Helping Women Invest Smarter: An Interview with Cassandra Cummings (2024)

“The following conversation was conducted over email and edited for flow and clarity.”

Damien Peters of Wealth Noir: Happy to be able to talk with you, Cassandra. We met a long time ago when Wealth Noir was just getting started. I’m so happy I could finally have you here. But for the readers, can you tell us a little about yourself?

Cassandra Cummings of the Stocks & Stillettos Society: Hi, I’m Cassandra Cummings, the founder of The Stocks & Stilettos Society. We are going on three years and are the fastest growing community of women investors.

In “The Society”, we pride ourselves on the “Each One, Teach One” model, where we provide a safe space for women to grow as a part of their investing journey. There are daily posts, courses, challenges and other informative components to assist women with becoming savvy and confident investors.

WN: I know you worked in financial services at a big bank before founding The Stocks & Stillettos Society. Tell us about how you originally became interested in personal finances.

Cassandra Cummings: I started in personal finance 15 years ago as a licensed financial advisor. My college mentor introduced and lured me into the business as a way to help others. It was also a way for me to have a considerable amount of autonomy in order to be present in my daughter’s life, as a single parent.

After years of not interacting with clients that looked like me and crossing paths with women who did not share the same enthusiasm about investing as I did, three years ago, I created The Stocks & Stilettos Society.

WN: I love those who come from finance and now preach the gospel of financial literacy to others. I like to know there is experience and knowledge behind the information I get.

I’ve seen you cover a range of different topics with your Society. And your conference last year touched on a large number of personal finance concepts. But what specifically does the Stocks & Stillettos Society offers to its community?

Cassandra Cummings: I offer what I like to call the 3Cs: The Courses, The Circle and The Clubs.

I offer investment literacy courses to help people become savvy and confident investors. My classes are designed for beginners and oftentimes will cover trending topics such as marijuana, bitcoin and real estate.

The Stock Success Circle is a premium, online investment community where we go more in-depth with investing topics and have great speakers.

Lastly, I enlisted an amazing group of women who helped me create an Investment Club platform for women, The Stock Sister Circles. Ladies meet online to pool resources and invest in the stock market.

WN: That sounds great. I think a lot of people are scared of the stock market and investing because they hear stories of investments gone bad. I’m glad to hear you cover a range of beginner and more advanced topics and help make it approachable.

Speaking of stories of bad investments, a lot of people are getting started now on their journey to wealth, so I always like to talk to people about how they got their start investing. Can you tell us about the first investment you remember making? How have you become a better investor from any mistakes you made?

Cassandra Cummings: My dad passed away when I was 17, and I received a death benefit. Along with the check, came a financial advisor who recommended high-commissioned financial products such as annuities and whole-life insurance policies. I was clueless about the asset allocation and products that were bestowed upon me.

One of the first investments the advisor recommended was an Equitable (now Allianz) California Muni Bond Income Fund. She recommended that I allocate $60K to the fund in A-Shares, which may not have been appropriate for a 17-year old. What did I know? Nothing.

Instead, she should have recommended to add that amount to the equity portion of my portfolio and set up a dividend income schedule to receive a monthly dividend payout, since income was needed for me at that time. I didn’t have much success with the fund, because I continued to make withdrawals to finance college expenses and the annual rate of return on the fund was less than 8 percent per annum (tax-adjusted rate), to really provide the income needed for my particular situation.

As an Investment Adviser Representative and a Registered Investment Advisory firm, I have a fiduciary responsibility to put my client’s interests before my own. It not only makes good business sense, but it’s the right thing to do. When I was younger, I had to take a crash course on investments. It taught me that you must know about money and have money mentors who genuinely have your best interest at heart. I would definitely share this piece of insight with my younger investors, today.

WN: I had a very similar experience with an advisor when I graduated college. My mom used him, so I went to him after graduating undergrad. I had my doubts when I dug into basic investing concepts with him. Eventually, I left him, but even with his fee-inducing judgment, I made thousands by dropping him and holding the money where he had invested it.

Thinking through all those learned lessons, what do you think is the greatest lesson you have learned about managing your money?

Cassandra Cummings: The greatest lesson that I’ve learned while investing is not to give your money back. It’s imperative that you learn how to protect your profits when investing in the stock market. Be careful, remain disciplined and don’t succumb to greed and fear.

WN: Truth. Staying disciplined and consistent has always produced better returns than trying to time the market. I still do it, but just with a little play money. I know my base is best sitting still.

We share the fact that we both left good corporate jobs to venture out and start personal finance companies. How did you decide to venture out on your own?

Cassandra Cummings: I made the decision to fly solo three years, ago. I knew I wanted to go into business for myself for a while but waited until my daughter was off to college. Also, I wanted the freedom to really serve clients the way they needed to be served. I knew that I could only do this by striking out on my own.

WN: That’s another thing I love to tell others about becoming an entrepreneur, timing is important. Starting a company is sexy, but it’s important to make sure the timing is right in your personal life before making the jump.

I know you talk to a lot of women in The Stocks & Stillettos Society. What is the most common question you hear from your community?

Cassandra Cummings: The most common question that I am asked is, “How do I get started?” People have been led to believe that the stock market is a big, scary place akin to a casino where people go to lose money.

In The Stocks & Stilettos Society, we help people overcome those fears, eliminate barriers and learn how to minimize risk in order to start investing. Many get started with micro investing apps such as Acorns and Stash. Others will start with platforms such as StockPile or Robinhood. The key is to just get started.

WN: I know exactly what you mean. Everyone thinks it’s so hard to get started or are filled with fears, but it’s the first step on the path to financial freedom.

Taking it way back for a second, is there a memory about your childhood that sticks in your mind as influencing who you are today? Is there a moment that put you on the path to mastering money?

Cassandra Cummings: The sudden and tragic loss of my dad at the age of 17 was a pivotal moment for me. Initially, I was thrust into adulthood without a means to adequately provide for myself. It would take nearly three months to discover that my dad had a college fund set aside for me in the form of a death benefit.

However, in that three months, I had worked extremely hard to secure scholarships and a part-time income to equip myself to make money and better manage my own money in college. Although I had the ability to just focus on school, I still managed to remain employed during my undergraduate years. The consistency of a paycheck forced me to be disciplined about budgeting, saving and later, investing.

I don’t think that you can ever really master money, but you can implement guiding principles and have financial objectives to help you live the life that you desire, financially.

WN: I love how you turned that hardship into your life as a challenge to get better and improve. It’s a core mindset that I think is important when trying to build wealth. Things will happen, but when you work harder to overcome it, you exit the situation stronger.

I really enjoyed getting to interview you today, Cassandra. Even though I’ve known you for a while, I learned a few new things and really enjoyed hearing more about your story. Is there anything you have coming up that you want to let our readers know about?

Cassandra Cummings: We recently launched The Build-A-Bag Challenge, where we are looking to help 10 ladies grow $500 into over $100K in less than 12 months through investing options.

Also, our fall/winter enrollment for The Stock Sister Circles was underway through Oct. 5th. It’s a chance for women to come together to create a money team with like-minded women, who want to pool resources to invest in the stock market.

Join The Stocks & Stillettos Society’s private facebook group to hear more from Cassandra and her community of women learning to invest. You can find out more about them at www.stocksandstilettos.co or on Facebook or Instagram

Related