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by The Real Money Pros
Money: you make it, you want more of it, and you want to protect it. We are The Real Money Pros, a show hosted collaboratively by experts who specialize in investing, financial and estate planning, taxes, insurance, and any other way to grow wealth. Plus, we make it fun! We help you know good advice from bad – especially when everyone seems to want a piece of your money.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 2 days ago2h 4m
Business Exit Planning, Capital Gains Taxes, & Donor-Advised Funds (7/25/2026)
Selling a business is one of the largest financial events many entrepreneurs will ever experience... But most owners spend years building their company without spending nearly enough time planning how they'll eventually leave it. Jeremiah and Nic discuss why successful business exits begin long before a purchase offer arrives. They explain why business owners should start planning two to three years before selling, the importance of obtaining a professional business valuation, preparing financial records for buyer due diligence, building enterprise value instead of simply generating income, and coordinating your CPA, attorney, valuation specialist, and financial advisor throughout the process. They also share real client examples that illustrate the dramatic difference between proactive planning and trying to figure everything out after the sale has already occurred. The guys also explore why nearly 92% of small businesses never actually sell, common succession planning mistakes, and why many owners underestimate the value they've spent decades creating. Listeners will hear practical discussions about treating a business as an investment asset, creating retirement income after a liquidity event, and avoiding costly tax mistakes once a large lump sum is received. Jeremiah and Nic cover advanced tax planning strategies, including donor-advised funds, managing large capital gains, charitable giving, and the distinction between ordinary income and capital gains taxation. For business owners and self-employed professionals, the hosts review tax-saving opportunities available through SEP IRAs, SIMPLE IRAs, Solo 401(k)s, Cash Balance Plans, Mega Backdoor Roth strategies, S-Corp elections, bonus depreciation, and other planning ideas that can help reduce taxes while building long-term wealth. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
- 1 weeks ago20 min
Before You Surrender Your Annuity...
Owning an annuity you no longer like does not automatically mean surrendering it is the right decision. Nic has the discussion of how to evaluate an annuity that no longer seems to fit your retirement plan. He walks through the reasons investors become dissatisfied with their contracts, the questions to ask before making a change, and the different options that may be available. Depending on the contract and your circumstances, the answer could be to keep the annuity, wait for surrender charges to expire, take partial withdrawals, complete a 1035 exchange, begin using its income features, or surrender it entirely. Nic also explains why frustration alone is not enough to make the decision. Taxes, surrender penalties, income riders, guarantees, opportunity cost, age, and retirement goals all need to be considered together. Sometimes remaining in an annuity can be costly. In other cases, leaving it may create even more damage. The right answer depends on what you own, why you bought it, and whether it still serves a purpose in your financial plan. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
- 1 weeks ago1h 22m
Retirement Tax Traps: Social Security, IRA Withdrawals & Smarter Tax Planning (7/18/2026)
Retirement taxes are rarely as simple as people expect, and making the wrong withdrawal at the wrong time can have consequences far beyond your tax bill. In our first hour, Jeremiah Bates and Alex Lundgren explain how IRA withdrawals, pensions, Social Security, brokerage accounts, Medicare IRMAA surcharges, and capital gains work together to shape your lifetime tax picture. They discuss why major purchases, home remodels, and other large withdrawals deserve careful planning to avoid unnecessary taxes and higher Medicare costs. The conversation later shifts to Social Security planning. The hosts cover when to claim benefits, how working before full retirement age can affect payments, filing strategies for married couples, survivor benefits, and why Social Security should be coordinated with the rest of your retirement income plan instead of viewed in isolation. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
- 2 weeks ago2h 4m
Business Owners Think Beyond Taxes: Structure, Exit Planning & Investment Decisions (7/11/2026)
Whether you're starting a business, growing one, or preparing to exit, the financial decisions you make today can have long-term tax and estate planning consequences. In Hour 1, Brian Wiley and Jeremiah Bates explain the differences between LLCs and S Corporations, when an S Corp election may make sense, how business structure affects taxes and liability, and why business owners should coordinate their entity planning with their estate plan. They also discuss cost basis, inherited assets, and avoiding costly mistakes before they happen. Hour 2 shifts to investing, covering concentrated stock positions, strategies for managing highly appreciated investments like Micron, investor psychology, and ways to think through market volatility, geopolitical events, and portfolio risk without letting headlines dictate your decisions. The final hour answers listener questions on business succession planning, selling a closely held business when family members don't want to take over, Qualified Opportunity Zones and the upcoming 2026 tax deadline, evaluating annuities within a comprehensive financial plan, and why fiduciary advice should focus on your entire financial picture—not just one investment account. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
- 4 weeks ago20 min
Direct Indexing: Managing Taxes as Your Wealth Grows
For many, index funds are one of the best ways to build long-term wealth. But as portfolios grow and taxable investments become a larger part of the picture, the conversation often shifts beyond investment returns. Today, Nic talks about how direct indexing fits into the next stage of financial planning. He explains why successful investors with large taxable brokerage accounts may begin looking for additional flexibility around taxes, portfolio customization, and managing highly appreciated assets. You'll learn how direct indexing differs from traditional index investing, why tax-loss harvesting is only part of the story, and how this strategy may fit into a broader financial plan. Nick also discusses who direct indexing is designed for—and just as importantly, who it probably isn't. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
- Jun 30, 20262h 3m
Think First: Better Financial Decisions, Roth Strategies & Long-Term Care Planning (6/27/2026)
Brian Wiley is joined by business coach and author Allison Dunn for a conversation about why critical thinking is one of the most valuable financial skills an investor, business owner, or retiree can develop. They discuss how better decision-making applies to retirement planning, leadership, investing, and navigating life's biggest financial choices. The show also answers listener questions on retirement planning, including how to coordinate 401(k)s, Traditional IRAs, HSAs, and Roth conversion strategies to improve tax efficiency. Brian explains why retirement accounts should be viewed both individually and as part of one comprehensive financial plan, while also discussing health insurance planning before Medicare eligibility. Later, the conversation turns to long-term care planning, estate planning, trusts, and the pros and cons of self-funding versus insurance-based solutions. They also explore fiduciary advice, family communication around money, Micron stock and concentrated positions, investor psychology, and why having a thoughtful process often leads to better financial outcomes than simply reacting to markets or emotions. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com Guest: Allison Dunn, Author and Business Coach https://deliberatedirections.com/think-first-allison-dunn/ ————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
- Jun 25, 202658 min
Navigating Medicaid: How Families Can Protect Assets and Pay for Care
Most families don't think about Medicaid planning until they're facing a health crisis—but by then, some of the best planning opportunities may already be gone. Nic and Jeremiah are joined by Brooke Baker and Jessica Young of Legacy Navigation for an in-depth conversation about the realities of long-term care, Medicaid eligibility, and protecting family assets. Together, they break down the differences between Medicare and Medicaid, the true cost of care, common misconceptions about qualifying for benefits, and why so many families find themselves overwhelmed when a loved one suddenly needs assistance. The discussion explores real-world planning considerations, including asset protection strategies, the five-year lookback period, spousal protections, estate recovery rules, and the challenges families face when trying to navigate the complicated system on their own. Guests: Brooke Baker & Jessica Young Legacy Navigation https://legacynavigate.com/ Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
- Jun 22, 20261h 22m
Wealth Traps: Rental Properties, Concentrated Stock Positions & Retirement Income (6/20/2026)
Brian Wiley and Jeremiah Bates open the show with a discussion on concentrated stock positions, portfolio rebalancing, and the challenges investors face after large gains. Using examples ranging from Micron stock to broader market opportunities, they explore diversification, risk management, investor psychology, and the ongoing battle between fear and greed. The conversation also examines what it really means to be wealthy, how to think about financial independence, and why having a plan matters more than chasing the next investment opportunity. The second hour focuses on retirement income planning and highly appreciated assets, particularly rental properties. They discuss capital gains concerns, 1031 exchanges, Delaware Statutory Trusts (DSTs), step-up in basis rules, and strategies for investors who want to simplify their lives without creating unnecessary tax consequences. They also cover Treasury bills, retirement withdrawal planning, income-focused investing, and how to evaluate whether your assets are positioned to support your long-term goals. Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com Hosts: Jeremiah Bates & Brian Wiley ————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————
About Real Money Pros
Money: you make it, you want more of it, and you want to protect it. We are The Real Money Pros, a show hosted collaboratively by experts who specialize in investing, financial and estate planning, taxes, insurance, and any other way to grow wealth. Plus, we make it fun! We help you know good advice from bad – especially when everyone seems to want a piece of your money.
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