I have a guarantee that I have never had to pay out. Not once. And it is not because the bar is low — it is a $10,000 guarantee. It is because every single contractor and small business owner I have worked with was overpaying on taxes before we started, and the savings we find always exceed that threshold.
That might sound like marketing. Let me explain exactly why it is not — and what it says about the state of tax planning for most business owners.
Key Takeaways
- 01The guarantee covers $10,000 in identified annual tax savings within the first 90 days
- 02It has never been paid out because qualifying contractors and business owners are almost always overpaying
- 03Most of the savings come from 4–5 core strategies: entity structure, retirement plans, equipment depreciation, income splitting, and proactive timing
- 04The strategies are legal, proven, and available to any business owner — most just do not have an advisor who implements them
- 05Qualifying typically requires $150,000+ in net business income and no prior proactive tax planning relationship
Table of Contents
What the Guarantee Actually Covers
The guarantee is simple: within 90 days of starting a TodayCFO engagement, we will identify at least $10,000 in annualized tax savings opportunities for your business. If we do not, we refund our fees for that period. No questions asked.
The word "identify" is important. Tax savings cannot always be fully realized in the first 90 days — some strategies like entity restructuring or retirement plan setup require time to implement properly. But the $10,000 in opportunities will be documented, explained, and presented to you within that window. You will see exactly what we found and what it is worth.
What the Guarantee Is Not
- It is not a promise of aggressive or borderline strategies — everything we recommend is legal, defensible, and IRS-compliant
- It is not a guarantee of $10,000 in cash back in 90 days — it is $10,000 in annual savings that, once implemented, reduce your ongoing tax liability
- It is not available to every business — qualifying requires minimum income thresholds and a review of your current situation
- It is not a trick to get you on a retainer — if we find the savings, you decide whether to engage further; the guarantee period stands on its own
Why It Has Never Been Paid Out
There is a reason I am comfortable making a $10,000 guarantee: the baseline tax situation for most contractors and small business owners is terrible. Not because they did anything wrong — but because the typical CPA or tax preparer is focused on filing, not planning. They report what happened. They rarely tell you what you should have done differently.
The result is that the average contractor earning $250,000 or more per year is leaving $30,000 to $60,000 per year on the table in completely legal deductions and tax strategies they simply were not told about. The $10,000 guarantee is not a stretch — it represents the floor of what I expect to find, not the ceiling.
EXPERT INSIGHT
"I have reviewed tax situations for dozens of contractors over the years. Almost every single one had at least one of these in common: they were operating as a sole prop or single-member LLC taxed as a sole prop (missing S-Corp savings), they had no retirement plan or a low-contribution plan, or they were not deducting all the equipment and vehicles they legally could. Any one of these mistakes can cost $15,000–$30,000 per year. Most clients had multiple." — Tom Woolley, MBA
This is not about finding loopholes. It is about using the strategies Congress built into the tax code for business owners — and actually using them, instead of leaving them on the shelf. For more on the difference between a filing CPA and a planning CPA, read: Is Your CPA Actually Planning Your Taxes — or Just Filing Them?
What We Find in the First 90 Days
The first 90 days of a TodayCFO engagement follow a structured process. Here is what a typical discovery and diagnostic phase looks like for a contractor client:
Week 1–2: Tax Diagnostic
- Review of prior two years of tax returns (personal and business)
- Assessment of current entity structure (sole prop, LLC, S-Corp, C-Corp)
- Review of current bookkeeping and expense categorization
- Analysis of retirement plan status (current contributions vs. available limits)
- Vehicle and equipment inventory review
Week 3–4: Opportunity Analysis
- S-Corp election analysis: calculate SE tax savings at current income level
- Retirement plan gap analysis: what you contributed vs. what you could have contributed
- Equipment and vehicle deduction audit: what was deducted vs. what qualifies
- Income splitting opportunities: spouse employment, children on payroll, management structures
- Missed deductions: home office, health insurance, professional development
Days 30–90: Strategy Presentation and Implementation Planning
- Present documented savings opportunities with specific dollar amounts
- Prioritize strategies by impact and implementation complexity
- Begin implementation: entity elections, payroll setup, retirement plan establishment
- Create a 12-month tax planning calendar
The 5 Sources of Most Tax Savings
In nearly every contractor engagement, the bulk of identified savings comes from the same five categories. These are not obscure strategies — they are mainstream tax planning tools that most business owners simply are not using.
1. S-Corp Election
This is typically the largest single savings opportunity. A contractor earning $250,000 operating as a sole proprietor pays self-employment tax (15.3%) on their entire net income. An S-Corp election allows them to pay a reasonable salary (say $80,000) and take the rest as a distribution — avoiding SE tax on the distribution amount. Savings: $15,000–$30,000+ per year for many contractors. See our full analysis: LLC vs. S-Corp for Contractors: Which Structure Saves More?
2. Retirement Plan Setup or Maximization
A contractor with no retirement plan is contributing $0 tax-deferred. A Solo 401(k) or SEP IRA allows contributions of $66,000–$76,500 (2023 limits), generating $23,000–$27,000 in annual tax savings at a 35% rate. Most contractors have no plan or a modest one — this is frequently the second-largest savings opportunity.
3. Equipment and Vehicle Deductions
Contractors who are not using Section 179 and bonus depreciation on equipment, or who are not properly deducting business vehicle use, frequently leave $10,000–$40,000 per year in unclaimed deductions. See our guide to contractor equipment deductions: Contractor Equipment Depreciation: The Complete Tax Guide.
4. Missed Business Deductions
Home office deduction, self-employed health insurance, professional development, tools and materials, cell phone, software — contractors frequently miss 5–10 legitimate deductions that cumulatively add up to $5,000–$15,000 in additional write-offs.
5. Income Splitting and Family Employment
Paying a spouse for legitimate bookkeeping, administrative, or site coordination work — or hiring children for real tasks — can shift income to lower tax brackets and generate additional retirement plan contributions. A spouse on payroll who contributes to their own Solo 401(k) can add $23,000–$30,000 in family retirement savings and reduce the contractor's business income simultaneously.
Real Examples: What Contractors Actually Save
Here are representative examples of what a TodayCFO diagnostic typically uncovers for contractors at different income levels. Names and details are composites, but the numbers reflect real patterns.
| Contractor Profile | Situation Found | Annual Savings Identified |
|---|---|---|
| Electrical contractor, $220K net income | Operating as sole prop, no retirement plan, minimal vehicle deductions | $34,200 |
| General contractor, $380K net income | LLC taxed as sole prop, small SEP IRA, not deducting equipment purchases | $58,400 |
| HVAC contractor, $175K net income | S-Corp already in place but under-contributing to retirement, missing equipment deductions | $22,800 |
| Plumbing contractor, $290K net income | Operating as sole prop, spouse not on payroll, no retirement plan | $47,500 |
In every case, the savings identified far exceeded the $10,000 guarantee threshold. The $10,000 guarantee is designed to give you confidence, not to represent the ceiling of what we find.
Who Qualifies for the Guarantee
The guarantee is not available to every business owner — that would not be a responsible offer. Here is what makes someone a qualifying candidate:
Qualifying Criteria
- Net business income of $150,000 or more — below this level, the strategy options narrow significantly and a $10,000 guarantee becomes harder to justify responsibly
- No current proactive tax planning relationship — if you already have a fractional CFO or tax strategist actively managing your taxes, the low-hanging fruit may already be captured
- Based in the United States — we focus on US tax law; international situations require specialized expertise
- Willing to share tax returns and financial data — we cannot identify savings without visibility into your actual situation
- Business type: contractors, tradespeople, dental and medical practices, consultants, and other service-based small businesses are ideal candidates
Who Is NOT a Good Candidate
- Employees with W-2 income and no significant side business income
- Businesses with complex international structures or offshore issues
- Anyone currently under IRS audit (we can refer you to appropriate counsel)
- Businesses in severe financial distress where tax planning is secondary to cash flow survival
What a TodayCFO Engagement Looks Like
The guarantee is tied to the first 90 days, but most clients continue with an ongoing engagement after seeing what we find. Here is what a full TodayCFO engagement typically includes:
- Initial tax diagnostic and strategy presentation — months 1–3; the guarantee period
- Entity restructuring support — S-Corp elections, payroll setup, operating agreement review
- Retirement plan establishment — Solo 401(k), SEP IRA, or defined benefit plan setup with a recommended TPA (third-party administrator)
- Quarterly check-ins — estimated tax review, year-to-date income tracking, strategy adjustments
- Year-end tax planning session — equipment timing, income deferral or acceleration, last-minute retirement contributions
- Ongoing access — answer questions, review major decisions (equipment purchases, new hires, contracts) through a tax lens before you commit
- Coordination with your CPA — we work alongside your existing tax preparer or can refer you to one; we focus on strategy, not filing
The fractional CFO model means you get the strategic benefit of a full-time CFO at a fraction of the cost. For more on what that looks like, read: 6 Tax Planning Strategies Every Small Business Owner Should Be Using.
THE BOTTOM LINE ON THE GUARANTEE
"I have put a $10,000 guarantee on every new engagement because I am that confident in what we find. It is not a marketing gimmick — it is a commitment that if I cannot identify meaningful savings in your tax situation within 90 days, I have not done my job. In the years I have been doing this work, I have never had to write that check. That is not luck. It is a reflection of how far most business owners are from optimal tax efficiency — and how clear the path forward is once you actually look." — Tom Woolley, MBA
Frequently Asked Questions
What is the TodayCFO tax savings guarantee?
TodayCFO guarantees that qualified clients will identify at least $10,000 in annualized tax savings opportunities in the first 90 days of engagement. If we do not find $10,000 in savings, we refund our fees for that period.
Who qualifies for the tax savings guarantee?
Qualifying clients are typically contractors, dental practice owners, or small business owners with net income of $150,000 or more who have not previously worked with a proactive tax strategist. Business structure, entity type, and current tax setup are reviewed during the discovery call.
Why has the guarantee never been paid out?
Because almost every business owner at the qualifying income level is significantly overpaying on taxes. The strategies we use — S-Corp elections, retirement plans, depreciation timing, income splitting — are legal, proven, and available to any business owner. Most simply do not have an advisor who implements them.
What does a TodayCFO engagement include?
A typical engagement includes an initial tax diagnostic, strategic recommendations, implementation support for entity structuring and retirement plan setup, quarterly check-ins, year-end tax planning, and ongoing access to your assigned advisor.
How quickly can tax savings be implemented?
Some strategies, like expense categorization and deduction identification, produce savings immediately on your next tax return. Others, like S-Corp elections, require advance planning and may take 3–6 months to implement. The $10,000 guarantee covers identified savings opportunities, not necessarily cash received in the first 90 days.
The Bottom Line
We offer a $10,000 tax savings guarantee because we have yet to work with a qualifying contractor or small business owner who was not significantly overpaying. The strategies exist. The question is whether you have someone implementing them. If you do not, you are paying taxes you do not legally owe — and that is a problem we can solve.
See If You Qualify for the $10K Guarantee
If you are a contractor or small business owner making $150,000 or more per year, there is a very good chance you are overpaying on taxes. Schedule a free strategy call and we will show you exactly what we find — and what it is worth.
Schedule Your Free Assessment