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Episode Overview

What if the biggest professional disappointment of your life was actually the foundation for your long-term wealth strategy?

In this episode of the Duct Tape Marketing Podcast, John Jantsch interviews Jack Ojo, founder of Ojo Wealth Strategies, one of the nation’s largest tax-focused wealth management firms. Before building a nationally recognized firm, Jack was a top-rated minor league baseball umpire on the verge of the Major Leagues.

After an unexpected release ended his umpiring career, Jack reinvented himself through education, discipline, and a relentless focus on tax strategy and client service. Today, he helps business owners and high-income professionals minimize taxes, maximize retirement savings, and protect against worst-case financial scenarios.

This conversation explores career resilience, proactive tax planning, retirement strategies, and the overlooked wealth-building tools most entrepreneurs ignore.

About Jack Ojo

Jack Ojo is the founder and lead advisor of Ojo Wealth Strategies, a nationally recognized tax-focused wealth management firm. He holds multiple professional designations, including CPA, CFP, and a Master’s in Taxation.

Before entering wealth management, Jack was a highly rated minor league baseball umpire, advancing to AAA and earning the Joe Ryan Award as the top minor league umpiring prospect. After his baseball career ended unexpectedly, he redirected his discipline into education, earning advanced credentials and building a firm focused on proactive tax reduction and long-term wealth preservation.

He is also the author of Too Smart to Be an Umpire, a book chronicling his journey from professional sports to financial advisory leadership.

Key Takeaways for Entrepreneurs and Business Owners

1. Your Biggest Expense Is Income Tax

Most business owners know what they owe in taxes but do not realize how much control they actually have. Tax planning should be proactive and strategic, not a once-a-year event.

2. Defined Benefit Pension Plans Are Massively Underused

High-income sole proprietors and small business owners can potentially write off hundreds of thousands of dollars annually through properly structured defined benefit plans.

This is one of the most overlooked strategies in small business tax planning.

3. Entity Structure Matters

• Over 100K to 150K income? An S-corp may reduce Social Security tax exposure.
• Under 20K income? A sole proprietorship may be sufficient.
• Compensation structure and reasonable salary must be defensible in an audit.

4. Documentation Wins Audits

Whether deducting vehicles, mileage, or home office expenses, documentation is critical.

• Use mileage tracking apps.
• Track business use consistently.
• Avoid aggressive deductions that cannot be defended as reasonable.

5. Banner Year? Buy Smart and Deduct Strategically

If revenue exceeds expectations:

• Consider Section 179 deductions for equipment purchases.
• Evaluate vehicles over 6,000 pounds for accelerated depreciation.
• Make strategic investments before year-end.

6. Bad Year? Consider Roth Conversions

A low-income year can be an opportunity to convert traditional IRA assets to a Roth IRA at lower tax rates, positioning yourself for long-term tax-free growth.

7. 401(k) Plans Are Essential

For most Americans earning under 400K to 500K annually, maxing out a 401(k) is one of the smartest wealth-building moves available.

• Immediate tax reduction
• Long-term compounded growth
• Predictable retirement income structure
• Potential seven-figure balances at retirement

8. Putting Children on Payroll Can Be Strategic

If structured correctly:

• Children working in a sole proprietorship can earn income free from Social Security tax.
• Income can be redirected into 529 plans.
• Proper documentation and legitimate work are essential.

9. Spouses on Payroll Create Double Retirement Power

When a spouse legitimately works in the business:

• Two retirement accounts can be funded.
• Social Security benefits increase.
• Long-term household wealth improves significantly.

10. Protect Against Worst-Case Scenarios

Jack’s firm grew 400 percent after the 2008 financial crisis because clients were prepared. Wealth strategy is not just about growth. It is about resilience.

Great Moments from the Episode

• 00:01 The Big Reframe: Sometimes the career setback you are replaying becomes the wealth strategy that makes you unstoppable.
• 01:00 From AAA Umpire to Financial Advisor: Jack shares how his near-Major League umpiring career ended and how he redirected his focus into education and credentials.
• 03:30 Poverty in the Minor Leagues: A candid look at the financial realities of minor league baseball.
• 05:35 The Honesty Factor: How umpiring shaped Jack’s approach to trust and client service.
• 07:00 Your Largest Expense Is Income Tax: Why most business owners underestimate their ability to control tax liability.
• 10:45 Handling a Surprise Banner Year: Strategies to reduce tax impact when revenue spikes unexpectedly.
• 11:15 Turning a Bad Year Into an Opportunity: Using Roth conversions strategically during income downturns.
• 13:30 Vehicle Deductions and Documentation: Where business use becomes defensible and where it becomes risky.
• 17:00 Why 401(k)s Are Essential: A strong defense of retirement plans for business owners and employees alike.
• 18:54 Paying Your Kids Through the Business: A practical look at compliant, strategic payroll for children.

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Memorable Quotes

Everybody knows what they owe or what their refund is, but they do not realize how much control they actually have over that number.

If you are a pig with deductions, you are going to get slaughtered.

If you are not maxing out your 401(k), you are making a mistake.

Final Thoughts

Jack Ojo’s story proves that career disappointment can become the foundation for financial mastery. His journey from AAA umpire to nationally recognized tax strategist underscores a powerful truth.

Discipline, education, and proactive tax planning create long-term wealth.

For entrepreneurs, this episode is a reminder that taxes are not just an annual event. They are a strategic lever that, when handled correctly, can transform your financial future.

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