Amy C. Cross is the CEO and founder of StillPoint Capital, established in 2004. With a career in securities dating back to 1991, Cross has expertise as a former American Stock Exchange (AMEX) floor trader, an index and equity options specialist and an ETF market maker. She’s also worked as a market correspondent and in mergers and acquisitions and private capital raising. Based in Tampa, Cross transitioned into middle-market investment banking and has received numerous accolades, including the Tampa Bay Business Journal’s “BusinessWoman of the Year Award.” She is a FINRA arbitrator and holds multiple securities registrations, a Florida real estate broker license and various insurance licenses.
I grew up in Monmouth Beach, New Jersey. My father was in the HVAC industry as a technical trainer, author, and business operator. My mother was a school teacher and guidance counselor for 34 years, then became an author, life coach and hypnotherapist, and is now also an Amazon best-selling author. Because we lived in a beach town, I loved going to the beach when it snowed. It was such an amazing sight to watch the snow collect on the sand and dissolve in the surf. I just love that memory.
My parents taught my sister and me to work very hard and always demonstrate responsibility. I remember that starting when I was 14, we would work both full-time and part-time jobs every summer. This taught me early on that hard work was natural and to appreciate my downtime. Later in life, when I had to work even harder to accomplish a goal, it didn’t seem extraordinary to me.
I worked at “the corner store” in my hometown as a cashier and later as a waitress in a restaurant. It was exciting to earn a paycheck and be given responsibility for the first time, rather than just being seen as a child or student. I learned how people can vary in their dispositions when you wait on them; some are naturally positive and talkative, while others are negative or more reserved. It was clear to me that the more positive the person, the more enjoyable the experience of working with them, whether it was during a 5–10-minute checkout or serving them for an hour or more. I recognized that I had the choice to determine how I would carry myself, and it was evident that a positive mindset was the most natural and beneficial approach.
I first became involved in the securities industry with a broker-dealer when I took a summer job in 1991, cold calling for stockbrokers. As crazy as it sounds, I loved the job and did extremely well. Later, in 1992, after college, I reached out to the same stockbrokers to see if they were hiring, and they referred me for an interview in New York City. I ended up getting hired as an administrative assistant for a high-producing broker.
Later in my career, I began to dabble in M&A and raising capital for my own personal projects. Then, in 2003, when I moved to Tampa, I met my first business partner, who was an intermediary for M&A transactions and private placements. He taught me the ropes of facilitating transactions for others. We decided to open our own broker-dealer to conduct our M&A securities transactions and to create a niche in the market by making securities registration available for others as well. That is why we launched StillPoint Capital, and we did just that.
StillPoint Capital provides a convenient solution for securities registration for independent investment bankers. For those independent bankers who conduct M&A and raise capital, StillPoint enables them to become securities registered with FINRA while they work in their own firms, still supporting their own brand names. StillPoint manages all of the compliance work for the transactions so that the investment bankers can focus on what they do best—working with their clients.
I’m most proud of StillPoint’s ability to reach its 20-year anniversary in April 2024. Standing the test of time with many of the same relationships intact from the beginning, or even before, brings me great satisfaction. Statistically, we beat the odds of any start-up lasting more than 2-5 years. Continuing to serve our market, evolve with the times, and manage all situations that come our way has been the adventure of a lifetime.
The last few years have taught me that I am more capable and more vulnerable than I ever knew. COVID is the first example that comes to mind. On that day in March 2020, I had to protect my staff by not only trying a work-from-home business model for the first time but also implementing and executing it all on the same day. Like all other businesses and facilities in the same situation, we had to lead our teams and answer questions we had never considered before. Emerging from that experience, along with other major economic challenges impacting my sector, has made me acutely aware of the need to be nimble to adapt and survive in these unprecedented times, and of how vulnerable we are and continue to be. The past 30+ years in the securities industry have been an extraordinary time to be alive and in business.
My business philosophy is “be the buffalo.” Have you heard the story of the buffalo and the cows? When faced with a storm, the buffalo walks toward it and faces it head-on. They weather the worst of it and come out on the other side more quickly. The cows, however, run from the storm, which chases them, causing them to spend more time in it and often letting it overwhelm them. It’s a powerful metaphor that applies to both life and business. Once I faced challenges head-on, on my own timeline and with the best intentions, it became clear that I could mitigate damages and see better days sooner. This is a motto I live by.
My biggest supporters, without a doubt, are my parents, my sister, my children, and my dear friends. As you know, life brings many ups and downs both personally and as a business owner. Despite learning how to weather the storm and take the good with the bad, the down days still hurt. Having a support system around me during the harder times has been invaluable. Their support has enabled me to rally when I’ve needed to, and I am deeply grateful to them for that.
My greatest extravagance is taking time for myself to renew and recharge. As a business owner, homeowner, and single mom for most of my children’s lives, I don’t often get to focus solely on my own needs. So, when I do, it feels like a true luxury.
My most surprising hobby or skill is that I thoroughly enjoy and seem to have a knack for seamlessly organizing personal travel adventures. I often wonder if I missed my calling as a travel agent. Additionally, documenting these wonderful memories is very rewarding to me. My poor children have had way too many pictures taken of them—thank goodness for digital photos.
Something people may not know about me is that while living in New York City, a friend from the American Stock Exchange decided to film a soap opera and offered me a role. I gladly accepted, and we would go to work early to film on the floor of the stock exchange. He later launched the series, which aired on public access TV in New York City during the early morning hours for many years. It was exciting to watch the show at 2 or 3 in the morning and see my friends and me performing our best as amateurs. While acting turned out to be far from my calling, we still had a great time and made some wonderful memories together.
My perfect day would be one filled with success and happiness, marked by great camaraderie, joy, and only favorable outcomes. I love surprises, so an exciting and thrilling surprise would be a welcomed bonus.
The biggest item on my bucket list is to explore Ireland with my significant other. It has been on my list for many years, and I am very excited to be in the planning stages of our trip to the beautiful and serene Emerald Isle. We look forward to visiting his family and exploring the countryside. It’s thrilling to experience a different lifestyle, culture, and geography, especially with some of the most amazing people I have and have not yet encountered. “Erin go bragh”!
The biggest honor of my life has been being a mother to my four beautiful children. It has been amazing to raise four distinctly different personalities with their own drives and motivations and to see them all striving for their greatest potential. This has eclipsed all of the other successes in my life, including peer recognition and the accolades I have received.
This interview has been edited for brevity and clarity.
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