The Invisible Advantage Middle Market Millionaires Are Missing

Carlos H. Lowenberg Jr., founder of Masterpiece Capital, has spent years challenging that mindset. He believes that for this segment of wealth, philanthropy is not simply a generous afterthought. It is one of the most powerful levers available for strategic wealth design.

“I was talking to a client worth $30 million, and he asked me if he was wealthy enough to be thinking about charitable giving,” Lowenberg recalls. “It is funny and equally troubling how skewed perceptions of wealth have become.”

This perception gap has led many business owners in the middle market to overlook one of the most effective financial tools available: what Lowenberg calls planned giving. While philanthropy is rooted in generosity, its real strength lies in how it can be structured. When designed correctly, it can unlock tax advantages, create enduring legacy assets, and expand long-term wealth rather than deplete it.

Most people in this bracket are paying a significant percentage of their income in federal taxes alone, while the ultra wealthy often pay proportionally less. “It is the two to five million dollar earners who are getting hit the hardest by taxes,” Lowenberg explains. “It is unfortunate, because they are the very ones who could benefit most from philanthropic strategies.”

When philanthropy is integrated into a broader plan, particularly through vehicles such as charitable trusts, it can create a rare financial trifecta: reducing income tax, deferring capital gains tax, and eliminating estate tax. Lowenberg is quick to point out that these strategies do not take money away from families. Instead, they give families more control over where their capital ultimately goes.

“Most people think it is charity versus family. It is not. It is charity versus taxation,” he says. “If you are giving away a million dollars in taxes every year, you are already a philanthropist. You are just not choosing where that money goes.”

Yet despite these advantages, most charitable gifts are still made in cash, even though much of the wealth in this segment sits in operating businesses and real estate. That imbalance means many middle market owners, who hold a large share of these assets, are missing out on the full potential of planned giving.

“We see it all the time,” Lowenberg notes. “People are making one off decisions. Setting up a retirement account here, buying into a captive insurance plan there, but it is rarely coordinated. They are taking scattered actions without a broader strategy, and that is where they leave money on the table.”

The opportunity cost can be enormous. Lowenberg offers a simple illustration.

“If you take a ten million dollar asset and sell it outright, it might become eight million after capital gains tax. Conservatively invested, it may generate around five hundred thousand dollars a year, which provides income but limited growth. If instead that same asset is placed into a charitable trust, with only ten percent committed to philanthropy, the tax bills can disappear and the full ten million continues to work. That extra two million, invested wisely, can double every six to seven years. Over twelve to eighteen years, that compounding can turn into two to four times the original amount, all while funding meaningful impact and legacy. This is not theory. It is real wealth creation.”

For nearly twenty five years, Masterpiece Capital has helped clients navigate this space and harness the strategic power of philanthropy. What distinguishes the firm is its commitment to full spectrum planning. Philanthropy is never treated as a stand alone tactic. It is introduced only after the rest of the financial landscape has been optimised.

“We optimise everything,” Lowenberg says. “From pension plans, captive insurance, and qualified plans to C corp structure and Augusta rules. We do not introduce philanthropy until every other low hanging fruit has been picked.”

The process begins with a thorough analysis of the client’s current position. The team reviews documents, structures, and assets, then maps goals, identifies resources, and designs an integrated plan that connects wealth building, tax efficiency, and legacy objectives.

Increasingly, Masterpiece Capital incorporates AI into this analysis. “AI allows us to model complex financial scenarios faster and more thoroughly than ever before,” Lowenberg explains. “It helps us see more angles in less time, which leads to better and more efficient decisions.”

For many clients, philanthropy becomes a natural extension of their strategy once they see the numbers.

“Once they understand the financial logic, they often choose to incorporate some form of philanthropic planning,” Lowenberg says. “We are helping them fulfil a sense of responsibility while also doing far more with what they already have.”

The firm’s clients include business owners, real estate investors, and tech professionals with concentrated stock positions. Many of them hold capital that could be restructured for significantly greater long term benefit. Without the right guidance, they either do nothing or pursue isolated tactics with limited effect.

“At Masterpiece Capital, our ethos is not about pushing philanthropy,” Lowenberg emphasises. “It is about opening up a wider field of possibility, with philanthropy as one of the most powerful options within that field, and showing clients what is genuinely possible.”

As middle market millionaires continue to shoulder a heavy tax burden, watching billions quietly transfer away in the form of avoidable tax, the question is no longer whether they can afford to consider philanthropy. The real question is whether they can afford not to.

Through planned giving, these owners can gain a higher level of control, growth, and long term impact, allowing their wealth to multiply rather than erode. Most importantly, it returns agency to the people who created the wealth in the first place.

“You are already giving,” Lowenberg says. “The only question is whether you want to decide where the money goes, or have that decision made for you.”

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