Legacy Planning – March to a Million

The Business Owner Opportunity (Mini Series Ep. 6)

By March to a Million | January 7, 2026

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The entity structure trap and how outdated business structures drain thousands in unnecessary taxes
And more!

Connect with Greg DuPont:

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When Life Changes Overnight: Why Real Planning Needs Resilience (Ep. 55)

By March to a Million | December 17, 2025

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
And more!

Resources:

GoFundMe for Matt Halloran’s family

Connect with Greg DuPont:

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From Legal Plan to Legacy Plan (Mini Series Ep. 4)

By March to a Million | November 5, 2025

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 about selling more; it’s about asking better questions, building alignment, and becoming a lifelong guide for your clients.

What to expect:

Why probate is getting worse, not better, for families
How to frame trust reviews without sounding “salesy”
What it really means to build a legacy plan
The conversation that separates good attorneys from great ones
And more!

Tag: Legacy Planning