how ultrawealthy – In a conversation with MISRYOUM, Rob Mallernee says the families that stay wealthy for generations treat culture, tax planning, long-term investing, and frugality as ongoing commitments rather than one-time decisions.
When you look at what it takes to stay rich for a century, Rob Mallernee argues it’s rarely one “brilliant” move. It’s the accumulation of hundreds of smaller, disciplined decisions over many years—habits he says he’s seen while working with ultra-high-net-worth families for more than 30 years.
The conversation is an as-told-to essay based on Mallernee’s account of his experience. He is 50 and CEO of a wealth management software company; he is based in North Carolina, and Business Insider has verified his employment.
Mallernee’s first point is about family culture.. He says the most successful families “instil a sense of purpose in the next generations. ” aiming to ensure children and grandchildren “don’t feel entitled. ” but instead feel motivated to make their own way and add value to the world.. In those families. he says. later generations don’t see wealth as something they own outright. but as something they steward for the future.
That stewardship, he adds, is visible in how the second and third generations pursue their own careers and achievements.. “Almost all of our clients do a really great job with that,” he says.. He also describes being “often amazed” that they build careers and accomplish things in their lives even though they “already have more than enough money.”
The second habit is how families handle taxes—treating it as continuous work rather than a checkbox.. Mallernee says the most successful families are “very intentional and thoughtful about expenses and costs.” Taxes. he notes. are “typically. one of the highest costs in these situations. ” and he frames investment choices as a major driver of whether the outcome is tax-efficient or tax-inefficient.
He offers a clear contrast: buying “an equity fund where the manager is buying and selling all the time” can lead to “a significant proportion of short-term capital gains” being taxed each year. which would reduce the client’s net return.. He then points to “a tax-loss harvesting strategy. ” where investors buy “a basket of stocks rather than a mutual fund” and sell positions at a loss “to offset gains elsewhere.” In that setup. he says the “gross return expectation is the same. ” but the “after-tax returns are significantly higher.”
Mallernee says these wealthy families devote time and resources to hiring people to avoid costly mistakes. He stresses that they “don’t treat tax planning as a one-time exercise but as an ongoing process that considers every financial decision from all perspectives.”
The third habit is a preference for long-term investing—holding core assets for extended periods to reduce both taxes and transaction costs.. He gives an example from real estate: if a family bought a house in Aspen and held it for decades. “the asset’s appreciation is likely to be significant and outweigh the cost of maintaining it over time.”
He says the same logic applies to financial assets.. “Ultra-high-net-worth individuals with well-planned equity portfolios almost never pay taxes on them because they buy and hold,” he claims.. When they need cash—he uses the example of needing $1 million to buy real estate—he says they “won’t sell investments and incur taxes.” Instead. he describes families borrowing against their portfolio or taking out a mortgage. and he adds that “Very wealthy people tend to avoid paying cash for their homes because it’s not the smartest way to do it.”
The final habit, he says, is frugality. “You may be surprised,” he tells readers. In his view, wealthy individuals can be “very frugal” and pay close attention to costs, including “the nitty-gritty stuff” that many people assume wouldn’t matter.
He acknowledges that this focus can reach extremes. “Sometimes that can go to extremes,” Mallernee says, and he adds he could provide examples of “people worth over $100 million” asking an advisor to look into “a cost worth less than $10.”
Throughout the conversation, Mallernee ties these habits back to a single repeated theme: staying wealthy isn’t about one standout decision. It’s about being “consistently intentional about all your financial decisions,” a mindset he says is how wealthy families retain their wealth.
The pattern he describes is consistent across each of the four habits: cultural expectations for heirs, ongoing tax attention rather than a single exercise, long-term holding to reduce taxes and transaction costs, and detailed cost scrutiny—even down to expenses “worth less than $10.”
ultra-high-net-worth families wealth management tax planning tax-loss harvesting long-term investing family culture frugality