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A Larger Future Than a Past: The Mindset Behind Financial Advisor Career Longevity
The single most important frame for my career longevity is simple: always have a vision of a larger future than a past. As long as you have something meaningful you're building toward, waking up energized is easy. And if you don't have it, no amount of past accomplishment fills the gap.

Greg DuPont
6 days ago4 min read


How a Repeatable Retirement Planning Process Can Improve Client Outcomes
Investments, taxes, estate planning, income, and healthcare all influence one another, making it difficult to know where to begin when it comes to retirement planning.
Where advisors fail is not having a repeatable process.

Greg DuPont
Sep 163 min read


The Fire-Sale Default
I’ve sat across the table from the family Taylor described more times than I can count. Dad built a real estate portfolio over thirty years. He can’t keep up with it anymore. The kids don’t want it. What happens next is usually a fire sale — no tax planning, no value maximization, no continuity through the estate plan.

Greg DuPont
Sep 74 min read


On Track Isn’t Protected: A sequencing case study in the difference between adequate and protected
Ron and Donna came to me earlier this year with a version of a question I hear constantly from dual-income couples closing in on the same retirement date: can we actually stop at 65, and what happens if one of us gets sick or doesn’t make it there at all?

Greg DuPont
Aug 315 min read


Premium Financing: The Tool with the Reputation
On Episode 66 of March to a Million, RJ and I sat down with Jacob Brigati of Simplicity UFC to walk through what the strategy actually is, when it fits, and — the part I asked most about — how a firm that does this at scale protects clients across the 15-to-20-year horizon these policies live on.

Greg DuPont
Aug 204 min read


How Artificial Intelligence Can Help Estate Planning Attorneys Build Better Systems
The attorneys who will thrive over the next decade are those who stop solving every problem themselves and start designing systems that solve problems on their behalf.

Greg DuPont
Aug 196 min read


March to a Million Mission Update: 8 years in 4 to Go
Eight years ago I made a commitment that would end up shaping everything I’ve done since. I called it March to the Million — a commitment to help one million people prepare for the future. Eight years in, four to go.

Greg DuPont
Aug 133 min read


3 Different Retirement Models: A Case Study
Mark came into our office in his mid-50s with a line I keep hearing from professionals like him. “I don’t want products — I want to understand the strategy.” He’s a long-tenured W-2 professional stepping into a consulting-and-entrepreneurship phase, mid-six-figures in his 401(k), meaningful after-tax assets across whole-life cash value, real-estate equity, and a modest brokerage, 10 to 15 years from full retirement. Sophisticated. Reads pro/con literature. Brings articulate s

Greg DuPont
Aug 64 min read


The Financial Advisor's True Role: A Quarterback
The single most expensive mistake on the list isn’t a portfolio choice or a tax election. It’s the absence of a financial quarterback coordinating across the investment advisor, the CPA, the estate attorney, and the insurance professional. Each is optimizing within their own lane. Nobody is integrating across lanes.

Greg DuPont
Jul 163 min read


What the Lanes Don't See: A Case Study in Financial, Tax and Insurance Integration
Their estate attorney handed them off with two questions. The first was Erin’s: should we buy more life insurance? The second was Dan’s: should we just become completely debt-free?
Both reasonable. Both, answered inside a single lane, wrong.

Greg DuPont
Jul 96 min read


We’ve Given You a Democracy, If You Can Keep It: What the 250th anniversary asks of the work we do for families
The founders knew the system was fragile. They studied history. They understood the gravity that pulls a republic toward chaos on one side and toward total control on the other, and they wrote the architecture knowing humans would have to figure out coexistence in practice, not just in theory.

Greg DuPont
Jul 23 min read


Phantom Stability: Private credit and what’s already in your clients’ 401(k)s
The product behind those headlines is private credit. It’s a $3.5 trillion market most clients have never heard of, and the executive order signed in August of 2025 opened the door to bring it directly to the $13 trillion defined contribution market — meaning the 401(k)s most clients think they understand.

Greg DuPont
Jun 163 min read


When Referral Partnerships Stop Working: What Estate Planning Attorneys Should Do Next
Referral partnerships once felt like the smart way to grow. You sent clients to a financial advisor or insurance agent, they sent business back, and everyone benefited. But through the years, you've also probably noticed some cracks. The referrals slow down. The quality drops. And your revenue starts to feel as unpredictable as the partnerships themselves.
This article explains why referral partnerships often become unreliable and what you can do instead.

Greg DuPont
Jun 126 min read


The Quietest Tax Window You’ll Ever See: Why the bridge years between W-2 and Social Security do more for a plan than most plans use them for
There’s a window most retirement plans don’t even map.
It opens the year a client’s W-2 income stops, and it closes the year Social Security starts. For most of the clients you and I see, that’s somewhere between two and six years of unusually quiet tax air — earned income gone, Social Security not yet on, required minimum distributions still a long way off.

Greg DuPont
Jun 93 min read


Sized to the Bracket: A bridge-years case study in sequencing what the window allows
A couple in their early 60s — came to me in March with a version of a question I bet you’ve heard a hundred times: when is the right time to start converting to Roth?

Greg DuPont
Jun 25 min read
How Human Connection Helps Estate Planning Attorneys Grow
Clients do not make major planning choices based on facts alone. They also respond to trust, clarity, and confidence. For an estate planning attorney who wants to expand into life insurance or broader financial services, that matters. It is often the difference between staying a document provider and becoming a true financial advocate.

Greg DuPont
May 285 min read
Prioritize Client Understanding Before Recommendations: A Better Growth Model for Estate Planning Attorneys
Clarity leads to better client outcomes, stronger trust, higher retention, and more ethical growth. For estate planning attorneys expanding into financial services, this approach reduces pressure, improves confidence, and helps you serve clients as a true financial advocate.

Greg DuPont
May 264 min read


Three Levers, Layered: A case study in PILOT Retirement Process stacking
I isolated the 401(k) and ran the analysis on it alone — leaving the self-directed IRAs, the syndication, and the cash-value insurance explicitly out of the model. That was a deliberate choice, not an oversight. If the 401(k) on its own can carry retirement, everything else becomes upside.

Greg DuPont
May 214 min read


5 Proven Strategies to Seamlessly Integrate Financial Services into Your Law Practice
If you run a successful estate planning firm, you have likely seen the shift already. Clients no longer want estate documents in isolation. They want guidance that connects wills, trusts, beneficiary designations, insurance, and long-term financial goals into one clear plan...In this article, you will learn five practical strategies to integrate financial services into your law practice in a way that is efficient, ethical, and sustainable.

Greg DuPont
May 148 min read


Family Wealth Planning: Two Conversations Advisors Should Lead
Two structured conversations can help professionals move beyond transactions and into true client leadership:
Family Financial Preparedness
Family Financial Priorities

Greg DuPont
May 79 min read
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