Our April Woman Crush, Chiara Figueroa, Is Teaching Us Why We Should Acquire Boring Businesses

I had the pleasure of working with Chiara at Bloomingdales many moons ago. Before she arrived, my friend had told me that she was transferring from the Scottsdale location in Arizona, which is where I’m from. Excited to already have something to talk about once we met—I’ll never forget when she arrived. She was this big ball of fun, loving, and vivacious energy! A Leo, for sure! Over time, we became friends and would do hikes, lunches, and dinners together. I always admired her determination, discipline, and assertive attitude. Additionally, I loved her passion for growth and how she was always stretching her mind by learning about new subjects that piqued her interest.

One of my favorite memories with Chiara is a lunch break moment we shared together in the MAC office. We were talking about something she had learned in one of her MBA classes. I listened to her passionately recite the new information she had gained and how it would help her become a better leader. That moment triggered a series of events in my life—first, the thought of, wow, she’s so intelligent— how do I become more like her? Not in the sense of how I abolish my individuality and adapt hers, but more in the sense of how I attain that passion for learning and apply it to my life. How do I acquire the skills and habits she has that I am so fond of? Then it triggered action because that day in the office—as I was admiring her as she taught me how to become a better leader—I decided to go back to school and later enrolled at The Los Angeles Film School, where I got my degree in Entertainment Business.

Your friendships matter because they have the power to encourage and inspire you, or they can hinder your growth and keep you from fulfilling your purpose. Choose Wisely.

Although we are miles apart and both of our lives get busy, it’s like no time has passed when we make ourselves back into one another’s orbit. Chiara's friendship is one I will always truly cherish, and I am so honored to feature her as this month’s woman crush and highlight her journey as she steps into a venture we can all learn from.

Tell us About Yourself!

To all the ladies in the place with style and grace, nice to meet you! I’m Chiara Figueroa, a Latina currently residing in Phoenix with my business partner as we pursue our dreams of purchasing recession-proof businesses. For my W-2, I am a maestro of global retail experiences, shaping end-to-end customer journeys from strategy to execution, turning transactions into connections, driving brand loyalty and success for a LVMH brand. The goal is to take what I have learned in my corporate career and apply those unfair advantages in successfully owning a handful of “boring businesses.”- if you want to hear more about our journey, go listen to the Deal Diary podcast (shameless plug!).

What inspired you to start the Deal Diary podcast and begin acquiring “boring” businesses? 

To be able to buy back my time, how I spend it and build generational wealth. Owning recession-proof, “boring businesses” can give you the ability to do just that; ~10,000 baby boomers are reaching retirement age each day in the United States. Additionally, with mergers and acquisitions being such a male-dominated industry, Ella and I wanted an outlet where we could share our journey of wins and pitfalls while also offering value with features from industry experts. We hope our stories resonate and help others who are also navigating m&a, but more importantly….inspire the girlies to take the leap and do the thing they believe in but looks crazy to most people.


Watch our IG Live Discussion: Mastering the Art of Acquiring Boring Businesses


What unique opportunities might arise for single women in owning "boring" businesses compared to more glamorous ventures?

"Boring" businesses can cater to niche markets with specific needs, allowing single women to specialize and differentiate themselves in the market. For example, there is a landscaping distribution company in Phoenix and everyone knows this company because it’s been owned for 20+ years by a mother and daughter. Being the only women-owned business selling rocks and sand to B2B companies in town?! Sounds like an opportunity to have community impact and leverage that as a selling point to do speaking engagements to share your expertise! 

In what ways might owning a "boring" business empower single women to challenge traditional gender roles in entrepreneurship?

Owning a "boring" business can be powerful by breaking stereotypes, achieving financial independence, and inspiring others to follow suit. Being at the helm of a business, even if it's in a less glamorous industry, gives women a platform to exercise leadership and authority. This challenges the notion that women are better suited for supportive or subordinate roles in business, showing that they can lead and manage enterprises effectively.

How might the steady income from a "boring" business provide single women with financial security and independence?

People need auto shops, laundromats, towing, ect. so you can count on consistent revenue streams. Additionally, it empowers you to take control of finances, reduce reliance on others, facilitate long-term planning, and offer career flexibility. We also just learned there are certain industries that have requirements for a percentage of government contracts to go to female-owned businesses - I love to see it!

What risks and challenges should single women be aware of when considering the purchase of a boring business, and how can they mitigate them?

Challenges are obvious in this male-dominated industry, there is skepticism or lots of  “mansplaining.” It was important for Ella and I to learn how to reroute a conversation to save both parties time and quickly communicate long-term vision while speaking with conviction. For business in general, your deal team is everything, so don’t just settle on the first people you meet.  It’s important for Deal Diary to have an all-female deal team, so we took our time selecting our banker and lawyer - still interviewing CPAs with m&a experience if anyone has a referral! 

Please drop your referrals in the comments.



What words of wisdom do you wish to share with other Single Women Entrepreneurs balancing 9-5 jobs?

Don’t underestimate networking events or joining local female communities. We have made 5x more connections and are that much closer to our first deal because of the support we have received from those we have met. Also, don’t forget about your immediate network! Tell everyone you can what you are doing! I thought I had no one, but Ella and I found an off-market deal, all from having a random conversation with a family member.  I’m a believer now, your network is your net worth!

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Meagan A. Culberson

Meagan A. Culberson is the Creator and Founder of SingleGirClub.com, a lifestyle brand that advocates for the empowerment of single women. With a degree from The Los Angeles Film School and impressive experience working with renowned brands like Chanel, Clarins, and Lancôme, Meagan has earned a reputation as a skilled professional in her industry. 

She is dedicated to making a positive impact on the world. When she isn't working on Single Girl Club, she organizes convivial events that encourage the establishment of authentic relationships. She has organized successful fundraisers for important organizations such as The Ghetto Film School, Art in Common INC, Single Moms Planet, and Los Angeles City Council Candidate Dulce Vasquez. She resides in the vibrant city of Los Angeles, CA.

https://substack.com/@meaganayana
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Our March Woman Crush, Minaa B, Is Showing Us How We Can Heal in Community