Dynamic Women & The Men Who Support Them – Ramsey D. Smith

The world is an amazing place. There are times when one experiences that “aha” moment. Learning more about Ramsey was one of those moments for me. Since the pandemic and not being able to travel and meet new people, I was on a mission to meet new amazing people virtually. Ramsey is one of those people who the more you learn about him, the more intrigued one is. I love his story about what he learned from millennials — just goes to show that we can always all learn from each other. I am so honored and privileged to share Ramsey’s journey with all of you. Thank you Ramsey for being such an inspiration to us all!

– Maree Moscati, CEO CTPRP

Ramsey D. Smith

Founder and CEO


How have you supported women throughout your career?

Ramsey: From the very beginning of my career, I have worked with a lot of super talented women, many of whom were my bosses. That includes Lisa Shalett, whom you’ve interviewed previously and is a good friend of mine. From the beginning of my career, I’ve been surrounded by extraordinary women who brought different perspectives and demonstrated excellence. Those were some of the people that I learned the most from about the craft of the work we did.

Frankly, I have always believed there is a lot of untapped potential in underrepresented groups generally. In the absence of being able to easily rely on strength of personality or shared experiences, many of these professionals focus on demonstrating their expertise to succeed. A lot of excellence comes out of that mindset.

When you realize that, it opens a lot of possibilities. At the same time, realizing that potential requires intentionality and awareness. The podcast I currently co-host is a good example. It has been developed through a very organic process. We happened to start out as four guys talking about personal financial products.

We are constantly looking for new ways to improve the show. The first step was to add guests. At a certain point, we stopped again, looked at the show and quickly realized, “Wow, way too many guys.” Since then, we have intentionally sought out more female voices and the show is materially better for it.

What advice do you have for new folks in the financial services industry?

Ramsey: Mentorship and seeking advice are very important, and I truly believe that no one goes it alone. There are lots of resources and great people to help you, and it’s great to seek that out.

The journey to success inevitably includes ups and downs.

Sometimes the pitfalls are of your own doing. Other times you may question whether you have been treated fairly.

Whatever the origin of the rough patch, it is in your best interest to be the driver of the corrective action.

This might mean staying in place and doing something differently or striking out on your own.

When things go right, we tend to over index that success to ourselves, and when things go wrong, we tend to over index that failure to other people, but the reality is every success and failure is some mix of skill and luck. You have to own your own fate as much as possible with the help of mentors and sponsors along the way.

What’s a do-over you wish you had in your career?

Ramsey: Looking back, if I could choose the way things progressed, I think I would have managed the sequence of my career a little bit differently. I would have perhaps compressed some of my working career and started what I’m doing now a little bit earlier.

I would also implement something that I learned from the millennials with whom I worked, and that is the idea that you need to be careful about totally giving yourself over to your employer. It’s important to work hard and try to achieve things, but at some point, you’re going to leave your company. The millennials I worked with were very hardworking but also aware that there are other options in life besides where they are, no matter how wonderful that place is. And that, I think, provides a lot of freedom to move on when it’s time. At first, I wasn’t so comfortable with it because I felt like that attitude was flouting tradition, but in retrospect, I have to say, more power to them. I’ve taken a page from that book ever since.

How did you choose the name Alex.fyi?

Ramsey: I wanted something simple and easy to remember, and people tend to trust brand names that are named after people. I’m a huge fan of Alexander Hamilton. My family is a huge fan of the show, of course, but for me, there’s also the Wall St. element to it, and he’s someone I admire. Then I looked at domain extensions, and I really like .fyi. It was expressive of what we were trying to do. So that’s it, really. That’s the story.


Ramsey D. Smith is an entrepreneur and founder of the digital insurance agency ALEX.fyi, a platform for retirement income solutions. He is focused on modernizing the distribution paradigm in the $230B annuities industry.

Ramsey currently serves as an Independent Director on the Board of Genworth Financial. He is a member of the Risk and Nominating and Corporate Governance committees.

Prior to starting ALEX.fyi, Ramsey spent 21 years at Goldman Sachs, where he served as a Managing Director. There, he pioneered and led multiple Equity Derivative businesses. In the Life Insurance space, he developed a franchise that provided corporate level risk management and investment strategies for the nation’s top carriers. Previously, he co-led the Equity Division’s Canadian Institutional Team, where he was responsible for providing risk management and investment tools to major governmental Pension plans and other institutional clients in Canada. Ramsey also served as co-head of the GS Firmwide Black Network.

He started his career at Credit Suisse as an analyst in the Mergers and Acquisitions Group where he covered the Natural Resources industry.

Ramsey serves as Vice Chair of the Board of SEO, a nonprofit organization dedicated to closing the opportunity gap in underserved communities. Ramsey served previously as a Trustee of the Dalton School.

He is a graduate of Princeton University and earned his MBA from Harvard Business School. Ramsey and his wife, Sabrina, live in Atlanta and have two children.