William White Winnetka

The goal of any leader should be to build a team that can function without you. Then go out and find your next opportunity.


Born in Ohio and raised in Maryland, William S. White Winnetka studied building construction for his undergraduate at the Georgia Institute of Technology. He then continued his education at Columbia University, where he received his law degree and an MBA in Finance.

White began working for Lehman Brothers’ real estate and investment banking but quickly decided to go into private equity at NorthStar Capital Investment Corp. He worked in New York for three and a half years, focusing on a large billion-dollar company that they owned. He helped oversee all the legal documents and all aspects of financing, acquisitions, and dispositions for hotel assets.

William S. White Winnetka continued working at various real estate companies in the condominium market and hospitality sector until 2005 when he co-founded the Montessori Academy of Chicago. A few years ago, they opened a middle school and now serve children from infant to grade eight. Currently, the school has 330 students in Chicago’s West Loop.

This father of two teenage boys enjoys all kinds of outdoor activities, from cycling to wakeboarding/surfing to skiing. White also enjoys woodworking and making furniture.

In addition to his position as co-founder and owner of the Montessori Academy, William S. White Winnetka is currently interviewing for a position in real estate asset management and development.

Where did the idea for Montessori Academy of Chicago come from?

When my co-founder and I came to Chicago, we noticed a lack of educationally based programs for kids from birth to three years old. With a background in Montessori, we decided to open a Montessori school to fill that need.

What does your typical day look like and how do you make it productive?

I spend a portion of my day doing research and reading, and I work to understand what’s going on locally and globally as well as across different industries. At this point, the school is largely self-sustaining. We have a strong executive team in place, so I spend a small portion of my time just updating myself on what’s going on. Lately, I have been spending more of my time trying to understand what the latest trends for the real estate industry are, what asset classes are growing, stabilizing, retracting, and the financing sources for the various parts of real estate ownership.

How do you bring ideas to life?

What I like to do is surround myself with intelligent people who are good at what they do. I work very hard to understand the steps necessary to reach an objective and then assign tasks to help meet that objective.

What’s one trend that excites you?

I like the inclusion of math and science as a hands-on endeavor. It’s transforming in education. When I was in high school and college, I did not like how you learned in the abstract and then eventually, you began to see the application in the tangible. It seems like education at this point is moving in the direction of understanding that making things tangible for students helps to teach you much better.

What is one habit of yours that makes you more productive as an entrepreneur?

I work very hard to distinguish the forest from the trees, that’s probably the best way to put it. Obviously, on a daily basis, one needs to tackle the day-to-day tasks that are in front of you, but always with an eye towards long-term goals or objectives.

What advice would you give your younger self?

Get to know the people around you. Relationships and human interaction are the most valuable assets that we have. Also, never quit, because even though life never goes as we plan, it never stops being interesting.

Tell us something that’s true that almost nobody agrees with you on.

I think you should always work to make yourself obsolete. The goal of any leader should be to build a team that can function without you. Then go out and find your next opportunity. I believe a lot of people are afraid of being replaced and therefore tend to protect and control information. That’s to the detriment of the business and ultimately to the detriment of on-going professional development. When you train people to do what you do and to know what you know, that in turn allows you to learn more and faster, and to grow.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I recommend that everyone keep learning. Education doesn’t stop with college. You’ve got to keep working towards the changes and growth within the industry and society and keep learning.

What is one strategy that has helped you grow your business?

Understanding your clients and their needs. Once you understand that, you create a service that meets those needs in a unique, intangible way while creating an environment that supports that objective.

What is one failure you had as an entrepreneur, and how did you overcome it?

I worked in a company that didn’t have operational excellence. As a finance-oriented person, it made it impossible to execute. This made me realize the importance of operations and how one cannot have good finance and grow without an operation team that is excellent at what they do.

What is one business idea that you’re willing to give away to our readers?

One area that I’ve seen a need in is for a logistics coordinator between foreign-produced production companies and US consumers. An intermediary for product delivery.

What is the best $100 you recently spent? What and why?

It’s not professional per se, but I bought my girlfriend a $100 spa coupon. It’s the best $100 I’ve spent in a while. She works in a very stressful environment, and she was very touched that I would think to do something to help her relax.

What is one piece of software or a web service that helps you be productive?

Excel. I live by it. My background was with a finance concentration. From my standpoint, unlike other self-generating software packages, you have to truly understand how your business works in order to create a useful file.

What is the one book that you recommend our community should read and why?

Lincoln on Leadership: Executive Strategies for Tough Times by Donald T. Phillips. It highlights the need to make decisions with limited information in the face of strong opposition and criticism.

What is your favorite quote?

“By endurance, we conquer.” – Ernest Shackleton.
“It is not the strongest of the species that survives, nor the most intelligent that survives. It is the one that is most adaptable to change.” – Charles Darwin.

Key Learnings:

● Know what you don’t know. It’s a skillset everybody should always have. It’s the ability to analyze what you don’t know and pick out what you need to do to fill those gaps, whether it’s through gathering information or surrounding yourself with people who have that expertise.
● Surround yourself with a diverse group of intelligent people.
● Be true to yourself. If you feel uncomfortable, something is not right. Figure out why and make a change.