RSUs: What to Do When They Vest
Between Sips
Your RSUs vest. The shares hit your account. Now what? For most high earners, RSUs sit in a kind of planning no-man's-land — not quite a paycheck, not quite an investment you picked, but treated like both without a clear strategy for either. The result is decisions made by default rather than intention. In this episode, Emily and Jessica walk through how RSUs actually work — from grant to vest to sale — and more importantly, what that means for your W-2, your tax bill, your concentration risk, and your broader financial picture. They get into when selling at vest makes sense, how to...
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Is There Something Your Tax Return Isn't Telling You?
Between Sips
You've got a good accountant. You trust them. You sign the return. But here's what Emily and Jessica see all the time: costly mistakes that aren't anyone's fault — they happen because your accountant can only work with what they're given. And there are things living at the intersection of your tax return and your busy life that fall through the cracks unless someone is paying attention to the whole picture. In this episode, Emily and Jessica walk through what your tax return is actually telling you — and what it should be driving. Because the number at the bottom isn't the point. The point...
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Real Estate Ownership: Personal vs. LLC – What You Need to Know
Between Sips
If you've spent any time on financial social media, you've probably heard some version of this: buy real estate, put it in an LLC, and watch the tax savings roll in. Here's the thing — that's mostly wrong. And in this episode, Emily and Jessica explain why. For most high earners, rental real estate is a passive activity. The deductions don't touch your W-2 income. The LLC doesn't change what hits your tax return. And qualifying for the tax treatment people are actually imagining? That requires a level of real estate involvement that most busy professionals simply don't have. So if it's not...
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Retirement Accounts and The Tax Surprise Hiding in Your IRA
Between Sips
There’s this belief a lot of smart, responsible people carry for decades: Save as much as possible in your retirement accounts, don’t touch it, let it grow, future you will thank you. And then…future you hits “RMD age”. Suddenly there’s a number attached to your birthday. A required withdrawal. A tax bill you didn’t fully picture. Medicare premiums reacting to your income. And the realization that most of your wealth lives in accounts the IRS still has a claim on. This conversation with Jessica and Emily feels like the moment when you zoom out and look at your entire financial...
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Trump Accounts: What’s the Catch With the Free $1,000?
Between Sips
With headlines, commercials, and social chatter everywhere, these new accounts are getting a lot of attention. But are they actually the best way to give kids a financial head start? In this episode of Between Sips, Emily and Jessica break down how Trump accounts work, where they fit alongside 529s and custodial accounts, and why your child’s future goals should drive every decision. They share what high-earning families need to know about tax treatment, flexibility, record-keeping, and the trade-offs that often get overlooked. If you’re saving for a new baby—or just trying to make...
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Do I Need a Trust? Here’s How They Work
Between Sips
Trusts aren’t just for the ultra wealthy, or something you deal with much later in life. For most people, that assumption just creates stress and delay. In this episode of Between Sips, Emily and Jessica slow things down and talk about trusts in plain language. What they are, why people use them, and why they are not magic tax loopholes. You’ll hear the difference between revocable and irrevocable trusts, explained with everyday examples. This conversation will help you feel less intimidated and more grounded. You don’t have to rush out and set something up tomorrow, but you should...
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The Conversation We All Keep Dodging: Estate Planning
Between Sips
Estate planning has a reputation for being heavy, uncomfortable, and easy to avoid. Between sips of a Rhode Island coffee, Jessica and Emily talk about why that avoidance is so common, even among thoughtful and successful people, and why it can create more stress down the road. This conversation reframes estate planning as a way to protect your life, your relationships, and the people you love, not a checklist for the end of life. From incapacity planning to outdated documents, they explore how small decisions today can create clarity and peace of mind later, without making it overwhelming....
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How to Set Goals Without Overhauling Your Life in 2026
Between Sips
A new year has a way of making people feel like they need to figure everything out at once. Goals, priorities, plans, all piled together in January, like our life restarts with the change in the calendar. In this first Between Sips episode of 2026, Emily and Jessica talk through a more realistic way of thinking about goals, one that leaves room for life stage, time constraints, and changing priorities. They share why so many people struggle to articulate what they want, and how narrowing goals too quickly can cause us to miss opportunities that really move the needle. The conversation takes...
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What People Get Wrong About Roth IRAs and Conversions: A Guide for Busy Professionals
Between Sips
Roth IRAs, backdoor Roths, conversions… most people know these terms, but not why they matter. In this episode, Emily and Jessica break it all down in plain English and focus on the real question: How do you create more flexibility for your future self? With uncertainty around tax policy and retirement rules, the way your money gets taxed can have as much impact as how it’s invested. The good news? You have more control than you may think. Emily and Jessica walk through the key moments when a Roth conversion might be worth considering—career pivots, sabbaticals, business transitions,...
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How to Plan for Your Child’s Education
Between Sips
College can feel far away when your kids are still young, but the questions around their future tend to show up early. Over a favorite cup of coffee, Emily Harper, CFP® and Jessica Gibbs, CFP®, talk through the mix of hope, uncertainty, and planning that surrounds education today. They share what they’ve learned as financial planners and college graduates, touching on rising costs, changing career paths, and the value of defining your own philosophy before focusing on numbers. The conversation wanders through personal stories, shifts in the education landscape, and the small steps families...
info_outlineMarkets are down, your retirement date’s circled on the calendar—now what? Emily and Jessica unpack how to protect your peace of mind, why your “sleep-at-night factor” matters, and what it really means to retire on your terms.
Tune in to hear how market volatility can impact your retirement portfolio if it happens at the wrong time. Plus, understand the value of stress-testing your portfolio and how to reduce your anxiety around retirement.
Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures
0:14 - Intro
2:39 - Can You Retire in a Down Market?
5:18 - Why Timing of Returns Matters
14:40 - Beyond Markets: Inflation and Rates
17:05 - The Cash Bucket Strategy
20:05 - Key Takeaways
26:11 - Disclosures & Closing
Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures
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Connect with Emily on LinkedIn: https://www.linkedin.com/in/emilyharpercfp/
Connect with Jessica on LinkedIn: https://www.linkedin.com/in/jessicagibbscfp/
Instagram: https://www.instagram.com/monumentwealth/#