As an AI language model, I don't have personal experiences or thoughts. However, I can provide you with some general insights on how often business owners may think about their insurance and the factors that can influence their decision-making process.

The frequency with which business owners think about their insurance can vary depending on various factors such as the nature of their business, industry regulations, and personal preferences. Here are some considerations:

1. Annual Review: It is common for businesses to review their insurance policies on an annual basis. This allows them to reassess their coverage needs, evaluate any changes in their business operations or risks, and compare insurance options from different companies.

2. Changes in Business: Significant changes in a business can prompt a review of insurance coverage. For example, if a company expands its operations, hires more employees, acquires new assets, or launches new products/services, it may need to adjust its insurance policies accordingly.

3. Industry Regulations: Certain industries have specific insurance requirements mandated by regulatory bodies. Businesses operating in these industries may need to regularly review their insurance to ensure compliance with regulations.

4. Claims or Incidents: Experiencing a claim or incident can draw attention to the adequacy of insurance coverage. Businesses may reevaluate their policies to ensure they are adequately protected against similar risks in the future.

5. New Insurance Companies: Some business owners may explore new insurance companies or policies annually to compare coverage options, pricing, and customer service. This can be particularly relevant if a business has experienced changes or if they believe they can find better coverage or rates elsewhere.

6. Technology and Apps: The availability of insurance apps can make it more convenient for business owners to manage their policies, access documents, file claims, and communicate with their insurance providers. Utilization of such apps may vary depending on the preferences of individual business owners and the features offered by their insurance company.

7. Agent vs. Direct Contact: Business owners have the option to work with a local insurance agent or directly contact insurance companies. The choice depends on personal preferences, the complexity of insurance needs, and the level of service and expertise desired.

It's important to note that these considerations can vary widely from one business owner to another. Some may be highly engaged with their insurance needs, while others may delegate the responsibility to trusted advisors. Ultimately, the frequency of thinking about business insurance will depend on the individual circumstances and priorities of each business owner.