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
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
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
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.
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
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 planning, and economic systems, while discussing the opportunities and disruptions that may emerge as these technologies scale across society.
Key takeaways:
Why the cost of advanced AI models is dropping rapidly, and how that trend may turn AI into a utility
How autonomous vehicles and robotaxis could reshape transportation and personal economics
Why humanoid robots may soon perform real work in logistics, manufacturing, and elder care
How rising electricity demand from AI may reshape energy production and infrastructure
Why digital finance and stablecoins could change how money moves across borders
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 potential future tax exposure, the rising national debt levels, and fiscal pressures.
Greg discusses:
Why no one truly predicted the 2025 market and what that means for how we plan going forward
How inflation has shifted, where it still lingers, and whether zero inflation is even possible
The housing market’s grip on retirees and why so many feel financially stuck in place
How 401(k)s and IRAs have become areas policymakers may evaluate for future revenue
Why the US national debt is a generational problem that demands honest conversation
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 points matters for families approaching or already in retirement. Greg emphasizes the importance of resilience, open-mindedness, and taking prudent steps to protect what matters most during periods of significant change.
Greg discusses:
Why the American constitutional system is historically rare and what happens when its principles erode
How turning points in history feel uncertain while living through them, and why context matters
The practical ways disruption shows up in families, from anxiety to financial paralysis
Why resilience and financial protection matter more than ever for people nearing retirement
The importance of staying open-minded and truth-seeking during polarized times
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 disruption and why resilience matters more than ever.
Greg discusses:
Why truth is starting to feel stranger than fiction in today’s economy
How AI and automation are quietly replacing knowledge-based roles What this shift means for people in their peak earning years
Why mindset, adaptability, and financial resilience matter more than specific skills
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 conversations advisors must initiate to protect their clients’ legacies. Greg also shares the “bag of tricks” approach that helps attorneys and advisors ask the right questions at the right time.
Greg discusses:
Why most small business owners can’t sell their businesses for a reasonable value despite years of work
How to structure exit strategies using key employees and golden handcuffs to maintain continuity
The power of asking “What needs to happen in 5-10 years for you to be happy?” to transform planning
Why business owners view their companies as family, and how legacy thinking drives all decisions
The entity structure trap and how outdated business structures drain thousands in unnecessary taxes
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 can impact even the strongest plans
Matt’s family emergency and the ripple effects it created in both his life and business
RJ’s personal health crisis, including a stroke, seizures, and the financial implications of caregiving
Why planning for resilience matters as much as planning for taxes or retirement
How the Four D estate planning model helps clients prepare for curveballs
The power of asking better questions and building guardrails into every plan
