We use AI not as a buzzword, but as a working tool — one that connects your investments, taxes, estate plan, and benefits into a single, continuously updated picture so that every decision we make for you accounts for everything else.
Your investment portfolio lives with one firm. Your taxes are handled by a CPA who never sees your holdings. Your estate plan is in a lawyer's drawer. Your benefits — VA, Social Security, RMDs — each operate in their own world.
None of these talk to each other. Which means a decision made in one area can quietly undermine another — and neither your advisor, nor your CPA, nor your attorney ever catches it.
By integrating AI into how we research, monitor, and plan, we maintain a living picture of your complete financial life — one where every element informs the others, in real time, before it matters.
Every domain of your financial life feeds into a single, integrated view — so decisions in one area automatically account for the others.
Holdings, performance, risk exposure, and rebalancing needs
Loss harvesting, gain timing, RMD coordination, bracket management
Trust structure, beneficiary alignment, and succession readiness
VA entitlements, Social Security optimization, Medicare coordination
Appreciated asset deployment, timing, and foundation strategy
Cash flow modeling, distribution planning, and lifestyle sustainability
Technology handles the monitoring, pattern recognition, and cross-domain analysis. Lee and Langdon handle the judgment, the relationships, and the decisions.
AI monitors your holdings daily — not just for performance, but for tax implications, risk drift, and opportunities that arise from market movements. When something surfaces that warrants action, it reaches us before it reaches you.
A position that has declined triggers a tax-loss harvesting flag — but before acting, the system checks your RMD schedule and charitable giving plan to ensure the move still makes sense in context.
Every decision we consider for you is automatically run against the full picture of your financial life. A change in your estate plan triggers a review of beneficiary designations across every account. A tax move is checked against income projections before it's made.
When you're approaching a Medicare enrollment window, the system flags how your current Roth conversion strategy might affect your IRMAA bracket — a connection most advisors miss entirely.
VA benefits, Social Security timing, pension coordination — these are areas where errors are costly and corrections are slow. AI helps us identify eligibility, optimize timing, and ensure nothing is left on the table.
A veteran client's disability rating, service history, and asset structure are cross-referenced against current VA benefit schedules — surfacing entitlements that four years of manual advocacy might otherwise miss.
Rather than waiting for an annual review to catch misalignments, our system monitors your plan continuously and surfaces issues as they emerge — giving us time to act before the window closes.
A shift in interest rates changes the relative value of individual municipal bonds versus bond funds in your portfolio. The system flags the rebalancing opportunity weeks before year-end, not after.
These are the kinds of situations our integrated approach surfaces — connections that siloed advisors routinely miss.
A client's estate plan calls for leaving a significant stock position to heirs. Meanwhile, tax-loss harvesting logic flags that same position as a candidate for a swap.
A veteran client begins taking required minimum distributions. The added income affects their countable assets for VA pension eligibility purposes.
A client retires in December and drops into a lower tax bracket — but only through year-end. The window for a Roth conversion at favorable rates is three weeks wide.
We are deliberate about what AI does and does not do at Hollingsworth. It is a tool for clarity and completeness — never a substitute for the relationship, the expertise, and the fiduciary accountability that defines how we work.
Every recommendation still comes from Lee. Every phone call still reaches the decision-maker. Technology makes that relationship more informed, not more distant.
We can explain every AI-surfaced insight in plain language. You will always know why we're recommending what we're recommending.
Every alert, flag, and recommendation is reviewed by Lee or Langdon before it reaches you. The system informs judgment — it does not replace it.
AI is excellent at pattern recognition and cross-domain monitoring. It is not a substitute for decades of fiduciary experience, relationship knowledge, or legal expertise.
Your financial information is never used to train AI models or shared with third parties. Our technology obligations to you are the same as our fiduciary ones.
Schedule a complimentary portfolio review and we'll show you specifically what we'd be watching for in your situation.
Request a Portfolio Review