Category: Finances
The Business Owner Opportunity (Mini Series Ep. 6)

The Business Owner Opportunity (Mini Series Ep. 6)

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  • The entity structure trap and how outdated business structures drain thousands in unnecessary taxes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

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

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

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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:

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How We’re Redefining Financial Advocacy for Families (Ep. 54)

How We’re Redefining Financial Advocacy for Families (Ep. 54)

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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 Estate Plan, a proprietary system that helps families document, defend, and deliver their legacy while avoiding costly tax and probate mistakes.

What to expect:

  • The origin of Greg’s “March to a Million” mission
  • The dangers of financial fragmentation
  • How to make longevity a blessing, not a curse
  • Why “Wealth Under Alignment” replaces “Assets Under Management”
  • And so much more!

Resources:

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The Attorney–Advisor Advantage (Mini Series Ep. 5)

The Attorney–Advisor Advantage (Mini Series Ep. 5)

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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 reason collaboration often fails (hint: it’s not about revenue splits), and explains how letting go of control can actually increase influence, effectiveness, and income. He shares a live client case that proves how powerful it is when legal and financial minds row in the same direction with the 4D Estate Plan as their compass.

What to expect:

  • The hidden insecurity behind control-seeking professionals
  • How family office thinking can transform small firms
  • The advisor’s mindset vs. the attorney’s wiring
  • A case study showing the 4D Plan in action with seven kids, charitable intent, and major tax savings
  • And more!

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

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

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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!

Resources: 

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The Trust Conversation: Selling Without Selling (Mini Series Ep. 3)

The Trust Conversation: Selling Without Selling (Mini Series Ep. 3)

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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 sabotage trust with legal clients
  • The “alignment” strategy that leads to better outcomes
  • How to introduce high-value offers without pushing
  • A powerful way to uncover your client’s real motivations
  • And more!

Resources: 

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How To Cut Benefits Costs, Not Coverage with Keefe Duterte (Ep. 53)

How To Cut Benefits Costs, Not Coverage with Keefe Duterte (Ep. 53)

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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 advisory relationships along the way.

Greg and Keefe talk about:

  • How PBMs are quietly inflating drug prices—yes, even generics
  • Why most employers are overpaying by 20%+ for the same coverage
  • A 3-step “Replicate, Reduce, Replace” approach to employer health plans
  • How attorneys can use health plan strategies to deliver more client value
  • And more!

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Connect With Keefe Duterte:

About Our Guest:

Keefe Duterte graduated from the University of Arizona in 2002 with a double major in Finance and Economics and earned his Life & Health Insurance license that same year. With over two decades of experience, he’s dedicated his career to helping individuals and families navigate the often confusing world of health insurance. Keefe is passionate about health and wellness and committed to finding creative, affordable solutions that make quality care accessible. His mission is simple: to put the “health” back in healthcare.

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The 4D Estate Planning Advantage for Modern Attorneys (Mini Series Ep. 2)

The 4D Estate Planning Advantage for Modern Attorneys (Mini Series Ep. 2)

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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 4D framework to:

  • Stay relevant in an AI- and tech-driven future
  • Deliver comprehensive value beyond documents
  • Protect clients from one-size-fits-all financial sales strategies
  • Structure their practice to attract higher-value engagements
  • And more!

Resources:

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The Big Picture: From Practitioner to Legacy Builder (Mini Series Ep. 1)

The Big Picture: From Practitioner to Legacy Builder (Mini Series Ep. 1)

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Estate planning professionals are at a crossroads. Those who stay stuck in transactional work will struggle to survive, while those who think bigger have the chance to build a true legacy.

In this episode of March to a Million, Greg DuPont kicks off a special 10-part series on moving from practitioner to legacy builder. Greg talks about why so many attorneys plateau, how outdated thinking holds them back, and what it takes to build a practice that creates lasting impact for clients, families, and the profession itself.

Greg discusses:

  • Why so many estate planning attorneys plateau in their practices
  • The critical differences between revenue models for attorneys and financial advisors
  • How outdated beliefs in the profession prevent attorneys from running their firms as businesses
  • The 4D Estate Plan model and how it shifts the attorney’s role from technician to strategist
  • Why this mini-series matters and what’s at stake for those who want to build a legacy
  • And more

Resources:

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The Private Insurance Strategy Every Business Owner Should Know with Craig Clemons (Ep. 52)

The Private Insurance Strategy Every Business Owner Should Know with Craig Clemons (Ep. 52)

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Private insurance isn’t just for Fortune 500 companies; it can be a powerful wealth-building and risk-mitigation tool for law firms, business owners, and entrepreneurs.

In this episode of March to a Million, Greg DuPont sits down with Craig Clemons, Vice President at Reinsurance Specialists, to uncover how private insurance structures can help business owners self-insure, unlock tax advantages, and even build new pools of investment capital. From protecting against reputational risk to leveraging captive insurance strategies for estate planning and retirement, Craig breaks down the opportunities most professionals don’t even know exist.

Here’s what you’ll learn:

  • How private insurance works as both protection and an asset-building tool
  • Why risk management strategies can be customized for any industry
  • Real-world examples of law firms, doctors, and construction companies using this model
  • How private insurance ties into estate planning and long-term wealth transfer
  • And more!

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Connect With Craig Clemons:

About Our Guest:

C-suite executive with extensive sales, marketing, business development, and leadership experience in diverse companies, including three Fortune 500s. In his current role with Reinsurance Specialties™, Craig recruits, coaches business development individuals / educates business leaders operating in 30 US states, delivering a best-in-class private insurance platform.

As recent vice president of public relations and business development for Express Employment Professionals™ (a $4 billion international enterprise), Craig worked directly with the CEO to develop new business and strategic partnerships serving 800 franchised offices, 65,000 clients, and 600,000 associates in the U.S., Canada, and South Africa.

Previously, Craig served in senior management positions with Oklahoma State University, Williams Companies, Advantage Media Group, Frito-Lay, and for eleven years with Anheuser-Busch as Senior Market Manager.

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