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.

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Disclaimer: 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.

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.

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Disclaimer: 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.

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.

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Learn more at https://www.robinglen.com

Disclaimer: 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.

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 wealth
• What Medicare and Medicaid actually cover (and what they don’t)
• The difference between traditional and hybrid LTC solutions
• How “inefficient” assets (like old annuities) can be repositioned to triple care value
• And how multi-generation planning protects not only parents, but your children’s future too

They 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 care
• LTC costs rise faster than general inflation (≈4.6% annually)
• Hybrid life insurance and annuity designs can turn dormant assets into 3–4× care leverage
• Proactive planning protects *three generations* — parents, you, and your kids

Resources

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Disclaimer

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.

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 motivation
• The importance of focusing on processes rather than outcomes
• Embracing discomfort and failure for personal and professional growth
• Positive self-talk and mindset-strengthening strategies
• Incremental progress and viewing goals as a series of small steps
• The significance of feedback and handling it constructively
• Cultivating an abundance mindset through gratitude and self-reflection
• The cognitive and emotional impact of labeling experiences
• The modern mindset challenges are rooted in our primal past

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.com

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

Key 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.

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.com

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

Key Topics Covered:

• Family meetings and the importance of teaching values
• Various methods of charitable giving
• The rise and impact of donor-advised funds (DAFs)
• Charitable planning involving cryptocurrencies
• The benefits and uses of life insurance in charitable planning
• The role of flexible legacy planning
• Financial tools like Charitable Remainder Trusts (CRTs) and Charitable Lead Trusts (CLTs)

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.com

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

Key Topics Covered:

• The mission and impact of Cafe Momentum
• Tristan Williams’s personal journey and transformation
• The importance of community involvement and support
• Challenges and misconceptions in establishing Cafe Momentum
• Personal growth through culinary and social skill development
• Systemic inequalities and infrastructure issues in urban areas
• The shift from focusing on recidivism to broader measures of success
• Stories of success from Cafe Momentum alumni

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.html

To connect with Katherine, visit: https://www.forvismazars.us/

For more information on Robin Glen, visit: https://RobinGlen.com

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

Key Topics Covered:

• Shifting terminology from budget to cash flow needs for a positive financial outlook
• The Five Areas of Active Wealth: investment structure, spending, leveraging assets, tax management, and asset protection
• Tailoring investment strategies based on risk tolerance and time horizons
• Utilizing tax strategies like donor-advised funds and annual exclusion gifts
• The significance of regular estate plan updates and understanding upcoming changes in the estate tax exemption
• Professional advice and the importance of a collaborative advisor team
• Preparing heirs for wealth management
• Emotional transitions post-business sale and the necessity of pausing to assess new financial realities
• Financial education resources and their role in long-term wealth management

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/ccmoya

To 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 chain
• The importance of community involvement and hiring practices
• Detailed insights into transitioning a business through an ESOP
• Emotional aspects and planning of a business exit strategy
• Recognizing key individuals and the role of advisors in business succession
• Lessons learned and common pitfalls in business transitions

In today's episode of Planning Reimagined, the team at Robin Glen are diving

into the world of business exit and succession planning. Celeste, Chris and Mike all share insights on ensuring robust estate and tax planning while thinking about how you would like to exit your business.

They discuss the critical aspects of business sale planning and its impact on both direct and indirect beneficiaries, like employees, ensuring that businesses remain stable and secure. From the importance of liquidity during estate tax payments to the strategic role of life insurance in maintaining financial flexibility, they cover it all. They also break down key strategies such as valuation discounts, charitable planning, and the significance of pre-sale preparations.

They offer real-life examples about the consequences of poor planning versus well-executed strategies and discuss the emotional complexities tied to family businesses, the tactical use of buy-sell agreements, and the many benefits of key person insurance. Additionally, the offer ideas about exit strategies, ownership structuring, and the importance of early and transparent planning.

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

To learn more about Robin Glen, visit: https://www.robinglen.com/

Key Topics Discussed:

• Estate Planning and Business Stability
• Life Insurance and Flexibility in Business Sales
• Exit Strategy Considerations
• Market Readiness
• Valuation Discounts
• Succession Planning
• Tax Mitigation Strategies
• Deferred Compensation Plans
• Buy-Sell Agreements
• Presale Strategy Benefits
• Ownership Structuring
• Planning for Changing Circumstances
• QSBS (Qualified Small Business Stock) Exemptions

The conversation covers everything from ensuring business stability and proper due diligence to the emotional and financial complexities involved in successfully passing down or selling a business. They also talk about importance of having the right advisers and detailed preparation to ensure smooth transitions, whether through a third-party sale or family succession.

Oliver and Israel provide real-world examples and practical advice on mitigating risks, maintaining business value, and preparing for unforeseen circumstances.

For more information and to connect with Oliver, visit:

https://bulkleycapital.com/team-member/oliver-cone/

And to connect with Isreal: https://www.lockelord.com/professionals/m/miller-isreal

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

To learn more about Robin Glen, visit: https://www.robinglen.com/

Key Topics Discussed:

• Importance of demonstrating stability in business
• Retention of owners post-sale for smooth transitions
• Due diligence and discovery of hidden liabilities
• Common issues impacting business sales
• Dynamics of negotiation and relationship preservation
• Role of experts in successful business transitions
• Realistic market expectations and professional valuations
• Formation and management of LLCs
• Updating buy-sell agreements and insurance policies
• Emotional and financial complexities in family business transitions
• Steps for preparing a business for future sale or succession

In this episode of Planning Reimagine, Celeste welcomes Susan Bryant, CEO and founder of Unboxed Advisors, who brings over 20 years of experience in CPA, tax planning, and investment advising. They dive deep into a critical yet often overlooked aspect of business management: insurance and risk mitigation. Susan and Celeste will share insights on the significance of proper insurance and the strategic steps needed to ensure long-term business stability.

They discuss how 80% of businesses lack adequate insurance for their key persons, often focusing solely on bank-required policies. Susan talks about the vital role of term policies, buy-sell agreements, and disability insurance in maintaining business operations when unexpected events occur. They also talk about the devastating effects of losing a key person, not just on business value but also on employees and stakeholders.

They also discuss working with a team of expert advisors to navigate these complexities, the challenges entrepreneurs face, and the necessity of continuous and proactive planning.

To learn more about Susan, visit: https://unboxedadvisors.com/

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

To learn more about Robin Glen, visit: https://www.robinglen.com/

Key Topics Discussed:

• Life Insurance for Key Persons and its Importance
• Lack of Proper Insurance and its Consequences
• Business Continuity and Value Preservation
• Funding Buy-Sell Agreements for Liquidity
• Importance of Diversified Investments and Proper Business Risk Management
• Need for Disability Insurance to Safeguard Revenue
• Role of Advisors in Comprehensive Risk Management
• Continuous Planning and the Importance of Revisiting Decisions
• Cybersecurity as an Emerging Risk for Small Businesses

In this episode of Planning Reimagined, Celeste and Kris welcome Phil Pilibosian, Senior Managing Director at US Capital Wealth Advisors, for an in-depth discussion on the critical importance of personalized, holistic advisory services in wealth management. Phil discusses the distinct limitations large financial firms like Goldman Sachs face when handling small, tailored deals and how boutique firms provide a more flexible, client-focused approach. The conversation moves into the intricacies of tax planning, employee contract negotiations, and estate planning, emphasizing the need for expert advice that's both comprehensive and customized.

Throughout the episode, the trio talks about the collaborative benefits of partnering with specialized firms and the invaluable human touch in providing financial guidance—something robo-advisors cannot replicate. Phil shares real-life examples, including uncovering $250,000 in unclaimed property for a client and demonstrating the tangible advantage of personalized service. They also talk about the importance of holistic financial planning to address the unique needs and goals of clients.

To learn more and connect with Phil, visit: https://www.uscallc.com/

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

To learn more about Robin Glen, visit: https://www.robinglen.com/

Key Topics Covered:

• The limitations of large financial firms in small, personalized deals
• The need for specialized advisory services in wealth management
• Collaboration between boutique firms and specialists to provide comprehensive solutions
• Real-life examples showcasing the impact of personalized financial services
• Importance of holistic planning and the human touch in financial advisory
• Tax-efficient management and structuring assets for long-term benefits
• Challenges and benefits of robo-advisors in the wealth management space

The episode also explores estate tax complexities, the taxation of foreign trusts, and the critical need for proper planning and professional counsel when dealing with cross-border financial matters. Steve and Robert share real-life examples to highlight the importance of strategic structuring, whether for business purposes or personal investments, to avoid unforeseen tax liabilities and ensure compliance on multiple fronts.

To connect with Robert Smith, visit: https://savillecpa.com/

To connect with Steve Hare, visit: https://www.ydklaw.com/

To schedule an appt with the Robin Glen team, visit: www.calendly.com/ccmoya

To learn more about Robin Glen, visit: https://www.robinglen.com/

Key Topics Covered:

• Impact of the 2009 Swiss bank scandal on financial disclosure
• Effects of the Corporate Transparency Act on financial privacy
• Pros and cons of increased financial transparency in the US
• Capital gains tax changes in Canada
• Tax obligations for non-US citizens owning US property or investments
• Estate and gift taxation nuances for US residents and non-residents
• Importance of thorough planning for cross-border business and real estate investments
• Tax implications for foreign trusts benefiting US persons
• Examples of real-world tax planning challenges and solutions
• Necessity of professional advice for global tax compliance

In this episode of Planning Reimagined, we continue the series of the family office and welcome Jay Judas to discuss the intricacies of using life insurance in estate planning for affluent families. This discussion covers the strategic implementation of irrevocable trusts to fund life insurance policies, highlighting the substantial gifting limits available for married couples. They explore the versatility of life insurance, especially Private Placement Life Insurance (PPLI), to offer tax-efficient solutions tailored for high net-worth individuals and families. They share various examples, stressing the importance of comprehensive planning, professional management, and the necessity of not viewing life insurance as a one-size-fits-all product.

They also talk about how life insurance provides liquidity, ensures harmony within family businesses, and supports generational wealth transfers. The conversation also touches on premium financing as a means to enhance cash flow, the potential of life insurance as a stable asset class, and the importance of avoiding common pitfalls like investor control issues with private placement policies.

To connect with Jay, visit: https://www.lifeinsurancestrategiesgroup.com/

To schedule an appt, visit: www.calendly.com/ccmoya

To learn more about Robin Glen, visit: https://www.robinglen.com/

Key Topics Discussed:

• Advantages of using irrevocable trusts to fund life insurance policies
• Gifting limits for funding life insurance in trusts
• Premium financing options for maximizing cash flow
• Overview of Private Placement Life Insurance (PPLI)
• Importance of estate planning, financial planning, and tax planning
• Tax-efficiency and stability of life insurance as an asset class
• Role of life insurance in liquidity and generational wealth transfer
• Case studies illustrating comprehensive planning before determining life insurance needs
• Avoiding investor control issues in private placement policies

Celeste welcomes Yadira Anzueto to dive into the intricate world of risk management and insurance for affluent families. Yadira, a licensed insurance expert, discusses the vital role of risk management in family planning, revealing how proper insurance can be a family's primary defense against unexpected catastrophic losses, and how the risk completely changes as wealth grows.

They also discuss how family offices integrate with wealth management, by defining their function and importance for affluent families. Yadira shares real-life scenarios that bring these complex themes to light, and why standard insurance just doesn't take into consideration the complexity of various assets and wealth. They wrap up by emphasizing the importance of regular insurance reviews and educating the next generation on social media risks.

To learn more about Robin Glen, visit: RobinGlen.com

To connect with Yadira, visit: https://www.linkedin.com/in/yadira-anzueto

Key Topics Covered:

• Importance of educating younger generations about family plans and risk management
• Comprehensive insurance reviews and asset protection
• Role of family offices in wealth and lifestyle management
• Specific insurance coverages like mechanical breakdown and cyber protection
• Determining appropriate umbrella limits for high-net-worth individuals
• Emerging threats such as cyber-attacks, kidnap and ransom coverage
• Customized insurance strategies for multiple state properties and high-end assets
• Advocacy at the time of a claim and real-life scenarios of substantial losses
• Educating the next generation about social media and potential risk exposure

They also emphasize the necessity of incorporating technology to professionalize and operationalize family office operations and discuss topics such as the importance of compliance, managing nonbankable assets, and understanding complex ownership structures. The conversation underscores the potential of technological solutions, like Orca ARC, which offers robust tools for managing family office assets and compliance requirements, thus helping family offices navigate the increasingly complex regulatory landscape.

To learn more about Orca, visit: https://www.withorca.com/en/

To learn more about Robin Glen, visit: RobinGlen.com

To schedule an appt, visit: www.calendly.com/ccmoya

Key Topics Covered:

• Importance of efficiency in family offices for risk mitigation
• Role of technology in keeping family office teams small yet efficient
• Anticipated wealth transfer over the next 25 years and its impacts
• Hard conversations around estate planning and wealth management aided by technology
• The importance of human understanding complemented by technology in advising
• Technology's role in providing transparency and organizational efficiency
• Introduction of Orca ARC and its functionality
• Compliance with international and local regulatory requirements
• Balancing technology and human capabilities in family office operations

The episode also discusses the challenges of intergenerational wealth transfer, highlighting the critical necessity of preparing the next generation to manage family assets effectively. They also touch on new investment opportunities, such as music as an asset class and the tokenization of real assets via blockchain. They also talk about the difficulty that family offices can face in a lack of technology in managing assets, and other gaps in how they are run.

Key Topics Covered:

• Connect technology platform for managing family data
• The friction in educating family members about risk
• Emotional decision-making in family offices
• Music and assets as new investment classes
• Blockchain's role in asset ownership transparency
• Risk management across family balance sheets
• Intergenerational struggles in wealth and leadership transfer
• The trend toward experiential investing and flexible living arrangements
• Cybersecurity and the risks of single-point failure in family offices

To connect with David, visit: https://www.linkedin.com/in/uhnw/

To learn more about Robin Glen, visit: RobinGlen.com

To schedule an appt, visit: www.calendly.com/ccmoya

Their conversation tackles various dimensions of estate planning, from choosing the right trustee who aligns with family goals to the intricacies of crafting a fair asset distribution among heirs. They also offer real-life examples of families facing challenges due to inadequate planning or lack of transparency, highlighting the urgency and importance of these discussions.

To connect with Courtney, visit: https://www.linkedin.com/company/mariposa-advisers/

To learn more about Robin Glen, visit: RobinGlen.com

To schedule an appt, visit: www.calendly.com/ccmoya

Key Topics:

• Selecting an appropriate trustee and the challenges of family members in this role
• Preparing the next generation for business inheritance
• Strategies for tax-efficient business sales and maximizing after-tax proceeds
• Importance of family dynamics and managing expectations in business succession
• The role of charitable planning and donor-advised funds in wealth management
• Effective communication strategies for discussing wealth and legacy within families
• Real-life examples demonstrating the impact of poor planning and conflict resolution

In this episode of Planning Reimagined, Kris and Celeste welcome Mark Auten to discuss personal and estate planning. They discuss that while many are meticulous in planning out the legacy of their businesses, they often don't put the same thought into their personal planning, to sidestep potential legal pitfalls and guarantee a seamless process. They underscore the emotional challenges that often accompany financial decision-making within the realm of estate planning.

The episode also talks about "estate planning paralysis," a state many find themselves in when confronted with the complexities of preparing for the future. But as Celeste points out, initiating the process is as simple as calling the right advisor. From rolling premiums into a life insurance trust to the craft of family business succession, the conversation discusses strategies to effectively manage and transition wealth. They also discuss the challenges faced in probate cases, the value of involving children in financial discussions early, and the indispensable role of education in preparing future generations to handle wealth responsibly. We have a wealth transfer of approximately $36 trillion ahead of us, making estate planning more important than ever.

To connect with Mark, visit: https://plunksmith.com/mark-auten/

To learn more about Robin Glen, visit: RobinGlen.com

To schedule an appt, visit: www.calendly.com/ccmoya

Key Topics Covered:

• Approaching personal planning with the same detail as business planning
• The balance between financial decisions and emotional factors in estate planning
• Overcoming estate planning paralysis and starting the process
• Life insurance trusts as a cost-saving tool
• Customized estate planning and the role of specialized advisors
• Family business succession and preparing future generations for wealth management
• The impact of probate and strategies to avoid it
• Estate planning in blended families and the use of corporate trustees

They also talk about the realities of managing family-owned real estate assets and why having the right team is crucial. In addition, they compare UPREITs and DSTs, breaking down the benefits, challenges, and considerations for smaller portfolios looking to engage with REITs.

They also discuss how 1031 exchanges operate, the critical role of a qualified intermediary, and the strict timelines investors must follow for a successful exchange. In addition, they compare the concerns of many individuals managing extensive asset portfolios, and Jeff offers his expertise, emphasizing the necessity of early and strategic planning.

To learn more about Robin Glen, visit: RobinGlen.com

To connect with Jeff, email at https://www.1031specialists.com.

To schedule an appt, visit: 

Topics Discussed

• Understanding Real Estate Ownership Transitions
• Mechanics of a 1031 exchange and its benefits
• Wealth Creation and Estate Planning
• Transitioning from Active Real Estate Management
• Navigating Complexity and Tax Implications in Real Estate Transactions
• Logistics of a 1031 Exchange with DST
• UPREIT Structures vs. DST
• Engagement with REITs and Accessibility for Small Portfolios

From discussing why placing all your money in one property type is a high-risk move to exposing the truth behind those too-good-to-be-true investment advice, our experts share actionable insights into becoming a material participant in real estate, the benefits a management company can provide, and how to plan for those essential tax-efficient exit strategies.

In the "Shiny Object Whack a Mole" segment, we challenge common investment rhetoric, promoting a skeptical approach to betting all on real estate or jumping straight into mega properties. We cover the advantages of starting small and exploring various investment avenues.

To learn more about Robin Glen, visit: RobinGlen.com

To schedule an appt, visit: www.calendly.com/ccmoya

Topics Discussed

• Introduction to Real Estate as a Wealth-Building Tool
• Diversification in Real Estate Investment
• Skepticism and Research in Investment Advice
• The Role and Impact of Taxes in Real Estate
• Being a Material Participant in Real Estate
• Client Success Stories and Strategies