Matt Sizemore, Financial Advisor at Morgan Stanley

Matt Sizemore, Financial Advisor at Morgan Stanley On a mission to help you find purpose and joy as you manage wealth! MSSB will not accept purchase or sale orders via social network messaging systems.

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A real conversation I had with a friend of mine on the golf course... "I got a surprise tax bill from my last stock vest...
04/01/2026

A real conversation I had with a friend of mine on the golf course... "I got a surprise tax bill from my last stock vesting, and my advisor told me there's nothing I can do about it."

Equity compensation can be a powerful wealth builder—but the tax details matter just as much as the potential upside.

A few quick reminders to keep in mind:
· Not all equity is taxed the same. RSUs are typically taxed as ordinary income when they vest, while stock options may have tax impact at exercise and/or sale depending on the type.
· Withholding may not equal what you owe. The default tax withholding on vesting/exercise can be a starting point—not the final bill—especially for higher earners. Check with your plan provider to see what they're withholding for you.
· Timing can change outcomes. The decision to exercise, hold, or sell (and when) can affect ordinary income vs. capital gains treatment and your cash flow.
· Concentration risk is real. If company stock is becoming a large portion of your net worth, it may be time to revisit diversification.

This is general information, not tax or legal advice. Tax rules are complex and can change—please consult your tax advisor for guidance specific to your situation.

Celebrating another year with my family and taking a moment to reflect on how important relationships are—both at home a...
03/11/2026

Celebrating another year with my family and taking a moment to reflect on how important relationships are—both at home and in the work we do. Although I'm a little late, thank you all for the birthday wishes.

Happy 70th birthday to my dad, Ken Sizemore—the steady example I've tried to follow both in life and in this business. G...
02/12/2026

Happy 70th birthday to my dad, Ken Sizemore—the steady example I've tried to follow both in life and in this business. Grateful for the laughs, the lessons, and a great family steak dinner to celebrate you!

I'm excited to share that the Cadden Sizemore Group was recognized in the 2026 Forbes Best-in-State Wealth Management Te...
01/21/2026

I'm excited to share that the Cadden Sizemore Group was recognized in the 2026 Forbes Best-in-State Wealth Management Teams ranking for the state of Virginia. This recognition is a testament to the hard work, collaboration, and care our team brings to work every day. I'm thankful for our clients and for my incredible colleagues who make this role so rewarding. and proud to belong to such a great team and firm!

2026 Forbes Best-In-State Wealth Management Teams
Source: Forbes. Awarded Jan 2026. Data compiled by SHOOK Research for the period 3/31/24–3/31/25.
https://www.morganstanley.com/disclosures/awards-disclosure/

Feeling grateful to celebrate 10 years with The Cadden Sizemore Group at Morgan Stanley this month!While I've worked har...
12/18/2025

Feeling grateful to celebrate 10 years with The Cadden Sizemore Group at Morgan Stanley this month!

While I've worked hard to get here, the truth is that I couldn't have scaled this business without the people around me. I'm especially thankful for Anne Southworth and Christy Goodman, our team's phenomenal proactive and reactive service partners in every sense of the word. I'm also deeply grateful for the mentorship and support I've received from Ken Cadden and my dad, Ken Sizemore.

I can't forget my lovely wife who has supported and celebrated me at every step of the way. No way I'd be here still without her.

I walked in the door in 2015 knowing almost nothing about markets or private client work and was thrown straight into the deep end. I cold-called nonstop and was told "no" more times than I can count. While it was painful at the time, with the rare glimpse of hope, I wouldn't trade that experience for anything now.

My motto was, "I need to work my tail off to find someone to help."

In that journey, I found the best clients I could ask for, and the clarity that I'm exactly where I'm meant to be. Excited to see where the next 10 years takes me!

Below: A throwback picture of my wife and I on our honeymoon in Bermuda, the same year I started at Morgan Stanley.

I tried something new this Thanksgiving… Amidst all the chaos of getting the house ready for guests, 3 kids screaming, a...
12/04/2025

I tried something new this Thanksgiving…

Amidst all the chaos of getting the house ready for guests, 3 kids screaming, and what felt like 20 trips to the grocery store….

I made a pumpkin pie from scratch. A caramelized honey custard pumpkin pie. And let me tell you, it did not disappoint.

I'm going to tie this to business, don't worry.

This thing was the real deal. I made the pie crust (which was surprisingly easy), even though everyone told me to just buy a premade one.

I browned the butter, caramelized the honey, added eggs, and yes Libby's 100% Pie, and heavy cream and Voila: PUMPKIN PIE!

I see people take the easy way all the time…in life…at the holidays…in business. And I'm all for conveniences believe me, especially raising 3 kids.

But some of the best things in life require you to roll up your sleeves and get to work, learn something new, or outright invent something.

If you want better results, make your own pie, or find someone who can do it better than you ever could.

Between end-of-year reviews, market updates, and the upcoming holidays, this time of year always moves fast. But even du...
11/20/2025

Between end-of-year reviews, market updates, and the upcoming holidays, this time of year always moves fast. But even during the busiest times, it's important to takes some time to pause and take everything in. Fall in Virginia is breathtaking, and a much-needed reminder to myself (and maybe to you, too) to slow down and appreciate the moment.

My wife and I just celebrated 10 years of marriage with a quick getaway to Washington, VA - our first real time alone si...
11/04/2025

My wife and I just celebrated 10 years of marriage with a quick getaway to Washington, VA - our first real time alone since welcoming baby #3. While we enjoyed the quiet, the views, and our first Michelin-star meal, for us the most luxurious part was slowing down and simply enjoying each other's company.
Life with three kids doesn't leave much time for stillness, but stepping away reminded me how important it is to stay connected as partners, not just parents. Grateful for the reminder, and for the amazing life and family my wife and I have built together over the past decade.

These past few weeks have been a special time for the Sizemore household as we adjusted to life as a family of five! We'...
09/24/2025

These past few weeks have been a special time for the Sizemore household as we adjusted to life as a family of five! We're thrilled to share that we welcomed our son, Sonny, on August 18, 2025.

I'm grateful to my incredible team, The Cadden Sizemore Group, for their support during this time, and to my clients for their well wishes and patience while I stepped away to be fully present with my family. As I return from paternity leave, I'm excited to reconnect with you all!

What if I could give you a year of your life back?Of course I can’t do that literally, but through some intentionality a...
06/26/2025

What if I could give you a year of your life back?

Of course I can’t do that literally, but through some intentionality and awareness, maybe?

Most of us have 2 places we spend most of our hours living: Home and Work.

That’s obvious, right?

According to ChatGPT, most Americans will spend about 8,000 hours at both places per year (Work: 2,000 hours + Home: 6,000 hours = 8,000 hours total).

And…people in the US spend 220 hours per year commuting to and from work. Just under ½ an hour each way.

There are only 8,760 hours in the year, people!

That leaves 540 hours for leisure and vacation somewhere other than home or work. Are you taking those? That’s 1 hour and 15 minutes each day if we assume 2 full weeks of vacation.

Maybe part of our anxiety, depression, and other health issues are that we’re not spending enough time at our 3rd place? And by that, I mean whatever place rejuvenates your body, mind, and spirit: the river, hiking mountains, playing golf, bike trails, time with your faith community, the gym, the art studio, the wood working bench, etc.

Though we spend a similar amount of time at home compared with the rest of the developed world, our time at work is vastly higher.

Japan spends 1,600 hours/year working. Canada 1,700 and Germany 1,300. Are these slack countries? I think not. They are incredibly hard working and productive cultures.

Let’s work it out:

Last 10-Year average GDP Per Capita (Per Person) numbers:

Japan: $37,537 USD

Canada: $48,813

Germany: $42,807

United States: $67,366

No doubt from this standpoint the US dominates, right?

But if we divide that by the number of hours we work, here’s what we produce:

Japan: $23.46/hour

Canada: $28.71/hour

Germany: $32.93/hour

United States: $33.68/hour

We work more and produce more overall, but we aren’t much more productive in the hours when we work. I also wonder if we would widen our economic gap even more with just a little more time off.

We could have an additional 700 hours/year to feed our souls yet be just as productive in each hour as our German counterparts.

What if we just took 300 more hours through the year?

That’s 3,000 hours over a decade. In 3 decades of our working lives, that’s more than a full year of time we would get back to spend on hobbies, rejuvenation, and enjoying life.

What could you accomplish with this? How much better could you have gotten at painting, fitness, or golf? Better yet, how much more enjoyment would you find in your life?

I think we’re doing it wrong here in the US. Our health outcomes would agree compared with the rest of the developed world.

Drop a comment on what 3rd place you’re exploring this Summer!

For Generous Givers, the most underrated tool is…Wait for it...The Donor Advised Fund. Did you know the largest contribu...
06/18/2025

For Generous Givers, the most underrated tool is…

Wait for it...

The Donor Advised Fund.

Did you know the largest contributor to charity is not Warren Buffet, Jeff Bezos, or the Gates Foundation? It’s one of Morgan Stanley’s competitors Donor Advised Fund. That entity gave over $14 Billion dollars to charity last year. That’s nearly as much as the top 50 individuals/foundations COMBINED and nearly 5x what Mike Bloomberg, the largest donor, gave last year.

DAFs can help you:

1️⃣ Leave a Legacy: Encouraging Charitable Giving from your heirs far beyond your life.

2️⃣ Can Help You stay below certain tax thresholds such as IRMAA, 20% Capital Gains, and Net Investment Income in the current year.

3️⃣ Grow your Charitable Dollars Tax Free in the market within the fund (increasing your impact).

DAFs are a 501(c)(3) that allows you the Donor and Advisor to give to other registered 501(c)(3)s and non-profit/faith-based organizations.

The key is, you could receive all the tax breaks you would normally get by giving cash or appreciated stock to charity.

But….

You get to take your time doling out funds to your favorite charities/non-profits.

All from one organized place that keeps track of your gifts (so you don’t have 20 different charitable gift receipts to keep track of yourself).

Forget having to staff your own Private Foundation (expensive!) and being forced to give out 5% of your assets each year, you are not forced to give anything annually from a DAF. We can debate whether that’s good or not. But a study from Fidelity showed that 74% of contributed assets were given to charity in the first 5 years. That’s a pretty good clip! You could argue that’s much more than foundations would give as a % of assets with the mandatory 5% annual granting.

Oh, and you can give almost any kind of asset to this account: Cash, Highly Appreciated Company Stock, Real Estate Interests, Crypto, Privately Held Business Interests, Alternative Investments, etc.

Click Here to Learn More about Morgan Stanley’s Donor Advised Fund: https://lnkd.in/ennBvsry

Click Here to Schedule a Meeting to Review Your Charitable Giving Strategy: https://lnkd.in/ee2Hy6ZX

As always, this is not tax-advice, consult your CPA/Financial Advisor for what strategy is right for you.

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