Life After Ownership: Defining Your Next Chapter After You Sell a Business
Release Date: 09/03/2025
Retiring Before 65: What It Really Means
Between Sips
We’ve all heard 65 is the magic retirement age, but who decided that, anyway? In this episode, Jessica Gibbs, CFP®, and Emily Harper, CFP®, share a fresh take on what it means to step away from full-time work before that milestone. The conversation moves between money and mindset, the realities of healthcare and savings, and the freedom of redefining what retirement even looks like. They talk through how to prepare, what “enough” might mean for you, and why the emotional side of this transition matters just as much as the financial one. For anyone wondering when work starts to give way...
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Should You Retire When the Market is Down?
Between Sips
Markets 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 0:14 - Intro 2:39 - Can You Retire in a Down Market? 5:18 - Why Timing of Returns...
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OBBBA Review: Tax Moves to Make Before 2025 Ends
Between Sips
The “One Big Beautiful Bill” is here—and it’s changing the math on deductions, income timing, and year-end tax strategy. In this episode we cut through the complexity to spotlight the most important moves to make before December 31, 2025. We unpack what high earners need to know about charitable deductions, the new 35% cap, clean-energy credits, and how to make the most of your AGI and MAGI thresholds—without drowning in details. Pour yourself a cup of your favorite brew and tune in for clear, actionable ideas on how to finish the year tax-savvy and confident. Please see important...
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Unique Ways to Donate to Charity Beyond Writing a Check
Between Sips
“Cash isn’t the only way to make an impact. Complex assets—like private business shares or alternative investments—can sometimes be the most powerful gifts.” Emily M. Harper, CFP® Charitable donations come in many forms: cash, stock, assets. In this episode, we’re talking about charitable donations in the form of complex assets, such as privately held business shares, crypto, oil and gas royalties, and more. Depending on your situation, it may make a lot of sense. It can help maximize the impact of your gift while also increasing your tax efficiency. That being said, there is much...
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Post-Exit Planning: How to Manage Your Investments & Cash Flow After Selling Your Business
Between Sips
For business owners, the day you sell your business can feel like you’re crossing the finish line. In reality, it’s actually just a new starting point for the beginning of your post-exit life. One of the biggest questions we hear after a successful sale is “What should I do with all this money?” In this episode, Jessica and Emily tackle the financial side of post-exit life: the benefits of a cash strategy, why you should be thinking about your portfolio’s total return (not just income), and why behavior is often the biggest threat to long-term investing success. Tune in to learn more...
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Life After Ownership: Defining Your Next Chapter After You Sell a Business
Between Sips
“Liquidity can open a lot of doors, but purpose tells you which ones to walk through.” Selling a business is an amazing accomplishment, but it is often followed by an identity crisis that can leave former business owners in a spiral. The purpose you committed yourself to every day is suddenly gone – what’s your purpose now? In this episode, we discuss how to approach life after business-ownership: how to find fulfillment, what to do with the money, and where to look for your next project.Whether that’s joining a board, angel investing, or pursuing philanthropic...
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A Gift that Changes the Game: How to Approach Transformational Giving
Between Sips
What if your giving could transform an organization’s future? In this episode of Between Sips, we share how to approach extraordinary charitable gifts—whether $25K or $25M—with intention and impact. We’ll cover the four factors to consider, smart questions to ask the charity, and how to navigate recognition, structuring your gift, and assessing impact. Tune in to learn how to turn generosity into truly strategic giving. Please see important podcast disclosure information at Connect with Monument Wealth Management:
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Thinking of Moving or Retiring Abroad? Listen to This Episode First
Between Sips
Welcome to the inaugural episode of “Between Sips,” a new podcast from Monument Wealth Management where we look at big questions at the intersection of money and meaning. In this episode, we’re answering the question: Should I move–or invest–abroad? We talk about what to expect, what’s involved, and how to prepare. When people dream of retiring abroad, they typically think of margaritas on the beach and sipping wine in the Riviera, not the intricacies of international tax laws. From visas to tax issues to cost of living and more, moving to a foreign country comes with a lot of...
info_outline“Liquidity can open a lot of doors, but purpose tells you which ones to walk through.”
Selling a business is an amazing accomplishment, but it is often followed by an identity crisis that can leave former business owners in a spiral. The purpose you committed yourself to every day is suddenly gone – what’s your purpose now?
In this episode, we discuss how to approach life after business-ownership: how to find fulfillment, what to do with the money, and where to look for your next project.Whether that’s joining a board, angel investing, or pursuing philanthropic endeavors–Jessica and Emily share ideas and scenarios to consider. Join us for a great conversation and great coffee!
Please see important podcast disclosure information at https://monumentwealthmanagement.com/disclosures
Connect with us!
Get our Free Private Wealth Advice Newsletter: https://www.monumentwealthmanagement.com/subscribe
LinkedIn: https://www.linkedin.com/company/monument-wealth-management/
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/#