of Business Transition

10:51 The Importance of Personal Planning

14:31 Clarity, Confidence, and Capability

22:13 The Importance of Clarity in Personal Planning

24:01 The Confidence Boost from Personal Planning

25:02 Overcoming Quadrant One Addiction

25:58 The Role of Personal Planning in Business Exits

29:48 Protecting Your Confidence at All Costs

33:12 Redefining Treats and Building Sustainable Confidence

34:33 The Power of Capability in Personal Planning

43:07 The Concept of No Arrivals in Business

44:23 The Importance of Personal Planning for a Bigger Future

45:21 Wrapping Up and Next Steps

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.