Back Bay Financial Planning & Investments

06/23/2026

Such an untapped opportunity — including the next generation in financial planning.

There was a great piece in the WSJ recently on family conversations around financial education, including bringing it to family reunions! One of the privileges of my work is getting to sit down with our clients' children, not to sell them anything, but just to educate and be a resource when they need one. Financial literacy continues to be something we don't prioritize in education in this country. (That is changing!)

For our clients, it's also a planning conversation: gifting strategies, opening accounts, tax-efficient wealth transfers that let compounding do the heavy lifting early.

But even when there's no money changing hands, the education itself compounds. I have more of these conversations every year, and watching those benefits unfold over time is a good reminder of how big a deal it can actually be.

The sprawling Rosenthal clan is meeting this weekend to reconnect and empower future generations with family wisdom on finding success.

06/16/2026

Getting a lot of questions about the SpaceX IPO lately. Here are my honest thoughts and what I've been telling our clients:

We generally recommend limiting any single position to less than 5% of a portfolio. That said, IPOs can be a bit different from any other stock - if you genuinely believe in a company's long-term story, getting in early can make sense. But price matters, and the first year after an IPO can be a rough ride due to some of the differences.

A few mechanics worth understanding:

Lockup expirations. Early employees and investors typically can't sell immediately. There are usually trigger windows 6–9 months post-IPO when that changes. When those lockups expire, it often creates significant selling pressure.

Reality creep. Once public, companies have to report quarterly numbers. The gap between the roadshow narrative and actual reported numbers can be humbling. SpaceX trades at a steep premium to its fundamentals right now. Most of that is excitement about a market that genuinely looks untapped. Hard to argue with the long-term thesis and excitement. But the short-term mechanics and financial realities are a different conversation.

My general guidance to our clients: if you really want to own it, let the dust settle for at least 6 months. The chart below shows 1-year returns on the largest U.S. IPOs. It's not an encouraging track record.

This is not investment advice. All investments involve risk, including the potential loss of principal.

06/10/2026

The Social Security Administration just released their 2026 Trustees Report. Not much has changed unfortunately, we continue to track toward the 2032 trust fund depletion date. That said, I still don't generally advocate for clients to claim benefits early based on the projected reduction.

When asked if I worry about the trust fund depleting, I usually respond with the "History doesn't repeat itself, but it does rhyme." In 1983, Congress reformed Social Security with just months before the last real deadline. We still have 6 years. What seems most likely, and what the report essentially lays out is a combination of higher payroll taxes and an extended full retirement age for younger workers, kicking the can down the road for another 60–70 years against our nations demographic challenges.

Bottom line is for most of our clients, this shouldn't keep you up at night.

I always think the SSA report is a fascinating read. It describes in great detail the challenges of the program as well as possible solutions for members of Congress.

You can read it here:

Baltimore, MD - The Social Security Board of Trustees today released its annual report on the financial status of the Social Security Trust Funds. The combined …

06/03/2026

Last week I had the privilege of speaking at the Community Foundation of the Eastern Shore, joining Coastal Hospice for an event on charitable giving and tax planning.

The passage of the OBBBA has meaningfully changed the landscape in 2026 and the changes cut in two different directions depending on how much you give.

For standard deduction filers, there's genuinely good news. For the first time since the pandemic-era provisions expired, non-itemizers can deduct up to $1,000 (single) or $2,000 (married filing jointly) in cash gifts directly on their return, no Schedule A required. For a lot of households, that's a real, tangible tax benefit from giving that simply didn't exist last year. Keep track of all those cash gifts!

For larger givers, the picture is more nuanced. Itemizers now face a 0.5% of AGI floor before any charitable deduction kicks in, plus a 35% cap on the tax benefit for high-income donors. That doesn't mean giving is less worthwhile, it means it has to be more thoughtful. Strategies like qualified charitable distributions, donor-advised funds, bunching, appreciated securities, and for those with significant assets - charitable remainder and lead trusts become more important when the straightforward deduction is squeezed.

The CFES and Coastal Hospice put on a wonderful event, it was a great opportunity to dig into all of it. The work these organizations fund in this community is hard to put a number on, and that's kind of the point.

05/28/2026

I've gotten a couple of questions about bonds lately. Yields have moved up, and when yields rise, the bonds you already own fall in price so a lot of folks see red on their statements and wonder what's happening. Not the same volatility you see in stocks, but some volatility nonetheless. The last couple of years of bond returns have been pretty darn good.

Here's the part that gets lost. Without writing a dissertation on it, I think of mid- and long-term rates as a rough proxy for expected inflation plus expected economic growth. Both have been pushed higher by structural forces, the enormous AI capex buildout and a federal government issuing a lot of debt, not by a one-off shock. Oil, as a result of our recent conflict, has nudged inflation slightly higher as well.

The silver lining is the chart below: a bond's starting yield has historically been one of the best guides to the return it delivers over the next decade. Higher yields today have historically been associated with higher returns going forward. It's the same idea across asset classes, when prices fall, future return expectations rise.

For retirees, that's genuinely good news. A bond sleeve that's actually paying you again does more of the heavy lifting, which means you lean on your stocks a little less for the income and stability your plan needs.

Past performance is of course not indicative of future results, and the chart is illustrative, not a specific forecast.

05/12/2026

Spent a few days in Leland, Michigan last week with a small group of RIA owners — no agenda other than working on our businesses together. It's a study group I've joined, and this was our annual time to get together in person.

I've always believed diverse perspectives sharpen me as both a practitioner and a business owner. I came away with great feedback on what we're building at Back Bay, and I like to think I gave some useful feedback in return.

One thing I've adjusted to as a new RIA owner: being a steward and fiduciary to clients isn't just about the planning and investing. It's about making sure the firm itself is built to serve them well for the long haul, a different kind of work you have to periodically step away for. Doing it on the heels of wrapping up our annual Spring reviews made for perfect timing.

And no, being out of state doesn't mean I started sleeping in. Early morning runs along Lake Leelanau were amazing. Cold air, cold water. Every morning, we jumped in to start the day. Wakes you right up.

05/02/2026

Yesterday I got to spend the morning judging the second annual Salisbury University financial planning competition.

Most of you know I teach as an adjunct for the Perdue School’s financial planning program and serve on its advisory board. So getting to watch these students present is personal for me. The preparation, the presentation, the depth of knowledge - it keeps getting better every year. The full academic and professional community support has been awesome.

The future of financial planning locally and across the country being developed here on the Eastern Shore is in good hands. I’m just glad to play a small part in it.

Congratulations to all the winners - well deserved!

04/27/2026

The market can feel confusing right now. Prices are up, headlines are noisy, and it's hard to know what to make of any of it.

The reality is over time, stock prices follow earnings. Not the news cycle, not the sentiment on social media, not whatever the talking heads said this morning. If businesses make more money, they're worth more. It really is that simple, even when the short-term noise makes it feel anything but.

This chart shows that relationship going back to 2000. Notice how the two lines tend to find each other, even after dramatic separations. Right now, 12-month forward earnings growth sits at +31.3%, one of the stronger readings in the past two decades.

Markets are forward-looking. They're already trying to price in what comes next. The question isn't what the headlines say today. It's what earnings look like six to twelve months from now.

Earnings season is underway, and so far the results are holding up. Markets are reflecting that, even with everything else going on.