Foundress Fridays: Chelsea Fabbro, Agency Owner at American Family Insurance

Chelsea Fabbro owns Cabanillas Headquarters at American Family Insurance.

“I own an insurance agency where we specialize in making an insurance purchase an understandable and empowering experience for our clients. We provide an agency community where new and current clients can trust that their individual insurance needs are being provided with integrity and their concerns thoughtfully handled. We focus primarily on the home, auto, umbrella and life insurance needs of our clients.”

AZF: Did you always know that you wanted to be entrepreneur? If not, when did you realize that it was the right path right for you?
CF: I did not always know but realized it by working for a female business owner who inspired me to see myself and my future in a new way. It was my first professional job and I was hired to answer phones for her insurance agency. This was my starting point but from there she encouraged and mentored me to take on a much bigger role within her agency. I was captivated, seeing my efforts turn into results and thought to myself “I am going to do this one day.”

AZF: What excites you most about being an entrepreneur?
CF: The ability to write my own story, and the freedom to win and lose on my own terms. There is something unique about knowing that even in the hardest of times, my decisions got me there and I get to decide how I will get through it.

AZF: How do you feel best supported?
CF: There are so many types of support on this journey that I greatly value, both big and small. I certainly benefit from the big stuff like my family and friends supporting me while I invest a lot of time, energy and financial resources to make this happen. I equally benefit from the smaller supportive moments or interactions with clients and colleagues. I am re-energized when a client has gone out of their way to share appreciation for our work, or a fellow entrepreneur asking, “How are you?” in a way that only you two really understand. Feeling like I have a community within my agency and one here locally through The Foundress gives me a sense of belonging and grounding no matter how crazy or stressful it all gets.

AZF: What is your “life motto”?
CF: I have a few life mottos that come to mind right away. The first being, “Never give up,” this motto is a must when trying to build a business and making endless sales calls. The second being “safety first,” this just makes sense for an insurance gal like myself. The third, and my personal favorite, “I can do hard things”, you must be your biggest believer and continuously remind yourself of your strength.

AZF: Describe your perfect Saturday morning.
CF: I would start with the breakfast routine I have with my husband. This consists of him making delicious cappuccinos and us eating a varied pastry item that he is ridiculously excited about; it is a contagious joy! I would then go to a themed Spin class, preferably 90’s Pop music. After this sweat sesh, I would head home and relax on the couch watching a true crime series.

AZF: What motivates you to keep going amidst of the challenges that come with being an entrepreneur?
CF: The belief that my agency has the power to make a positive impact in my small pocket of the world, and even beyond. I am motivated by three significant passions, which are, to create a space for fellow women to start and build careers within my agency, using my agency to spread kindness throughout our community, and protecting our clients with the proper coverage and insurance education they need to advocate for themselves when it matters most.

AZF: What’s one piece of advice you’d give to a young entrepreneur who is just starting out?
CF: Seek out rejection. It is so beneficial to be wrong more than you are right when you are just starting out because it is how you get to the good stuff. It is important to realize that trying and failing to your next best idea is a part of the journey and to not let it be why you feel like crap about yourself or question if you should even try anymore. You can do more than you know with the strength that comes after you push through the momentary feelings of failure, shame and embarrassment after messing up. It is your fuel. That is your hard-earned foundation, that is where you build the stamina to choose you and believe in YOU!

Follow Chelsea on Instagram and LinkedIn

About The Foundress

The Foundress is a creative community of female entrepreneurs established by Coley Arnold and Lindsey Holt, owners of Junk in the Trunk Vintage Market. The women-led networking group currently has over 120 members who receive exclusive access to mentorship from experienced female entrepreneurs and industry leaders; community gatherings that feature expert speakers and the opportunity to connect with like-minded women; as well as monthly Mastermind Groups where members can brainstorm and collaborate together.

Every Friday AZF will spotlight a member of The Foundress and her business in the online series Foundress Fridays. Learn more about The Foundress and join the community at

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