How to support an entrepreneur client with multiple businesses

Serial entrepreneurs, or those who own more than one business at a time, are more common than you think.

In fact, GoDaddy’s February 2026 U.S. National Survey of 2,454 microbusiness owners found that one in three respondents have more than one business.

Unfortunately, many of these entrepreneurs may not have a clear understanding of their insurance needs.

“Coverage is often bought piecemeal over time, from different agents, with nobody looking at the whole picture,” said Jeff Kroeger, broker and division leader in New York and New Jersey for World Insurance.

As an advisor, it’s important to recognize this issue and take a holistic approach to each client’s financial and insurance needs.

Common challenges to consider

When they aren't viewed as a cohesive unit, the various risks and businesses an entrepreneur client has can be overwhelming.

“Stepping back and evaluating them from a risk management perspective levels the field,” said Lisa Holt, CEO of Ivy Risk Strategies.

In many cases, a client’s businesses share employees, technology, and funding, so a disruption in one can affect the others. When reviewing coverage, you should account for these interrelated risks.

Also, as a client’s business grows through acquisitions, its insurance program can become increasingly fragmented, with overlapping policies and uncovered exposures.

“As an example, I recently picked up a new account that had grown over the years through acquisitions and ended up with 54 policies, redundant coverages, and gaps in exposures where coverage was needed,” Holt explained.

After a total restructuring, Holt brought them down to seven policies and created a consistency that allowed them to operate more efficiently, saving money in more ways than just premium reductions.

In addition, many entrepreneurs will buy insurance from direct writing carriers and not through a broker, and buy based on price and not what their actual exposures are.

Furthermore, they may choose policies because they’re simply required and settle for the bare minimum when their business warrants a more comprehensive plan.

How to evaluate insurance needs

To determine what type of insurance coverage an entrepreneur client needs, perform a complete inventory of their businesses.

Then, map out the ownership, revenue, debt, employees, contracts and major exposures associated with each one.

“You should understand not only what each business does, but also how the businesses are connected,” said Zachery Candow, licensed agent at Universal Insurance Company Inc.

Are they commonly owned? Do they share employees, equipment, property or contracts? Does one company provide services to another? Does the owner personally guarantee obligations?

Then, look at risk on both a business-by-business basis and at the overall enterprise level. The goal shouldn’t simply be to accumulate policies.

“It should be to identify the financial consequences of the major risks and then determine how much of each risk should be transferred to insurance versus retained by the client,” Candow noted.

Ultimately, the appropriate coverage will depend heavily on the industries involved.

Oftentimes, however, these policies make sense: property and casualty coverage, general liability, commercial auto where applicable, workers’ compensation, professional or errors-and-omissions liability, cyber coverage, employment practices liability, and umbrella or excess liability coverage.

Align personal protection with business ownership

“The more businesses an owner has, the more personal coverage they may need,” Kroeger said.

Life insurance can help cover guaranteed loans, buy-sell agreements, and estate taxes. Disability coverage, while often overlooked, may also come in handy, especially when owners take income through distributions.

Then, there’s long-term care planning.

“Long-term care planning can help entrepreneurs avoid a forced or rushed sale of the business or large withdrawals that could weaken the company’s financial security in order to cover care costs,” Kroeger added.

Ideally, you’d help a client assess their available resources and insurance options. This way they won’t have to rely on business ownership to provide them with the liquidity they need most.

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