Sherilyn Williams Casiano, Founder & CEO, S.I. Williams Wealth Management, LLC

When I was about 13, my mother was working for an accounting firm and when I told her that’s what I wanted to do, she brought home some teaching materials – a guide and a workbook for teaching accounting.
Sherilyn Casiano is the Founder and CEO of S.I. Williams Wealth Management, LLC, in New York City. She holds an MBA from Columbia University. On her first summer job at the age of 14, she wound up balancing the books for the island of St. Croix in the US Virgin Islands – the first time in anyone’s memory that the books had been balanced. She was a key member of KKR’s personal wealth group for the New York general partners, including one of the billionaire founders.
She has headed her own profitable multi-family office for 14 years. She teaches financial management at the Fashion Institute of Technology (FIT), as well as a financial literacy course for the Harlem Empowerment Zone.


Click here to download your free copy of the Female Leadership in Our Time



I always wanted to be an accountant. Numbers really fascinated me. Also, my mom was very entrepreneurial and supportive. When I was about 13, my mother was working for an accounting firm and when I told her that’s what I wanted to do, she brought home some teaching materials – a guide and a workbook for teaching accounting. So that summer, while my brothers and sisters were all out playing, I was inside going through the exercises in the workbook. I still remember the excitement I’d experience when I’d figure out a problem which I had been stuck on!  You go from the frustration of two columns of numbers just not matching, trying repeatedly to figure out the error… then you finally find it, the columns match, and in an instant, you’re on top of the world! That’s what I call the exquisite integrity of accounting. The numbers don’t lie. Certainly people can lie with numbers, or make up something that looks legit. But the beauty of accounting is that once someone runs those numbers through the real process, the truth comes out. The numbers will ALWAYS tell the truth if you let them. So, in any case, by the time I got the job that next summer, working in the Finance Department of St. Croix, I already knew how to do reconciliations.



That was the family entrepreneurial gene kicking in. Beside my mom’s many businesses, other relatives owned the island’s largest bakery, and preceding generations had entrepreneurs in various kinds of businesses. So I think it was only natural for me to want to start my own business. Also, I thought what we were doing for the partners at Kohlberg Kravis Roberts & Co.’s (“KKR”) was pretty cool and very different from what I was taught in accounting school. In any case, by the time I was ready to go out on my own, we had really developed a reliable process for managing the partners’ wealth that let us give them a level of detail and insight that they had never had from even the best outside vendors. It was my conviction that there were many other people with complex wealth needs, who could benefit from my experience, expertise, and the system I had developed in my work at KKR.



Well, the Dynamic Wealth Information Management Businesses Solution is a software application I created to automate my Dynamic Wealth Management System. I already had the system in place, but I was looking for software that would make the job easier. Delivering the kind of comprehensive and detailed reporting provided through my system is very labor-intensive. I used to have to pull information from many different applications, and use 3 or 4 others to combine and produce reports that showed anything more than just invested assets. But most people’s wealth is not in the market; it’s in various forms of hard assets, some liquid, most not very liquid at all. My system brings all the information related to an asset into one place, so that it’s readily available when needed. For instance, for a piece of art, a Picasso, my system brings information not just relating to the purchase price, but additional information that is relevant and important to that asset into one place, such as ownership, market value, insurance value and policy, location of the asset etc.

So an essential part of my system is to collect all such information and retain it together, in one place, so you don’t have to search in a dozen places and call a dozen people to put all of it together when the client asks for it.

I looked at everything available on the market that claimed to be for the Family Office. But to my surprise and then my frustration, there was nothing that was designed to make the administrative tasks any easier. All the products were designed for the type of Family Office dominated by an Investment adviser/manager – to make their job easier. So it could show you the balance in portfolios over 50 mutual funds, but was useless for trying to track the costs and insurance for the staff and animals at the horse farm. Out of desperation I hired a set of programmers to create something to MY specifications. Designed for the Family Office by a Family Office Owner/Manager. That’s how the Dynamic Wealth Information Management Business Solution – DWIMBS – was born.



DWIMBS moves the focus for effective wealth management from strategy to High Quality Information (“HQI”) and evidence-based decision making. In the 2008 crisis, all the elegant and clever strategies of the best in the business failed. “Balanced portfolios” – that darling of investment adviser wisdom – were clobbered as the crisis hit all sectors. The few who, like my clients, or Goldman Sachs, were getting HQI and paying attention to the real numbers, parked their money on the side, and waited for the smoke to clear… and then snapped up bargains.

In addition, DWIMBS is the first software created to specifically address the desire and need of High Net Worth Individuals and their Families for true control, the needs of the Family Office for operational efficiency and ease of creating accurate, strategic reporting, and the needs of advisers to get relevant and accurate information that empowers them in their work for the wealthy family. No other product serves all three groups equally well, the way DWIMBS does.

Lastly, it is built around a proven and reliable methodology and process that is unique in the wealth management arena, one that addresses all aspects of one’s wealth, not just invested assets.



For me there have been three key points to balancing work and family life.

•  Straight talk with the kids
•  Setting boundaries and responsibilities
•  Giving options and choices

Being a widowed mother of 2 young boys, I felt it was very important to be even more involved in raising them. I did not want a nanny to replace me as their mom, as I’ve seen happen in other families. So it’s been essential to make my children part of the balancing process, if you will. The first step in doing that was to speak frankly with them about how our family life was different from that of their friends, since there was no father in our home.  I did not want to pretend everything was perfect or that they have no responsibilities. I felt it was important that they understand my responsibilities as both a business owner/entrepreneur and as a single parent, now that my husband was no longer there to share the duties of raising them as in the past.  I made sure that they understood what work I do, why it takes many uninterrupted  hours, and requires frequent meetings or phone conferences. As a result, whenever I’ve needed them to step up and do what they need to do, they have.

The second part is making sure they know they are part of a family and as such have a right to make their own wishes and opinions known. However, I’ve also made sure they know that there is only one adult in the family – only one person in charge. And I remind them frequently. They have specific responsibilities such as completing their homework each day, which I still supervise. And nowadays they are often responsible for making their own breakfast or starting dinner.

In line with that, the third key I think is giving them choices. I’ll often say “Okay, you guys decide. Here are your options.” I usually stick to 2 options. Never more than 3. Other times I’ll have to say ”There are NO options here – you Have to do this.”

My boys each have their own calendars and I make sure I am synchronized with them so that I can manage my scheduling to account for my parental responsibilities, such as school functions and other duties.

That’s how I balance my family life.

I am also blessed with a large family who is very supportive. For instance, I have a nephew who comes over regularly to take my boys to Central Park, play video games and sports like basketball. This has provided the kind of male bonding and sense of belonging to our extended family that they needed. One of my sisters, who lives in Florida, is also the project coordinator for my software business, will come to New York to stay with my boys while I’m at this years Global Female Leaders Conference. In addition, I also rely on a very capable team of consultants and other advisors who help me immeasurably, and who all go the extra mile for me.

The other thing I do is plan weekend road trips and, 2 or 3 times a year, longer vacations of a week to 10 days where my boys and I can discover new places and have great experiences together. For example we spent a week in New Mexico, looking at dinosaur fossils and Indian ruins. We drove from San Diego, California all the way to the Grand Canyon by car – a 10 hour trip! It was also a great adventure, giving them a real sense of the size and diversity of the geography of our country, so different from the concrete canyons of Manhattan. My boys are also at the age where they can now be trusted to be away from me for a period of time. This past summer they spent a month with my brother and his family in St. Croix. While I spoke to them every day, they were excited to be with my brother, who teaches aeronautics and is an airplane engineer. . They learned to fly and get a feel for Caribbean culture.



I don’t think of those things much, so this is a tough question. Better that you ask are there any challenges I haven’t met. But I think the biggest challenge has been getting people to see me as more than a bookkeeper. I’ve had men say to me at a networking event “Oh you do bookkeeping stuff” as if that’s all I do. The truth is, nobody does what I do. I know that’s a bold claim. But, since leaving KKR, I’ve spent over 15 years looking and haven’t found anyone who gives their clients the level of insight and control my clients get, though many make similar claims. If you speak to the “guy/woman on the street”, they’ll think that wealthy people can afford to hire the best, and therefore they must have their financial life together. But the fact is that virtually no wealthy person has a clear picture of ALL their wealth and even more important, true control of their wealth. My particular skill set – a unique combination of training, experience and mindset – has enabled me to deliver a level of certainty and control to my clients that I’ve not seen anywhere else, even at KKR. I originally thought that other family offices must provide the same level of insight and detail, but as I looked at other operations, and especially the big names in the family office market, I realized what I did was very different and much more designed around the client’s REAL needs and interests.

So most people automatically assume they know what a personal CFO is and does. But they are wrong. For instance, many financial planners claim to act as a Personal CFO, but they are only involved in the creation of a financial plan, employing the recommended products they represent. They have no part in the day to day tracking and reconciliation of transactions, or in accurately determining the changes in distribution as partners enter and leave an investment partnership. Most people would be amazed at how incomplete traditional wealth management really is. So, clearly communicating to people the uniqueness and immense value of what I do in a way they can “get it”, has been one of my biggest challenges.

“I think every female entrepreneur MUST have a team of competent and tough attorneys. Tough is possibly even more important, because the other side will often come after you without a solid case, hoping to win by shear intimidation.”

I have been fortunate that in all my jobs working in someone else’s business I have had an excellent experience with all of the decision makers and leadership. My intelligence, my organizational abilities, my penchant for innovation, and my belief that doing a good job was incredibly important, were always quickly noticed and appreciated. As a result, I rapidly took on more and more responsibilities, even in my first summer job at age 14. At KKR, for instance, within two years, I was promoted to the second in command position in the personal wealth group, over other older employees who had been there years longer.  This, needless to say, was not popular with those employees, and I had to deal with the cattiness and meanness of those other women for the remainder of my time there.

It is surprising that women for the most part have not developed the kind of robust support networks in the workplace that men have. While they tend to have more developed social networks, I’ve seen all too often that women in the workplace, work against each other rather than for each other. Hopefully more events that bring women together can help change this.

A challenge I’ve encountered as an entrepreneur and software developer is having my easy-going style, sense of fairness, and respectful professionalism mistaken for weakness. When the first version of my software had been completed by the South American programmers I had hired, the owner of the company tried to add on a charge of $30,000 for cost and time over runs, a breech of our agreement. He also wanted exclusive rights to sell the product and hinted they could go ahead and sell it anyway if I didn’t agree. He was holding my brainchild hostage, and claiming I had no chance of bringing it to market without him! I immediately turned the matter over to my attorneys, who straightened things out very quickly. I promptly got my software at the the price originally agreed upon. I think every female entrepreneur MUST have a team of competent and tough attorneys. Tough is possibly even more important, because the other side will often come after you without a solid case, hoping to win by shear intimidation, as happened when a Canadian bank challenged our trademark. Again, my lawyers negotiated a workable solution.

One of the big gifts of being an Entrepreneur is the certainty that you’re not stuck in a place where you are not respected and valued – that you can walk away. Once you’ve created something from nothing, you have the sense that you can do it again if you need to. I have created four businesses since I left KKR, and effectively manage all of them.



I think I will continue to refine DWIMBS. I also have in mind some additional software products, one for Estate Advisers and one for the Private Equity Market. I am also concerned that few people ever mention “information integrity” in all the conversations around “big data.” It seems no one has a reliable process for verifying whether the data being collected has been properly vetted, if at all, and is relevant and timely, and how to organize it to be useful and easily understood. So I have my work cut out for me.


Well, if you mean what’s my mind-set for starting the day, the 3 things I take with me are:

•   The knowledge that I’m innovative
•   That I can learn and teach others
•   My commitment to doing an excellent job

If you’re asking what physical things do I never leave home without, they are:

•   My digital office i.e my iPhone and personal hot-spot
•   My Keys
•   My pocket book (usually the large one that can hold my laptop and what ever else I need for the day, such as a change of shoes, lunch, etc.)


Click here to download your free copy of the Female Leadership in Our Time



Please enter your comment!
Please enter your name here