Episode 148-How to Keep Your Hard-Earned Money Through Good Tax Planning with Ron Palmiter and Shawn Roberts
In this episode of The Prospecting Show, Dr Connor Robertson sits down with Ron Palmiter and Shawn Roberts, two tax professionals who have built careers helping business owners structure wealth efficiently. Together, they explore how entrepreneurs can reduce tax liability legally, build long-term strategies that protect assets, and stop losing money through reactive accounting.
The Mindset Behind Tax Strategy
Dr Robertson opens, “Ron, Shawn — people see taxes as punishment. But you both treat the tax code as an opportunity. What changes when you start thinking that way?”
Ron smiles, “The moment you stop treating taxes as a once-a-year event and start viewing them as part of your business model, everything changes. The IRS gives you a rulebook; those rules can either cost you money or save you money depending on how you play.”
Shawn adds, “We tell clients all the time — the tax code rewards those who build, invest, and create jobs. You can’t avoid taxes completely, but you can direct where your dollars go.”
Dr Robertson nods, “So it’s about alignment, not avoidance.”
The Difference Between Tax Filing and Tax Planning
Shawn explains, “Filing is reporting what already happened. Planning is deciding what will happen. Most business owners only do the first.”
He continues, “By the time your CPA files your return, all the opportunities for strategy are gone. We want entrepreneurs thinking quarterly — adjusting entity structure, compensation, and deductions proactively.”
Ron adds, “The smartest clients treat us like part of their management team, not just once-a-year consultants.”
Dr Robertson comments, “That’s the same in deal structuring — the value’s in the forward planning, not the paperwork.”
Structuring Entities for Efficiency
Ron breaks down why entity selection matters. “Sole proprietors pay the most in taxes because every dollar is subject to self-employment tax. By converting to an S corporation or partnership, you can split income between salary and distributions — reducing payroll taxes legally.”
He says, “The key is documentation. You can’t just move money and call it strategy. You must keep clean books, pay yourself reasonably, and document intent.”
Dr Robertson adds, “That’s discipline — using structure to create efficiency.”
Deductions Most Owners Miss
Shawn lists deductions that entrepreneurs frequently overlook:
- Home Office Deductions — actual-use percentage for workspace.
- Accountable Plans — reimbursing personal expenses through the business.
- Health Reimbursement Arrangements (HRAs) — letting the company pay for medical costs tax-free.
- Retirement Plans — solo 401(k)s or defined benefit plans for higher-income earners.
- Depreciation — accelerated deductions for vehicles, equipment, and property.
He says, “Most of these require setup, not discovery. You can’t claim what you never planned for.”
Dr Robertson laughs, “Exactly. You have to plant before you harvest.”
The Power of Depreciation
Ron explains how depreciation drives wealth creation. “When you buy an asset — a building, a vehicle, or equipment — you can write off the cost over time. But with accelerated depreciation or bonus depreciation, you can claim much of that value upfront.”
He continues, “That’s how investors and entrepreneurs legally reduce taxable income without losing cash flow.”
Dr Robertson adds, “That’s identical to real estate syndication models — paper losses, real profits.”
Tax Strategy and Exit Planning
Shawn notes that planning for an exit should start years before selling. “If you wait until you’re in negotiations, it’s too late. We restructure ownership, reallocate equity, and prepare for capital gains optimization long before the deal closes.”
He gives an example: “By using qualified small business stock (QSBS) exemptions or 1031 exchanges, clients can defer or eliminate massive taxes legally.”
Dr Robertson comments, “That’s exactly why due diligence must include tax modeling.”
Avoiding Common Tax Traps
Ron outlines five costly mistakes small business owners make:
- Mixing personal and business accounts.
- Paying family members without documentation.
- Overpaying estimated taxes instead of adjusting mid-year.
- Missing quarterly filing deadlines.
- Ignoring state-specific tax incentives.
He says, “Each of these is avoidable — but only if you have consistent review cycles.”
Dr Robertson adds, “That’s management by intention — prevention instead of repair.”
Leveraging Retirement and Insurance Vehicles
Shawn emphasizes how tax strategy overlaps with wealth planning. “Entrepreneurs should use retirement plans not just for savings, but for tax control. A defined benefit plan or cash balance plan lets you defer significant income.”
Ron adds, “And permanent life insurance creates liquidity that’s tax-deferred while alive and tax-free at death. It’s not for everyone, but when integrated correctly, it’s powerful.”
Dr Robertson reflects, “That’s the compound strategy — integrate insurance, investment, and entity structure.”
State and Local Incentives
Ron explains that tax incentives vary widely by state. “Manufacturers, solar installers, and even tech startups often qualify for credits or grants they never claim.”
He adds, “Local economic development agencies literally pay you to create jobs. But if you don’t ask, you don’t get.”
Dr Robertson says, “That’s the same with business funding — opportunity hides in bureaucracy.”
Building a Year-Round System
Shawn advises implementing quarterly reviews:
- Q1: Entity checkup and W-2 salary adjustments.
- Q2: Mid-year deductions and credit reviews.
- Q3: Tax-loss harvesting and retirement funding.
- Q4: Final optimization before December 31st.
He says, “This rhythm prevents surprises. Taxes become a forecast, not a fire drill.”
Dr Robertson nods, “That’s operational cadence — consistency compounds savings.”
Integrating Tax Strategy with Business Growth
Ron summarizes, “Taxes touch every part of business — hiring, real estate, investments, even marketing. Once you understand that, every decision becomes a tax decision.”
He adds, “The goal isn’t to pay nothing — it’s to pay strategically.”
Dr Robertson comments, “That’s sustainable growth — protecting the fuel that powers reinvestment.”
The Emotional and Ethical Side of Tax Planning
Shawn concludes, “There’s nothing unethical about using the tax code as designed. The government incentivizes business activity because it strengthens the economy.”
He adds, “When you reinvest wisely, you’re not just protecting yourself — you’re contributing to job creation and innovation.”
Dr Robertson closes, “Ron Palmiter and Shawn Roberts show that mastery of taxes isn’t about avoidance — it’s about awareness. Smart entrepreneurs don’t fear the system; they use it.”
Listen to the Full Episode:
How to Keep Your Hard-Earned Money Through Good Tax Planning with Ron Palmiter and Shawn Roberts