Built on Trust: How Duncan Supply Found a Better Fit for Its Risk Strategy 

Duncan Supply knows a thing or two about longevity. 

Founded in 1936 by Russell Duncan, the fourth-generation family-owned business has grown from its refrigeration roots into a heating, air conditioning, and refrigeration wholesale distributor with locations across multiple states. 

Through that growth, some principles have stayed remarkably consistent. 

“We truly live that depression mindset of buy what you can afford and operate within your limits,” said Christopher Duncan Hendricks, president and CEO of Duncan Supply Company. “Four generations later, we’re still running the business in the eyes of how it was founded 90 years ago.” 

That approach to business has shaped the way Duncan Supply thinks about risk. 

A relationship built around trust 

For Hendricks, strong business relationships start with people. 

“People love to do business with people,” he said. “Really, relationships mean everything.” 

Duncan Supply had worked with Gregory & Appel Insurance before 2019, but that year brought a new conversation: whether a captive insurance program could be a fit for the company. 

The concept was unfamiliar at first. 

Duncan Supply was accustomed to a traditional insurance structure. A captive offered something different: greater ownership of its insurance program, along with a stronger connection between the company’s risk performance and its financial results. 

Hendricks admits he had questions. 

“The idea was foreign,” he said. “I was a little hesitant and kind of unsure because it’s a change.” There was a fear that if something bad happened, his company could be removed from the program. What helped was having an advisor who understood Duncan Supply’s business and history. 

“I had Gregory & Appel saying, ‘Listen, this is what we do. We know you. We know your history. This will be a good thing, please trust us.’ And I went on that journey.” 

Turning insurance into a resource 

As Duncan Supply became more familiar with the captive, Hendricks began to see value beyond the financial side. 

“This isn’t just insurance, this is learning from each other,” he said. “We unlocked a whole new asset, a whole new resource.” 

Education became an important part of that experience. 

Since joining the captive, Duncan Supply has invested further in its safety program, including adding a dedicated safety professional who participates in training, monitors regulatory developments, visits company locations, and works with branch leaders on areas that need improvement. 

For Hendricks, having that focus inside the organization has brought greater visibility into risk across the business. 

“The fact that I have somebody paying attention to the risk management in-house every day means the world,” he said. 

As Duncan Supply has continued to grow, it has expanded that commitment by training an additional person to help support safety and risk management across its footprint. 

Finding a partner who understands the business 

Industry experience also matters to Hendricks. 

Duncan Supply wanted an advisor who could understand its operations, communicate clearly, and share what similar businesses were seeing before those same issues reached Duncan Supply. 

“We look for somebody who understands our type of business, who can relate to us and explain things in basic terms, but who’s also staying ahead of the industry,” Hendricks said. 

That proactive education has become part of the relationship. 

According to Hendricks, Gregory & Appel helps Duncan Supply stay aware of regulatory changes and risk concerns affecting other companies in its space, giving its team more information to act on before a problem develops. 

“It’s great to have somebody who really stays ahead of our industry and looks out for people in our industry,” he said. 

Betting on your own performance 

Hendricks is also clear that captives are not the right fit for every company. 

For business owners considering one, he recommends starting with the fundamentals: understand your claims history, what you are paying for insurance, and how much risk you are prepared to take on. 

For Duncan Supply, the company’s safety record and operating philosophy made the captive worth exploring. 

“When you’re first coming into a captive, the initial capital investment you have to make is that you’re really investing in yourself,” Hendricks said. “I thought, hey, if I’m going to bet on myself, this is what comes with it.” 

That mindset has carried forward as the company grows. 

More locations mean more exposure, but they also mean a continued investment in the people, processes and risk management practices that support the business. 

For Hendricks, the relationship still comes back to the same thing it did in the beginning: trust. 

“Find somebody that you trust and that’s genuine. Find somebody who you can connect with,” he said. “And that was everybody at Gregory & Appel.” 

A risk strategy built for the road ahead 

Duncan Supply has spent generations building its business around disciplined decisions, strong relationships, and taking care of what it has built. 

Its approach to insurance now reflects that philosophy, too. 

With greater ownership of its risk program, access to education, and a partner that understands its industry, Duncan Supply has built a strategy that can grow alongside the company. 

Ready to take a closer look at your risk strategy? 
Talk with Gregory & Appel Insurance about whether a captive or another risk management approach could fit your business. 

What Are Employee Benefits Captives and Why They Matter for Employers

At Gregory & Appel, we’ve spent over a century helping businesses navigate the complex world of insurance and risk management. We’ve seen firsthand how rising healthcare costs can strain companies and limit their ability to provide meaningful employee benefits. That’s why we’re passionate about employee benefits captives: a powerful solution that puts control back in your hands. In this short guide, we'll walk you through everything you need to know about employee benefits captives. Let's get started with the basics:

What is captive insurance?

Employee benefits captives are groups of companies that form their own insurance company to cover their own claims. This setup helps employers save money, gain more control over their policies, and better manage costs by pooling risks together instead of relying on traditional insurers.

What are employee benefit captives?

Employee benefits captives are a specialized type of captive insurance. It's an alternative risk transfer mechanism where organizations form their own insurance company to cover risks related to employee benefits, like health insurance and healthcare benefits. This captive insurance structure acts as a form of self-funded plan, allowing employers to gain greater control over their healthcare costs and employee benefits.

How Do Employee Benefits Captives Work?

Participating in this type of captive arrangement means that you as an employer pools your premiums into a shared fund rather than paying premiums to a traditional fully insured employer. This pooled fund serves as a shock absorber for larger claims and unexpected catastrophic claims, providing financial protection and risk mitigation.

Members of your captive benefit from cost savings through risk pooling and improved risk management strategies. The captive insurer offers medical stop loss insurance and other employee benefit options tailored to the needs of you and your fellow participating organizations. Employee benefits captives provide an innovative captive solution that empowers employers like you with more control, flexibility, and potential cost savings compared to traditional insurance coverage.

Why Are Risk Management Strategies Important for Employee Benefits Captives?

Captive insurance works best when employers have a good handle on their risks. In fact, having strong risk management is a must if you want to be part of a captive. Risk management strategies play a big role in employee benefits captives because they help employers handle healthcare costs and employee benefits more effectively. Without it, the financial ups and downs from big, unexpected claims can quickly become overwhelming and disrupt the whole plan. If risk management isn’t in place from the start, it’s tough to keep things stable and avoid surprises.

Risk management is the foundation that keeps captives running smoothly, controls costs, and makes sure that benefits are sustainable for your employees.

Benefits of Employee Benefits Captives

Employee benefits captives offer a range of advantages that can help you better manage your healthcare costs and provide tailored benefits to your workforce. The main benefits for employers participating in these captives are:

Overall, employee benefits captives empower employers with the ability to take ownership of their health insurance, reduce costs, and create benefit plans that truly align with their workforce’s needs.

Potential Downsides of Employee Benefits Captives

At Gregory & Appel, we understand that while employee benefits captives can be a powerful tool for managing healthcare costs and gaining greater control over your benefits, they aren’t the right fit for every business. Captives require a serious commitment and come with considerations that every employer should carefully evaluate.

First, managing a captive demands significant time and resources. Your team will need to be actively involved in overseeing claims, compliance, and risk management efforts to ensure the captive operates smoothly. Additionally, captives face complex regulatory requirements that can vary by state or region, so staying compliant requires ongoing attention.

Forming a captive also involves upfront costs, including capital contributions and administrative expenses. It’s important to recognize that realizing meaningful financial returns often takes several years, so a long-term commitment is essential.

Because captives involve retaining a portion of risk, your business must have the financial strength and willingness to assume that responsibility. Without strong risk management practices in place, unexpected high claims can impact all members of the captive, increasing risk exposure.

Finally, captives are not a one-size-fits-all solution. Smaller businesses with highly volatile claims or those not prepared to engage in proactive risk management may find captives less advantageous.

At Gregory & Appel, we work closely with you to assess whether an employee benefits captive aligns with your company’s goals, risk tolerance, and capacity to manage the program. When the fit is right, captives can offer significant cost savings, greater control, and tailored benefits that truly meet your workforce’s needs.

What is an example of a captive for employee benefits?

At Gregory & Appel, we often share stories to help illustrate how employee benefits captives can transform the way businesses manage healthcare costs. Let’s take the example of “Midwest Manufacturing Co.,” a mid-sized company with about 300 employees, located in Illinois.

Midwest Manufacturing was struggling with rising health insurance premiums year after year. Their traditional fully insured plan was becoming a financial burden, and they felt like they were paying for coverage their employees didn’t fully use. The company wanted more control over their employee benefits and a way to stabilize costs without sacrificing quality.

That’s when they came to us to explore employee benefits captives. Together, we helped Midwest Manufacturing join a group captive made up of several like-minded employers in their region. Instead of sending premiums off to a traditional insurer, Midwest Manufacturing began pooling their premiums with other captive members into a shared fund. This fund acted as a safety net, absorbing larger-than-expected claims and protecting the company from catastrophic healthcare expenses.

With the captive structure in place, Midwest Manufacturing gained greater flexibility to customize their health plan to better suit their employees’ needs. They also received detailed claims data and insights, enabling them to implement targeted wellness programs that improved employee health and reduced claims over time.

Over the first two years, Midwest Manufacturing saw a noticeable reduction in overall healthcare costs, saving approximately 10% compared to their previous fully insured plan. Plus, because the captive returned unused funds when claims were lower than expected, the company was able to reinvest those savings into enhanced benefits and employee incentives.

This example highlights how an employee benefits captive can empower businesses like Midwest Manufacturing Co. to take ownership of their health insurance, manage risks proactively, and create a benefits program that truly supports their workforce all while achieving meaningful cost savings.

Is my business a good fit for an employee benefits captive?

Wondering if an employee benefits captive is the right move for your business? It really comes down to a few important things. Captives tend to work best for companies with a steady number of employees and a real interest in managing risks proactively. If you’re a mid-sized business between 50 and 1,000 employees, you might find group captives especially helpful because they let you team up with similar employers to share risks and save money.

You’ll also want to be financially prepared to take on some of the risk yourself and invest in the process. That means having the resources and time to stay on top of claims, compliance, and risk management. If you’re looking for more control over your benefits and want access to detailed claims data to make smarter decisions, a captive could be a great fit.

Captives can help improve your cash flow, keep premium increases steadier, and protect you from those big, unexpected claims with medical stop loss coverage. Just keep in mind, joining a captive is a long-term commitment that requires active involvement.

Group Captive Options

Group captive options allow like-minded employers to join forces, pooling their risks and sharing costs to better manage employee benefits and healthcare expenses. This collaborative approach lets smaller employers, who might otherwise face challenges in self-funding, to access the advantages of captive insurance through a group benefits captive. Larger companies can also benefit from group captive options by leveraging collective purchasing power and risk management resources to reduce healthcare costs and improve cash flow.

Explore Captive Insurance with Gregory & Appel

At Gregory & Appel, we’ll work with you to see if a captive matches your company’s goals, risk tolerance, and capacity. When it’s the right fit, captives give you the power to take charge of your health insurance, manage costs better, and create benefits that truly support your team. Fill out the form below for more information about captive insurance. We're looking forward to chatting with you!

This content is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice.



Balancing Cost, Care, & Risk: Lessons from Our CFO & HR Executive Roundtable 

Recently, Gregory & Appel brought local CFOs and HR leaders together for our Balancing Cost, Care, & Risk roundtable. We brought together leaders wrestling with the same fundamental challenge: how do we protect our people without breaking the bank?  

Here's what we learned together. 

1. Start with Shared Organizational Values 

When HR and finance agree on what the organization values as an employer, they can look at investments in the same way. This kind of alignment takes effort and planning. 

Angie Woods, our VP of HR, and Sarah Robison, our CFO, started at Gregory & Appel on the same day, which made that alignment a priority from the start. As Angie put it: "The best HR professionals are the ones who, more than just looking through the lens of people, understand the business, understand the findings, understand all of that... we know that the cost of our people are the greatest cost on balance sheet, right? So just having that constant cost trade-offs, and it's a balance." 

Sarah added her own perspective on why this matters: "While HR has the full purview of people, finance has the whole purview of the company and where we invest the dollars. And every dollar that's invested in any particular area means it can't be invested somewhere else." 

2. Replace an Immediate "No" with a Conversation About Trade-Offs 

Think about what the organization could move, delay, or add to a long-term plan instead of seeing every decision as just a yes or no. 

"Instead of I try and I'm always great at it, but I try not to always say no," Sarah explained. "It's what's the trade-off? What are we willing to give up? Or what are we willing to shift? Or what are we willing to adjust? Or can it be no for now, and we can put it onto the roadmap to look at in a year? And trying, as much as I can, to bring folks along in those conversations versus just making those decisions and saying this is the way it has to be." 

3. Build a Long-Term People Plan Alongside the Financial Plan 

Plan out benefit decisions, workforce investments, and key milestones for the next three to five years. 

"Just like in finance, we're used to doing budgets or three-to-five-year plans," Sarah said. "There needs to be a three-to-five-year people plan along with it. It's not just the recruiting and the attraction side, but what are the things that we're going to do? What is our benefit planning going to look like? When are we going to make these next decisions? What are the gates or the milestones that need to happen where we can make this next investment, so we all know what we're looking towards." 

4. Treat Benefits as an Investment, Not Simply an Expense 

Healthcare costs will likely keep rising, so the goal is to slow that growth and make sure both employees and the organization get more value. 

"While we like to say we want to reduce or lower healthcare costs, the reality is they very rarely ever go down," Sarah said. "But it's how can we slow the increase? How can we get the value? What can we do on the preventative side? If you look just at the numbers, it's always an expense, but you have to look at it as an investment in our people and all the other aspects that go with it." 

5. Use Benchmarking Selectively 

Big reports can be overwhelming. Focus on data from similar industries, company sizes, and workforce groups, and look for plan features that matter most for hiring and keeping employees. 

Matt Heincker, our Employee Benefits Practice Leader, explained how G&A approaches this with clients: "There are certain areas of your plan that are pretty important if they're in line with your competitors—just basic plan design. But things like PTO, mental health services, there are a lot of ancillary things that are becoming a lot more important. The younger generation really values their lifestyle. So there's specific parts of this 40-page report we're going to really direct your attention to." 

Angie described how she narrows the data down internally: "I want to get as close to apples-to-apples as possible. So looking at certain things in our industry—what are our competitors doing, organizations that are similar in our size, headcount, revenue, geographical differences... We're not benchmarking against the Googles and the Metas, because we're not them. We're a smaller company." 

6. Listen to Employees Before Investing 

Surveys and feedback show which benefits employees actually value. This helps organizations avoid spending on programs that people rarely use. 

"I love doing surveys," Angie said. "The last thing I want to do is spend money on a benefit that we think people find important and they don't. And so we want that information so that we can make some trade-offs—so we can invest that money somewhere else for a benefit that we don't have that is important to our employees." 

Sarah pointed to a related discipline: tracking utilization after the fact. "With some of our benefits, we actually get utilization reports to be able to understand: is it driving what we're looking for? There's been a couple of items here at G&A when Angie and I came in, and utilization's high... we're like, how can we redeploy those dollars?" 

7. Account for the Work Behind Cost-Containment Strategies 

Many strategies mean employees have to change how they use their benefits. Think about the training, communication, and support needed to help them adjust. 

"There are a lot of things that are effective," Matt said of cost-containment strategies. "But what comes with it is employee education. Most of them require education with your employees to relearn how to interact with their benefits and how to access them. So what is your appetite for that? And what's your organization's bandwidth for that?" 

8. Evaluate the Support Behind Your Benefits Strategy 

Your broker or benefits advisor should offer more than just renewal numbers. Find a partner who provides useful benchmarking, explains the pros and cons of different strategies, helps share changes with employees, and ties benefit decisions to your bigger business goals. 

Matt described how this plays out in practice: "We really rely on a lot of benchmarking because your benefits need to look very different depending on what industry you are in to be an employer of choice... So we show you what that looks like for your industry—maybe there's some small tweaks you can make that really elevate it quite a bit, but don't cost a lot. And the second part of that is really: what are the most effective ways to contain cost? We've got our finger on the pulse of the more innovative strategies to contain cost." 

The Path Forward 

The best benefits strategies balance financial responsibility with what employees really need. This takes teamwork, good data, and regular conversations between HR, finance, and leadership. 

Ready to align your people strategy with your bottom line? Reach out to our Employee  Benefits team for a one-on-one strategy session to review your current benefits, benchmark against your industry, and explore innovative cost-containment options. 

Creating an Employee Handbook: Common Legal Mistakes

Your employee handbook is an important document. A well crafted handbook gives legal protection and effective communication for your organization. Ideally, it help employees understand company policies, promotes solid company-employee communication, and sets a consistent standard of expectations. However, a poorly crafted handbook can have serious legal ramifications.

In many employment lawsuits, your handbook will be a key piece of evidence that can either protect your company or provide ammunition for the employee (or former employee) who is suing you. With stakes this high, it’s quite important for your handbook to be thorough, up to date, legally compliant, understandable, and readily available to all employees. It’s also wise to make employees sign a form stating they received and reviewed the employee handbook, so that they cannot later claim during a lawsuit that they were unaware of a particular policy.

In this short guide, we’ll explore more of what your handbook should legally include and look at examples of common legal mistakes employers make with their employee handbook.

What Legally Needs To Be in an Employee Handbook?

An employee handbook must include several legally required elements to stay in compliance with federal, state, and local laws, and to protect both you and your employees. These elements serve to clarify workplace expectations, employee rights, and the legal framework governing the employment relationship. Your employee handbook should include:

At-Will Employment Statement

The handbook should explicitly state the nature of the employment relationship, typically that employment is “at-will.” This means either the employer or the employee can terminate the employment at any time, with or without cause or notice, unless otherwise specified by contract or law. Clearly defining this relationship helps prevent misunderstandings and potential legal claims related to wrongful termination.

Equal Employment Opportunity (EEO) Policy

A comprehensive EEO should affirm your company’s commitment to providing equal employment opportunities to all employees and applicants without discrimination based on protected characteristics such as race, color, religion, sex, national origin, age, disability, or any other status protected by law. This policy demonstrates compliance with federal laws enforced by agencies like the Equal Employment Opportunity Commission (EEOC) and helps foster an inclusive workplace culture.

Anti-Harassment and Anti-Discrimination Policies

These policies should clearly prohibit harassment, discrimination, and retaliation in the workplace. They should define unacceptable behaviors, provide examples, and explain the procedures for reporting incidents. Including information on how complaints will be investigated and the protections afforded to complainants also helps meet legal standards and protect your employees.

Wage and Hour Policies

Your handbook needs to address compliance with wage and hour laws, including the Fair Labor Standards Act (FLSA). This includes detailing employee classifications (exempt vs. non-exempt), overtime eligibility and compensation, pay schedules, and timekeeping requirements. Clearly explaining these policies helps prevent wage disputes and makes sure your employees understand how they will be compensated.

Leave Policies

Legally required leave policies should be outlined, like those relating to the Family and Medical Leave Act (FMLA), medical leave, sick time, and any state-specific leave laws. Your handbook should explain eligibility, the process for requesting leave, employee rights during leave, and the company’s obligations. Including information on paid time off (PTO), bereavement, family leave, and other benefits related to time away from work is also important. Be sure to clarify how employees accrue paid time off, including the accrual process and any rollover policies, and specify the need to provide notice when requesting time off to ensure smooth scheduling and compliance.

Workplace Safety and Health Policies

Employers must include policies that comply with the Occupational Safety and Health Administration (OSHA) regulations and any applicable state safety laws. This includes outlining safety procedures, reporting accidents or unsafe conditions, and the company’s commitment to providing a safe work environment. It is essential to include dress code and remote work policies, tailored to the specific needs of different workplaces, to ensure clarity and compliance with current work arrangements.

Benefits

Clearly outline employee benefits, company benefits, and the full range of what the company offers, such as health insurance, retirement plans, wellness programs, and flexible scheduling. Distinguish between employee benefits (direct perks for employees), company benefits (broader organizational offerings), and the overall package the company offers to attract and retain staff. Make sure these benefits are relevant, easily accessible, and clearly described so employees understand what is available to them.

Department-Specific Policies and Responsibilities

Include department-specific policies and clarify the responsibilities for each department. Outlining these helps ensure that employees understand their roles, duties, and expectations within the organization, and supports interdepartmental cooperation and clarity.

Discipline and Termination Procedures

This section should explain the expectations for employee conduct, the process for addressing violations, and the circumstances under which termination may occur. Clear guidance helps set expectations and reduces legal risks related to wrongful termination claims.

Technology Use and Confidentiality Policies

Policies regarding the use of company technology, including computers, email, internet, and social media, should be clearly stated. Your handbook should specify that company devices and communications are the property of the employer and outline acceptable use, monitoring, and privacy expectations. Confidentiality policies protecting sensitive company information and intellectual property should also be included.

Legal Compliance

Be sure to include all required policies and address legal liability by determining which practices are essential for your organization. Regularly review and update your handbook to ensure all content remains relevant and compliant with current laws and regulations.

Acknowledgment of Receipt and Agreement

In order for your handbook to be enforceable, it should include an acknowledgment form that your employees sign, confirming they have received, read, and understood the handbook. This form should also reiterate that the handbook is not a contract and that policies are subject to change. Ensure employees have access to the entire document and understand their responsibilities as outlined in the handbook.

Including these legally required components in your employee handbook keeps you compliant and helps create a clear, consistent, and fair workplace environment.

This employee handbook blog is provided for informational purposes only and does not constitute legal advice. It may not include all requirements applicable to your specific state or locality. Employers should consult with legal counsel or qualified HR professionals to make sure your handbook complies with all relevant federal, state, and local laws and addresses the unique needs of your organization.

What Are Common Legal Mistakes Made in an Employee Handbook?

Many employers inadvertently include errors in their handbook that can open your business up to liability. Here’s a few common legal pitfalls to avoid:

Go Beyond Employee Handbooks with Gregory & Appel

Creating a solid, compliant employee handbook is just the beginning. What really counts is putting those policies into action every day, whether that’s running performance reviews or keeping your workplace safe and fair.

At Gregory & Appel, we’re here to help you go beyond the handbook. From designing employee benefit plans that really work to crafting smart risk management strategies, we show up to help your business succeed.

Want to stay on top of the latest legal and compliance news? Sign up for Gregory & Appel’s Legal and Compliance Roundup and get practical tips and updates delivered straight to your inbox. Let’s make compliance simple together!

This content is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice.

These HR Insights are published in partnership with Zywave, and are not intended to be exhaustive, nor should any discussion or opinions be construed as professional advice. © 2011, 2019 Zywave, Inc. All rights reserved.

Insurance for Healthcare Organizations

A healthcare organization can look calm from the waiting room. Patients check in, phones ring, clinicians move from one room to the next and the day keeps moving. But anyone who leads a healthcare organization like a hospital system knows how much is happening behind the scenes. A staffing shortage changes the rhythm of the da or a patient complaint needs careful documentation. A system outage creates pressure fast or compliance issue raises questions that reach far beyond a single policy.

This is what makes insurance for healthcare organizations so different from a standard business insurance program. The risk is complicated and layered. It is clinical, operational, financial, regulatory and deeply human, all at the same time. It lives in the exam room, the break room, the server room, the boardroom, and every process that keeps your organization moving.

Building a strong insurance program for a healthcare organization starts with looking beyond premium and policy terms. You'll need to understand where claims are developing, where coverage may be misaligned, where loss prevention can make a meaningful difference, and how data can help guide better decisions. You'll want to work with a broker who knows how to connect those layers instead of treating them as separate conversations.

This guide breaks down the insurance coverages, risk strategies, and broker support healthcare organizations should understand as you build a stronger program. It is designed to help you look past the renewal date and think more clearly about the risks that affect your people, your patients, and your path forward.

What are the core coverages for healthcare organizations?

Healthcare organizations face a wide range of risks, from patient care and employee safety to data privacy and property damage. A strong insurance program brings these exposures together into one coordinated plan, helping your organization protect its people and its assets. This applies across various healthcare settings, including hospital systems, physician-owned practices, federally qualified health centers, specialty practices such as neurologists, facilities and surgery centers, and ancillary services like laboratories.

Core coverages often include:

The right mix of coverage depends on your organization’s size, services, workforce, contracts and risk profile. Gregory & Appel Insurance helps healthcare organizations evaluate exposures, identify coverage gaps, and build insurance programs that support both day-to-day operations and future growth.

Why is healthcare risk management so complicated?

Healthcare organizations don’t face risk from one direction. Their exposure is shaped by patient care, daily operations, workplace safety, privacy obligations, contracts and leadership decisions. One small issue, like incomplete documentation or a missed safety protocol, can grow into a much larger liability event.

That’s why risk control matters. For many healthcare organizations, loss prevention is still underused. Some rely on generic carrier resources that may not reflect how their teams actually work, where incidents tend to occur, or what pressures employees face day to day. Those tools can be helpful, but they are rarely enough on their own.

A stronger approach starts with understanding your organization’s real operations. High-impact areas often include patient safety protocols, infection control, documentation accuracy and workplace safety concerns tied to lifting, nursing duties and ergonomics. Each of these areas can affect claims, compliance, employee wellbeing, and patient trust.

Better risk management also looks ahead. Leading healthcare organizations track incident trends and risks like equipment failure and on-site violence in addition to filed claims. They use root cause analysis to understand what went wrong and why. They also connect risk management with clinical leadership, so prevention becomes part of how the organization operates rather than a separate administrative task.

What are the top risks that healthcare organizations should be aware of?

For healthcare organizations, risk tends to show up where pressure is highest: a busy care team, a system that cannot go offline, a compliance requirement that changes faster than internal processes do... the issue is rarely one isolated exposure. More often, it's the way clinical, operational, financial, and technology risks connect.

The areas below are a good place to start when evaluating where your organization may be most vulnerable.

Cyber and technology risk in healthcare

Healthcare organizations are prime targets for cyber crime because they hold sensitive patient data and cannot afford long disruptions. A cyber event can create:

The challenge is that many organizations believe they are protected because they have a strong IT team. IT is important, but cyber risk also needs leadership attention, employee training, tested response plans, and insurance coverage that matches your organization’s actual exposure.

Common gaps include:

Cyber risk should be treated as an operational risk, not a separate technology issue.

Workforce risk and workers’ compensation

Your workforce is your biggest asset and your largest risk exposure. Healthcare work is physically and emotionally demanding. Employees face injury risks from lifting, repetitive motion, long shifts, and high-stress environments. When teams are stretched thin, burnout can also contribute to errors and more frequent claims.

A stronger workers’ compensation strategy looks ahead instead of waiting for claims to happen. Practical opportunities include:

It's also important to track the right signals. These metrics can help show whether your program is improving or falling behind:

Staffing shortages add another layer. When teams are stretched thin, fatigue-related incidents become more likely, which affects your liability exposure.

Regulation, compliance, and governance

Healthcare organizations operate under close scrutiny, and compliance requirements continue to shift. Think about a leadership decision that feels routine at the time: a staffing change, a new service line, a contract update or a response to a patient complaint. In healthcare, decisions like these can carry regulatory, employment, insurance, and reputational implications.

Risk also sits in the space between teams. Compliance may be tracking one concern, legal may be focused on another, and insurance may not enter the conversation until after a claim, investigation, or renewal challenge. This disconnect can affect both coverage and cost.

A few questions can help reveal where governance risk may be building:

A stronger approach connects governance decisions to the broader risk strategy. This translates to bringing risk management, legal, compliance, finance, clinical leadership, and insurance advisory into the same conversation before a problem escalates. When these groups are aligned, your organization can make better decisions, reduce avoidable gaps, and present a stronger risk story to the market.

How should healthcare organizations build their coverage strategy and program structure?

A strong insurance program should reflect the way a healthcare organization actually operates. A small outpatient practice, a multisite specialty group, and a larger health system may all need core healthcare coverage, but your risk profiles are not the same. Patient volume, services provided, staffing model, contracts, locations, and claims history all shape what the right program should look like.

The problem is that many insurance programs do not keep pace with the organization. Some healthcare organizations are underinsured in emerging risks, while others are still paying for legacy program structures that no longer fit.

Common gaps include:

Program structure matters, too. Healthcare organizations should understand how claims-made and occurrence policies work, where tail coverage may apply, and whether larger systems could benefit from captives or other alternative risk financing strategies.

What do sophisticated buyers do?

It's important to remember that the lowest premium is not always the best program. In many cases, it is simply the cheapest starting point, and it may leave the organization with more risk than leadership realizes. Sophisticated healthcare buyers look at more than the renewal premium. They ask better questions, use better data, and evaluate insurance as part of a broader financial strategy.

They often start with total cost of risk, or TCOR. This gives leaders a clearer view of what risk is really costing the organization.

TCOR may include:

Many healthcare organizations track premium because it is easy to see. TCOR gives a fuller picture. It shows whether the organization is reducing risk over time or simply shifting costs around.

Sophisticated buyers also benchmark limits against meaningful operational factors, including:

This helps leadership avoid two common problems: buying limits based on habit or reducing coverage based only on price.

For larger or more complex organizations, advanced strategies may also come into play. Deductible optimization, loss-sensitive programs, and captives can give leaders more control, but only when the organization has the resources to support them.

How does data improve healthcare insurance decisions?

Claims information, incident reports, staffing trends, patient volume, and department-level loss activity can all point to where risk is building. When that information is reviewed only at renewal, your organization misses opportunities to improve operations throughout the year.

High-value analytics may include:

Better data can help leaders see what needs attention first. It can also support stronger conversations with underwriters, especially when the organization can show what it is doing to reduce risk.

How do you choose the right insurance broker?

Choosing an insurance broker for a healthcare organization is about finding someone who can help you manage risk before, during, and after a claim. The right broker should understand how your organization operates, not only what policies you buy. They should ask about your services, patient volume, provider count, contracts, staffing model, claims history, and growth plans. Those details shape your coverage needs and help underwriters see a clearer picture of your risk.

A strong broker should also bring healthcare-specific experience. Healthcare risk is different from general business risk. You need a partner who understands your risk profile and can help you build a program around it. .

Look for a broker who can help with:

The best broker relationships are proactive. They do not begin the renewal conversation a few weeks before expiration. They help you review data, monitor claims, identify coverage gaps, and prepare for market changes before those issues become urgent.

It's also worth asking how the broker measures success. Lowest premium is not the same as the best outcome. A better measure is whether the program fits your risk, supports your operations, and gives leadership confidence when a claim or disruption happens.

Claims management and advocacy

Claims advocacy is one of the clearest tests of broker value. Premiums matter, but the outcome of a claim can have a much larger financial and operational impact. For healthcare organizations, claims services should be specialized because medical malpractice claims and other complex exposures require close management.

Early claims handling can influence:

Healthcare claims require active participation. Medical malpractice litigation, employment claims, and workers’ compensation losses can move quickly, and small decisions early in the process may shape the final outcome. A strong broker helps create structure around that process. Strong claims support often includes dedicated claims professionals who help organizations understand exposures and maintain business continuity. They should help you understand what is happening, what information is needed and when to challenge a carrier’s position.

Best-in-class organizations often:

The right broker should bring claims into the larger risk strategy. That means connecting claim outcomes to loss prevention, coverage decisions, staffing practices and renewal planning. As you review options, explore how each broker structures claims support and ongoing service.

Strengthen Your Healthcare Organization From the Inside Out

Healthcare organizations are built around a clear purpose: caring for people. But supporting that mission takes more than clinical expertise. It requires a strong understanding of the risks surrounding the organization, from patient care and workforce safety to cyber threats, regulatory pressure, contracts, claims activity, and cost control.

When those risks are managed in separate conversations, important details can be missed. Coverage limits may fall out of step with actual exposure. Claims patterns may develop quietly. A risk control opportunity may not get attention until after a loss. Over time, those small disconnects can create larger financial and operational challenges. A stronger insurance strategy brings the full picture into focus.

The right partner can help your organization look beyond premium and ask better questions. How is the program structured? Where are claims starting to develop? Which risks are changing fastest? What does the data show, and how can it support better decisions? This kind of guidance matters at renewal, but it should not stop there. As your organization grows, adds services, manages staffing pressure, or responds to new operational demands, your insurance strategy should be able to keep up.

Gregory & Appel Insurance is an independent risk management advisor helping organizations navigate the complexities of insurance and employee benefits. For healthcare organizations, including hospital systems, physician-owned practices, federally qualified health centers, specialty practices like neurologists, facilities and surgery centers, and ancillary services like laboratories, this means taking the time to understand how your operations, people, data and long-term goals shape your risk. We are committed to a holistic approach that supports healthcare organizations as those needs evolve.

Our healthcare team helps organizations build insurance programs that reflect how they actually work. We connect coverage strategy, risk control, claims advocacy, benchmarking and data-driven insight, giving leaders a clearer view of their program and the confidence to make informed decisions.

Whether you are reviewing malpractice limits, strengthening cyber coverage, addressing workforce injury trends or rethinking your total cost of risk, Gregory & Appel Insurance can help you find the right path forward. We work with healthcare organizations to identify gaps, support stronger claims outcomes, and align insurance strategy with the realities of day-to-day operations.

Ready to build a stronger insurance strategy for your healthcare organization? Fill out the form below.

This content is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice.

Resort and Timeshare Insurance: Coverage Guidance for the Hospitality Industry

Running a resort or timeshare takes a lot of behind-the-scenes work. Guests may only see the finished experience, but boards and property leaders are thinking about everything it takes to protect the property, support the team, and keep operations moving.

Insurance is a big part of that, but it can be hard to know what needs a closer look. Are the right coverages in place? Are there exclusions that could create problems later? Is the property ready for renewal, storm season, or a claim?

This guide is designed for the people responsible for keeping those properties protected. We'll cover practical insurance and risk management guidance tailored to resorts and timeshares, with insight into the coverages, market trends, and planning conversations that matter most.

Here at Gregory & Appel Insurance, we work with hospitality properties like yours to help you understand complex risks, ask the right questions, and build insurance programs that fit the way your properties actually operate.

What Types of Insurance Policies Do Resorts and Timeshares Need?

Resorts and timeshare properties face a wide range of risks, from property damage and guest injuries to employment issues, board decisions, cyber events, and severe weather. Because of that, most need an insurance program that addresses both day-to-day operations and larger, less predictable events.

Common policies may include:

Why Does Your Program Need To Be Customized?

A beach resort with hurricane exposure will have very different needs than a mountain timeshare community, an urban resort or a property with golf, marina or spa operations. All of these details matter and you shouldn't settle for generic coverages. You need to build your insurance program around how your property actually operates.

A strong advisor can help the board or ownership team review:

How Do Timeshare Insurance Programs Differ From Resort Insurance Programs?

While timeshare, vacation ownership, and resort hospitality operations share many of the same property and liability exposures, each requires an insurance program tailored to its operational structure, ownership model, and governance responsibilities.

Timeshare and vacation ownership programs often involve additional complexities surrounding association governance, shared ownership interests, fiduciary responsibilities, and coordination between associations, management companies, and owners.

Resort hospitality programs, meanwhile, are typically centered on operational risk management, guest exposures, property protection, workforce risks, and business continuity for centralized hospitality operations.

For resorts and timeshares, your insurance program should support the full risk management strategy. The goal is to protect your property, the people who visit and work there, the property owners and board members, and the financial stability of your organization when something unexpected happens.

How Much Does Insurance Cost for a Resort?

The cost of resort insurance can vary a lot depending on your property's unique features and operations. Factors like the size of your resort, its location, the amenities and activities you offer, and your overall risk profile all play a role. For example, if your resort is in an area prone to natural disasters like hurricanes or earthquakes, your premiums might be higher because of the increased risk. Resorts with luxury facilities, extensive guest services, or specialized operations like spas, restaurants, or recreational camps usually need more comprehensive insurance with optional coverages tailored to your specific needs.

Other things that affect your cost include your resort's claims history, the coverage limits you choose, and whether your insurance is placed through admitted carriers or surplus lines. If you have strong risk management programs that include things like safety protocols and staff training, you may be eligible for better rates and terms.

To get an accurate quote, you'll need to provide detailed info about your resort’s operations, facilities, and exposures. At Gregory & Appel, we work closely with resort operators and national insurance carriers to assess your unique risks and design insurance solutions that give you value and peace of mind.

And when we say we show up, we mean it. In most cases, that means walking the property ourselves, spotting exposures that may not be obvious on paper, and helping you uncover coverage needs carriers might miss from a distance. Whether your resort is in Florida, California, Texas, Utah, Hawaii, or elsewhere, partnering with an experienced broker like Gregory & Appel means you can secure comprehensive coverage that protects your assets, employees, and guests from a wide range of potential events.

Why Is Risk Management So Important for Resorts and Timeshares?

Resorts and timeshares are built around creating a positive experience for guests and owners, but behind the scenes, they are complex operations with a wide range of exposures. A single property may include lodging, pools, restaurants, fitness centers, shuttle services, beach access, elevators, vendors, employees, board members and shared ownership interests. Each of those areas can create risk, and incidents such as slips, trips, and falls can occur on the premises, requiring appropriate coverage.

That is why risk management is so important. It helps resorts and timeshares move from reacting to problems after they happen to identifying potential issues early and making informed decisions before a claim, storm or major disruption occurs. A strong risk management strategy can help boards and property leaders:

For coastal resorts and timeshare properties, risk management becomes even more important as hurricane season approaches. Planning ahead gives boards and property managers time to review property values, assess wind deductibles, update emergency response plans and complete mitigation work before a storm is in the forecast. Once a storm is named, options may become limited.

Risk management can also help improve how the property is viewed by the insurance marketplace. Carriers want to understand more than the location and building values. They want to see that the property is well managed, that leadership understands its exposures and that there is a clear plan for reducing preventable losses. Your advisor should be helping you craft this underwriting narrative to help you with the most favorable program.

When a resort can show proactive maintenance, safety planning, thoughtful documentation and a clear understanding of its risk profile, it may be in a stronger position during renewal conversations. That can be especially valuable in a market where conditions can shift quickly after major weather events or large industry losses.

At its core, risk management helps protect more than the buildings. It helps protect the guest experience, the people who visit and work there, the financial health of the association or ownership group and the trust of owners who expect the property to be managed responsibly.

For resorts and timeshares, the right risk management strategy creates a clearer path forward. It helps leaders make confident decisions before the unexpected happens.

What Are the 2026 Trends for Resort Insurance?

Resort and timeshare insurance is moving into a more favorable market than we’ve seen in recent years. Carrier capacity is increasing, more insurers are entering the space and competition is creating better options for many boards and property owners.

One of the bigger shifts is the return of more “ground-up” programs. Instead of building coverage through several carriers across multiple layers, some properties are finding opportunities for one carrier to cover the full program. That can create a cleaner structure, easier administration and a more straightforward story for the board.

We’re also seeing deductible profiles improve. In recent years, many coastal and catastrophe-exposed properties had to accept higher percentage deductibles. Now, depending on the property, location and loss history, some programs are seeing wind deductibles come down to 2% or even move to a flat dollar amount. That is a positive trend, especially for boards trying to manage budgets and explain risk financing to owners.

At the same time, hurricane season remains the big variable. The Atlantic hurricane season officially runs from June 1 through November 30, and the National Hurricane Center notes that regular Tropical Weather Outlooks resume May 15. While the market is more competitive right now, an active wind season or major storm losses could shift conditions quickly. Colorado State University’s April 2026 outlook anticipates somewhat below-normal Atlantic hurricane activity, but early-season forecasts still carry uncertainty.

The best move for resort and timeshare properties is to use this window wisely. Review your program early, understand your deductible options, update property values and take mitigation steps before storms are in the forecast. A softer market can create opportunities, but preparation is still what gives boards the strongest position when it’s time to renew.

How To Choose an Insurance Broker for Resorts and Timeshares

Choosing the right insurance broker matters because resorts and timeshares do not fit neatly into standard insurance forms. These properties often combine hospitality, shared ownership, property management, board governance, guest amenities, coastal exposure and long-term capital planning. A broker who does not understand that mix may miss important gaps or accept policy language that does not match how the property actually operates.

The right broker should start with a full review of the coverages already in place. That means looking beyond premiums and limits to understand what the policies include, what they exclude and where coverage may be restricted. In recent years, some carriers have limited the types of coverage they are willing to offer, including flood, wind and other catastrophe-related exposures. For boards, knowing those details before a loss occurs is critical.

A broker with resort and timeshare experience can also help identify coverage opportunities that may be overlooked. For example, certain on-site property features, like sea walls, may be insurable in some cases. Many boards assume those items cannot be covered, but the answer depends on the policy, the carrier and how the coverage is structured. That is why it helps to work with someone who understands what can be negotiated, clarified or added.

Ongoing support should also be part of the conversation. A strong broker should help make the insurance program easier to manage, including aligning renewal dates when possible, keeping documentation organized and helping the board understand what is changing in the market. The relationship should not be limited to renewal season.

A good broker should also provide education throughout the year. Many resorts and timeshares have significant cyber liability, for instance, but may not carry cyber insurance or may not fully understand their exposure. Boards need practical guidance, clear explanations and resources that help them make informed decisions.

Risk management support is another important factor. The broker’s team should be willing to get out to individual properties, walk the site and help identify risks that could lead to future claims. That may include trip-and-fall hazards, maintenance concerns, life safety issues, contract gaps or areas where additional controls could reduce risk.

Questions To Ask When Choosing a Broker

What To Look for in a Resort and Timeshare Insurance Broker

Look for a broker with a niche focus. The insurance industry did not develop every policy form with timeshares or resort properties in mind, so the broker needs to understand how to adjust, negotiate and explain coverage to match the intent of the program. They should know how the property management company is protected, how the board is protected and where the association or ownership group may still have exposure.

The worst-case scenario is working with a broker who treats a resort or timeshare like a standard commercial property. These risks require a deeper review, stronger education and year-round support.

The right broker should act as an advisor, not a transaction partner. They should help the board understand the current program, uncover gaps, prepare for market changes and build a practical risk management plan that protects the property, the people who visit and work there and the long-term financial health of the organization.

Gregory & Appel: Help for Whatever Is Ahead

Here at Gregory & Appel, we help boards and property leaders like you look closely at what is covered, what may be excluded, and where hidden gaps could affect your property.

Our team brings a niche understanding of resort and timeshare exposures, from wind and flood to cyber liability, board protection, property management relationships, on-site risk concerns, and beyond. With the right guidance throughout the year, you can make more informed decisions before your program is put to the test.

Fill out the form below to download the Regional Guide to Risk. This guide shows what properties in your area should be watching, planning for, and discussing with the Gregory & Appel resort and timeshare team.


This content is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice.

Cyber Risk at Home: What Successful Families Should Do This Year 

While many people think of cyber risk as a business issue, affluent families are often targets because of their personal, financial, and lifestyle information connected to their accounts and devices. Unfortunately, a cyber incident can affect far more than a laptop or email account. It can disrupt access to financial records, expose private information, trigger fraudulent transfers, or create expensive cleanup costs.  
 
Even more unfortunately, cyber risk is not hypothetical, especially for high-net-worth families and family offices. Deloitte reports that 43% of family offices globally said they experienced a cyberattack in the last 12 to 24 months. In North America, that rose to 57%. For family offices with more than $1 billion in assets under management, it rose to 62%. Among those that were attacked, one-third suffered loss or damage. The most common impacts were operational damage, including loss of confidential or sensitive data, at 20%, and financial loss at 18%. 
 
Luckily, there are things you can do to mitigate your risk and get help when incidents occur. Cyber insurance is designed to help with those losses and connect you with resources when something goes wrong. In this guide, we’ll cover common cybercrimes, tips to protect your family, and coverage you should consider. Let’s get started. 

What Are Common Cybercrime Tactics? 

Cybercriminals use a range of tactics to steal money and personal information, often relying on manipulating human behavior. Understanding how these schemes work can help families spot warning signs earlier and respond more carefully.  

Deepfakes 

AI-generated video or audio used to impersonate someone in your family or network. This can include something posted in an attempt to hurt you or your company’s reputation or used to gain illegitimate access to bank accounts or other sensitive information.  

Deepfake Example

You receive a phone call from your son. It sounds exactly like him and came from his phone number. He is extremely upset because he’s lost his passport and wallet while traveling. He needs you to wire him enough money to get a plane ticket home. Scammers can actually use social media videos to create extremely realistic deepfakes like this and use spoofing devices to make it appear to come from a specific number.  

Phishing

Emails, texts or phone calls that appear legitimate but are meant to fool someone into giving up login information, financial details or other personal data, or into clicking a harmful link or attachment.  

Phishing Example  

It’s a Tuesday, and you just got a text from your bank asking you to verify a recent transaction. The message has a link and says that urgent action is needed. You click on it, worried your card is going to get shut off, and it takes you to a login screen where you enter your username and password. Then something goes wrong and your login doesn’t go through. You shrug, thinking it’s just a normal error. Unfortunately, that message and website were both fake and now bad actors have your bank username and password.  

Ransomware 

Malicious software that locks files, devices, or systems and blocks access until a ransom is paid. 

Ransomware Example 

A household employee opens what appears to be a routine invoice. The file installs ransomware that locks the family’s shared drive, financial records, travel details, and personal documents, leaving your family unable to access important information. A message appears demanding payment in exchange for restoring access. 

Data Breaches 

Sensitive, confidential, or private information that is accessed, exposed, or stolen by someone who should not have it. This can happen through a hacked account, a weak password, a phishing scam or even an accidental disclosure. 

Data Breach Example 

A private bank experiences a cyberattack that exposes confidential client records. For a high-net-worth family, that could mean sensitive financial documents, account information, personal identification and even estate planning materials end up in the wrong hands, creating both financial and personal risk. 

Confidence and Romance Scams 

A scheme where a criminal gains someone’s trust through an online or personal relationship, then uses that connection to ask for money, collect sensitive information, or carry out fraud. 

Romance Scam Example 

A family member begins an online relationship with someone who appears charming, successful, and trustworthy. After months of frequent messages, the person claims to be dealing with an urgent financial problem and asks for help with a wire transfer. In some cases, the scammer may also gather personal details about the family’s lifestyle, travel plans, or financial resources, which can open the door to larger fraud or security risks. 

While these tactics may seem simple, the truth is that cyber criminals are constantly refining and improving their scams and can catch even educated individuals.  

Tips To Protect Yourself and Your Family 

Despite bad actors becoming more and more sophisticated with these types of tactics, the good news is that many cyber risks can be reduced with a few thoughtful habits. Small steps can go a long way toward protecting your personal information, finances, and privacy. 

Pause before you act 

Be wary of emails, texts or calls that feel urgent, unusual or too good to be true. Scammers often try to create panic so people react before thinking things through. Slow down, ask questions, and confirm the request before taking any action. 

Verify payment requests every time 

Before sending money electronically, confirm the recipient through a trusted method, even if the request appears to come from someone you know. A familiar contact can still be compromised. 

Share less personal information 

Only provide sensitive details when there is a clear reason to do so. If someone asks for information like your Social Security number or banking details, ask why it is needed and whether there is another way to verify your identity. 

Confirm identity before sharing information 

Scammers can now use technology to imitate the voice of a family member, advisor or other trusted contact. Before approving a transaction or sharing private information, confirm the person’s identity in person or by calling a number you know is legitimate. Some families also use a shared password or security question for added protection. 

Use stronger passwords 

Avoid simple passwords tied to birthdays, pets, names, or other personal details. Choose long, unique passwords for each account, ideally with a mix of letters, numbers, and symbols. A trusted password manager can help keep them organized and secure. 

Turn on multi-factor authentication 

Add an extra layer of protection to your accounts whenever possible. Multi-factor authentication makes it harder for someone to get in, even if they have your password. Use it on email, banking, social media, health care portals, and any other account that stores personal information. 

Be thoughtful about social media 

Who you add and what you share online may be riskier than you realize. Do not accept friend requests, follows or messages from people you do not know. Criminals often use fake profiles to gather information and build trust before attempting fraud. Avoid posting details that expose your location, routines, travel plans or other personal information. Pay attention to what appears in the background of photos and videos and use strict privacy settings to limit who can view your content.  

Review app and privacy settings regularly 

Check what information your social platforms, apps, and third-party tools can access. Adjust permissions to match your comfort level, especially for apps connected to your contacts, photos, location, or account data. 

Protect your devices 

Phones, tablets, and computers can all be targeted. Use reputable antimalware software and keep your systems updated so you are better protected against viruses, spyware and ransomware. 

Freeze your credit or set fraud alerts when appropriate 

These tools can make it harder for someone to open new accounts in your name. They are worth considering if you want an added layer of identity protection. 

Monitor your digital footprint 

Keep an eye on unusual account activity, exposed passwords, and leaked personal information. Regular monitoring can help you catch issues early before they become more serious. 

Keep work and personal accounts separate 

For executives, family office staff, and others with access to sensitive information, it’s best to maintain clear boundaries between business and personal communications, logins, and devices. 

Stay current on new threats 

Cyber risks change quickly. Keeping up with common scams and new tactics can help you recognize a problem sooner and respond more carefully. 

Bring in outside experts when needed 

High-net-worth families and family offices may benefit from professional cybersecurity support. Specialists can assess vulnerabilities, test defenses, monitor for threats and provide training for family members and staff. 

Coverage To Look For 

Cyber insurance is not a substitute for strong cyber habits, but it can be an important backstop when prevention fails. For high-net-worth families, the right policy can help cover financial loss, support recovery and provide access to professionals who know how to respond when a cyber event affects your privacy, your accounts or your day-to-day life. The right policy can help your family recover faster and with more support when an incident occurs. Here’s some things to keep in mind when looking for coverage:  

Gregory & Appel: We’re Here to Help 

Cyber risk is personal, and for successful families, the impact can reach far beyond a single account or device. It can affect your finances, your privacy, and your peace of mind. Taking thoughtful steps to protect your information is a smart place to start, and having the right coverage provides valuable support when something goes wrong. 

At Gregory & Appel Insurance, we help families think through risk from every angle. That includes understanding where cyber exposures may exist, reviewing whether current protections still fit your needs and helping you find coverage that supports your lifestyle. When the stakes are high, it helps to have a partner who knows how to ask the right questions and guide the conversation. If you’re wondering whether your current approach still fits your needs, we’re here to help. Fill out the form below to talk to one of our experienced private client advisors.  

This content is not intended to be exhaustive, nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice. 

What Are the Disadvantages of Captive Insurance for Your Business?

Think of captive insurance as moving from "renting" your insurance to "owning" it. Instead of sending premiums to a traditional carrier, you’re basically building your own in-house insurance company. It gives you the driver's seat when it comes to coverage and costs, but like owning any business, it comes with a few extra responsibilities you’ll want to be ready for.

The main purpose of a captive insurance company is to cover risks that are unique, difficult to insure, or inefficiently priced in the commercial market. When managed well, captives can deliver cost savings, improved risk management, and greater control over coverage.

However, captive insurance may not be the right fit for every business. Like any alternative risk financing strategy, it involves tradeoffs. Understanding the advantages and disadvantages of captive insurance is essential before deciding if a captive is appropriate for your organization.

Below are the most common challenges and considerations businesses encounter when evaluating captive insurance.

What Are the Disadvantages of Captive Insurance?

Initial Setup and Costs

Let's talk about the biggest hurdle for forming a captive insurance company: the startup costs. Building a captive isn’t quite as simple as opening a new bank account. You’ll need to factor in things like feasibility studies, licensing fees, and hiring a management team to keep the gears turning.

In addition to these costs, captive insurance companies must meet regulatory capital requirements set by their chosen domicile. This capital ensures the captive can pay claims and remain financially stable, but it may require a significant cash or collateral commitment.

These funding requirements can be a significant burden. Even when the long-term economics are favorable, the short-term financial commitment can be a significant hurdle.

Regulatory Requirements for Captive Insurer

Captive insurance companies are regulated entities, and the regulatory environment can be complex.

Each captive operates under the oversight of a regulatory authority in its chosen domicile. Regulatory requirements vary by jurisdiction but typically include:

Failure to meet these requirements can result in penalties, fines, loss of licensure, and reputational harm to the parent company.

Tax compliance is another area to navigate with captives. Captive insurance companies must be structured and operated carefully to maintain favorable tax treatment, including compliance with Internal Revenue Service guidelines on risk distribution, premium pricing, and claims activity. Poor execution can undermine tax advantages and create unexpected exposure.

Insurance Company Operations and Management

When you start a captive, you’re not just a policyholder anymore; you have all the responsibilities of an insurance company. This means you are responsible for handling claims, picking investment strategies, and staying on top of paperwork.

Your captive should also align with your company’s broader business strategy. Decisions about risk retention, coverage limits, and claims philosophy have real financial consequences. Poor alignment between business objectives and captive operations can lead to volatility and inefficiency.

Forming a captive is definitely not a hands-off solution. It requires a bit of a learning curve, but that’s exactly where having a brokerage comes in to help you navigate the tricky parts.

Increased Need for Risk Management

Captive insurance shifts risk back to the business, making a strong risk management practice essential.

With a captive, you genuinely have "skin in the game" with your risk policy. If your safety programs are well defined and claims are low, you’re more likely to keep the profits. On the flip side, if safety slips, it hits your bottom line directly. This accountability is a huge plus, turning safety from a tedious compliance chore into a strategic way to save your business money.

Because captive insurance companies retain risk, poor claims experience directly affects financial performance. High losses, unmanaged exposures, or inconsistent safety practices can erode underwriting profits and strain capital reserves.

Why Do Businesses Still Choose Captive Insurance?

Given these challenges, it is reasonable to ask why businesses still pursue captive insurance. But for the right organization, the advantages often outweigh the disadvantages.

Captive insurance can deliver:

Captives also encourage better risk behavior. When companies benefit directly from improved safety and lower claims, risk management becomes a strategic advantage rather than just a compliance exercise.

That said, captives are not for everyone. Businesses considering this path should have:

This is where working with an experienced insurance broker and captive advisor can make a difference. A thorough feasibility study, realistic financial modeling, and a clear understanding of responsibilities can help determine whether a captive or an alternative, such as a group captive, is the right fit for your organization.

Captive Insurance: A Strategic Tool, Not a One-Size-Fits-All Solution

Captive insurance can be a powerful risk financing strategy, but it is complex.

Initial costs, regulatory requirements, operational demands, and the need for strong risk management are important considerations for any business. For some organizations, these challenges outweigh the benefits. For others, they provide greater control, transparency, and long-term value.

The key is to approach captive insurance with a clear understanding of its complexities.

At Gregory & Appel, we help businesses objectively evaluate captive insurance by considering both advantages and disadvantages to determine alignment with their goals, risk profile, and financial strategy.

If you are considering captive insurance or would like to explore alternatives such as group captives, we are available to discuss your options. Fill out the form below to take the next step.

This content is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice.

Understanding the Benefits of Captive Insurance

A captive insurance company is formed to insure the risks of its parent company or a group of related businesses. By funding their own insurance company, businesses gain flexibility and long-term financial advantages.

Captives can be structured to provide insurance coverage to a broad range of risks, including general liability, auto, casualty, property, workers’ compensation, and specialized exposures such as professional liability or cyber risk. All areas that can be difficult or costly to insure through traditional markets.

Captive programs can support more effective risk management by allowing businesses to tailor insurance coverage to their needs, allocate costs more accurately, incentivize loss control, and manage risk in alignment with actual operations.

Captive insurance companies are subject to regulation, including requirements for capitalization, solvency, financial reporting, and actuarial review. This oversight adds complexity but promotes financial discipline and long-term stability.

For businesses seeking to reduce reliance on commercial insurers, gain greater control over premiums, and implement a strategic approach to risk, captive insurance with both its advantages and disadvantages is a great option to consider.

What Are the Benefits of a Captive Insurance Company?

Captives are attractive for a reason! Benefits include:

How Does a Captive Insurance Company Make Money?

Captive insurance companies primarily make money in two ways: underwriting profit and investment income.

Underwriting profit results when premiums collected exceed claims and operating expenses due to effective risk management. Investment income is generated by investing unearned premiums while claims are pending.

These revenue streams allow businesses to retain value that would otherwise go to a traditional insurer. Success depends on strong governance, adequate capitalization, disciplined risk management, and compliance with regulatory and tax requirements.

Is Captive Insurance Right for You?

Captive insurance can offer significant benefits, but it’s definitely not a "one-size-fits-all" solution. It’s a strategic move that requires a long-term mindset and a real commitment to safety. Before you dive in, you’ll want to look at your financial goals and your appetite for managing risk. It’s about weighing those great advantages against the trade-offs to see if it’s right for your business.

Ready to Explore Captive Insurance?

At Gregory & Appel, we’re here to help you pull back the curtain on captive insurance. Our captive experts look at your goals and unique risks to see if a captive program is the smartest move for your future.

Whether you’re interested in forming your own standalone captive or joining forces with a group captive, we’re ready to walk you through it. Let’s start the conversation and find the strategy that puts you back in control.

This content is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice.

Captive Insurance: Advantages and Disadvantages

If you’ve ever wondered how some businesses manage to keep their insurance costs down while still having solid coverage, captive insurance might be the secret sauce. Simply put, a captive insurance company is like having your own in-house insurance provider, created just for your business and its unique risks. It’s a smart, flexible approach that’s gaining popularity as an alternative solution and choosing the captive route can be a strategic option for businesses seeking greater customization and cost control. In this article, we’ll walk you through the key advantages and disadvantages so you can decide if captive insurance is the right fit for your business.

What Are the Advantages of Captive Insurance?

At Gregory & Appel, we often see businesses benefit in some pretty meaningful ways when they choose captive insurance. We’ve seen captive insurance arrangements help companies:

What Are the Disadvantages of Captive Insurance?

While captive insurance offers many benefits, we believe it’s important to be upfront about the fact that it may not be suitable for every business. Here’s a few points to consider when forming your own captive:

The other option is to join a captive insurance program. Here are a few potential drawbacks to be aware of:

Whether you form, join, or stick with traditional insurance, getting your business “captive ready” can really pay off. By putting solid risk management practices in place, you make your company stronger and keep your claims history looking good, which helps your overall risk profile. Staying financially stable also puts you in a better spot with insurers and gives you more control over your costs and risks, no matter what kind of insurance you use. Plus, being prepared means you keep your options open, so if a captive insurance program feels like the right move down the road, you’ll be ready to take it on.

Considerations for Captive Insurance

Before jumping into captive insurance, it’s important to take a close look at a few considerations. It’s not something to take lightly! Success means committing to managing risks well and having the right funding. Doing a thorough feasibility study upfront, including a detailed cost benefit analysis, can really help you get the most out of a captive insurance program while avoiding the common pitfalls. Before starting your own captive, factors you should consider are:

Most of these considerations involve starting your own captive insurance company, which can feel like a big commitment with plenty of moving parts. The initial steps of captive formation require meeting financial requirements and regulatory capitalization set by the domicile's regulatory body. But here’s the good news: you might not have to go it alone. You can partner with an experienced insurance broker like Gregory & Appel to help you along the way.

Or, many businesses choose to join an existing group captive insurance program instead. This approach lets you tap into the benefits of captive insurance without shouldering all the startup costs and administrative burdens yourself. It’s a way to share risks and resources with other like-minded companies, making it a more accessible and manageable option for businesses that want to explore captives but aren’t ready to build one from scratch. So, if the idea of forming your own captive feels overwhelming, joining a group captive could be a smart alternative to consider.

How Do Captive Insurance Companies Make Money?

Captive insurance companies make money mainly in two ways: through underwriting profits and by earning investment income. When your business pays premiums to your captive, some of that money is set aside as unearned premium reserves until claims are paid out. During that time, the captive invests these funds, generating investment income that can really boost its financial health. Since claims can sometimes take a while to be paid, this investment income becomes a crucial part of the captive’s earnings.

Other financial factors to be aware of with captive insurance companies are:

By forming a captive, companies get to keep the underwriting profits and investment income that would normally go to traditional insurers. This blend of cost savings, better cash flow, and more control over finances makes captive insurance a compelling option for businesses looking to take charge of their insurance costs and risk management.

Gregory & Appel: Your Partner for Captive Insurance Success

While captive insurance requires a commitment to risk management, funding, and careful evaluation of regulatory and capital requirements, it can be a powerful alternative for businesses seeking cost savings, improved risk management, and increased flexibility. With Gregory & Appel’s expertise, you gain access to customized coverage options and solutions you won't find in traditional insurance markets.

Ready to find out if a captive insurance program is the right fit for your business? We'd love to talk with you and help you explore your options. Fill out the form below to start the conversation with Gregory & Appel today.

This content is not intended to be exhaustive nor should any discussion or opinions be construed as legal advice. Readers should contact legal counsel or an insurance professional for appropriate advice. Gregory & Appel is neither a law firm nor a tax advisor; information in all Gregory & Appel materials is meant to be informational and does not constitute legal or tax advice.