Back Bay Financial Planning & Investments

Back Bay Financial Planning & Investments Fee-Only, Fiduciary, Retirement & Tax Planning Expertise on the Eastern Shore of Maryland & Delaware

Well, it's time to announce the big surprise for Back Bay. Please welcome Matt O'Keefe, CFP® to the firm as our newest f...
09/01/2026

Well, it's time to announce the big surprise for Back Bay. Please welcome Matt O'Keefe, CFP® to the firm as our newest financial planner. You can read more about Matt on our website: https://backbayfp.com/meet-our-team/

But the long and short of it is Matt and I go back to my first day in the business. Ironically, he's responsible for why I have a practice on the shore. It's a full circle moment. It shores up our firm's continuity and also allows the firm to handle some growth without any advisor being oversaturated with too long a list of clients.

We're excited for this next chapter. Please welcome Matt and his clients to the Back Bay family.

Ryan Carrado was our summer intern (and first intern ever at Back Bay!) this year. Many of you know how involved I am wi...
08/28/2026

Ryan Carrado was our summer intern (and first intern ever at Back Bay!) this year. Many of you know how involved I am with Salisbury University and their Financial Planning program. As part of that, I try to allow space for an intern at our firm to see and hear real world financial planning in action, along with what running a firm looks like. I consider our internship a success because Ryan told me it wasn't at all what he thought it was going to be. Financial planning can be like that.

Ryan got to sit in on over a dozen client and prospective client meetings. For those who were able to meet him, I appreciate your grace in allowing him to watch where the rubber meets the road. He's intimately familiar with our planning software, RightCapital, after helping me update all of our clients' plans, and our tax planning software, Holistiplan. He may be more familiar than he wanted to be. ;) We also got him a professional headshot for his future ventures — turns out he cleans up nice.

Overall, I hope it was a great experience for him. It's always one for me, as I find teaching to be one of the easiest ways to keep sharp on so many aspects of our business. He has a bright future ahead of him, one that hopefully has the CFP Board marks behind it sooner rather than later.

EDIT: I totally forgot to mention as part of Ryan's internship, I asked him to guest write a blog post detailing his experience. You know there was going to be some work involved. You can read about his time in his own words here: https://backbayfp.com/my-summer-at-back-bay-guest-post/

08/17/2026

I hear alot about people who are worried about Required Minimum Distributions, or paying taxes in retirement. Something like: "I don't want a big pre-tax balance, RMDs are going to crush me in taxes later."

The instinct to avoid forced taxes is right. But when you run the numbers, it usually doesn't hold up. And that fear is quietly pushing a lot of pre-retirees to over-Roth. The youth are calling it "Roth-maxxing"

What most people miss: you save on the way in at your marginal rate. You pay on the way out at your effective rate. Those are not the same number.

Take someone earning $150,000 a year, married filing jointly. Every dollar they defer into a 401(k) or traditional IRA saves them 22 cents in federal tax, off the top, at their marginal rate.

Now fast-forward to retirement. Say RMDs force that same person to pull, oh, $150,000–$175,000 out of the account in a given year. That withdrawal fills up the 10%, 12%, and part of the 22% bracket starting from zero, landing at roughly a 10–12% effective federal rate.

22% saved going in. 10–12% paid coming out. That's a real, durable tax edge as good as a market return. It comes purely from understanding how brackets work, not from any clever strategy.

For scale: to actually reach a 22% effective rate (not marginal) on withdrawals, a married couple would need to pull something like $565,000+ out of pre-tax accounts in a single year, under today's brackets. Most RMDs don't come close. Ironically, over "Roth-maxxing" via Roth conversions in retirement erodes the edge from making pre-tax deferrals in the first place!

None of this is a knock on Roth accounts, they absolutely have a place. But "I'm afraid of RMDs" isn't, on its own, a reason to pay more tax today than you have to. Understood correctly, this math should make you less afraid of a pre-tax balance, not more.

Marginal vs. effective. Not exciting. Might be the most underrated (and misunderstood!) concept in retirement tax planning.

White Marlin Open 2026 in the books. Got to take our kids to the scales to see the 600 pound blue marlin, which my kids ...
08/09/2026

White Marlin Open 2026 in the books. Got to take our kids to the scales to see the 600 pound blue marlin, which my kids think is a dinosaur. It's about as close as it gets nowadays.

Anyways, some big money handed out, congratulations to the winners.

Interesting question hopefully they are thinking about (you know I am) - how is this taxed? Since I've never won (or participated) I can only guess they'll be receiving 1099-MISC income. Which means, no taxes withheld. But these prizes are indeed taxable. These individuals will want to make sure they have a plan to pay estimated taxes (the win falls in the quarter due September 15, so that's the one that matters most), and should consider other strategies to minimize their income this year.

Unless they plan on winning every year (as we talked about, statistically unlikely) they should be looking to maximize their available deferrals through their 401(k)s, HSAs or other tools. Pushing portfolio management decisions that would capture gains until next year, or looking for opportunities to create losses such as direct indexing their winnings or using a tax aware long-short strategy if they have big gains coming into the year. For those with philanthropic goals, a donor advised fund might be a great thing to start.

Unfortunately, while it is an awesome gesture that many do, I don't think donating the fish meat to the food bank counts. Despite how much that fish was "worth." Would be a fascinating case for the tax court.

Good tax planning can help those lucky anglers with more of their hard earned prize money!

2026 White Marlin Open is underway. Always an awesome event for our area. I'll head down to the scales this week. The ki...
08/03/2026

2026 White Marlin Open is underway. Always an awesome event for our area. I'll head down to the scales this week. The kids love seeing the fish, and it's quite a spectacle if you haven't been. Marlin Fest at the Inlet is an awesome addition too.

It's known as the richest gamefish tournament in the world, and this year 334 boats are chasing nearly $10 million. I always like thinking about the economics of such a gamble.

In investing and economics, we use a concept called expected return: basically, what you'd expect to make on average once you factor the odds. Here's how it shakes out for 2026. To compete for the real money, a boat pays over $100,000 to enter all the calcuttas. Split the whole purse evenly across 334 boats and the average take is about $30,000. So you're putting up six figures for an expected payoff of maybe a third of that.

However, that's just the economic theory version, because the money doesn't get split evenly. Obviously the headlines you'll read are about the winner-take-all where a few boats haul in millions, and most come back to the dock with nothing. That's the asymmetry people chase. There are few things rational about the economic decision, but the passion and the excitement are what make the event so awesome.

With those probabilities, I wouldn't quite view it as an investment idea. But sometimes it's about more than the numbers. See you at the scales!

07/28/2026

I saw another advisor post this recently, and it felt so aligned with my thinking that I wanted to echo it for those looking for an advisor or those of you who are thinking about entering the industry. It's exactly what I've been focused on this time of year.

The most valuable work I do for a client almost never happens in the meeting itself. It happens in the quiet hours in between: reading a tax return closely, sitting with someone's retirement income plan, working through a Roth conversion three years before anyone thinks to ask about it. Or how about just getting back to you right away!

That kind of thinking just doesn't scale, and I don't think it ever will. The uncomfortable part: most of the industry isn't designed to protect that time. A lot of advisors carry two, three, four hundred households. At that size the math forces the job into something else entirely: gather assets, run the meetings, keep the machine moving. The deep thinking is the first thing that gets squeezed out, because it's the one thing you can skip without anyone noticing right away. In a world where professional services are just taking on as much as they can, quality is what gets whittled away.

That's the entire premise of capping the number of households I take on. I'd rather know your situation cold than collect a long list of names I can't keep straight. In a world of AI, I think that is the value proposition for our profession: knowing your finances as well as or better than you do.

At the end of July, it's hard to believe, but I'm just about at that cap. Which is exactly why we've got a big announcement coming September 1st.

As I reflect on one year in, it's the part I'm proudest of: the time to actually think about the people I work for. Zero compromise on protecting it.

Genuinely surprised by this one - Back Bay Financial Planning & Investments was voted Best Financial Investment Firm in ...
07/23/2026

Genuinely surprised by this one - Back Bay Financial Planning & Investments was voted Best Financial Investment Firm in Sussex County in Coastal Style Magazine's 2026 Best Of readers' poll.

We're literally one year into this. To be on that list already isn't something I expected. I like to think this is what evidence looks like when you do good work for people. That's the only scorecard I'm keeping, awards or not.

Most importantly, I just want to say thank you to all who took a second to vote for us. It means the world. We're doing our best to make year 2 even better.

(Coastal Style Magazine 2026 Best Of, voting conducted spring 2026. Back Bay paid no compensation to be nominated or to receive the award. An award is not indicative of future performance or of any client's experience.)

History doesn't repeat itself, but it often rhymes.....
07/21/2026

History doesn't repeat itself, but it often rhymes.....

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19930

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