The Anatomy of a Latina Entrepreneur

Lily Winsaft Latina entrepreneur

Hard work, a thirst for learning and giving back are the building blocks of success.


Editor’s note: This is part one of a three part series spotlighting Lily Winsaft a successful Latina entrepreneur and her successful journey.

Latin Business Today: Lily please tell us about yourself and your family.

Lily Winsaft's parents left and parents with siblings today

Left photo: Lily Winsaft’s parents; right photo Lily left with parents with siblings today

My parents are originally from Colombia, my dad from the coast of Colombia and mom from the capitol – Bogotá. I’m the oldest of four siblings, all of us Colombian born. When I was four my father immigrated to the United States, secured a job and saved until he could reunite our family in the states a year later.

We settled in Brooklyn, NY but the weather and environment took its toll on my health. I suffered from asthma and a host of allergies. To this day I can recall the distinctive sound of an ambulance and the blur lights on numerous occasions when whisked off to the emergency room in the middle of the night.

My father would take me into the city every Saturday to get oxygen. The doctor’s office was near the Museum of Natural History and we would go there afterwards. That museum is one of the fondest memories I have from my childhood. At twelve years old we moved to Miami and I never again had an issue with being short of breath.

My parents made a great impact on my life.

They instilled the love of books, the passion for education and learning.

Mom gave up her career as a teacher and became a stay at home mom. There was never a day that she wasn’t there when we came home from school.  Dad followed the steps of the family trade and became a watchmaker and jeweler. He worked two or three jobs at a time to keep food on the table and make ends meet.

Today they’re happily retired and run a nonprofit school in Miami teaching “The Art of Living through the Qaballah”. My parents taught me the love and commitment to help people and make a difference in the world.


As a result I have always recognized the importance of volunteerism and “giving back.”

One of my fondest memories was of a mission to Guatemala sponsored by Care International. I was a member of a volunteer group of corporate executives and entrepreneurs.  We experienced the beautiful work Care is doing to support women in underdeveloped nations.

I was accompanied by executives from Coca Cola, UPS, Delta, the Atlanta Community Foundation among others. Channel 2 in Atlanta filmed a three-part documentary about this journey.

It was very inspiring!

Lily with CARE kids and Lily with CARE volunteers

Left photo Lily with CARE kid, Right photo: Lily center with Corporate volunteer executives and Channel 2 crew in Guatemala

Latin Business Today: Lily tell us about the factors that shaped your career or business aspirations.

Lily addressing team and speaking

Right photo: Lily addressing team and left photo Lily speaking

Becoming a Latina business owner was not something I specifically aspired to as a young woman, but it eventually became the natural course of things for me.

My personality, however, is very suited for business. I am a freedom seeker, fearless and capable of moving through risky situations. On another note, when I was twelve I began a ferocious journey into learning about and understanding human behavior, which led to me getting a degree in Psychology.

When you put together the need for freedom, the ability to take risks, and a passion for understanding and interacting with people, you get…a career in sales!

My lifetime sales career began at seventeen working for a national distributor of auto parts, it paid for college. I like, actually prefer the “hunt” and to only eating what I catch. For the most part I earned a living through straight commissions.

For many people starting a business can be scary because of the financial implications.

When you’re used to a steady stream of income, going without while your business is launching can be trying. Starting a business is difficult and certainly was in my case. At least I had some of the basic foundations from a personality perspective and knowing that I was 100% responsible for making it work.

My parents have always been teachers and I certainly have followed that path. I love to facilitate workshops, give inspirational/motivational talks and provide career/life coaching.

All theses practices that support our company’s mission – “To Create a World Where People Love What They Do For a Living.”

LBT: Lily tell us about past business successes and failures and impact on choices.

I have succeeded in every sales job I have ever had, and there have been over 20 in my life.

But there was always one consistent thought in my head – “I am working my butt off for the owners of this business and I am giving away more than half of what I am earning to them. This does not make sense! Yet, even though the only thing that made sense was for me to start my own business, I believed it would require lots of money to get a business started, so I didn’t even consider it.

At some point I gave in and landed a big corporate job that paid me a lot of money and benefits to do what I did best…sell stuff.

But even though I received several promotions in a 5-year span, along with the big salary came loss of freedom; so it wasn’t long before I had to seek an alternative. That’s when I decided to take what I had learned at this company and turn it into my own business.

I resigned without having something clearly lined up or without really knowing what I was doing.

LBT: Have you ever had had a formal mentor?

Lily Winsaft and son

Lily Winsaft and son

Not a formal mentor, but it hasn’t been because I didn’t want a mentor.

I strongly believe in mentoring, coaching and in leveraging the counsel of key individuals within one’s circle of influence. My mentors have been my parents and my children.

From them I have learned about values such as commitment, discipline, integrity, authenticity, perseverance, focus, etc. Additionally, my spiritual practices have led me to being an avid reader of books that have to do with self empowerment, expansive thinking, creative presence, enlightened leadership, conscious decision-making, etc.

One of the most beautiful things anyone ever said to me and that truly impacted me was, “Failure is not an option.”

It came out of my oldest son’s mouth at a time when I was considering throwing in the towel with the business. ten years later, Lance is pretty much running the business and I am so happy that I did not give up.

He recently opened our office in San Diego and is doing a great job building a sales team that he is training and mentoring.

In part two we’ll cover Lily’s business in depth and how her upbringing and experience contributed to its success.

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