How to get your boss to pay your medical bills with High Fiving Dollars Sarah Li Cain


High Fiving Dollars' Sarah Li Cain had a contract that said her company had to pay her medical costs, but when she got pregnant, she and her husband had to come up with a strategic plan to actually collect the cash they were owed. Plus her tips on how to make sure you get the luxuries you want in life, without feeling nickel and dime’d

In Sarah’s money story you will learn:

-The challenge Sarah faced when pregnant as a teacher in China

-How the healthcare system there required employees to pay upfront, and then fight to get re-imbursed

-The financial risk that created for Sarah and her colleagues

-How careful documentation helped to get her money back

-The technique Sarah used to negotiate with her employer and her boss for both her healthcare needs and those of her colleagues

In Sarah’s money lesson you will learn:

-That is is essential to read your contract when you take a job, and not assume it will provide things, even if it is the law.

-The importance of standing your ground when you are entitled to something. 

In Sarah’s every day money tip you will learn:

-Why she is willing to pay more for homes that have the amenities that are important to her and her family

-The importance of building in value-add activities and facilities into your home or community, so you don’t have to spend extra cash to have services and other things that you value but might not pay for on an individual basis. 

In My Take you will learn:

-The importance of documentation especially when you need to be re-imbursed by an employer

-The tools and apps I personally use for document management and scanning

-My take on lifestyle amenities where you live

-The crazy and outrageous amenities that may not be worth paying for in many cases

Episode Links

Learn more about Sarah at

Listen to her podcast with Garrett Philbin (from Be Awesome not Broke) Beyond the Dollar!

Follow Sarah Li Cain!

Twitter: @sarahlicain




The tools I use to  store and track documents are




The App I use to scan documents is Jotnot

Here’s a fun article from on The Most outrageous amenities in NYC apartments

Here is one from on over the top amenities

And here is one from on What Building Amenities to New Yorkers Want Most?