The Duct Tape Marketing Podcast
Episode Title: How to Reduce Taxes and Build Real Wealth
Host: John Jantsch
Guest: Jack Ojoe, Founder of Ojoe Wealth Strategies, Author of Too Smart to be an Umpire
Release Date: February 12, 2026
Episode Overview
In this episode, John Jantsch sits down with Jack Ojoe, founder of Ojoe Wealth Strategies and author of Too Smart to be an Umpire, to discuss tax-smart strategies for building real wealth, with actionable insights tailored for entrepreneurs, small business owners, and professionals. Jack shares his unique journey from being a minor league baseball umpire to becoming a prominent tax-focused wealth advisor. The conversation dives deep into practical tax planning, the overlooked power of defined benefit plans, entity structuring, leveraging 401ks, family payroll tactics, and best practices for documentation—plus memorable anecdotes and actionable advice to help listeners minimize tax burdens and grow wealth.
Key Discussion Points & Insights
1. From Umpire to Wealth Advisor: Turning Setbacks into Success
- Jack’s Background and Career Pivot
- After an unexpected setback as a minor league umpire, Jack used offseasons to build accounting experience and pursued extensive financial education after leaving baseball.
"I was so hurt from the baseball experience that I'd work 9 to 5 and then at night I spent the next four years getting my CPA, CFP, master's in taxation... trying to reinvent myself from the ground up." —Jack Ojoe [02:43]
- Discovered public accounting was unfulfilling; transitioned into wealth management to combine people skills and financial expertise.
- After an unexpected setback as a minor league umpire, Jack used offseasons to build accounting experience and pursued extensive financial education after leaving baseball.
2. The Honest Approach and Preparing for the Worst
- Grounded in “umpire” honesty, Jack’s approach centers on client trust and preparing for unforeseen scenarios.
- Emphasized anticipating “worst case scenarios” post-9/11 and during the 2008 financial crisis, which fueled his clients' loyalty and firm’s growth.
"I did believe in protecting against worst case scenarios... And the business really prospered, like went to a whole nother level after 2008, growing by 400%." —Jack Ojoe [05:26]
3. Biggest Myths About Taxes and Wealth Planning
- Business owners often miss that their largest expense is not their mortgage—it's income tax.
"I always ask them what their biggest expense is and they say their mortgage. And I go, no, it isn't." —Jack Ojoe [06:36]
- Most people vastly underestimate their control over tax liability, mistakenly thinking tax planning is only about refunds or end-of-year numbers.
4. Actionable Tax Strategies for Business Owners
- Defined Benefit Pension Plans:
- Dramatically underused, especially by high-income sole proprietors or those with few employees.
"We've had clients that have million-dollar incomes that we are able to get $500,000-600,000 write-offs by having defined benefit plans." —Jack Ojoe [07:36]
- Dramatically underused, especially by high-income sole proprietors or those with few employees.
- Choosing the Right Entity Structure:
- S-Corp advantageous if income over $100k–$150k; enables legitimate payroll/distribution strategies to reduce Social Security taxes.
"If your income is over $100,000... you should be an S corporation... avoid Social Security taxes." [08:28]
- S-Corp advantageous if income over $100k–$150k; enables legitimate payroll/distribution strategies to reduce Social Security taxes.
- Use the Best Pension Plan:
- Maximizing retirement accounts and utilizing the right plan based on income level is key.
- Timing Income and Expenses:
- Smart year-end actions: defer income, accelerate deductible purchases (e.g., Section 179 for equipment or vehicles), and leverage these to manage tax brackets.
5. Real-World Deductions & Credits
- Focus on solid, practical deductions—“no magic loopholes.”
"A lot of loopholes have been closed. What used to be pretty cool in the 70s and 80s, they're gone now. Start with pension plans." —Jack Ojoe [09:27]
- Section 179 deductions for large qualifying purchases (vehicles, equipment) in banner years; use Roth conversions in low-income years.
6. Salary vs. Distributions: Walking the Line
- Reasonable compensation is crucial; don’t play games as the IRS looks for justifiable figures.
"If you're a pig, you're going to get slaughtered." —Jack Ojoe [11:19]
- Keep clear documentation and aim to defend your numbers to a “reasonable person”—the standard in audits.
7. Depreciation: Making Documentation Sexy
- Meticulous mileage and expense tracking (through apps like MileageIQ) are essential.
- Over £6,000 vehicles can be written off in full, but only if business use is documented.
"You're playing a game of documentation I found with the office." —Jack Ojoe [13:50]
8. Distributed Workforce & Home Office Deductions
- Employees can restructure compensation for home office expenses:
"They can change their compensation structure around. So that part of this is salary and part of it is a direct employee business expense." —Jack Ojoe [14:18]
- For multi-state earners, domicile/travel tracking apps (Domicile365) can support tax filings and credits for days worked per state.
9. Health Insurance & HSAs
- Employer reimbursement for health insurance via Section 125 or HSA contributions can be a win-win for both employer and employee.
10. 401(k)s: Don't Believe the Hype Against Them
- Maxing out 401(k) plans is one of the best retirement and tax strategies for nearly everyone.
"Anybody that bashes 401ks you should run away from like the place was on fire." —Jack Ojoe [16:14]
- Encourage both spouses to contribute, even if one works part-time, as both can benefit from the tax deferral and future nest egg.
11. Putting Family on Payroll: The Overlooked Tax Win
- Children: Sole proprietors can hire kids legitimately, pay up to tax-free thresholds, and fund college savings or Roth accounts.
"You probably save $3,000-4,000 just having your kid on the payroll for $10,000." —Jack Ojoe [18:03]
- Spouses: Putting a working spouse on payroll unlocks a second retirement plan and social security benefits.
"My wife Eileen has been on the payroll for 30 years, always maxing out the 401k plan. She could tell anybody what she did because she did work in the office and worked very hard." —Jack Ojoe [19:53]
Notable Quotes & Memorable Moments
- On using past failures as strategy:
"What if the career setback you're still replaying is actually the best wealth strategy you'll ever stumble into?" —John Jantsch [00:00]
- On client trust:
"People like the honesty and I think that's from the umpire in me." —Jack Ojoe [05:26]
- On IRS audits:
"I found the IRS auditors to be very reasonable people. Believe it or not. ... If you're a pig, you're going to get slaughtered." —Jack Ojoe [11:19]
- Advice to children about 401ks:
"My three adult children, I preach that to them and I'm glad they listened to me on it. I go, max it out, max it out." —Jack Ojoe [16:14]
- On family payroll stories:
"My son worked on the shredding machine in the office. He stuffed envelopes and he told everybody at his preschool what his father did for a living, which significantly resulted in new business..." —Jack Ojoe [18:45]
Timestamps for Important Segments
- [02:43] Jack’s transition from baseball to financial advising
- [05:26] Importance of honesty and crisis preparedness in wealth management
- [06:36] The true biggest expense for most (income taxes)
- [07:36] Underused pension plans for entrepreneurs
- [08:28] Entity structure: S Corp vs. sole proprietor
- [09:27] Practical deductions (pension plans, Section 179)
- [11:19] Reasonable salary vs. distributions, audit experiences
- [13:50] How to document business use of vehicles/equipment
- [14:18] Multi-state/home office tax strategies
- [16:14] The value of 401(k)s for all earners
- [18:03] Family payroll strategies for tax minimization
Resources & Where to Learn More
- Jack Ojoe’s book: Too Smart to be an Umpire
- Ojoe Wealth Strategies: ojswealth.com
- Retirement and payroll tracking tools mentioned: MileageIQ, Domicile365
Summary
This episode blends compelling personal narrative with a practical, no-nonsense approach to wealth building through smart, legal tax minimization. Jack Ojoe’s advice is especially crucial for entrepreneurs and small business owners looking to take proactive—and often overlooked—steps to reduce taxes and grow wealth. The focus: there are no gimmicks, but plenty of proven strategies, from maximizing retirement plans to structuring family involvement, all rooted in a mindset of preparation and full documentation. For business owners, this conversation is a must-listen (or read!) for actionable steps that can directly impact financial security and growth.