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Jim Dew on Invest Like a Billionaire: How to Vet Your Financial Team

Written by Dew Wealth | Oct 12, 2026, 12:30:00 PM

Jim Dew, Founder and CEO of Dew Wealth Management, joined host Ben Fraser on Invest Like a Billionaire to discuss how entrepreneurs can bring the coordinated team ultra-wealthy families rely on into their own financial lives, without building a full family office.

The episode originally aired on July 6, 2023, but Invest Like a Billionaire recently re-released an edited version highlighting the strongest moments, which is the cut linked below.

Jim walks through what a family office does, why he believes a version of the structure can serve entrepreneurs well below billionaire wealth, and how the Fractional Family Office® model approaches that coordination differently. He also covers how to evaluate the professionals already on a financial team, how investment considerations shift as wealth grows, and why a common piece of investing advice deserves a closer look.

 

What is a family office, and why do ultra-wealthy families use one?

Jim defines a family office as a structure where a single family hires the tax, legal, insurance, and investment professionals they need as full-time employees working for that one family.

The appeal is coordination. Rather than assembling advisors piecemeal over the years, the family has a team under one roof, accountable to one set of goals. The structure requires substantial wealth to build and operate, which is why it has historically been limited to families at the very top of the wealth spectrum.

Can an entrepreneur get the benefits without that level of wealth?

This is the question Jim built his firm around.

His view is that the expensive part of a family office is employing the professionals directly, not the coordination itself. Many entrepreneurs already have an attorney, an accountant, an insurance agent, and a banker. What they often lack is anyone making those people collaborate or holding them accountable, which leaves the entrepreneur doing that coordination personally.

Jim describes a Fractional Family Office® model where an outside firm takes that coordinating seat, so the entrepreneur can set direction without living in the details.

How do you know whether the professionals on your team are the right ones?

Jim offers five things to examine:

Regulatory records. Start with the regulatory body for that profession, such as a state board of accountancy, bar association, or insurance department. Complaint history may appear there even when it doesn’t show up in a general web search.

Education and credentials. Straightforward and frequently skipped.

Specialization. Entrepreneurs typically need specialists rather than generalists. The attorney who handles corporate work is often not the right person to build an estate plan, and treating those as one job tends to produce weaker results in both.

Experience. How long they have been doing the specific work you need.

Personality and follow-through. Jim notes that follow-through shows itself from the first contact with a firm, well before anyone becomes a client. On personality, he cautions against assembling a team entirely of people you enjoy being around, since some healthy tension can produce better decisions than easy agreement.

How often do advisors need to be replaced?

Jim says it varies case by case. In his experience it is uncommon to keep an entire existing team unchanged, and equally uncommon to replace everyone.

He emphasizes that replacement is not always a judgment on quality. Entrepreneurs frequently outgrow advisors who served them well at an earlier stage. The accountant who takes a business from startup to its first million in revenue may not be the right fit at thirty or forty million, and the same pattern can hold for attorneys as entity structures grow more complex.

How might an investment approach change as wealth grows?

Jim’s view is that a growing balance sheet can open access to investments that weren’t previously available. Those investments often carry added risks, such as limited liquidity, higher minimums, and less transparency, and they aren’t suitable for everyone.

He points to asset allocation as something ultra-wealthy families tend to approach deliberately: deciding in advance how much belongs in each category rather than reacting to whatever opportunity a friend happens to mention. He suggests slicing categories into smaller pieces, so an investor knows not only how much belongs in real estate but how that breaks down across property types.

His central framing is a question: are you trying to build wealth or preserve it? Concentration can accelerate growth but adds risk, and diversification works the other way, though it does not ensure a profit or protect against loss. The answer shapes everything downstream.

How allocation changes as wealth grows

Is “only invest in what you understand” good advice?

Jim pushes back on this advice because he sees it as incompatible with real diversification.

No individual develops deep expertise across every asset class, and a diversified portfolio will include things the investor does not know inside and out. Jim uses air travel as an analogy. He cannot explain aerodynamics, but he still flies, because he trusts the pilots, the maintenance crews, and a safety record he can look up.

His conclusion is not that investors should be careless. It’s that the answer is trusted people with expertise in those areas. That’s why his five-point checklist above matters: trust should be earned through due diligence, not assumed.

What is a compelling focus?

Jim describes it as something that pulls a person forward, as distinct from the grinding and pushing that building a business requires. Effort alone is exhausting and can lead to burnout. A vivid picture of what the wealth is actually for can make the work more sustainable.

His own example is modest and personal. As a schoolteacher, he promised himself he would one day support his mother. Years later, that took the form of hiring a cleaning service for her every two weeks. She cried when he told her.

He notes that a compelling focus does not need to be large or expensive, and that the more specific it is, the more effective it tends to be.