Masterclass Listing

Program Agenda
Session 1 of Tax Planning Masterclass: Tax Bracket Management
  1. Understanding the Multi-Dimensional Tax System
    1. Ordinary income tax brackets and capital gains brackets
    2. Strategies for High-Income Earners with W-2
    3. K-1 and Schedule E Strategies
    4. Passive vs. non-passive
    5. Grouping Elections and 469 planning
    6. 3.8% Net Investment Income Tax (NIIT)
    7. Alternative Minimum Tax (AMT)
  2. Core Bracket Management Strategies
    1. Capital gain harvesting and tradeoffs
    2. Capital loss harvesting and offset rules
    3. Flying below the radar: strategic income timing
    4. Income smoothing and Roth conversions
  3. Asset Location
    1. Tax-free assets: Roth IRAs, life insurance, municipal bonds
    2. Tax-deferred assets: IRAs, annuities, retirement accounts
    3. Taxable assets: dividends, capital gains, interest income
    4. Tax-preferred assets: real estate, oil & gas investments
  4. Planning Impacts of Medicare Premiums
    1. Bracket creep and IRMAA surcharges
    2. How income strategy affects Part B and Part D costs
  5. Additional Planning Opportunities
    1. Use of NUA (Scenarios: Client laid off; Possible Roth conversion with NUA)
    2. Use of annuities, and life insurance in tax management

    3. Strategies for high-income clients in transition years

       

 

Session 2 of Tax Planning Masterclass: Foundational to Advanced Strategies for Individual Clients
  1. Tax-Advantaged Accounts
    1. Contribution optimization for IRAs, 401(k)s, SEP, SIMPLE plans
    2. Brief overview of HSAs
    3. Education funding: 529s and Coverdell ESAs
    4. Multi-year funding; Grandparent 529s, 529-to-Roth conversions
  2. Deductions and Credits
    1. Itemized vs. standard deduction strategy
    2. Tax bunching and charitable bundling
    3. Key credits: CTC, EITC, and education-related credits
  3. Investment Tax Planning
    1. Capital gains timing, harvesting, and stacking strategies
    2. Concentrated positions
    3. Examples of cap gains stacking by income bracket
  4. Income Shifting and Splitting
    1. Using family trusts and gifting
    2. Employing family members and setting reasonable compensation
  5. Other
    1. Social Security benefits and taxes
    2. Capital gains from homeowners insurance proceeds

6. TCJA Sunset: The Possible Impact and What You Can Control

Session 3 of Tax Planning Masterclass: Strategies for Business Clients
  1. Business Structures and Tax Implications
    1. Tax pros and cons of LLCs, S Corps, C Corps, and Partnerships
    2. How distributions are handled for each entity type
    3. S Corp Wage Optimization
    4. Restructuring strategies to improve tax efficiency
    5. Section 199A Qualified Business Income Deduction
  2. Section 1202 Qualified Small Business Stock
  3. Business Deductions and Credits
    1. Key deductions: depreciation, operating expenses, Section 179
    2. Tax credits: R&D, Work Opportunity Credit, Health Care Credit
  4. Timing and Revenue Deferral
    1. Aligning income and expenses for optimal timing
    2. Techniques to accelerate deductions and defer income
  5. Owner & Employee Compensation
    1. Solo 401(k) vs. SEP IRA
    2. Aggregation rules under Section 199A
    3. Tax-efficient fringe benefits (e.g., wellness, tuition programs)
  6. Medical Professionals
    1. Entity Structuring & Deduction Stacking for Independent Physicians
    2. Backdoor Roths, Mega Backdoor Roths, and Tax-Efficient Retirement Saving
    3. Real Estate, Passive Income, and Material Participation for Doctors
  7. Tax-Efficient Exit Planning: Practice Sales, Equity, and Asset Transfers
    1. Structuring installment sales to spread capital gains
    2. How to sell goodwill tax-efficiently (especially for sole proprietors)
    3. 1031 exchange strategies for doctors selling real estate
    4. Gifting or selling business interest to trusts (e.g., IDGT)
    5. Planning around the TCJA sunset and estate tax exemption compression in 2026
Session 4 of Tax Planning Masterclass: Roth Conversions, Executive Compensation, Trusts and Taxation

Join nationally renowned CPA Bob Keebler for this session when he educates you on the topics listed below.

  1. Roth Conversions
    1. Roth rules recap: taxability, recharacterization, and five-year rule nuances
    2. Visualizing brackets: Ordinary vs. LTCG brackets, ACA cliffs, IRMAA bands
    3. Conversion strategies by life stage: Pre-SS, post-SS, RMD phase, and after spouse passes
    4. Combining Roths with QCDs, bunching charitable deductions, and DAFs
    5. Case study: Using Roths in a 5-year glide plan to reduce lifetime taxes
    6. Inherited IRA considerations under SECURE Act
  2. Executive Compensation & Equity Planning:
    1. RSUs vs. ISOs vs. NSOs
    2. 83(b) elections
  3. Trusts and Taxations: Estate & Legacy Planning with Tax Efficiency
    1. Understanding Simple vs. Complex vs. Grantor Trusts (and Why It Matters)
    2. Distributable Net Income (DNI) and the Income Distribution Deduction
    3. Why Trusts Hit the Top Tax Bracket So Quickly (and How to Plan Around It)
    4. Capital Gains in Trusts: When They’re Taxed, When They Can Be Passed Through
    5. Lifetime Gifting Strategies:
      1. Annual exclusion and unified credit planning
      2. Using trusts for tax control (SLATs, IDGTs)
    6. Charitable Legacy Techniques: CRTs, CLATs, and remainder interests
    7. Step-Up in Basis Planning:
      1. Community property vs. joint tenancy considerations
      2. Managing highly appreciated assets near end-of-life
    8. State Estate Tax Planning:
      1. Planning for clients in decoupled states