Is captive insurance right for your business?

October 27, 2026
Managing Director Alex Toskovich speaks with Andy Lewis, CEO and Principal of Keystone Risk Partners, to get his perspective on captive insurance – how it works, who it benefits, and how the right businesses can turn insurance into a strategic asset.

A conversation with Andy Lewis, CEO and Principal of Keystone Risk Partners

Captive insurance is gaining traction as a strategic tool for middle-market businesses, but it’s not a fit for everyone. In this conversation, Andy Lewis, CEO and Principal of Keystone Risk Partners, explains how captives work, who they benefit, and what business owners should weigh before making the shift from traditional insurance to a more controlled, long-term approach to risk.

Let’s start simply – what is a captive insurance company?

A captive is a licensed insurance company owned by the business it insures. Instead of paying premiums to a third-party carrier each year, your operating business pays those premiums to an insurance subsidiary that you own.

That subsidiary is a real, regulated insurer – it’s licensed, capitalized, issues policies, sets reserves with actuarial support, and ultimately pays claims.

The idea is straightforward: If you’re consistently a better-than-average risk, why give the underwriting profit to someone else?

How should business owners think about this in practical terms?

A helpful way to frame it is disciplined self-insurance.

Most companies already retain risk through deductibles, exclusions, or gaps in coverage. A captive formalizes that reality – it prices the risk, funds it in advance, and converts what would otherwise be an expense into a balance sheet asset.

Over time, you’re building reserves and surplus that you control and can invest.

A captive is a licensed insurance company owned by the business it insures. Instead of paying premiums to a third-party carrier each year, your operating business pays those premiums to an insurance subsidiary that you own.”



However, the IRS has been very clear, especially with smaller “micro-captive” structures, that arrangements lacking real risk transfer or business purpose will be challenged. The guiding principle is simple: If it doesn’t work as insurance, it won’t work for tax.

Who is the right candidate for a captive?

The profile is fairly specific. The businesses that tend to benefit most share a few common traits:

  • They spend meaningful amounts on insurance – typically $1 million or more annually, though smaller entry points exist through group or cell structures.
  • Their loss experience is better than average. They’re paying more in premiums than they’re getting back in claims.
  • They have strong, stable cash flow and can comfortably capitalize the program.
  • They face risks the commercial market prices poorly, including cyber, liability, or certain property exposures.
  • They operate across multiple entities, locations, or lines of business.
  • And importantly, they think long term. This is not a one-year strategy.

In practice, that often describes middle-market family- or founder-owned businesses.

What industries tend to explore captives most often?

We see a lot of activity in construction, manufacturing, transportation, healthcare services, energy distribution, staffing, franchising and real estate. These are businesses where risk is meaningful, insurance is expensive, and management teams are focused on operational discipline.

If a business owner is interested, what does the process look like?

To answer this, businesses go through a formal feasibility study, which guides them to their final decision. The process typically unfolds like this:

    1. Preliminary review of your insurance history and loss data

    2. Formal feasibility study, where actuaries model expected losses and optimal program design

    3. Structural and tax review to confirm it operates as real insurance

    4. Domicile selection and licensing

    5. Implementation, where the captive begins issuing policies and receiving premiums

From start to finish, you’re typically looking at six to nine months. Even if the answer is “not yet,” the study itself is valuable since it gives a clear picture of your total cost of risk.

What are the primary benefits for business owners?

There are several, but the most meaningful ones are economic and strategic:

  • You retain underwriting profit instead of giving it to an insurer.
  • You reduce long-term cost of risk, removing layers of carrier overhead and margin.
  • You gain control over coverage, especially for risks the market avoids.
  • You smooth pricing volatility and reduce dependence on the commercial cycle.
  • You build an investable pool of assets – reserves and surplus.
  • You improve risk management, because better performance directly benefits you.

For disciplined operators, those advantages compound over time.

What needs to change with the existing insurance policy structure?

Typically, the policy structure transitions from a guaranteed cost or first dollar policy to a large deductible.

  • The utilization of a large deductible reduces your traditional premium.
  • The captive’s premium mirrors the cost savings of the deductible structure.
  • If the losses within the deductible are less than the captive premium, the owner keeps the profits.
  • The captive premium earns investment income for the benefit of the captive owner.

What about the trade-offs?

It’s important to be clear about those:

  • You need to commit capital upfront and maintain reserves.
  • There are formation and ongoing operating costs.
  • You are taking on the risk. A bad loss year affects your captive directly.
  • There’s a governance burden. This is a regulated entity with audits and oversight.
  • If structured poorly, there can be meaningful tax risk, particularly with smaller captives.

A captive is a strategic decision. It rewards strong businesses but requires discipline and a long-term mindset.

Tax often comes up in these conversations. How should business owners think about that?

Tax can be a benefit, but it should never be the primary driver. A properly structured captive is generally treated as an insurance company, which can provide deductibility of premiums and tax-deferred growth of reserves.

A properly structured captive is generally treated as an insurance company, which can provide deductibility of premiums and tax-deferred growth of reserves.”



Can you explain what “fronting” means as it relates to captive insurance?

Certain types of insurance, like workers’ compensation, require an admitted, rated insurer. In those cases, a commercial carrier issues the policy and then reinsures the risk to your captive. Because the carrier remains legally liable, it requires collateral – typically a letter of credit. That’s where a bank such as BBH can become an essential partner.

What questions should business owners be asking to gauge whether this is worth exploring?

A few key ones that come to mind are:

  • Are we spending enough on insurance for this to matter?
  • Are our losses consistently lower than what we pay in premiums?
  • Can we commit capital and absorb volatility?
  • Are there risks we’d like to insure that the market won’t handle well?
  • Are we thinking long term?
  • And importantly, is our motivation rooted in risk management – not tax or short-term gain?

Any final advice for a business owner considering a captive?

For the right company, a captive turns insurance from a recurring expense into a strategic asset. It rewards operational discipline, strengthens control over risk, and builds long-term value on the balance sheet. It’s not for everyone, but for well-run, growth-oriented businesses, it’s one of the most powerful tools that often goes unexplored.

Andy, thank you for your time.

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