Ryan Carrado, Summer Intern 2026
Prologue: Robert here. This summer we hired our first summer intern (ever!). I’m proud to say Lisa and I were very impressed when we met and interviewed Ryan. He is a finance student at Salisbury University, where I am currently an adjunct faculty member and a member of the advisory board for the Financial Planning program. An important part of being a practitioner, for me, is helping shape the next generation and trying to leave the profession that has given me so much better than I found it. When able, that means giving students real-world experience into how our firm works, the things we do, client meetings, and all the things you just can’t learn in a classroom. My goal was to give Ryan just that in his internship. This summer alone, Ryan sat in on over a dozen client and prospective client meetings. Real experience most students only read about in a textbook. We’re grateful to everyone for their grace in welcoming him into those rooms and giving him an environment where he could learn.
With Back Bay being so new, there were many moving pieces and things we’re still figuring out how to optimize. I like to think maybe the most valuable thing I could have taught Ryan is just how fluid business is, and that sometimes you’re making it up as you go. There isn’t anything wrong with that; in fact, it’s how you keep the blade sharp and do your best to be on the leading edge. I told Ryan at the beginning of his internship that his big project would be to write a blog (you know we had to assign some homework) detailing his experience, and it would have to stack up to be worthy of our blog. After all, this is the best retirement blog on the Eastern Shore and beyond. I think he did just that. And beyond his detailing of his experience, the work he helped with took a good bit of pressure off me and helped with numerous projects that brought Back Bay forward. I only hope his knowledge and experience grew in kind.
But that’s enough of me. Below is Ryan’s blog about his summer spent at Back Bay. But Ryan, if you read this, we’re grateful for the time and effort you put in this summer. You have a bright future ahead of you.
For those who I have not had the chance to meet yet, my name is Ryan Carrado. I am a senior at Salisbury University majoring in Financial Planning and I am very thankful to be the first intern at Back Bay.
I remember walking into the office on my first day feeling both nervous but also excited. This was my first experience with real clients and real money, vs. the basic foundations and theoretical scenarios that I had been learning during my coursework at Salisbury. I hit the ground running from day one. My first day was filled with learning brand new software that at the time was like understanding a different language, while also being fortunate enough to sit in a client meeting. This was my first experience of the client-facing side of the business. What stood out to me was the understanding between advisor and client and the respect clients have for the advisor. After that first client meeting, I knew I was in good hands having Robert as my mentor. The more he taught me, the more I understood about the importance of operating as a fee-only fiduciary and what it means to act in the best interest of your clients.
I spent the first few weeks watching training videos on how to use a new suite of software, RightCapital, our planning software; Orion, our trading and performance reporting software; and Holistiplan, our specialized tax planning software. All were software that I saw no connection to. The first month of my internship, I spent reviewing annual meetings and using RightCapital to update clients’ information such as account values, insurance details, loan details, updating beneficiaries (very important — I would go read Robert’s blog on Beneficiaries), and ensuring everyone has estate documents. Overall, I made sure our planning software in RightCapital was up to date and accurate with our clients’ information. I was also lucky enough to use RightCapital to assist in planning with hourly clients, entering portfolio holdings that aided in our analysis for them. Robert always described this as a broadsword in financial planning. I did not truly grasp what he meant by this until later in my internship. While working in RightCapital, I was able to familiarize myself with Orion, where I created portfolio tags for each client’s individual portfolio to make our analysis more efficient. Using Orion and Koyfin together, we are able to track how our clients’ portfolios are doing compared to their benchmarks and identify when rebalancing or other changes need to be made.
Transitioning into the second part of my internship, I began to model out pro forma tax returns for the current year. I was tasked with forecasting taxable income by looking at any IRA distributions, any updates to possible wages, new claims to Social Security, pensions, and annuities. Robert always described this software as the scalpel, being surgical and very precise. And after all I have learned during my time here, I finally understood why RightCapital is the broadsword and Holistiplan is the scalpel. Holistiplan is very important for our clients because this allows us to identify room for any necessary Roth conversions, analyze current or nearing tax brackets, and, most importantly, project this year’s potential AGI. This allows us to see which clients would slowly phase out of important deductions, such as the enhanced senior deduction. Holistiplan also allows us to identify other year-end tax moves such as harvesting gains, QCDs, any IRA contributions… I’m sure you have all heard this from Robert so I won’t repeat it, but it was for the purpose of reducing your tax bill, increasing generational wealth for your family, and pursuing any philanthropic wishes.
By this point, the software that had once felt completely foreign had become tools that I would put to use on a daily basis. I began building out the next year’s plan, and it was rewarding to see how a band of software that all had their unique purpose came together and created plans tailored to each individual client.
Although my internship has been very technical and analytical, I was lucky enough working under Robert to see the ins and outs of how a business works, from client relationships, to marketing tactics, to back-of-house operations. It was fascinating to see what you can do when you are the owner of your own practice and the complexities that come with it. Back Bay prioritizes providing extra value to clients through welcome letters to new clients, monthly newsletters, mid-year market updates, and extensive year-end tax planning, which all lead back to Back Bay’s three principles: Transparent Communication, Expert Guidance, and Proactive Planning. These are all things that give clients peace of mind and ensure that they have made the right choice choosing Back Bay.
Many people believe that finance is just crunching numbers, but during my time here I have realized it is more of an art and science than a math game. It goes deeper into the psychology of people’s minds, goals, and how willing some people are to take on risk while others might not be. It is very important to understand this when constructing plans for clients because not everyone will be the same, and that has been a fun part of my internship. Everyone I have met has been different in their own way, whether it’s their financial goals, the legacy they want to leave, or just how they want to enjoy retirement. One thing that I enjoyed is seeing an advisor tell people to spend money. It is very interesting because people have been told to save their whole lives for retirement, and then once they get into retirement, they are supposed to do a 180 and start spending it. It’s rewarding to help clients finally enjoy the money they have spent a lifetime saving and sacrificing for and watch them step into retirement and be able to use it.
Something that surprised me while working at Back Bay is the importance of learning and progressing. Ever since my first day, I have never stopped learning and progressing in my time here. I went from sitting in my office attempting to learn software that was so foreign to me and sitting in my first client meeting, hearing words and phrases I have never heard before, to beginning to work on hourly client plans, creating new 2027 plans for current clients, and now writing a blog for our website (seems cheesy).
For the majority of my internship, the learning curve was very steep and never seemed to end, which at the start was what I dreaded the most. Unfortunately, now that my time here is coming to an end, it has become my favorite part. I enjoy going into work each day knowing that I will know more by the time I leave, and knowing that the hours I spent in the office would translate to more than anything possible to learn in a classroom. Although this is just the start of my career, I have been very blessed and grateful for this opportunity. This experience has solidified my goals of obtaining my CFP® certification and a career in fee-only financial planning. I am very thankful to Robert, Lisa, and Back Bay as a whole for taking me on as their first intern. Thank you!
