Navigate Retirement and Change

Retirement planning has a habit of collapsing into a single number — a nest egg, a withdrawal rate, a probability of success. Jason Branning spent years pulling it back apart. The question that started him down that road wasn't academic at all: it was a married couple sitting across from him where one spouse could get long-term-care insurance and the other, because of a health condition, could not. How do you plan for a risk you can't insure away?

That problem is the seed of Modern Retirement Theory, the framework Branning developed with an academic collaborator and now teaches through his firm. On this episode of Advisor Ally, he walks Vineet Mohan through the theory, the crises that shaped his thinking, and why he believes the most human part of advising — actually understanding a client — is the one thing technology can't do for you.

A circuitous route into the business

Branning didn't set out to be a financial planner. He was a humanities major who expected to work in a university setting, and he only landed in the industry through an internship at a wealth management company that liked him enough to offer training. He told them plainly he knew nothing about financial services — a couple of economics classes, not a major. They said they'd teach him, and he stuck around for years learning from the ground up: client services, the financial planning department, shadowing advisors who'd been in practice for decades, then working through the Series exams and the CFP program.

The firm he grew up in shaped how he sees advice. It was built by two people from opposite sides of the business — one from insurance, one from a brokerage and CPA background — at a time when those were largely separate channels. That blend taught him early that advice runs a continuum, not a product silo.

"Advice runs a continuum. It's not just about insurance products or brokerage services — it's about where all these things fit together for an individual family."

That conviction carries into how he thinks about the craft itself. The best advisors, he says, listen and learn before they solve; they try to inhabit a client's thought processes and uncover the issues beneath the issues. Jump straight to answers and you miss things, which leads to advice that doesn't fit and expectations that go unmet down the road. It's a fitting philosophy from someone whose whole method is built on asking better questions.

Founding a firm in the wreckage of 2009

Branning started Branning Wealth Management in 2009, at the tail end of the great financial crisis — the worst market, he notes, since 1931. He'd already lived through the tech bubble's collapse in the early 2000s, and the pattern he took from both was the same: the clients who had a plan they understood and believed in, and who expected downturns, rode through and came out fine.

The firm's own beginning was turbulent for reasons beyond the market. The regional brokerage that had acquired the practice he grew up in collapsed after three of its owners committed malfeasance against clients, forcing a limbo period while a receiver took over and transferred credentials across the country. Branning came out of that determined to serve clients directly, and a back-office relationship with a Portland TAMP — with client funds custodied at Fidelity — made restarting under a new entity far less painful than it could have been.

That experience hardened his belief in preparation. He runs what he calls a premortem — stress-testing a client's plan against bad markets and bad life conditions before they happen.

"You can never take away the emotions. But the actions aren't informed only by the emotion — they're informed by a third party, which is the plan."

Modern Retirement Theory

The framework itself came out of conversations around 2006 and 2007 with Ray Grubbs, an academic and dear friend, initially about long-term-care planning. That uninsurable spouse crystallized the problem: how do you handle a contingency you can't mitigate the traditional way? Branning and Grubbs kept meeting, and what emerged was a liability-matched protocol. Start with the liabilities — the expected expenses for life and the possible contingencies — then structure income streams and assets to match them in a way that makes definitional sense.

The heart of it is the base fund. Branning asks clients to separate essential expenses — food, transportation, shelter, insurance they have to pay — from discretionary ones, and then insists that essentials get matched with like-kind income. If an expense is inflation-adjusting and will recur every month for life, it should be covered by an income source that behaves the same way. Social Security becomes the benchmark precisely because it's inflation-adjusted and impossible to outlive. Fill the base fund to an acceptable ratio first, then solve contingencies — home equity conversion mortgages, a long-term-care policy, asset-based insurance, or simply cash set aside. Branning is careful to note his firm is fee-only and sells no insurance; the theory is product-agnostic by design.

From there the model layers into four tiers: base, contingency, discretionary, and legacy. Discretionary goals are the things you want but can delay — buy the car next year if the market's down. And legacy, he stresses, is not just about money. It's about the values transmitted to the next generation, carried through conversations and documents as much as dollars. The two risks the whole structure is built to absorb are longevity and the unknown conditions — of health and of markets — that unfold across it. The framework has since shown up in retirement-planning curricula, which Branning treats as the point: it belongs to anyone who finds it useful, insurance or portfolio, because there's a slot for any approach.

Remote-first before it was normal

Long before COVID made it unremarkable, Branning Wealth was a location-independent firm serving clients from Hawaii to Canada — roughly 40 percent of them outside Mississippi, where the firm is based. The habit started early, when a principal at his original firm moved to Colorado and the practice digitized its entire paper repository into a secure electronic filing system. Branning has been a digital native ever since; he doesn't want paper anywhere near his desk, preferring to make notes and shred them for security. When the pandemic hit, the firm barely changed its workflow. It was already meeting clients over video and running on tools like Loom and Zoom, which is why he thinks COVID didn't invent the remote advisor so much as give everyone permission to admit it was possible.

Coding is not understanding

Branning is genuinely enthusiastic about AI, but he draws a firm line around what it can and can't do. His firm is testing the AI systems, and his verdict is unsentimental: they give wrong answers, often, which is why you need a domain expert in the loop to catch what's actually incorrect and push the tools to iterate.

"Coding is not understanding. That is something deeply human that an adviser is going to be required to do. But wow — how much better can the adviser serve their clients if we engage the tools?"

The upside he sees is scale and depth. This is a personal business with a hard ceiling on how many relationships one advisor can serve well, because real planning rests on understanding the people involved. If technology handles more of the coded, mechanical work, advisors can deliver more value, more personalization, and more of it more often — and push good planning out to more people than was ever possible before. Concretely, his firm has stitched together CRM workflows and automations with a consultant's help, and adopted a meeting notetaker that writes notes straight into the CRM as assigned action items. The team rereads every set of notes to confirm it captured what the meeting actually was, then publishes them to the client within 24 hours so the client can confirm they were heard and correct anything that's off. It's the accuracy and comprehensiveness, not just the time saved, that he values — and, he admits, once you work that way it's very hard to go back.

Branning closes on the same organic note that runs through his career. The firm's niche serving professional athletes came not from a strategy deck but from a conversation with a former NFL player, Kelly Jennings, who wandered into planning after a marriage-and-family-therapy degree and turned out to understand athletes' finances better than anyone. Off the clock, Branning's time goes to his wife of nearly 28 years and their four children, to books, and to the walks that have replaced his old running habit. For an advisor whose entire method is built on sitting down, listening, and letting the right answer emerge, it's exactly the ending you'd expect.