Episodes

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, i...

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...

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 sign...

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, ...

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,...

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 creat...

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 re...

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 adap...

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 s...

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 af...

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...

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 transparenc...

Technology is evolving at a pace that feels almost impossible to keep up with. What happens when multiple breakthroughs accelerate at the same time and begin reshaping industries, careers, and the global economy? In this episode, Greg DuPont unpacks the key ideas from ARK Invest’s Big Ideas 2026 report. Greg explains how falling AI costs, autonomous transportation, robotics, and digital finance are converging at the same time. He explores how these shifts could impact labor markets, retirement p...

Looking back at a full year of markets, inflation shifts, and economic change can reveal more than any forecast ever could. What did 2025 actually teach us about investing, housing, taxes, and the future of our savings? And how do those lessons change the way we plan for what comes next? In this episode, Greg DuPont walks through his top 10 lessons from 2025 now that we are firmly into 2026. He covers everything from market unpredictability and the importance of true diversification to the poten...

Uncertainty can feel overwhelming when political, economic, and social pressures converge at once. What happens when the systems we’ve relied on for stability begin to shift in ways we can’t predict? How do families prepare when the future feels less certain than ever before? In this episode, Greg DuPont steps back from tactical advice to examine the bigger forces shaping our current moment. He reflects on the fragility of self-governance, the lessons of history, and why understanding turning po...

Rapid technological change is no longer theoretical. In this episode, Greg DuPont reflects on how science fiction is becoming real life, and what that means for professionals, families, and the future of work. In this episode, Greg DuPont explores how AI, automation, and exponential technologies are reshaping the economy faster than most people realize. Drawing from personal reflection, current events, and future-focused thinkers, Greg explains why knowledge workers are especially exposed to dis...

Most small business owners work tirelessly for decades building something meaningful, yet many walk away with far less than they deserve. What separates those who capture real value from those who simply close their doors? This week, Greg DuPont explores the hidden planning gaps that prevent business owners from realizing the full value of their life’s work. He reveals why most businesses under $10 million struggle to sell, how to structure exit strategies that actually work, and the critical co...

Life changes fast, and sometimes it changes in ways none of us ever saw coming. This episode opens the door to an honest conversation about resilience, uncertainty, and the responsibility advisors carry when guiding clients through unexpected moments. In this episode, Greg DuPont is joined by guest host RJ Malyk as they unpack how sudden life events can reshape families, careers, and long-term plans. Greg discusses: Why Matt Halloran is temporarily away from the mic and how unexpected events ca...

What if one moment could redefine your life’s mission? Greg DuPont shares the story behind his new book, March to a Million, a vision born from his own near-death experience as a “blue baby” and a lifetime of seeing families lose control over their finances because of fragmented advice. Together with co-host Matt Halloran, Greg explores how the Wealth Solutions Network (WSN) is training attorneys to step beyond traditional legal roles and become true financial advocates. They discuss the 4D Esta...

What happens when attorneys stop working next to financial advisors and start working with them? Greg DuPont dives into the next evolution of the Wealth Solutions Network: regional attorney-advisor teams trained in the Financial Advocate model. He exposes the tension that’s long plagued professional estate planners who feel sidelined, advisors who feel unsupported, and reveals a better path forward built on mutual trust, shared responsibility, and aligned outcomes. Greg also breaks down the real...

Most estate planning attorneys stop where the real work begins after the documents are signed. In this powerful continuation of the “Back to Basics” mini-series, Greg DuPont and Matt Halloran expose the widespread consequences of binder-only estate plans and the probate nightmares they leave behind. Greg shares why the 4D Estate Plan is the missing framework for attorneys who want to stay relevant, serve at a higher level, and avoid becoming obsolete in a world of online legal forms. It’s not ab...

When estate planning attorneys try to sell like traditional salespeople, they lose the very thing their clients are looking for: trust. In this powerful part three of the March to a Million mini-series, Greg DuPont unpacks what it really means to “sell without selling.” They share how attorneys can let go of outdated scripts, ditch commission breath, and start crafting human conversations that naturally lead to alignment, clarity, and long-term value. What to expect: Why most sales scripts sabo...

It’s no secret: health insurance costs are crushing business owners, and most don’t even know why. In this episode of March to a Million, Greg DuPont sits down with Keefe Duterte, co-founder of Smart Health Benefits, to expose the hidden culprits behind rising healthcare costs, specifically, Pharmacy Benefit Managers (PBMs). But this isn’t just an exposé. It’s a strategic roadmap for estate planning attorneys looking to bring real, measurable savings to their business-owner clients and deepen ad...

The legal profession is facing a reckoning, and estate planning attorneys are at a crossroads. In this episode of March to a Million, Greg DuPont outlines the 4D Estate Planning Advantage: a transformative model designed to help attorneys evolve from document drafters to holistic, family-office-style advisors. With AI tools like wealth.com gaining traction and financial advisors moving aggressively into the estate planning space, the time to adapt is now. Greg explains how attorneys can use the ...