March to a Million

How much investment return do you really need in retirement? If you’re within 5 to 10 years of retiring, should you still be trying to beat the market, or should your retirement plan focus on replacing your paycheck?

In this episode, Greg DuPont explains why people approaching retirement may be watching the wrong financial scoreboard. Retirement income planning looks at how your savings and investments can work together to provide income after you stop working. Greg explores how market losses, investment fees, Roth conversions, inflation, and required minimum distributions may affect your retirement income and future tax bill.

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A retirement plan can overlook important risks when every decision depends on memory, disconnected tools, or separate advisors. 

What changes when each case follows the same detailed process?

In this episode, Greg DuPont explains how he developed WSN OS 3.0, an AI-supported planning system built from decades of work across estate planning, financial advice, taxes, and insurance. He walks through how the system organizes client information, identifies planning concerns, and helps attorneys educate families before recommendations are made. Greg also breaks down the PILOT process for retirement income, taxes, longevity, life events, ownership, probate avoidance, and risk transfer.

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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.

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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. 

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.

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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.

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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.

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.

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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.

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.

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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.

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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.

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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.

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