If you are like most, the answer is probably “never.” Most of us buy our first insurance policy when we buy our first automobile. The second when we buy our first home. More often than not from the same insurance agent. Why not? It was easy. 

Fast forward 5, 10, 15, 20 years—children, an au pair, a newer larger home, a vacation home, a rental property or two, a trust or LLC to hold title to these properties, a liquidity event, board positions, world travel. Sound familiar? Life has changed but your insurance likely has not. And equally as likely, your insurance agent hasn’t taken the time to help you adjust your program as these events have unfolded.  

Each of these events introduces a new and different risk into your life and unless properly addressed could put your hard earned assets in jeopardy. With the right insurance advisor, insurance carrier, and properly designed insurance program, these risks can be easily mitigated and it needn’t cost any more money to do so.


Do I have a personal umbrella? What does it really cover?  What’s my limit? Is that enough? 

What if I travel domestically or internationally and rent a vehicle? How would my insurance respond? Would it even respond?

What is my homeowners deductible? Would it ever be waived? When is the last time that I submitted a homeowners claim? Have I ever?  Should I ever?

If I lost my home in a total loss, would I be required to rebuild? Or could I take the cash value in my policy instead?

I have an old home. Would my insurance rebuild my home to current code or would that expense come out of my pocket?

What exactly is a flood? Or an earthquake? Are these events covered by my insurance? If not, should I add coverage and would it even be cost effective to do so?

I have an au pair and a housekeeper. 
What if either were injured on the job?
Am I responsible for their lost wages and rehabilitation, potentially indefinitely? What if my employee sues me?

What if I lose a piece of jewelry? Why if my housekeeper damages a piece of art? Or it falls off the wall in an earthquake? Or is damaged in a hurricane?  Am I covered?

Am I unknowingly putting my personal assets at risk? I hold both not-for-profit and for-profit board positions. Will my own insurance respond to a claim made against me?

How much would I receive for my car in the event of a total loss? How would the deductible apply, or would it apply?   

When do I add my children to my automobile insurance policy? When is the right time to take them off?

My home is titled to my trust. If someone were to be injured at my home, is my trust exposed?

What if a sewer or drain backs up inside of my home? I think that I am covered, but am I?

Will my insurance carrier visit my home in advance of a wildfire or a hurricane to make it safer? And not charge me for doing so?



The process is actually very simple, and for some it’s even fun.

Although not an exhaustive list, asking yourself these questions may be the start to having an intelligent conversation about the risks that you or your family faces and how insurance can help. 

To learn more about our process, please visit How We Work.