Tax Planning - Post 11 - Never Paid Out Guarantee

Tax Planning 2026

February 09, 2026•8 min read

I've Never Paid Out the Guarantee. Here's Why.

Meta Description: In 11 years, I've guaranteed $10K+ in tax savings to hundreds of business owners. I've never had to pay out. Here's exactly what I find every time.

Target Keywords: tax planning guarantee, business tax savings, proactive tax planning, CPA alternative, tax strategy

Cross-Links: 10K Tax Guarantee, CPA Planning vs Filing, Section 179 vs Bonus

When I tell business owners I guarantee $10,000+ in tax savings within 14 days—or I'll pay them—the first question is always the same:

"How often do you have to pay out?"

The answer: Never. Not once in 11 years.

Not because I'm cherry-picking easy cases. Not because I'm being selective about who I work with. But because the opportunity is always there—and most CPAs never look for it.

Here's exactly what I find, every single time.

The Five Things CPAs Miss (And Why)

Most CPAs aren't incompetent. They're busy. They're focused on filing, not planning. And they're working with incomplete information.

Here are the five areas where I find savings in almost every business I analyze—and why most CPAs never surface them.

1. Entity Structure (Average Savings: $5,000-$15,000/year)

What I find:

Sole proprietors paying full self-employment tax
Single-member LLCs that should be S-Corps
S-Corp owners with the wrong salary/distribution ratio
Businesses that outgrew their entity structure 3 years ago

Why CPAs miss it:

They file what you give them
Entity changes require proactive conversation
Most businesses set up their LLC at formation and never revisit it

Example:

Client: General contractor, $450K net income
Structure: Single-member LLC (default)
Self-employment tax: ~$36,000/year
After S-Corp election with $165K salary: ~$25,000/year
Annual savings: $11,000

And that's just Year 1. Compounded over 10 years, that's $110,000+ in tax savings from a single entity election.

2. Retirement Contribution Limits (Average Savings: $15,000-$50,000/year)

What I find:

High-income owners "maxing out" at $23,500 (401k employee deferral only)
No profit sharing contributions
No awareness of Cash Balance or Defined Benefit plans
Owners age 50+ not using catch-up contributions

Why CPAs miss it:

Retirement plan design isn't part of tax preparation
They don't know the owner's age, goals, or capacity
Plan providers sell what they offer, not what's optimal

Example:

Client: Dental practice owner, age 54, $550K income
Current: 401(k) at $31,000 (catch-up included)
Optimal: 401(k) + profit sharing + Cash Balance = $220,000
Tax savings at 37% bracket: $70,000/year

Over 10 years before retirement, that's $700,000 in tax-deferred growth. On a $220K annual contribution compounding at 7%, that becomes $3M+ in retirement wealth.

3. Depreciation Timing (Average Savings: $3,000-$25,000/purchase)

What I find:

Equipment purchased in December but not "placed in service" until January (missed deduction)
Major purchases made in low-income years (lower tax benefit)
No conversation about Section 179 vs Bonus Depreciation
Businesses buying when they need equipment, not when it's optimal for taxes

Why CPAs miss it:

They see the depreciation schedule after the purchase
Timing decisions require knowing next year's income projection
Most CPAs don't get involved until tax season

Example:

Client: Construction company planning $200K equipment purchase
2026 projected income: $320K (marginal rate: 32%)
2027 projected income: $480K (marginal rate: 35%)
If purchased in 2026: $200K × 32% = $64,000 tax savings
If purchased in 2027: $200K × 35% = $70,000 tax savings
Waiting 3 weeks saved $6,000

That's one purchase. Over a career of equipment decisions, proper timing saves hundreds of thousands.

4. Missed Deductions (Average Savings: $2,000-$8,000/year)

What I find:

Home office not claimed (even though owner does admin from home)
Mileage tracked poorly or not at all
Continuing education and conferences under-documented
Cell phone, internet, vehicle use not allocated properly
De minimis expenses not expensed immediately

Why CPAs miss it:

They work with the numbers you give them
They don't ask probing questions about what you're missing
Conservative CPAs avoid "aggressive" deductions (even legitimate ones)

Example:

Client: Medical practice owner
Discovered during analysis:

Home office: 250 sq ft office in 2,500 sq ft home (10% allocation) → $1,800/year
Unreimbursed CME travel: $4,200/year (not tracked)
Cell phone: 70% business use → $840/year
Mileage: 4,000 business miles/year not logged → $2,800/year

Total recovered: $9,640/year

5. Quarterly Tax Planning Opportunities (Average Savings: $5,000-$20,000/year)

What I find:

No mid-year income projection
No year-end planning conversation until December (too late)
Estimated tax payments not optimized
Opportunities to shift income or accelerate deductions not discussed

Why CPAs miss it:

They're buried in tax season February-April
They don't have time for quarterly strategic calls
Most CPA relationships are transactional (you call them, they respond)

Example:

Client: Legal practice, $380K projected income in October
Analysis showed:

On track for $400K actual (higher tax bracket)
Could defer $30K in December billings to January
Could accelerate $15K in equipment purchases before 12/31
Could max out defined contribution plan ($25K more than budgeted)

Result: Stayed in 32% bracket, avoided 35% bracket on $30K = $900 saved, plus full deductions on accelerated purchases

The difference between a CPA who files and a CFO who plans is this quarterly conversation. Over a year, it's worth $10,000-$20,000 in optimized decisions.

Why the Guarantee Works

The guarantee works because the opportunity is structural. It's not about finding a loophole or a clever trick. It's about:

Looking at the full picture (not just last year's tax return)
Knowing what's available (retirement vehicles, depreciation strategies, entity structures)
Timing decisions proactively (not reactively in April)
Asking the right questions (not waiting for the client to know what to ask)

Most business owners don't know what they don't know. Most CPAs file what they're given. The gap is where I find the $10,000+.

The Actual Process

Here's what happens during the 14-day guarantee analysis:

Days 1-3: Information Gathering

I collect:

Last 2-3 years of tax returns
Current year P&L and balance sheet
Entity structure documents
Retirement plan details
Compensation breakdown
Equipment and depreciation schedules

Most business owners have this. It's just sitting in files, never getting analyzed strategically.

Days 4-10: Deep Dive Analysis

I'm looking at:

Entity optimization opportunities
Retirement contribution capacity vs. actual
Depreciation strategy and timing
Missed deductions and credits
Quarterly planning opportunities

This is where I find the money. Every single time.

Days 11-14: Presentation

I present:

Specific dollar savings identified
Implementation steps for each strategy
Timeline and priority order
Year 1 savings vs. ongoing annual savings

If it's under $10,000, I pay you $500. That's never happened.

The Most Common Question

"If it's this obvious, why isn't my CPA doing this?"

Because they're doing what you hired them to do: file your taxes accurately and on time.

But filing taxes and planning taxes are different services. Most CPA relationships are structured around filing.

The difference:

Filing: Looking backward at what happened and reporting it correctly.
Planning: Looking forward at what's coming and structuring it intelligently.

Your CPA probably isn't bad at what they do. But if you're not having quarterly planning conversations, if they're not calling you with strategies, if you only hear from them at tax time—you have a filer, not a planner.

And the gap costs you $10,000-$30,000+ per year.

Who This Works For

I've done this analysis for:

Construction companies ($250K-$3M revenue)
Dental practices ($400K-$2M revenue)
Medical practices (solo practitioners to 10+ doctor groups)
Legal practices (solo to 20+ attorney firms)
E-commerce businesses ($500K-$5M revenue)

The industry changes. The income level changes. The specific strategies change.

But the pattern is always the same: the opportunity is there, and nobody's looking for it.

The Risk to You

None.

If I can't find $10,000+ in annual tax savings within 14 days, I pay you $500.

What do you have to lose?

How to Start

Step 1: Book a 15-minute discovery call.

We'll talk about:

Your current structure
Your income and growth trajectory
Whether the guarantee makes sense for you

Step 2: If it's a fit, we start the 14-day analysis.

Step 3: In 2 weeks, you see specific dollar savings—or you get paid.

Most business owners who do this analysis become clients. Not because I'm a good salesperson, but because when you see $25,000/year sitting on the table, the decision makes itself.

Book Your 14-Day Guarantee Analysis →

What Clients Say

"I thought my CPA was good. Turns out, they were just good at filing. Tom found $32,000 in Year 1 savings I didn't even know existed."

— Michael R., General Contractor

"The retirement optimization alone saved us $48,000 in taxes. That's real money going into our retirement instead of to the IRS."

— Dr. Sarah K., Dental Practice Owner

"We've been in business 15 years. Why didn't our CPA tell us about this stuff?"

— James L., Medical Practice

The Bottom Line

I've never paid out the guarantee because the opportunity is always there.

Every business owner I analyze is overpaying by at least $10,000/year. Usually more.

Not because they're doing anything wrong. Because nobody's looking.

The question isn't "Can you find $10K in savings?" It's "How much am I leaving on the table right now?"

Let's find out.

Book Your Free Discovery Call →

Tom Woolley is the founder of Today CFO. He's helped business owners discover over $3.2 million in tax savings through proactive planning. Email [email protected].

Tom Woolley

Founder and creator of TodayCFO

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