.png){kind=spacer}
Every Dollar You Keep Is a Dollar That Compounds
Tax planning isn't something that happens once a year in April. At Bull Run Investment Management, it's embedded into every investment decision, every account structure, and every financial planning conversation — year-round.
Working in close partnership with Brian Wendroff, CPA at Wendroff & Associates — or coordinating with your existing CPA — we build a proactive tax strategy that integrates directly with your investment management, estate plan, and financial goals. Every trade, every Roth conversion, every gifting decision is evaluated through a tax lens before it's executed.
The result? You keep more of what you earn, more of what you grow, and more of what you transfer — with full compliance and zero surprises come filing season.
- Proactive tax projections — not just year-end filing
- Roth conversion timing calibrated to bracket thresholds
- Tax-loss harvesting integrated with portfolio rebalancing
- Asset location optimization across taxable, deferred, and Roth accounts
- Personal, trust, and business returns prepared by your CPA
- Entity structuring for business owners and complex income
What Tax Planning & Preparation Covers
Our tax strategy spans investment-level decisions, income planning, entity optimization, and full return preparation — all coordinated under one roof to eliminate gaps and reduce your lifetime tax burden.
Tax-Loss Harvesting
We systematically harvest losses within your portfolio to offset gains — reducing your current-year tax bill while maintaining your target allocation. Losses are banked and carried forward when they exceed current gains.
Asset Location Strategy
Different account types are taxed differently. We place high-growth, tax-inefficient holdings in tax-advantaged accounts and tax-efficient positions in taxable accounts — optimizing your after-tax return across your entire portfolio.
Roth Conversion Planning
We model multi-year Roth conversion strategies to fill specific tax brackets — converting pre-tax assets to tax-free Roth accounts at optimal times, especially before Social Security and RMDs begin to push you into higher brackets.
Entity & Income Structuring
For business owners and executives with complex income — W-2, K-1, equity compensation, rental income — we work with your CPA to optimize entity structure, owner compensation, and income timing to minimize both income and self-employment tax.
Tax Return Preparation
Personal, trust, and business returns — prepared by Brian Wendroff, CPA or your own tax professional. Because your CPA works alongside our investment team, every return reflects the full picture of your financial activity for the year.
Charitable Tax Offsets
Donor-advised fund contributions, qualified charitable distributions from IRAs, appreciated stock donations, and charitable trust strategies — each timed and structured to generate maximum deductions aligned with your income and estate plan.
Tax Strategy Isn't a Season — It's a System
Most people think about taxes once a year. We think about them every quarter — coordinating investment, income, and planning decisions across a continuous calendar so nothing is left to chance.
Tax Return Preparation & Filing
Brian and his team prepare personal, trust, and business returns using the prior year's full financial data — including all investment activity, Roth conversions, charitable contributions, and entity income. Every return is reviewed alongside your financial plan before filing.
Mid-Year Tax Projection & Strategy Reset
After filing, we run a mid-year tax projection to assess your current trajectory. This is where we begin modeling Roth conversion opportunities, identify harvesting candidates, and flag any income events — equity vesting, real estate sales, or business distributions — that require proactive planning.
Harvesting, Conversions & Estimated Payments
With half the year's data in hand, we execute tax-loss harvesting, initiate Roth conversions to fill targeted brackets, and calibrate estimated tax payments. If you have K-1 or business income, we coordinate quarterly estimates with Brian's team to avoid penalties.
Year-End Optimization & Charitable Giving
Final push: we review the full tax picture, complete any remaining Roth conversions, execute charitable contributions (DAF, QCD, appreciated stock), finalize required minimum distributions, and ensure all year-end transactions are coordinated with both your investment strategy and your CPA's filing prep.
Working with Brian Wendroff, CPA
For clients who need tax preparation and proactive tax strategy, we work closely with Brian Wendroff — an experienced CPA who serves as an extension of our advisory team. Already have a CPA you trust? We coordinate with them seamlessly.
.png)
Brian Wendroff, CPA
Brian founded Wendroff & Associates in 2006 after four years of military service, including a tour at the Pentagon. Recognized as an "Entrepreneur's CPA," he pioneered complete online accounting solutions and specializes in outsourced CFO consulting, tax strategy, and accounting automation for businesses and high-net-worth individuals.
Brian works hand-in-hand with our investment team — ensuring every decision from Roth conversions to asset location to charitable giving is tax-optimized. He doesn't just file your return; he helps shape the strategy that determines what's on it.
Tax Strategies We Implement & Manage
Beyond basic filing, we deploy a range of proactive strategies that reduce your tax burden across income, capital gains, estate, and generational transfer — each integrated with your broader financial plan.
Roth Conversion Laddering
We model multi-year conversion plans that fill specific tax brackets — typically the 22% or 24% bracket — converting pre-tax assets to Roth before Social Security, RMDs, or a surviving spouse's higher filing status push you into costlier brackets.
Tax-Loss Harvesting & Gain Deferral
Systematic harvesting across your portfolio to offset realized gains. Losses are carried forward to future years when needed. We also manage lot-level selling — choosing specific tax lots to minimize the tax impact of each trade.
Donor-Advised Funds & QCDs
Contributing appreciated stock to a DAF avoids capital gains entirely while generating a full fair-market-value deduction. For clients over 70½, qualified charitable distributions from IRAs satisfy RMDs while keeping the income off your return.
Entity Optimization & Compensation
For business owners, we coordinate with Brian to evaluate S-Corp elections, reasonable compensation thresholds, profit-sharing and defined benefit contributions, and income timing strategies — all designed to reduce combined income and self-employment tax.
Gifting & Transfer Tax Strategy
We coordinate with your estate attorney to time and structure gifts — annual exclusion gifts, lifetime exemption transfers, and trust funding — with full tax modeling to ensure each transfer is optimized from both income and estate tax perspectives.
IRMAA & Net Investment Income Tax
For higher-income clients, we model Medicare surcharge brackets (IRMAA) and the 3.8% net investment income tax — planning income events and conversions to avoid triggering costly thresholds that can persist for two years.
Tax Decisions Don't Happen in Isolation
Your CPA, your portfolio manager, and your estate attorney need to be in sync. We serve as the central hub — ensuring every tax-sensitive decision is coordinated across your entire advisory team.
Tax Planning for Complex Financial Lives
If your tax situation involves more than a W-2 and a standard deduction, you'll benefit from integrated tax planning that connects your returns to your investments, your estate, and your long-term goals.
High-Earning Professionals
Executives with RSUs, stock options, deferred compensation, and bonus structures that create unpredictable income spikes requiring proactive bracket management and AMT planning.
Business Owners
Entrepreneurs navigating entity structure, owner compensation, pass-through income, retirement plan contributions, and the intersection of business and personal tax strategy.
Retirees & Pre-Retirees
Clients managing the transition from accumulation to distribution — where Roth conversions, Social Security timing, RMDs, IRMAA, and withdrawal sequencing determine how much of your nest egg actually reaches you.
Real Estate Investors
Clients with rental properties, 1031 exchange opportunities, depreciation recapture, and passive income that requires coordination with active investment and business income strategies.
Cross-Border Clients
U.S. residents with foreign assets, green card holders, expats, and clients with international income requiring FBAR, FATCA, and cross-jurisdictional tax compliance and planning.
Charitable Givers
Philanthropically-minded clients who want to maximize the tax benefit of their giving through DAFs, QCDs, appreciated stock donations, CRTs, and private foundation strategies.
Why Filing a Return Isn't Tax Planning
The Annual Filing
- CPA receives 1099s in March, files return, done until next year
- No communication between CPA and investment advisor
- Tax-loss harvesting opportunities missed because no one is watching
- Roth conversions done reactively — or not at all
- Charitable giving is a last-minute scramble in December
A Year-Round Tax System
- Proactive quarterly projections that shape investment and planning decisions
- CPA, portfolio manager, and estate attorney in constant coordination
- Systematic harvesting integrated with every portfolio rebalance
- Multi-year Roth conversion ladders modeled to specific bracket thresholds
- Charitable strategy planned in Q1, executed throughout the year
Ready to Stop Overpaying in Taxes?
Schedule a complimentary consultation to review your current tax strategy — or build one from scratch. We'll assess your income picture, identify opportunities, and outline a plan that saves you real money every year.