Market headlines tend to focus on whether the Dow or S&P 500 is up or down. But those numbers don’t always tell the full story of what’s happening in the market, or what it means for an individual investor. Changes in interest rates, the rise of passive investing, market concentration, and investor behavior can all …
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 …
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. …
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, …
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 …
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 …
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 …
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 …
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 …
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 …