Planning Around Stock Compensation: Taxes, Timing, and Down Markets with Emily M. Harper, CFP®
Release Date: 06/09/2025
Greenland, China, Market Rotation and What Actually Matters for Your Money
Off The Wall
Some weeks call for rain boots because the conversation is going somewhere most people would rather avoid. This episode steps into charged territory on purpose: geopolitics, tariffs, China and Taiwan, Greenland, and the policy decisions shaping today’s headlines. There’s no posturing here and no outrage bait, just a willingness to talk through complex questions instead of skirting around them. From there, the focus shifts to what actually matters for investors: how markets tend to react when policy dominates the news cycle, why short-term volatility shows up, and how data and discipline...
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What Last Year Taught Us About Staying Invested
Off The Wall
A new year always brings fresh predictions, louder headlines, and plenty of pressure. In the first Off the Wall episode of the year, Nate W. Tonsager, CIPM and David B. Armstrong, CFA take a step back and anchor the conversation in the reality of what happened in 2025, and why that context is essential as we head into 2026. They reflect on the surprises that shaped last year and connected those lessons to the environment ahead. Key topics: Global markets and why international equities outpaced U.S. stocks in 2025 Volatility, drawdowns, and what last year revealed about investor behavior ...
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What Investors Asked: Predictions, Bitcoin, and Gold
Off The Wall
In this Ask Monument Anything episode, we’re answering real questions from listeners of the show. From a question about Michael Burry’s bold predictions and why they continue to draw attention, to a discussion of Bitcoin’s unusual performance in 2025 and the renewed curiosity around gold as a potential safe-haven asset, the conversation then shifts to private credit’s emerging role inside 401(k) target-date funds. Key takeaways: • The patterns that show up again and again when attention-grabbing forecasts circulate • Forces that pushed Bitcoin into an unexpected...
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The Guide to Less Stressful Holiday Giving
Off The Wall
The holidays come fast and somehow the shopping and gifting part always seems to catch us by surprise. In this episode of Off The Wall, host David B. Armstrong, CFA is joined by Cathleen Phelps and Cecelia Gilliam from our Client Experience team as they sit down in full holiday mode to share ideas that make gifting feel fun again. From opening Roth IRAs for teens, funding 529 plans for nieces and nephews, and introducing kids to charitable giving, to practical strategies like shared family experiences, subscriptions, organizing spreadsheets, and even planning for parents who “don’t need...
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The Biggest Questions Shaping Portfolios Right Now
Off The Wall
Markets feel noisy right now, and investors are asking sharper questions than usual. In this episode of Off The Wall, Nate W. Tonsager, CIPM® and David B. Armstrong, CFA open with the surge in tech valuations and the unusual weight a handful of companies now hold inside the S&P 500. We’ll hear about what that concentration means for volatility, why some portfolios feel out of sync with the index, and how listeners can think about risk when the market feels lopsided. Next, they talk about the current labor environment, which is a mix of hiring freezes and productivity changes, and what...
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3 Trends in Charitable Giving that May Change How You Give This Year
Off The Wall
2025 has been a rough year for charities. Economic uncertainty, decreased federal funding, political polarization – in many ways, nonprofits are facing a lot of the same challenges they did during Covid, as well as a few new ones. Charitable organizations need your donations now more than ever. In this episode, we’re joined by former OFF THE WALL co-host and Partner at Monument, Jessica Gibbs, CFP® as she highlights three current trends in charitable giving and how you can adjust your giving strategy to help make a bigger impact. If you’re currently looking at end-of-year giving...
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Q3 Market Recap: Alternatives, Gold, and the Bull Market Debate
Off The Wall
It’s the start of a new quarter, which means it’s time for a market recap and our special “Ask Monument Anything” segment. David Armstrong, CFA, gets back together with Erin Hay, CFA, CMT, and Nate Tonsager, CIPM, to walk through the latest market moves, where momentum is showing up, and what investors should be paying attention to. This quarter, they dig into alternatives, gold’s surprising surge, and whether today’s bull market has more room to run. They also share candid thoughts on cash, dividends, and why being intentional with your portfolio matters more than chasing the...
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5 Years Until Your Last Day: How to Handle the Shift from Career to Retirement
Off The Wall
When you hit 60, there’s a mental shift that begins to occur. After spending 30+ years earning and saving, you are suddenly just a few years away from beginning to spend your retirement income. It’s a challenge every retiree faces: How do you step away from regular paychecks to drawing down your savings every month? In this episode, we discuss how to create an option-rich life in retirement, where your money will come from, how to handle taxes, how to stay flexible, and much more! Tune in to hear the whole conversation. 0:00 – Disclosure 0:48 – Kicking off the 75th episode...
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Dow Jones, S&P, NASDAQ: What’s the Difference (and Which Should You Use to Track Your Own Portfolio)?
Off The Wall
For many investors, the Dow Jones or S&P 500 or NASDAQ might as well be the same thing, but that’s not true at all. In today’s episode, Dave, Nate, and Erin dive into the differences between the big three indices and whether you should look to them as indicators of how your own portfolio is doing (spoiler alert: no, you shouldn’t). So what should you be tracking to get the best picture of your performance? And how can you avoid the most common mistakes people make when trying to track their portfolio on their own? Tune in to find out! Please see important...
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Should You Wait to Invest? The Q2 Market Review
Off The Wall
In this special Q2 Market Review episode of Off the Wall, we’re introducing a new segment: Ask Monument Anything (AMA). Dave, Nate, and Erin answer questions from clients and listeners, and also cover what went down in the markets during the second quarter of 2025. They cover everything from interest rates and inflation to timing your investment strategy and understanding international diversification. If you are wondering how to approach market timing, if cash is still king, or if international stocks should fit into your portfolio, this episode is for you! Dedicated email address for...
info_outlineIf stock-based compensation is a major part of your wealth portfolio, down markets can be stressful. In this episode, Jessica Gibbs, CFP® and Emily M. Harper, CFP®, break down how to approach equity compensation, even when the markets are rocky.
From tax planning to direct indexing and long-term diversification, they explore some ideas that can potentially reduce risk and create opportunities. Strategies like mapping out your vesting schedule and cash needs can keep you focused and on track during market swings.
If you’re an executive with stock compensation, this conversation will help you understand how to make informed decisions and respond with intention, instead of emotion.
Resources Mentioned in the Episode:
What is Direct Indexing and How Does it Work? with Pat McStay
Top Executive Compensation Strategies You Should Know with Laura Balser
Please see important podcast disclosure information at https://monumentwealthmanagement.com/
Episode Timeline/Key Highlights:
0:00 Important Disclosure
1:00 Introduction to Stock-Based Compensation
1:40 Common Mistakes for Building Wealth Through Stock Compensation
2:40 Common Risk Mentalities of Executives
5:26 Assessing Concentration Risk
9:00 Building a Sell Strategy
15:40 Market Volatility and Stock Comp
22:00 Episode Wrap-Up and Resources
23:20 Important Disclosure
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About “Off the Wall”:
OFF THE WALL is a podcast for business professionals and high-net-worth investors who want to build wealth with purpose. A little bit Wall Street, a little bit off-the-wall; it's your go-to for straightforward, unfiltered wealth advice on topics that founders, business owners, and executives care about.
Learn more about our hosts, Dave and Jessica on our website at https://monumentwealthmanagement.com.