The Show

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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00:00 Why Disciplined Investors Tend to Win
05:20 Asset Location: Where You Hold Investments Matters
09:00 How Different Accounts Are Taxed
11:40 Building Different Tax Buckets
14:30 Matching Investments to Your Financial Plan
17:30 Why Financial Accounts Are So Complicated
24:30 Capitalism, Socialism & Government Regulation
31:30 When Government Policy Goes Too Far
35:30 Trump Accounts: Investing for Children
38:30 Trump Accounts vs. UTMA & UGMA Accounts
42:40 Trump Accounts vs. 529 Plans
44:00 Best Ways to Invest for Your Kids

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

—————————————————————
Ataraxis PEO
https://ataraxispeo.com
 
Tree City Advisors of Apollon:
https://www.treecityadvisors.com
 
Apollon Wealth Management:
https://apollonwealthmanagement.com/
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00:00 Hour 1 – Why Business Valuations Matter
04:20 When Does a Business Need a Valuation?
14:55 Building a More Valuable Business
24:10 Common Valuation Mistakes Business Owners Make
34:20 Preparing Your Business for an Exit
39:55 Hour 2 – Retirement & Tax Planning for Business Owners
49:00 Turning Your Business into Retirement Income
58:30 SEP IRA vs. SIMPLE IRA vs. Solo 401(k)
1:12:10 Choosing the Right Retirement Plan for Your Business
1:19:30 Final Thoughts

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/
—————————————————————

00:00 Introduction
03:09 Market Update: Earnings, AI & Oil Prices
11:05 Business Exit Planning Starts Years Before You Sell
16:00 How Business Valuations Really Work
23:40 Preparing Your Business for Buyer Due Diligence
33:15 Listener Questions & Retirement Planning
39:53 Hour 2 Kickoff
40:06 Donor-Advised Funds Explained
51:02 Using a DAF to Offset a $600,000 Capital Gain
57:45 Charitable Giving & Tax Planning Strategies
01:04:11 Retirement Plans for Business Owners (SEP IRA, Solo 401(k) & More)
01:13:30 Final Thoughts & Wrap-Up