You need cash for a major purchase or investment opportunity. You could sell appreciated investments and potentially trigger capital gains taxes—or borrow the money and leave your investments alone.

Borrowing can sound like the obvious choice. After all, loan proceeds generally aren't taxable income. But what happens when it's time to pay the loan back?

In this episode, Nic breaks down the planning behind selling investments versus borrowing, including when debt can be an effective short-term tool, when paying the tax may actually leave you better off, and why avoiding taxes today shouldn't be the only goal.

The takeaway: Don't just compare taxes today. Consider interest, risk, time frame, repayment, and how the decision fits into your overall financial plan.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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The financial world looks very different than it did just a few years ago. Brian Wiley is joined by Steve Cilley of Ataraxis PEO for a wide-ranging conversation about how changes in technology, the workplace, housing, and the economy are reshaping the way people build and protect wealth.

The show begins by looking back at the economic fallout from COVID, including stimulus, inflation, changes in employee expectations, and the lasting impact on businesses. A listener with gains in XRP brings the conversation into cryptocurrency, tax-loss harvesting, cost-basis tracking, cold wallets, and the challenges of proving and protecting ownership of digital assets. Brian and Steve then look ahead to AI and robotics, discussing which jobs may be disrupted and why owning capital could become increasingly important as technology changes the labor market.

The discussion shifts to whether homeownership still makes financial sense, especially for younger generations facing higher prices and interest rates. They compare buying versus renting, home equity versus investing, the changing age of first-time buyers, and the financial and lifestyle tradeoffs behind the American dream of owning a home.

The final hour focuses on business owners and the modern workplace: employee classification, remote workers across state lines, payroll and employment-law risks, compensation agreements, managing employees, and why growing businesses eventually need their systems and advisors to grow with them.

Listen, Watch, & Connect!

https://www.therealmoneypros.com

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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Where you invest your money is only part of the equation. Which accounts hold those investments, how they're taxed, and where you eventually take income from can have just as much impact on your financial plan.

Brian Wiley and Jeremiah Bates begin with a listener looking for conservative retirement income, breaking down Treasury bills, notes and bonds, buying at auction versus the secondary market, bond ladders, CDs, annuities, interest-rate risk, and why avoiding state income tax shouldn't be the only consideration when choosing an investment.

The conversation then turns to asset location and retirement income—how taxable accounts, traditional IRAs, 401(k)s and Roth IRAs should work together, and how taxes can influence which accounts you spend from in retirement. The hosts also discuss staying disciplined through market volatility, investing for younger generations, and compare Trump Accounts with 529 plans and custodial accounts.

The show closes with listener questions on Backdoor Roth IRAs, the pro-rata rule, consolidating old retirement accounts, and how to fund large retirement expenses without creating unnecessary taxes.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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For many entrepreneurs, their business is their largest financial asset, but very few know what it's actually worth or what it takes to maximize its value before an exit.

This week, our team is joined by Jeff Szczypinski of WR Valuation for an in-depth discussion on business valuations and why they're about much more than determining a sale price. They explain how valuations support retirement planning, succession planning, estate planning, buy-sell agreements, gifting strategies, and ownership transitions. The conversation also covers the biggest drivers of business value, including management teams, key-person risk, customer concentration, financial records, and buyer due diligence, along with practical ways business owners can increase the value of their company before going to market.

The discussion continues with retirement and tax planning for self-employed business owners, covering SEP IRAs, SIMPLE IRAs, Solo 401(k)s, contribution strategies, employee considerations, and how choosing the right retirement plan can help reduce taxes while building long-term wealth. Throughout the show, the hosts emphasize that a business valuation isn't just about selling your company—it's one of the most valuable planning tools a business owner can have when preparing for retirement and protecting their family's financial future.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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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

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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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

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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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

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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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/

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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

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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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/

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Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

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