Why Are Middle Market Millionaires Overlooking the Power of Philanthropy in Business Succession Planning?

At a time when billionaires are dominating headlines and social media success stories, many middle-market millionaires, those with net worths between $10 and $100 million, are often finding themselves in a strange state of financial invisibility. Despite their substantial wealth, such millionaires live with a misconception that their finances aren’t large enough to take advantage of advanced planning tools like philanthropy. Carlos H. Lowenberg Jr., the founder of Masterpiece Capital, is shattering this mental barrier through his firm and a fervent belief that philanthropy is one of the vital ways to unlock strategic wealth potential.  

“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’s funny and equally troubling how skewed perceptions of wealth have become.”  

This rising mindset has enabled many to overlook the most powerful financial strengths available, what Lowenberg calls planned giving. While philanthropy is rooted in generosity, at its core, its power goes well beyond. It could potentially allow them to leverage tax benefits, create legacy assets, and strategically build wealth.  

Most people in the middle-market millionaire bracket are paying a notable percentage of their income, in federal taxes alone, while the ultra-wealthy, the billionaires, often pay significantly less. “It’s the $2 to $5 million earners who are getting hit the hardest by taxes,” Lowenberg explains. “It’s unfortunate, because they’re the very ones who could benefit exponentially from philanthropic strategies.”  

Philanthropy, particularly when structured correctly through tools like charitable trusts, has the potential to offer a rare financial trifecta, including reducing income tax, deferring capital gains tax, and eliminating estate tax. Lowenberg points out that these strategies don't take money away from the millionaire’s families but rather empowers them with the choice of where they want it to go. “Most people think it’s charity versus family. It’s not. It’s charity versus taxation. If you’re giving away a million dollars in taxes every year, you’re already a philanthropist. Only you’re not choosing where that money goes.”  

Despite the palpable benefits, most charitable gifts still come in the form of cash, even though most of the individual wealth in the country may be held in assets like businesses and real estate. That imbalance means that middle-market millionaires, who hold a substantial portion of those assets, are missing out.  

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

The opportunity cost is staggering. An example Lowenberg shares illustrates his idea: “If you take a $10 million asset, and have it sold, it could become $8 million after capital gains taxes. Conservatively invested, it might generate $500,000 annually, just enough for steady income, but little growth. On the other hand, if it's placed in a charitable trust, committing just 10% to philanthropy, the tax bills disappear, and the full $10 million continues to work. That extra $2 million, when invested wisely, could double every six to seven years. And over 12 to 18 years, the compounding could result in two to four times the original amount, all while creating a meaningful impact and legacy. This is not theory, it’s real wealth creation.”  

At Masterpiece Capital, founded nearly 25 years ago, Lowenberg and his team have been dedicated to helping clients navigate this space and empowering them with the power of philanthropy. What sets the company apart is its emphasis on full-spectrum strategy. At the firm, philanthropy is never treated as a standalone solution, but as a comprehensive and holistic strategy. “We optimize everything,” Lowenberg says. “From pension plans, captive insurance, and qualified plans to C-corp structure, and Augusta rules, we don’t introduce philanthropy until every other low-hanging fruit is picked.”  

The company begins the process through a deep analysis of the client’s present situation, dissecting through their documents, structures, and assets. From there, the team maps out goals, identifies resources, and builds a coordinated plan that integrates wealth building, tax optimization, and legacy planning.  

Increasingly, Lowenberg has leveraged the use of AI to facilitate the analysis process as well. “AI allows us to model complex financial scenarios after and more thoroughly than ever before,” he shares. “It helps us to visualize more angles in less time, and that means better and efficient decisions.”  

For many clients at Masterpiece Capital, philanthropy becomes a natural part of their strategy once they realize the financial logic behind it. “Once they’ve been shown the numbers, they choose to incorporate some form of philanthropic planning,” Lowenberg notes. “We’re helping them not only fulfill an obligation but also guiding them to do more with what they already have.”  

The firm’s work spans business owners, real estate investors, and even tech professionals sitting on large stock portfolios. Many of these individuals have capital that could be restructured for greater long-term benefit. Yet without the right guidance, they either do nothing or pursue siloed strategies with limited returns. “At Masterpiece Capital, our ethos is rooted in not just pushing philanthropy, but opening up a whole new set of possibilities, philanthropy included, and showing them what’s really possible.”  

As middle-market millionaires continue to carry a heavy tax burden, watching billions of dollars quietly slip away, the question is no longer whether they can afford to consider philanthropy, but whether they can afford not to.  

Through planned giving, millionaires can access a strategic level of control, growth, and long-term impact, allowing wealth to multiply, not shrink. And most importantly, it puts the power back in the hands of those who built their wealth in the first place. “You’re already giving. The only question arises: Do you want to decide where the money goes, or do you want to have it decided for you?” Lowenberg asks.  

The information provided in this article is for general informational and educational purposes only. It is not intended as legal, financial, or professional advice. Readers should not rely solely on the content of this article and are encouraged to seek professional advice tailored to their specific circumstances. We disclaim any liability for any loss or damage arising directly or indirectly from the use of, or reliance on, the information presented.