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We Get to Be Here: A Thanksgiving Reflection on Longevity and Attitude
We get to be here, in this work, in this year, with the households that trust us to walk them through it. The markets will do what the markets do. he political ramifications are unknowable. The technological acceleration is going to keep accelerating. None of that is ours to control. The posture we bring into the room and the longevity assumption we price into the plan — those are both ours.

Greg DuPont
1 day ago3 min read


Why Financial Plan Longevity Assumptions Need to Go Past 95: A Case Study
Their plan on file was built four years ago, ran to age 95 for both of them (software default), came back on-track, and nobody had reopened the horizon since.

Greg DuPont
Nov 36 min read


The AI Operating System Behind a Family Office
WSN OS 3.0 is an estate planning operating system that puts AI at the center of how retirement and estate planning gets done.

Greg DuPont
Oct 283 min read


Every Dollar with a Job - A Five-Slice Retirement Income Case Study
They came in sounding like people with a complaint about their provider. What they had was a complaint about the shape of their plan. The portfolio was in pieces, and no one had ever assembled the sentence that says which dollars pay for which parts of their life in which year.

Greg DuPont
Oct 135 min read


Identifying the 'Season' Your Clients Are In
Every one of those households is in a season. Reading which one they’re actually in is one of the most under-appreciated diagnostic moves in this work.

Greg DuPont
Oct 63 min read


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
Sep 224 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 13 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
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