Meet Sisters Maija Benincasa and Anne Stockstill, of Benincasa Milano

Tell us about Benincasa Milano.

Benincasa Milano is a line of luxury heels with made-to-measure custom insoles. Our patent-pending technology takes a foam impression of your foot to create a pair of Italian-made pumps, boots or sandals made just for you. We are most proud of our customer’s feedback that reinforces our mission, with reviews like, “the most comfortable, stylish heels ever.”

How did you and your sister get started?

Benincasa Milano was born when Maija decided to quit her corporate job in brand marketing and move to Milan to study the art of shoemaking. She had a singular focus: to create a beautiful shoe that didn’t hurt like hell. She studied with Italian pattern makers and artisans to understand how to create more comfortable designer shoes. She was living in Los Angeles at the time but decided to move to Dallas temporarily to live with her sister Anne while she developed the business plan. While in Dallas, Maija partnered with a biomedical engineer at UT Southwestern to develop the patent-pending insole technology. Just before launch, Maija invited Anne to join her on the new venture and the sisters decided to focus their business on the local Dallas market. Anne’s background in sales and engineering was the perfect pairing to Maija’s work in product development, and they started selling shoes in November 2017.

What is the best thing about working with your sister?

Working with my sister is fun. It makes the business feel less like work when you have your sister by your side. We travel a lot and produce a lot of events, and quite frankly it’s not always sexy. Having my sister in those moments makes it feel more like an adventure. I’m grateful to be able to totally be myself and be accepted and understood. There’s no “get to know you” phase because we have a 34-year relationship to leverage. We know each other strengths and weaknesses, communication style, etc.

Are you and your sister similar or different? How does that help your business? 

We are very different and our complementary personalities and skill sets balance our business. I am very analytical, strategic, and a big picture thinker. I am more of a visionary that pushes the business forward. Anne is very detail-oriented and executional. She holds down the fort and makes the business run day to day, while I am working on the next big thing. Both are crucial to our survival.

Can you share a funny childhood story about you and your sister? 

When we used to travel as a family, Anne and I always packed a separate, shared suitcase just for shoes. This drove our dad insane. We are the same size, so we figured the more the merrier. The shoe suitcase must have been an omen!

What’s your funniest story in working with your sister? 

I once did a photoshoot for D Magazine in Anne’s bathtub. We needed a set and she offered her house. Somehow, I ended up wearing heels in her bath tub. It was really fun and a good memory from the early days of the business.

What is the saying/phrase your sister always says? 

“Gotcha” and now I’m saying it! Gotcha, gotcha, gotcha all day long.

What is your favorite thing about your business? 

Our customers. The direct-to-consumer nature of our business model lets us play retailer as well, and we love interacting directly with our customers on a daily basis.

What is your biggest short-term and/or long-term goal for your business? 

Our long-term goal is to change the way women think and feel about wearing shoes. We want to empower women to move with ease and shed the belief that you have to be in pain to feel fashionable and beautiful.

What has been the biggest challenge along the way? 

My biggest challenge is sticking to the vision despite the varying feedback I get from potential investors, customers, and colleagues along the way. It’s hard to know when to act on feedback versus take it with a grain of salt. This goes back to following your intuition and not letting others get you off track.

What advice would you give an entrepreneur who is just starting out? 

Make sure you are really, REALLY passionate about the product or service you want to create. The more your business is tied to a mission or purpose, the more likely you will be to push through the tough times.

How are you finding balance? 

I am passionately dedicated to wellness. I make time every day to cook fresh food, exercise, meditate, and keep a gratitude journal. Starting a business is a marathon, not a sprint, and you have to take care of yourself if you’re going to survive several years without a burnout.

What have we not asked you that you want to share about entrepreneurship, sisters, or business advice?

Your siblings seem like a natural place to start when looking for a business partner. I recommend you really consider if this is the right thing for your relationship and make sure you are able to weather disagreements or challenges along the way. Anne and I have very honest and direct communication style, but I could see how it could become challenging if we did not. Also, if you’re naturally good at the same things, it’s probably not a good fit. Luckily Anne and I have complementary skill sets.

Lightning Round:

Favorite restaurant? True Food Kitchen

Favorite spot to hang out with your sister? Milan

Favorite place to work out? One Lagree

Favorite product? “One Night Only” Body Bronzer – we both use it.

Favorite road trip? Los Angeles to San Francisco

Favorite Instagram account to stalk? Chiara Ferragni, @chiaraferragni

Favorite song you and your sister love from growing up? Like a Prayer, Madonna

Favorite podcast? Goop

Contact Info:

Website URL:

Instagram Handles: @benincasa_milano @maijabenincasa @annebstockstill

Business Address: 3800 Commerce St #216 Dallas, TX 75226