Planning Reimagined

Hosted by Robin Glen

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Feb 2026

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About the show

Welcome to Planning Reimagined, a podcast by Robin Glen that gives you an exclusive peek into the wealth-building strategies of high-net-worth individuals. In every episode, we discuss the intricate world of securing wealth and creating a lasting legacy, exploring actionable strategies and insightful discussions to empower you on your journey.

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24 recent

February 22, 202624 min

Handshakes Don’t Survive Heartbreak: The Real Cost of an Unfunded Buy-Sell

A family business can survive competition. It usually doesn’t survive silence.In this episode of Planning Reimagined, Celeste Moya and Kris Stegall unpack a real-world business succession breakdown: the Smith family’s multi-subsidiary landscaping company is thrown into chaos after the unexpected death of a key-owner—because there was no buy-sell agreement, no funding, and no clear plan for ownership transfer.They break down why “we’ll work it out” is not a strategy, what it actually means to fund a buy-sell, how liquidity can prevent conflict (and litigation), and the practical steps business owners can take now to protect the company, the surviving family, and everyone who depends on the business.Subscribe to Story of the Week(ish) for planning insights in your inbox:https://zc.vg/P36ORLearn more at:https://www.robinglen.comDisclaimer: This podcast is for educational purposes only and should not be considered tax, legal, or investment advice. Please consult your professional advisors regarding your personal situation.

January 13, 202617 min

The Power of a Policy Review: How One Annual Check Saved $80,000 a Year

In this episode of Planning Reimagined, Celeste Moya and Kris Stegall discuss why routine policy reviews are one of the most overlooked tools in effective financial planning. Through a real-world case, they show how a simple review of a premium-financed life insurance policy uncovered an inefficient loan structure—saving the client $80,000 per year without changing the insurance itself.The conversation explores how life insurance, premium financing, indexed universal life, disability insurance, long-term care, and annuities should be treated as living financial tools that require ongoing attention. Celeste and Kris also address common misconceptions around policy performance, loan spreads, crediting caps, and illustrated returns—and why complexity makes regular reviews even more critical.This episode reinforces a core planning principle: implementation is only the beginning. Ongoing review and education are what keep strategies aligned with real-world conditions and client objectives.Subscribe to Story of the Week(ish) for planning insights in your inbox:https://zc.vg/P36ORLearn more at:https://www.robinglen.comDisclaimer: This podcast is for educational purposes only and should not be considered tax, legal, or investment advice. Please consult your professional advisors regarding your personal situation.

November 24, 202519 min

Planning for a Loved One With Special Needs

In this episode of Planning Reimagined, Celeste Moya and Kris Stegall discuss the critical importance of proactive planning for individuals with special needs, focusing on the case of Edward Whitmore, a retired executive concerned about his son Daniel's future. They explore the complexities of financial management for vulnerable individuals, the creation of a special needs trust, and the role of corporate trustees in ensuring financial dignity and protection. The conversation emphasizes the need for comprehensive planning that considers both financial and non-financial aspects of care, including long-term care considerations and the importance of flexibility in trust management.t.Key Takeaways:Proactive planning is essential for vulnerable individuals.Financial management challenges often arise for those with special needs.Creating a safety net involves more than just financial assets.Corporate trustees can provide impartial management of trusts.Long-term care planning is crucial for future needs.Flexibility in trust management allows for changing circumstances.It's important to consider both financial and non-financial aspects of care.Planning should be tailored to the individual's unique situation.Don't delay in establishing a special needs trust.Engaging professional care managers can enhance support for vulnerable individuals.Subscribe to our *Story of the Week(ish)* for planning insights in your inbox: https://zc.vg/P36ORLearn more at https://www.robinglen.comDisclaimer: This podcast is for educational purposes only and should not be considered tax, legal, or investment advice. Please consult your professional advisors regarding your personal situation.

October 13, 202519 min

The Hidden LTC Risk That Can Derail Your Plan (and How One Family Fixed It)

Welcome back to Planning Reimagined, now reimagined for real-life stories, shorter episodes, and actionable insights.In this episode, Celeste Moya and Kris Stegall share the story of Philip and Danielle Lawson (names changed), a couple in their 40s who thought their planning boxes were checked… until they realized one major blind spot: long-term care for aging parents.When Philip’s parents, living on pensions and Social Security, faced potential care needs, the couple discovered just how quickly those costs could derail their own goals for college savings, retirement timelines, and charitable giving.Celeste and Kris walk through:Why long-term care is one of the most underplanned risks in family wealthWhat Medicare and Medicaid actually cover (and what they don’t)The difference between traditional and hybrid LTC solutionsHow “inefficient” assets (like old annuities) can be repositioned to triple care valueAnd how multi-generation planning protects not only parents, but your children’s future tooThey also explore the emotional side, including how caregiving can strain families, drain assets, and fracture relationships, and what you can do now to prevent it.Key Takeaways:75% of people over 65 will need some form of long-term careLTC costs rise faster than general inflation (≈4.6% annually)Hybrid life insurance and annuity designs can turn dormant assets into 3–4× care leverageProactive planning protects *three generations* — parents, you, and your kidsResourcesSubscribe to our Story of the Week(ish) for planning insights in your inbox: https://zc.vg/P36ORLearn more at https://www.robinglen.comDisclaimerThis podcast is for educational purposes only and should not be considered tax, legal, or investment advice. Please consult your professional advisors regarding your personal situation.

January 13, 202556 min

Reimagining Goal Setting: Emphasizing Process and Mindset for Lasting Achievement

In this episode, Celeste welcomes Dan Lappin, Founder of Lappin 180, to discuss a whole new way to approach goal setting through building a resilient mindset. Through personal anecdotes, professional insights, and practical strategies, they unravel the often misunderstood concept of detachment from outcomes, emphasizing a focus on processes rather than end goals. Dan discusses how embracing discomfort and failure can be pivotal for growth. Celeste talks about how her father's advice to be "comfortable being uncomfortable" has shaped her career and personal life.They also talk about the power of incremental progress, positive self-talk, and adopting a mindset that sees each action as a step toward greater goals. They discuss the importance of feedback, handling failures constructively, and cultivating an abundance mindset. Dan offers insights into the cognitive and emotional impact of labeling experiences, highlighting the necessity of maintaining a neutral and objective stance for better decision-making. To find out more and connect with Dan, visit: https://www.lappin180.com/Key Topics Discussed:Detachment from outcomes and its impact on motivationThe importance of focusing on processes rather than outcomesEmbracing discomfort and failure for personal and professional growthPositive self-talk and mindset-strengthening strategiesIncremental progress and viewing goals as a series of small stepsThe significance of feedback and handling it constructivelyCultivating an abundance mindset through gratitude and self-reflectionThe cognitive and emotional impact of labeling experiencesThe modern mindset challenges are rooted in our primal past

December 16, 20241 hr 2 min

Building Strong Family Legacies: Insights on Values, Wealth, and Communication

In this episode, Celeste and Kris welcome Jeff Savlov, a family business and wealth consultant, to discuss the intricate dynamics of family values, communication, and wealth management. Jeff introduces an exercise for families to identify their core values and highlights the importance of creating a family mission statement. He also shares his purposeful legacy family project designed to engage young children in meaningful discussions about values and needs. Through compelling anecdotes and practical advice, they discuss the challenges families face in maintaining open communication, particularly about financial matters, and offer tools to foster healthier dynamics.They also talk about the complexities of fairness in family financial planning, addressing how perceptions of unequal love among siblings can impact relationships. They emphasize that successful wealth management requires honesty and vulnerability, especially when discussing inheritance and estate planning. The episode also touches on the significance of early financial education, humor in family dynamics, and integrating open dialogue into the family culture to mitigate the impact of generational differences.To learn more about or connect with Jeff, visit: https://blumandsavlov.com/For more information on Robin Glen, visit: https://RobinGlen.comTo schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoyaKey Topics Discussed:Engaging children in value discussions through the purposeful legacy family project.Importance of addressing fairness and perceptions of unequal love in financial matters.Integrating open communication about money, death, and healthcare into family culture.Anecdotes illustrating children’s wisdom and insights on family needs.Role of professionals in resolving family conflicts.Tools to facilitate conversations on family values and wealth management.

December 2, 20241 hr 14 min

Strategic Charitable Planning: From Donor-Advised Funds to Private Foundations

In this episode, Celeste and Kris sit down with philanthropy adviser Rick Peck to explore the intricacies of strategic charitable planning. They discuss the significant role that transparency and education play in family meetings, where younger generations are taught the "why" behind family values and decisions. Rick shares practical strategies for charitable giving, from simple checkbook donations to more complex approaches like commercial donor-advised funds (DAFs) and private foundations, highlighting the importance of aligning philanthropic goals with personal and financial objectives.They also discuss the evolving landscape of philanthropy, noting how changes in tax laws and the rise of digital assets like cryptocurrency influence nonprofit strategies. The episode wraps up with essential tips for engaging families in philanthropy, crafting flexible legacy plans, and the financial nuances of charitable trusts and life insurance. To find out more and connect with Rick, visit: https://www.thephilanthropyguy.com/For more information on Robin Glen, visit: https://RobinGlen.comTo schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoyaKey Topics Covered:Family meetings and the importance of teaching valuesVarious methods of charitable givingThe rise and impact of donor-advised funds (DAFs)Charitable planning involving cryptocurrenciesThe benefits and uses of life insurance in charitable planningThe role of flexible legacy planningFinancial tools like Charitable Remainder Trusts (CRTs) and Charitable Lead Trusts (CLTs)

November 18, 202453 min

Building a Brighter Future for Youth at Cafe Momentum

In this special episode of Planning Reimagined, Celeste is joined by Chad Houser, Founder of Cafe Momentum, and Cafe Momentum Ambassador, Tristian Williams to discuss the transformative journey of Cafe Momentum and its significant impact on justice-involved youth. Chad discusses his motivations and the evolution of the organization, which combines a dining experience with social impact. Tristan shares her powerful story of personal growth and transformation, transitioning from a troubled past to becoming a community ambassador and mentor.Tristan's journey is a testament to the power of community support, education, and personal development, demonstrating how programs like Cafe Momentum can alter life trajectories. Through engaging discussions, the episode highlights the critical role of community involvement, the importance of providing second chances, and how collective efforts can create meaningful change and uplift underserved populations.To find out more about Cafe Momentum, visit: https://cafemomentum.org/For more information on Robin Glen, visit: https://RobinGlen.comTo schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoyaKey Topics Covered:The mission and impact of Cafe MomentumTristan Williams’s personal journey and transformationThe importance of community involvement and supportChallenges and misconceptions in establishing Cafe MomentumPersonal growth through culinary and social skill developmentSystemic inequalities and infrastructure issues in urban areasThe shift from focusing on recidivism to broader measures of successStories of success from Cafe Momentum alumni

November 4, 202451 min

Post-Sale Financial Planning for Entrepreneurs

In this episode of Planning Reimagined, Celeste is joined by Judy Barton and Catherine Sharp to discuss the intricacies of post-sale wealth management for business owners. Judy highlights the importance of shifting the conversation from budgeting to cash flow needs and wealth longevity, emphasizing investment structure, efficient tax management, asset protection, and more. They also discuss valuable tax strategies and estate planning insights, underlining the necessity of regular estate plan re-evaluation and proactive financial education across generations.They also talk about the importance of the emotional impact of business sales, financial goal prioritization, and the role of professional advisors in shaping a robust financial future. From leveraging balance sheets to utilizing Opportunity Zones and trusts, you'll learn some of the most important areas where you may be leaving massive money on the table.To connect with Judy, visit: https://www.bny.com/corporate/global/en.htmlTo connect with Katherine, visit: https://www.forvismazars.us/For more information on Robin Glen, visit: https://RobinGlen.comTo schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoyaKey Topics Covered:Shifting terminology from budget to cash flow needs for a positive financial outlookThe Five Areas of Active Wealth: investment structure, spending, leveraging assets, tax management, and asset protectionTailoring investment strategies based on risk tolerance and time horizonsUtilizing tax strategies like donor-advised funds and annual exclusion giftsThe significance of regular estate plan updates and understanding upcoming changes in the estate tax exemptionProfessional advice and the importance of a collaborative advisor teamPreparing heirs for wealth managementEmotional transitions post-business sale and the necessity of pausing to assess new financial realitiesFinancial education resources and their role in long-term wealth management

October 21, 202444 min

Creating Co-Owners: An Employee Stock Ownership Plan Journey

Celeste is joined by Gina Schaefer, Founder of Logan Hardware, who shares her remarkable journey from being laid off in tech three times, to building a flourishing chain of hardware stores in Washington, DC. Gina discusses the significant challenges she faced, including opening her first store in a neighborhood still reeling from the 1968 riots, and the rapid growth that followed due to strong community involvement and seizing timely opportunities. She details her decision to exit the business through an Employee Stock Ownership Plan (ESOP), offering insights into the emotional and logistical challenges of the transition.They also discuss the importance of succession planning, adaptability, and understanding one's strengths and weaknesses, and Gina's well-researched and structured approach to the ESOP. The episode also covers the specifics of transitioning a business, the significant tax advantages of an ESOP, and lessons learned from Gina's extensive experience. To find out more or connect with Gina, visit: https://ginaschaefer.com/To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoyaTo learn more about Robin Glen, visit: https://www.robinglen.com/Key Topics Discussed:Gina’s journey from tech industry layoffs to building a successful hardware store chainThe importance of community involvement and hiring practicesDetailed insights into transitioning a business through an ESOPEmotional aspects and planning of a business exit strategyRecognizing key individuals and the role of advisors in business successionLessons learned and common pitfalls in business transitions