Naples Finance Professional Bobby Garon Warns That America's Wealth Boom Is Leaving a New Generation of Newly Wealthy Americans Underinsured

As business sales, equity compensation, and a strong stock market create wealth faster than ever, Bobby Garon of Naples, Florida, says insurance coverage is failing to keep up, leaving newly wealthy clients exposed to losses that could unravel years of financial progress.

NAPLES, Fla., Oct. 5, 2026 /PRNewswire/ -- Bobby Garon, a Naples, Florida-based finance and insurance professional, is raising concerns about a pattern he's noticed accelerating among clients whose net worth has grown quickly in recent years. According to Garon, a rising number of people who've come into significant wealth, whether through a business sale, vested equity compensation, or strong investment returns, are underinsured, simply because their coverage was never revisited once their financial outlook changed.

"People will call me the moment their portfolio moves, but insurance rarely gets that same attention," said Bobby Garon. "The insurance gap is more important than most people realize, because the more visible your wealth becomes, the more likely you are to get sued for your full net worth."

What Is the Insurance Coverage Gap Newly Wealthy Americans Are Facing?

The insurance coverage gap Garon describes happens when someone's net worth increases, often quickly, while their insurance coverage stays exactly where it was before that increase. It shows up most often in personal liability limits, coverage sized for an earlier financial chapter that no longer reflects what someone actually stands to lose in a lawsuit or major claim.

How a Liability Coverage Gap Can Threaten Wealth

Liability coverage exists specifically to cover the difference between what someone is sued for and what their policy pays out. When a judgment exceeds that coverage limit, the difference becomes personally owed, which can mean a lien on a home, garnished wages, or a court ordering the sale of investments to satisfy the judgment.

"A lawsuit doesn't check your account balance before deciding how much to ask for," Bobby Garon said. "It often works the other way. The more visible your wealth is, the larger the number someone's attorney puts on the table. If your coverage hasn't kept pace with that visibility, a single bad afternoon can undo years of careful financial planning."

Why Umbrella Insurance Coverage Falls Behind First

Bobby Garon says the clearest sign of this gap tends to show up in personal liability coverage. Many people are still carrying liability limits on their home and auto policies in the range of $300,000 to $1 million, numbers that made sense earlier in their financial life but no longer reflect where they stand today. He points to umbrella coverage, the policy that sits above home and auto insurance to absorb larger liability claims, as the place this gap becomes visible fastest, and the place where a shortfall does the most damage.

"An umbrella policy only functions properly if the coverage underneath it is sized correctly," Garon said. "I've sat down with people who've built real wealth but are still carrying liability limits set for a much earlier chapter of their life. If a claim exceeds those old limits, there's no cushion left to absorb it."

Why the Insurance Coverage Gap Goes Undetected

According to Bobby Garon, this gap in insurance coverage often has a lot more to do with timing than anything else. Insurance reviews typically happen on a fixed annual schedule, while wealth events, a business sale, a vesting date, a strong run in the market, tend to happen suddenly and outside that schedule entirely. The distance between those two timelines is exactly where the risk lives.

"Nobody sets out to underinsure themselves," Garon said. "It happens because a renewal notice gets treated as paperwork instead of a real checkpoint." He recommends that anyone who has recently experienced a meaningful increase in net worth, whether from a large bonus, appreciated investments, or an inheritance, treat that moment as a trigger point to revisit their entire insurance picture, rather than waiting for the next scheduled renewal to roll around.

About Bobby Garon

Bobby Garon is a finance and insurance professional based in Naples, Florida, where he lives with his wife and infant son. He holds FINRA Series 6, Series 63, and Securities Industry Essentials (SIE) licenses, along with Florida Life and Annuity and Property & Casualty insurance licenses. His professional experience includes client-facing roles at JPMorgan Chase & Co. and Morgan Stanley, as well as work as a Licensed Commercial and Personal Lines Insurance Advisor at Brown & Brown Insurance. He writes about financial education, leadership, personal growth, family, and community involvement on his website bobbygaron.com, as well as on Substack and Medium. His licenses and employment history can be independently verified through FINRA BrokerCheck.

SOURCE Bobby Garon