Category: Legal Profession
Building a Family Legacy That Goes Beyond Wealth with Vince Covino (Ep. 69)

Building a Family Legacy That Goes Beyond Wealth with Vince Covino (Ep. 69)

By |

Many families spend years building wealth, yet far fewer spend time discussing the values, relationships, and purpose they hope that wealth will support.

What would future generations remember if all they had was the story your financial decisions told? How do advisors help families create a legacy that’s measured by more than investment returns?

In this episode, Greg DuPont welcomes Vince Covino, Founder of VC Strategic Capital, to discuss how his view of financial planning changed after a significant personal transition. Together, they explore how meaningful legacy conversations can strengthen family relationships, why financial advice becomes more valuable when it reflects a family’s purpose, and how capital allocation can express personal values. Vince also shares why advisors can play a much deeper role by helping families think beyond products and toward the lives they hope future generations will inherit.

Key takeaways:

  • Creating space for honest family conversations about values, purpose, and the legacy parents hope to leave behind
  • Looking beyond portfolio performance to align financial decisions with personal meaning and long-term family goals
  • Helping families use wealth as a tool that reflects who they are rather than simply what they own
  • Guiding future generations through thoughtful discussions that strengthen relationships before wealth transfers occur
  • Reframing the advisor’s role from investment selection to helping families make purpose-driven financial decisions
  • And more!

Connect with Greg DuPont:

Connect With Vince Covino:

About Our Guest:

Vince Covino is an entrepreneur and investor with over 25 years of experience building, capitalizing, and scaling organizations across multiple industries. As the founder of Legacy Wealth, now a $1B+ registered investment advisory firm, and a national zoo and aquarium chain that has welcomed over 20 million visitors, Covino operates from direct experience with the full capital lifecycle: raising capital, deploying it, structuring complex deals, managing through disruption, and executing exits. 

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
Turning Failure Into Better Systems With AI (Ep. 68)

Turning Failure Into Better Systems With AI (Ep. 68)

By |

What if the biggest setback in your business became the reason you built something stronger?

Growth rarely follows a straight path. Sometimes the lessons that change your thinking come after plans fall apart, systems break down, or expectations aren’t met.

In this episode, Greg DuPont reflects on the ideas that stood out during CoachCon and how they reshaped his thinking about leadership, AI, and business growth. He explains how failure often creates the conditions for meaningful breakthroughs, why human qualities like curiosity and imagination become even more valuable alongside AI, and how better systems can free professionals to build stronger client relationships. Greg also shares how these lessons are influencing the next evolution of Wealth Solutions Network.

Key takeaways:

  • Failure often reveals the lessons needed to build stronger systems and better long-term decisions.
  • AI should reduce technical work so professionals can spend more time listening and connecting.
  • Human judgment, curiosity, imagination, and emotional insight remain difficult for AI to replace.
  • Building systems from experience creates greater resilience for businesses facing future change.
  • New technology becomes more valuable when it’s embraced as a practical tool instead of feared.
  • And more!

Resources: 

Connect with Greg DuPont:

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
Should a Rental Property Be Part of Your Retirement Plan? With Taylor Vick (Ep. 67)

Should a Rental Property Be Part of Your Retirement Plan? With Taylor Vick (Ep. 67)

By |

Should rental property be part of your retirement plan? What happens when it’s time to transfer investment property to the next generation, create retirement income, or reduce taxes without creating new challenges? Those decisions can have lasting financial and tax implications, making thoughtful planning just as important as the property itself.

In this episode, Greg DuPont welcomes Taylor Vick, Founder of Blue Ridge Asset Management, to discuss how real estate can fit into retirement planning, estate planning, and long-term wealth management. Taylor shares how he built his own real estate portfolio, why leverage and cash flow have played an important role in his approach, and how seller financing can create opportunities for families. Greg and Taylor also explore real estate professional status, self-directed IRAs, depreciation recapture, and why business owners and families should have a plan before transferring or selling real estate.

Greg and Taylor discuss: 

  • How rental properties can support retirement income, estate planning, and long-term wealth
  • How leverage, cash flow, and appreciation can work together when building a real estate portfolio
  • How seller financing may help families transfer investment property while creating ongoing income
  • What investors should understand about self-directed IRAs, real estate ownership, and tax planning
  • Why business owners and families should prepare real estate assets before selling or passing them to the next generation
  • And more!

Resources:

Connect with Greg DuPont:

Connect with Taylor Vick: 

About Our Guest:

Taylor Vick is the Founder of Blue Ridge Asset Management, where he works with investors, families, and business owners on real estate investment, portfolio management, and long-term planning. He also serves as a fractional director of real estate, helping clients maximize the value of their real estate holdings while navigating tax considerations, estate planning, and multi-generational ownership strategies.

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
Premium Financing Strategies for Estate Liquidity and Legacy Planning with Jacob Brigati (Ep. 66)

Premium Financing Strategies for Estate Liquidity and Legacy Planning with Jacob Brigati (Ep. 66)

By |

Building wealth is one thing. Creating enough liquidity to protect that wealth for future generations can be an entirely different challenge.

How can business owners, real estate investors, and high-net-worth families address estate taxes, business succession concerns, and outstanding loans without disrupting the assets they’ve spent years building?

In this episode, Greg DuPont welcomes Jacob Brigati, Premium Financing Consultant at Simplicity UFC, to discuss how premium financing can help create estate liquidity, support business succession plans, and address leveraged asset concerns. Jacob explains how financing life insurance through bank leverage may help high-net-worth families manage estate planning challenges while preserving valuable assets. 

He also shares real-world examples, discusses underwriting requirements, and explains the importance of conservative planning, ongoing policy management, and creating flexible strategies that can evolve over time.

Jacob discusses:

  • How premium financing helps create estate liquidity while reducing upfront out-of-pocket costs
  • Why leveraged real estate owners often use insurance planning to address outstanding loan obligations
  • How business owners can create liquidity to balance inheritances among children fairly
  • The importance of conservative projections and ongoing policy reviews over many years
  • Financial and medical underwriting factors that determine premium financing eligibility
  • And more!

Connect with Greg DuPont:

Connect With Jacob Brigati:

About Our Guest:

Jacob Brigati is a Premium Financing Consultant with Simplicity UFC, specializing in helping high-net-worth families, business owners, real estate investors, and advisors use premium financing strategies to address estate planning, business succession, and liquidity needs. He works closely with attorneys, financial advisors, CPAs, and family offices to design life insurance solutions that can help create liquidity for estate taxes, outstanding obligations, asset equalization among heirs, and legacy planning goals. Jacob’s focus includes structuring and managing premium-financed life insurance strategies, coordinating with insurance carriers and lenders, and providing ongoing policy reviews to help clients monitor performance over time.

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
Building a Retirement Strategy Beyond the Investment Account (Ep. 65)

Building a Retirement Strategy Beyond the Investment Account (Ep. 65)

By |

Retirement planning can feel clear when markets are rising, but harder when income, taxes, inflation, and risk all collide.

Is your plan built around a portfolio, or does it actually account for what could go wrong?

In this episode, Greg DuPont reflects on 20 years in financial services and the lessons that changed how he thinks about retirement planning. He shares why mutual funds, ETFs, tactical investing, and annuities each taught him something different, and why no single tool can carry a retirement plan on its own. He also explains the six risks retirees need to plan for and why structure matters more than chasing returns.

Key takeaways:

  • Why low-cost investments can still leave retirees exposed when markets fall at the wrong time
  • How Greg DuPont’s early years in financial services changed his view of client protection
  • Why fixed indexed annuities became useful only when matched to the right retirement need
  • How six retirement risks shape the planning process before product choices are made
  • Why a retirement strategy needs structure, income planning, liquidity, tax planning, and timing
  • And more!

Connect with Greg DuPont:

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
The Future Is Closer Than We Think (Ep. 64)

The Future Is Closer Than We Think (Ep. 64)

By |

Technology is advancing faster than most people realize, and the ripple effects could reshape industries, economies, and everyday life in ways that once seemed impossible.

In this episode, Greg DuPont discusses how emerging technologies could transform mobility and human performance, why long-term thinking matters amid global uncertainty, and how media, markets, and political narratives influence public perception. He also shares insights into the importance of preparation, perspective, and adapting to a future that may arrive faster than most people expect.

Greg discusses: 

  • The breakthroughs happening in artificial muscle and soft robotics technology
  • How wearable exoskeletons and assistive devices could change everyday life
  • Why global disruptions can have long-term economic and social consequences
  • The importance of staying grounded during periods of uncertainty and rapid change
  • How innovation and preparation can coexist in an unpredictable world 
  • And more!

Connect with Greg DuPont:

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
The Biggest Retirement Mistakes Most Families Never See Coming (Ep. 63)

The Biggest Retirement Mistakes Most Families Never See Coming (Ep. 63)

By |

What if the biggest retirement risks aren’t market crashes, but the quiet mistakes most people never see coming?

In this episode of March to a Million, Greg DuPont unpacks the inspiration behind his new book, The Twenty-Five Biggest Retirement Mistakes, and why so many families enter retirement feeling uncertain despite “doing everything right.” Greg explains why retirement is not simply an extension of the accumulation years, but an entirely different financial phase that requires a different strategy, mindset, and level of coordination.

Greg discusses:

  • Why accumulation and distribution require completely different financial strategies
  • The hidden tax traps tied to IRAs, 401(k)s, and required minimum distributions
  • Why claiming Social Security too early can create long-term financial consequences
  • Estate planning mistakes families often discover too late
  • How having a coordinated “financial quarterback” strategy may help reduce uncertainty in retirement
  • And more!

Resources: 

Connect with Greg DuPont:

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
Challenging the Status Quo After a Financial Loss (Ep. 62)

Challenging the Status Quo After a Financial Loss (Ep. 62)

By |

Life can change quickly after losing a spouse, especially when financial decisions suddenly become your responsibility. What looks stable on the surface may still carry hidden risks, tax exposure, and missed opportunities for future generations.

In this episode, Greg DuPont walks through a real client case involving a recently widowed woman navigating retirement income, RMDs, and estate planning concerns. He explains how market risk, the SECURE Act, and taxable retirement accounts can quietly affect a family’s future. 

Greg also shares how income planning, annuities, and gifting strategies helped reduce projected taxes while creating more predictability and support for future generations.

Key takeaways:

  • How the sequence of return risk can create pressure during retirement withdrawals and market downturns
  • Why large IRA balances may create unexpected tax burdens for children under SECURE Act rules
  • How predictable income strategies helped reduce stress after the loss of a spouse
  • Ways gifting strategies and structured planning may reduce long-term estate tax exposure
  • Why reviewing older financial plans matters when life circumstances and tax laws change
  • And more!

Resources: 

Connect with Greg DuPont:

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
Supporting Families with Special Needs Planning with Mary Anne Ehlert (Ep. 61)

Supporting Families with Special Needs Planning with Mary Anne Ehlert (Ep. 61)

By |

Caring for a family member with a disability touches every part of life, from daily routines to long-term financial survival. What happens to the people who depend on you completely when you are no longer here to protect them?

In this episode, Greg DuPont interviews Mary Anne Ehlert, CFP®, Founder of Protected Tomorrows, about her 38-year mission helping families plan for loved ones with disabilities. She shares how her personal experience as a sister, mother, and caregiver shaped her conviction that families cannot navigate this alone, and why the professionals they turn to are rarely equipped to help. 

Mary Anne walks through the critical role of special needs trusts, ABLE accounts, and proper estate documents, and explains why a social worker and financial professional working together changes everything for these families.

Key takeaways:

  • Turning personal caregiving experiences into a mission to support families facing similar challenges
  • Recognizing gaps in financial and legal guidance for families with loved ones with disabilities
  • Building structured plans that include trusts, benefits, and long-term care considerations
  • Supporting caregivers by prioritizing their well-being alongside their loved ones
  • Creating systems that document personal details to maintain continuity of care
  • And more!

Connect with Greg DuPont:

Connect With Mary Anne Ehlert:

About Our Guest:

Mary Anne Ehlert is a nationally recognized expert in special needs planning. As a Partner of Simplicity Group and Founder of Protected Tomorrows, a Simplicity Group commitment, she leads the organization in providing advocacy, education, and planning support to families with loved ones who have disabilities.

Mary Anne founded Protected Tomorrows more than 35 years ago after her family’s personal journey with special needs planning for her sister Marcia’s future revealed a lack of available resources. She has since dedicated her life to building those resources for others.

Prior to founding the company, Mary Anne spent over two decades in corporate financial services. Today, she speaks at national conferences, hosts educational webinars, and leads virtual training programs for families and caregivers of people with special needs and disabilities.

Mary Anne has served on the boards of several disability-focused organizations, including the National Disability Institute, Special Olympics Illinois, a SEDOL Foundation and Gateway to Learning. She currently serves on the boards of the Special Olympics Illinois Foundation, Cornelia de Lange Syndrome Foundation, Integrative Touch, and the Tails for Life Advisory Board.

Mary Anne resides in Barrington, Illinois with her life partner and her three pups. She is a proud mother of three stepsons, one who lives independently and shares his life experiences with his peers with disabilities.

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More
Private Credit Risks: What Investors Need to Know Before It Spreads (Ep. 60)

Private Credit Risks: What Investors Need to Know Before It Spreads (Ep. 60)

By |

Markets often look stable until they are not.

What risks are quietly building beneath the surface, and how could they impact your future?

In this episode, Greg DuPont, Founder of Wealth Solutions Network, breaks down the rapid rise of private credit and why it is gaining attention across the financial system. He explains how this $3.5 trillion market grew after banks pulled back from lending and why it now plays a major role in portfolios. Greg also outlines the risks tied to limited transparency, liquidity constraints, and valuation concerns. 

Additionally, Greg shares steps investors can take to review exposure and strengthen their financial positioning.

Key takeaways:

  • How private credit replaced traditional bank lending after regulatory shifts following the 2008 crisis
  • Why limited transparency and internal pricing models can mask real risks in private credit funds
  • How withdrawal limits and fund gating reveal liquidity challenges during periods of stress
  • Why exposure may already exist inside pensions, insurance products, and retirement accounts
  • What steps investors can take to review holdings, diversify assets, and assess risk tolerance
  • And more!

Connect with Greg DuPont:

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

Archives

Categories