March to a Million

You’ve saved for retirement, but how do you know when another year of work is helping rather than delaying the life you planned? In this episode, Greg DuPont examines the “One More Year Trap” and why retirement decisions can become driven by uncertainty rather than financial need. He explains how accumulated savings should translate into retirement income, why Social Security may leave a smaller gap than expected, and how taxes can affect the value of working longer. Greg also explores the cost

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,