Client Stories

Steve (58) is a regional sales director who's worked for three different employers across his career, leaving behind a 401(k) at each stop. Karen (56) has taught part-time for years and carries a small pension that has never really been factored into their overall picture. They both save diligently, they've never carried unhealthy debt, and by every reasonable measure they've done the right things for a very long time.

The problem is that no one has ever looked at the whole thing together. Their retirement accounts sit in four different places. Their Social Security decision has never been modeled. They have no idea what to do about health insurance in the roughly nine-year window between when Steve wants to stop working and when Medicare kicks in. And with retirement now only about three years away, the fear of a bad market at the wrong moment has quietly become the loudest voice in the room.

They came to us after attending a retirement workshop. They had known for a while they needed a real plan, and they had put it off just as long. What they wanted was simple. Someone to tell them, honestly, whether they were actually in position to retire when they hoped to, and what the next three years should look like to make sure the answer was yes.

Jake and Ryan came to us in 2017 as 50/50 owners of a fast-growing construction and remodeling company. The business was scaling quickly, revenue was climbing into the millions, and they were reinvesting heavily into trucks, buildings, and real estate to support the work. On paper, everything looked great.

In practice, it didn't feel that way. Despite doing serious top-line revenue, they felt like they were hitting zero at the end of every month and every year. There was no buy-sell agreement in place, no cash management system built around the business, and no coordinated plan for how the growing asset base should actually be structured. They were two strong operators running hard, but the financial side of the business was starting to strain.

There was also a generational gap to plan around. Ryan, in his 60s, was beginning to think about what life looked like after the jobsite. Jake, in his 40s, still had a long runway and the appetite to keep building. Same business, same partnership, two very different timelines. Without a real plan, that gap could have quietly turned into a problem. With a plan, it became the blueprint for everything that followed.

A couple in their late 70s approaches us with a revocable trust that was set up more than a decade earlier. Life has changed significantly since that original planning. The portfolio has grown, real estate has been added, business interests have been sold, and the original estate attorney is no longer practicing. They are confident the trust exists. They are much less confident about what is actually inside it.

There is no current will coordinated with the trust, which means any assets not properly titled into the trust could fall outside the plan and potentially end up in probate. Their two adult children and several adult grandchildren are the intended beneficiaries, but the mechanics of how wealth would actually move to them have never been tested against current estate tax rules.

Their biggest concern is straightforward. They have worked hard to build something meaningful. They do not want taxes, courts, or family confusion to take more than necessary. They also want to give generously to the causes they have supported quietly for years, but have no formal vehicle to do it through.

A couple in their early 40s approaches us after receiving a significant inheritance. Both parents are high earners at public tech companies, both have equity compensation as a meaningful part of their pay, and they have three kids between the ages of 5 and 11. On the surface, their financial picture is strong. Two strong careers, two growing sets of company stock, and now an inheritance that changes what the next several decades could look like.

The challenge is that none of it is coordinated. The inheritance arrived with tax implications they didn't fully understand. Their W-2 income pushes them into the top federal brackets. Their equity compensation adds another layer of complexity, with concentrated positions in two different employers. They are funding their 401(k)s and have some cash in the bank, but beyond that, there is no clear plan for where dollars should go next.

Retirement isn't a stress point in the way it is for most clients. They already know they will be comfortable. What they don't know is what comfortable actually looks like, which accounts they should be building up versus drawing down, and how to make sure the inheritance does more than just sit in a brokerage account for the next twenty years. They also have no current estate plan of their own, which means everything they just inherited, plus everything they've built on their own, has no structure to protect it for their kids.