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Tax Planning

The Implementation Gap: Why Even Legitimate Tax Strategies Fail During Audits

Earmark Team · April 10, 2025 ·

What’s the biggest mistake tax professionals make? Great ideas that never get implemented. That’s according to Jasmine DiLucci, a tax attorney, CPA, and enrolled agent who has built an impressive following of nearly 500,000 YouTube subscribers by debunking viral tax myths on social media.

I sat down with Jasmine for a conversation on the Earmark Podcast. We kicked things off by discussing the issue of false information about taxes that spreads on social media. Jasmine also highlighted an even deeper concern: even legitimate tax strategies can face serious issues if implemented incorrectly.

Why Social Media Fuels Tax Misinformation

Jasmine says one reason so many “loopholes” and sketchy strategies go viral is that true tax expertise rarely gets posted online. Skilled professionals are busy running firms, while less experienced creators spread half-truths. This leads to flawed tips on topics like clothing deductions or marking up the inside of a shirt with a tiny business logo, all to claim a tax write-off.

The clothing deduction test is a great example. The test has existed for decades, complete with court rulings stating clothes are only deductible if they’re unsuitable for personal wear. But many influencers ignore this, telling people to slap a hidden logo on their regular clothes. As Jasmine points out, these strategies often fail in an audit. Taxpayers who rely on them risk penalties and extra scrutiny.

Implementation Over Theory: The Real Reason Plans Fail

For Jasmine, the greatest pitfall is the implementation gap—the space between hearing a tax idea, reporting it correctly on a return and documenting what was done. 

She highlights the short-term rental loophole as a perfect example. While the idea is legal, most filers never produce the logs, election statements, or rental agreements proving they qualify.

“If it’s not on the return that way,” Jasmine says, “then what did we just do? Nothing.”

Clients often pay thousands for big-picture “plans” but fail to handle bookkeeping or gather the right records. By the time they’re under audit, there’s no backup for the deduction. Those clients face costly disputes with the IRS, sometimes losing deductions they could have secured with basic documentation.

The Shift in Responsibility: Why Clients End Up Holding the Bag

Misinformation creates tension between clients and professionals. Many taxpayers see social media videos telling them they can write off anything. Then, when their tax expert says “no,” it causes conflict. Some preparers cave and let questionable deductions slide. Others keep warning clients but never clearly explain the “why.”

During an IRS audit, that defense of “my tax preparer said I could” means little. The IRS holds taxpayers responsible for their returns. Jasmine notes that low-level auditors sometimes miss legal details, so a wrong deduction might slip by. But if a client’s case goes to appeals or tax court, illusions fall apart without real support.

Bridging the Gap with an Integrated Service Model

Jasmine’s firm avoids the implementation gap by offering an integrated approach: tax planning, accounting, and preparation, all under one roof. She insists on year-round contact, keeping detailed records, and ensuring clients follow the steps for valid deductions. Her team also handles IRS resolutions, so she knows firsthand where taxpayers slip up.

Working with a single provider can prevent the “blame game.” Instead of paying one person for theory, another for the return, and a third for bookkeeping, Jasmine’s clients get everything in one place. This structure helps them stay organized, meet documentation rules, and rely on correct returns from the start.

Scaling Through Delegation and the Right Tools

While her integrated model works, Jasmine admits it wasn’t easy to build. She did almost everything herself early on—sales calls, tax returns, and marketing. Eventually, she found experts who could handle each function at a high level.

She also credits technology for streamlining processes:

  • Canopy for practice management
  • CCH for tax software
  • Calendly for scheduling
  • Slack for team communication
  • Superhuman for email management

For tax research, she recommends the Bradford Tax Institute because it clearly cites legal authority. She warns that AI chatbots sometimes invent court cases, so relying on them can be risky.

Join Jasmine’s Free Community

Jasmine welcomes taxpayers and fellow professionals to her free tax community at actualtaxlaw.com. There, she shares detailed answers about IRS notices, audits, and new tax updates. Users can post questions or upload documents for possible video reviews.

Earn Free CPE for Listening to the Episode

Tax ideas don’t save you money if you don’t implement them correctly. Closing the gap between theory and execution can shield taxpayers from costly audits and give professionals a clear advantage. Whether logging short-term rental days or documenting a true business expense, proper follow-through matters more than any buzzworthy trick.

If you’d like to hear the full interview and gain more insights on best practices, listen to the full episode of the Earmark Podcast. You can also earn free NASBA-approved CPE by registering for the course on the Earmark app and taking a quick quiz to verify your learning.

Maximizing Tax Savings with Defined Benefit and Cash Balance Plans

Earmark Team · January 27, 2025 ·

What if you could help your high-income business owner clients convert a $500,000+ tax liability into retirement wealth—while maintaining complete IRS compliance? That’s the power of defined benefit and cash balance plans, a strategy that many CPAs overlook but that can transform your clients’ financial futures.

In a recent webinar, David Podell of Business Benefits Consultants shared how strategically designed defined benefit plans can provide CPAs with a powerful tax optimization tool. 

Identifying Ideal Clients

According to Podell, the best candidates for these plans are high-income business owners who:

  • Have consistent, significant profits
  • Are comfortable with their current income
  • Run companies with fewer than 50 employees
  • Have stable employee bases
  • Are currently overpaying in taxes
  • Have underoptimized retirement planning

With these criteria in mind, let’s see how these plans have delivered results for real businesses.

Real-World Success Stories

Podell illustrated how defined benefit and cash balance plans can help business owners significantly lower their tax liabilities while enhancing their retirement savings.

Case Study 1: Law Firm Achieves $874,000 Contribution

A small law firm with two partners experienced an unexpected surge in income after winning a significant case that awarded them a substantial fee—much larger than their typical annual earnings. Facing a hefty tax bill, they sought a strategy to minimize their tax liability while making the most of this financial windfall.

They consulted with Podell to explore their options. By implementing a customized defined benefit plan, they were able to contribute $874,000 toward their retirement, with $814,000 being deductible. Remarkably, 96% of this contribution was allocated directly to the two partners.

The plan was meticulously tailored to account for the partners’ differing ages and financial situations:

  • Partner A was older and closer to retirement, making it advantageous for him to maximize his retirement contributions.
  • Partner B was younger, with student loans and young children, and preferred to contribute a smaller amount.

“This was very specific and customized in the design,” explains Podell. “We adjusted the plan to reflect the age difference and individual needs of each partner. By doing so, we turned a potentially large tax burden into a significant retirement asset for them.”

The result was a win-win:

  • Immediate Tax Savings: The firm significantly reduced its taxable income for the year, saving hundreds of thousands in taxes.
  • Retirement Growth: The partners boosted their retirement savings without disrupting cash flow or day-to-day operations.

Case Study 2: Solo Attorney Maximizes 1099 Income

A solo attorney was earning a substantial W-2 salary from his primary employer while also generating significant 1099 income through consulting work. Faced with a hefty tax bill on his consulting earnings, he sought a strategy to mitigate his tax burden and enhance his retirement savings.

He approached Podell with a straightforward question: “What if I can put away all the 1099 money? How would this work?”

By implementing a customized defined benefit plan, the attorney contributed $105,000 entirely for his own benefit. This strategic move not only provided a significant tax deduction but also allowed him to convert his side income into a substantial retirement asset.

Case Study 3: Family Business Secures Nearly $1 Million Deduction

A family-owned enterprise, involving multiple entities and several family members, faced a significant tax burden due to high profitability. The business had a complex ownership structure, including two primary owners, a minority owner, and other family members employed within the company.

Seeking a solution to minimize taxes while benefiting the entire family, they consulted with David Podell. By designing a highly customized defined benefit plan, they were able to make a $948,000 deductible contribution, with 86% of the benefits allocated directly to the owners and participating family members.

Key aspects of the customized plan included:

  • Inclusive Design: The plan incorporated not just the main owners but also the minority owner and other family members, maximizing benefits across the family.
  • Age and Role Considerations: Adjustments were made based on the ages and roles of each family member to optimize retirement contributions where they were most needed.
  • Multiple Entities Coordination: The plan seamlessly integrated various business entities under the family’s control, ensuring compliance and optimal benefit distribution.

“We tried to maximize the family as best as possible, determining ages and everything else,” explains Podell. “We really created this in a way that was very customized.”

The outcomes were substantial:

  • Significant Tax Reduction: The nearly $1 million contribution substantially lowered the company’s taxable income, providing immediate tax savings.
  • Enhanced Retirement Benefits: Family members received considerable boosts to their retirement savings, strengthening their financial futures.
  • Unified Financial Strategy: The plan aligned the family’s financial interests, promoting cohesion and shared goals within the business.

This case exemplifies how defined benefit plans can be tailored to accommodate complex family businesses while turning substantial tax liabilities into valuable retirement assets.

Strengths: Flexibility and Customization

The success of these case studies stems largely from the inherent flexibility of defined benefit and cash balance plans. “Every single plan design is different,” notes Podell. “That is not the world of the 401(k); that is not the world of a SIMPLE or a SEP plan.”

Key considerations for implementing these plans include:

  • Plan Design Variations: Options like floor offset, new comparability, and cash balance designs can drastically affect outcomes.
  • Flexibility in Contributions: Plans can be adjusted annually to match business performance, with options to freeze or reduce contributions in lean years.
  • Coordination with Existing Plans: These strategies can often be layered on top of existing 401(k) plans without disruption.

While traditional plans may cap out at basic 401(k) limits, defined benefit plans can support pension balances up to $3.1 million per person, with annual tax savings often exceeding $100,000. For CPAs looking to deliver measurable value to clients, these numbers represent a compelling opportunity.

The impact of proper plan design cannot be overstated. Consider a young real estate investor who received three different plan proposals:

1. First design: Offered a $100,000 contribution—not insignificant, but far from optimal.

2. Second design: Increased the contribution to $140,000 through a cash balance approach with a 401(k) component.

3. Third design: Incorporating pre-funding and ancillary benefits, achieved a remarkable $216,000 contribution—more than double the initial proposal.

This dramatic range demonstrates why sophisticated plan design is crucial for maximizing client outcomes.

A Strategic Combination: Defined Benefit + Roth 401(k)

Beyond plan design, there’s another powerful strategy available to enhance the overall tax benefits.

While many business owners avoid Roth 401(k)s due to losing the tax deduction, pairing them with defined benefit plans creates powerful tax diversification. 

When you’re already getting a $200,000+ deduction from your defined benefit plan, you can afford to make Roth contributions without the immediate tax benefit. This creates tax-free growth potential while controlling when and how taxes are paid—ideally during retirement when income levels and tax brackets may be lower.

Key Technical Considerations

While defined benefit plans offer powerful tax advantages, several important technical factors must be considered during implementation and ongoing management:

  • Plans should typically remain open 3-5 years minimum to minimize audit risk
  • For S-Corps, W-2 income levels are crucial for plan funding
  • Plans can work with multiple entities and control groups
  • Plans can be coordinated with existing 401(k)s without disruption

Given these technical complexities, successful implementation requires a coordinated effort among key professionals.

Implementing Success: The Team Approach

A successful defined benefit plan requires coordination among several professionals:

  • Tax advisor/CPA
  • Financial advisor
  • Record keeper
  • TPA/Actuary
  • Plan consultant

Consider working with a consultant who can quarterback this process, bringing together the necessary expertise while simplifying implementation for you and your clients.

By mastering this coordinated approach and becoming fluent in these sophisticated strategies, you can transform your practice and your client relationships.

Elevate Your Practice Through Strategic Planning

By mastering these advanced tax strategies, you can:

  • Deepen Client Relationships: Offering sophisticated planning sets you apart and fosters loyalty.
  • Attract High-Income Clients: Demonstrating expertise in significant tax-saving strategies can attract referrals.
  • Transform Your Role: Move from being a tax preparer to a strategic advisor who provides substantial, measurable value.

“Advice requires guiding your clients toward strategies that can improve their outcomes,” emphasizes Podell.

Ready to Transform Tax Outcomes?

Ready to explore defined benefit plans for your clients? Start by:

  1. Reviewing your client list for those with $100,000+ in potentially pensionable income
  2. Identifying business owners currently paying more in taxes than they’d like
  3. Considering clients with existing retirement plans that might benefit from optimization
  4. Reaching out to a qualified consultant to explore specific client situations

The difference between an ordinary retirement plan and an optimized defined benefit strategy can mean hundreds of thousands in tax savings for your clients—and a transformed advisory relationship for your practice.

Watch the full webinar to explore how you can implement these plans and transform your practice.

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