Earlier this week a clip from The Pat McAfee Show made the rounds. Mid-conversation, one of the commentators stopped and asked, with complete sincerity, "What even are percentages?"

The room laughed. The internet laughed. I laughed too.

Then I stopped laughing, because I realized how many of our clients are asking similar questions. They just never say it out loud.

In wealth management, we build almost everything on an assumption: that the person across the table understands the language we speak. We hand over performance reports full of basis points, allocation pie charts, trailing returns, and fee schedules expressed as a percentage of assets. Clients nod. We move on.

That nod is doing a lot of heavy lifting.

The data says it shouldn't. According to the TIAA Institute and GFLEC Personal Finance Index, U.S. adults answered only 49% of basic financial literacy questions correctly in 2025. That's the same score as 2017. Across eight years of fintech apps, money influencers, and investing content on every platform imaginable, the number has never climbed above 52%.

Only about a third of adults can correctly answer all three of the classic "Big Three" questions on compound interest, inflation, and diversification. In one survey, 65% understood inflation, but just 45% understood how compound interest works.

Sit with that for a second. Compound interest is the engine of everything we do. If a client doesn't understand percentages, they can't truly understand growth, risk, fees, or returns. They're trusting us on faith.

It's tempting to assume this is a problem for someone else's clients. Our clients are successful. They built businesses, sold companies, climbed career ladders.

But having wealth and understanding wealth are separate skills. A surgeon, a founder, or an heir can carry a seven or eight figure balance sheet and still have only a loose grasp of what drives it: why the portfolio is built the way it is, what they're paying, and what would actually move the needle. Success in one domain often makes people less likely to admit confusion in another.

So they nod.

Our industry has a habit. We explain things in the most sophisticated way possible, because sophistication signals competence. The vocabulary, the credentials, the charts all quietly say: I know everything, so surely you can trust me with everything you have.

I understand the instinct. People study for years for the CFA. They want it to show.

But that performance rarely connects with real clients. It creates distance. It makes people feel like the problem is them. And people who feel like the problem is them don't ask questions, don't engage, and eventually don't stay.

Clients don't fire you for being too clear.

Nearly every advisory firm segments clients. A, B, and C. Platinum, diamond, titanium. Pick your branding. Those tiers almost always measure one thing: how valuable the client is to the firm.

What if they also measured something that matters just as much: how confident the client is in understanding their own financial life?

We should be asking, directly, and without judgment: How comfortable are you reading this report? Do you know what you pay us, in dollars? Would you be able to explain your plan to your spouse or your kids?

The answers would change everything downstream. A highly fluent client might want the full attribution analysis. A novice might need a single page that says, in plain words, what happened, why, and what it means for them. Same data. Different conversation. Both clients served well.

For a long time, the honest reason firms didn't do this was capacity. Producing tailored materials for every comprehension level, for every client, was expensive and slow.

That reason is gone. With the data infrastructure and AI tools available today, firms can generate reports, statements, and explanations that meet each client where they are, rapidly and at scale. At Milemarker we've seen firsthand that an empathetic, novice-friendly version of a report can be built just as easily as the expert version.

This matters for the clients you have today. It matters even more for the ones you want tomorrow. The next generation of wealth isn't impressed by jargon. They're used to products that explain themselves. Firms that speak simply and clearly will earn their trust, and firms that don't will lose them before the first meeting ends.

The McAfee clip was funny because it was honest about something that seems obvious. Someone said what they were thinking out loud and demonstrated their own lack of knowledge. All of us laughing only makes the next question nearly impossible to ask.

Our job is to make it safe for every client to ask and then to answer in a way they actually understand, without any shame. Clarity is a form of respect. It's also, increasingly, a competitive advantage.

More on how we're putting this into practice soon.

— Jud

Episode 168: This week on Next Mile, Kyle Van Pelt is joined by Matt Celenza, Managing Director and Partner at Americana Partners. Matt began his career at Morgan Stanley before joining Smith Barney, where he spent more than a decade with the Citi Family Office. He later led Boulevard, the firm he sold to Americana Partners in 2025. 

Matt shares why adding services in-house doesn’t make a firm a family office, and why the real work is coordinating each family’s needs in the order that matters to them. He outlines how complexity, not net worth alone, signals the need for that model, and why investing is often one of the last pieces of the conversation. Kyle and Matt also unpack how families with illiquid wealth find liquidity, how disciplined collateral management protects large loans, and why Matt expects firms using the family office label to be held accountable for it.

In this episode:

(00:00) - Intro

(01:13) - Matt's money moment

(04:07) - What separates a true family office from an RIA

(08:10) - When wealth becomes too complex for traditional wealth management

(11:24) - Balancing customization with scale

(12:59) - What brings families to a family office

(14:42) - Managing liquidity when wealth is tied up in illiquid assets

(18:59) - Managing collateral around concentrated wealth

(21:57) - When wealth becomes collateral

(22:59) - Why service still matters more than technology

(26:53) - Matt's outlook on the future of the wealth management industry

(29:39) - Matt's Milemarker Minute

AI tools change fast, but your firm's decisions still have long-term consequences.

Kailash Duraiswami and I discussed how wealth management firms can evaluate AI tools, focus on lasting foundations like data and governance, and avoid chasing every new release.

Missed the session? Learn how to make smarter AI decisions for your firm by watching the webinar replay here:

If you would like to arrange a meeting time, please reply to this email, and we’ll schedule something on the calendar.

Jud Mackrill