The Pain Behind the Gain: Your Capital Gains Strategy Guide 2025
Everything you need to know about maximizing your 2025 capital gains tax strategies
The Bottom Line Up Front
If you’re sitting on significant capital gains in 2025, this is the most important year for tax planning in decades. The “Big Beautiful Bill” is in the process of reshaping the entire landscape — creating new opportunities, changing timelines, and eliminating others. Here’s your complete guide to several of the major strategies available, when to consider each one, and why timing matters more than ever.
You’ve Made It. Now What?
Congratulations — and condolences.
You built something valuable. You sold it at the right time. You made the smart moves.
So why does success feel like a problem?
Because now you’re facing the part nobody prepared you for: realizing that your financial success has created your biggest financial challenge.
The business sale that secured your future just triggered a tax bill that could derail it. The real estate portfolio you built over decades now feels like a burden but selling means losing 30% to taxes. The stock position that made you wealthy is keeping you awake at night.
This is the pain behind the gain. Every dollar of profit creates roughly 30 cents of tax liability. Every smart move forward feels like it penalizes your past success.
Worse? When you start shopping for advice, you discover that most professionals are about to make your problem bigger.
The Advisor Problem That Nobody Talks About
Here’s what happens when you start seeking help:
The real estate guy pushes 1031s. The wealth manager suggests traditional portfolios. The tax attorney focuses on write-offs. The insurance agent talks about annuities.
Meanwhile, you’re sitting on the largest financial decision of your life, wondering if anyone is actually thinking about YOUR specific situation.
The truth they won’t tell you: Most advisors know one primary approach. Not because it’s always optimal, but because it’s what they’ve built their practice around.
You deserve better than a solution that fits their business model instead of your circumstances.
Why This Moment Is More Critical Than You Think
Breaking Legislative News
Senate Finance Committee published their text earlier this month (June 16), proposing to make permanent both 100% bonus depreciation AND Opportunity Zones — transforming both from temporary programs into permanent features of the tax code, though the specific implementation details and final passage remain subject to Congressional negotiation.
What This Could Mean:
- Potential elimination of sunset dates
- Possible permanent certainty for long-term planning
- Potential advantages for sophisticated strategies
Why This Matters Now:
You have roughly 180 days to make decisions that will determine:
- How much of your wealth you actually keep (vs. lose to taxes)
- How much liquidity you maintain for new opportunities
- Whether you’re tied to investments you don’t want to manage
- How much income you generate starting Year One
- What you leave to your heirs
- Whether you position yourself for the next phase of wealth building
Most advisors ask: “How do we defer these taxes?”
At IREXA, we ask: “How do we optimize your entire wealth transition?”
The IREXA Diagnostic: How We Think Differently
Traditional Advisor Approach:
“Here’s our solution. How can we make your situation fit it?”
IREXA Diagnostic Approach:
“Here’s your complete situation. Let’s determine the optimal path.”
Our Diagnostic Questions:
- What’s your primary objective? (Income now, tax elimination, liquidity preservation, growth)
- What are your constraints? (Time horizon, liquidity needs, risk tolerance)
- What’s your complete tax picture? (Not just this gain, but your entire strategy)
- How sophisticated is your current portfolio? (Traditional 60/40 or institutional-style allocation)
Our Five Core Strategies:
- Professional Real Estate Management (DSTs): Income-focused with zero landlord duties
- Long-Term Tax Elimination (Opportunity Zones): Building tax-free wealth permanently
- We recently posted a blog answering most common questions from clients regarding opportunity zones, check it out here.
- Immediate Tax Offset (Bonus Depreciation): Keep 60%+ of proceeds while eliminating taxes
- Private Market Access (Syndications): Institutional-style portfolio allocation
- Estate Optimization (IRA Conversions): Maximizing retirement and legacy wealth
What makes this different: Each strategy unlocks access to private market opportunities that institutions use but most individual investors never see. Most importantly: sophisticated investors don’t choose just one approach — they blend strategies based on their complete financial picture.
See how our diagnostic works for your specific circumstances. [Get Your Custom Analysis]
The Diagnostic Results: Which Path Fits Your Situation
If Your Primary Need Is Income Starting Immediately
The Challenge: You’re tired of active management but need cash flow.
Why It May Work: Professional management may eliminate landlord duties while potentially seeking to provide distributions within 30-60 days through institutional-grade properties.
At IREXA, We’ve Learned: The key is sponsor selection. We focus on DST sponsors who have substantial track records, though past performance does not guarantee future results.
If Your Goal Is Eliminating Future Taxes Entirely
The Challenge: Traditional strategies defer taxes, but you want them gone forever.
Why It May Work: Opportunity Zone investments may potentially eliminate taxes entirely on appreciation after 10 years, though this depends on meeting all IRS requirements and holding periods.
At IREXA, We’ve Learned: The Senate’s proposed move toward permanence could represent a fundamental shift in OZ planning. Some newer opportunities now offer quarterly distributions and exit options after one year, reducing lock-up risk while maintaining OZ benefits.
If You Need Immediate Tax Relief But Want to Keep Most of Your Money
The Challenge: Every strategy seems to lock up your capital.
Why It May Work: Depending on your situation, you may potentially invest ~35% of your gain to offset 100% of taxes, keeping ~65% liquid — though results vary and are subject to IRS rules.
At IREXA, We’ve Learned: Location quality and operator experience are critical factors, though no investment is guaranteed. We focus on high-traffic, established locations with experienced operators.
If You Want Institutional-Style Portfolio Optimization
The Challenge: Traditional portfolios offer limited yield in current conditions.
Why It May Work: Access to private market opportunities similar to those used by institutional investors may provide enhanced returns and reduced correlation to public markets, though performance varies widely.
At IREXA, We’ve Learned: Many clients combine this approach with others, depending on risk tolerance, liquidity needs, and suitability.
If You’re Focused on Retirement and Estate Optimization
The Challenge: Current retirement accounts will face huge tax bills later.
Why It May Work: Converting traditional IRA assets during downturns could allow you to pay taxes on temporarily discounted values — but timing and valuation risks are high.
At IREXA, We’ve Learned: This works best in coordination with tax professionals and only for qualified investors.
Why Most Clients Don’t Choose Just One Strategy
The “Income Now, Growth Later” Approach
- DST for income and professional management
- Opportunity Zone for long-term tax benefits
- Result: Potential for current cash flow plus future tax benefits, though both involve significant risks
The “Liquidity + Institutional” Approach
- Bonus depreciation to eliminate taxes while retaining liquidity
- Private syndications for portfolio diversification
- Result: Potential tax benefits with portfolio diversification, though both strategies involve substantial risks
The “Complete Wealth Transition”
- Primary tax strategy based on liquidity/timing
- Estate optimization for retirement accounts
- Private markets to modernize portfolio allocation
- Result: Comprehensive approach, though increased complexity and risk
At IREXA, We’ve Learned: Comprehensive planning requires careful consideration of risks and may not be suitable for all investors.
The Three Mistakes That Cost Clients Hundreds of Thousands
Mistake #1: Accepting Your Advisor’s Specialty
What Happens: You work with an advisor based on referral rather than comprehensive evaluation of available strategies.
The Potential Cost: Missed opportunities for income, growth, and tax optimization over time.
What We Do Differently: We evaluate multiple approaches before making recommendations, though not all strategies will be suitable for every investor.
Mistake #2: Focusing Only on Taxes Instead of Wealth Strategy
What Happens: You address immediate tax issues without considering broader investment strategy modernization.
The Potential Cost: Remaining in traditional portfolios while potentially missing alternative investment opportunities.
What We Do Differently: We may explore using tax solutions as potential gateways to institutional-style investing, where suitable and appropriate.
Mistake #3: Waiting for Perfect Information
What Happens: Extended research periods while deadlines pass and opportunities expire.
The Potential Cost: Loss of deferral options and acceptance of tax liabilities that might have been mitigated.
What We Do Differently: We provide clear timelines and decision frameworks to help qualified investors make informed decisions with available information.
Real Client Transformations
The Manufacturing Business Owner
The Problem: $4.2M gain from business sale, needed capital for next venture, facing $1.2M+ tax bill.
Traditional Advisor Approach: “Let’s put you in bonds and some blue-chip stocks after you pay the taxes.”
Our Diagnostic: Primary need was liquidity preservation while addressing taxes. Secondary goal was sophisticated portfolio allocation.
Our Approach: Opportunity Zone strategy for potential tax deferral combined with private syndications for retained proceeds, creating a blended approach that addressed both tax liability and portfolio positioning, though both involved substantial risks.
The Outcome: Tax liability deferred, capital positioned for potential institutional-style returns, liquidity preserved for venture opportunities. Client results will vary and are not guaranteed.
The Defensive Positioning Investor
“I have substantial gains but everything feels overvalued. I want defensive positioning but refuse to lock money up for 10 years in traditional OZ deals.”
Our Diagnostic: Primary need was defensive asset allocation without traditional OZ liquidity constraints. Secondary goal was maintaining tax advantages while preserving flexibility.
Our Approach: Exploration of emerging OZ opportunities in defensive asset classes with potentially enhanced liquidity features quarterly options and annual exits that eliminate traditional OZ constraints.
The Outcome: Defensive positioning explored, tax deferral benefits evaluated, liquidity flexibility preserved. All alternative investments involve substantial risks and may not be suitable for all investors.
What Harvard’s Endowment Knows That Your Advisor Doesn’t
The Institutional Approach: Top endowments and pension funds typically allocate 30-50% to private markets, though individual investor circumstances differ significantly from institutional investors.
Why Most Advisors Don’t Offer This:
- Limited access to institutional-quality private investments
- Regulatory and suitability constraints for individual investors
- Due diligence requirements for sophisticated strategies
- Comfort with traditional approaches
What We May Provide Access To:
- Enhanced Return Potential: Opportunities with institutional backing, though returns are not guaranteed and involve substantial risks
- Potential Reduced Correlation: Performance that may be less dependent on daily stock market volatility, though correlation can increase during market stress
- Income Generation Potential: Regular distributions that may exceed traditional fixed income, though distributions are not guaranteed
- Tax Structure Considerations: Potential depreciation and other benefits, though tax laws may change
Important Note: Institutional strategies are not automatically suitable for individual investors and involve substantial risks including illiquidity, high minimums, and potential for total loss.
At IREXA, We’ve Learned: Capital gains solutions that also provide access to institutional-style investing require careful evaluation of suitability and risk tolerance.
Why IREXA Exists
We founded IREXA because we observed sophisticated investors receiving advice that defaulted to advisor specialties rather than comprehensive evaluation of client-specific optimal outcomes.
Our Core Belief: Your specific situation should determine the strategy recommendation, subject to suitability and risk considerations.
Our Diagnostic Process:
- Complete Situation Analysis Your entire financial picture, not just the immediate issue
- Strategy Evaluation Relevant approaches that may be suitable for your circumstances
- Custom Recommendations Based on your specific situation, risk tolerance, and suitability requirements
- Implementation Through Qualified Partners Access to institutional-quality due diligence and opportunities where appropriate
- Ongoing Strategic Partnership Monitoring and adapting as your situation evolves
Our Distinction: We explore using tax solutions as potential gateways to institutional-quality wealth strategies, where suitable.
Your Next Step: The Strategic Consultation
What Makes Our Consultation Different:
- Real-Time Legislative Intelligence: We monitor tax law developments daily, though final legislative outcomes remain uncertain.Diagnostic Before Solutions: We spend time understanding your complete situation before discussing any strategies.Institutional-Quality Analysis: Comprehensive strategic thinking and due diligence similar to family office approaches.
No Product Pitches: We evaluate what may be optimal for your specific situation and risk tolerance.
Clear Action Plan: You’ll receive specific next steps and timing, not vague recommendations.
What You’ll Discover in Your Consultation:
- Which strategies may fit your specific situation (suitability varies by individual circumstances)
- How capital gains solutions might complement your broader investment approach
- What institutional-quality opportunities may be available and suitable for your situation
- Relevant timelines and deadlines for your potential strategy
- How to coordinate with your existing advisors (CPA, attorney) for seamless implementation
Investment Required: Complimentary strategic consultation for qualified investors
What Happens Next: If strategies appear suitable for both parties, we’ll outline potential implementation steps. If not, you’ll still have clarity to make informed decisions.
The Reality Most Clients Discover: There may be solutions available that they weren’t aware of, though not all will be suitable for every investor.
Important Disclosures
Investment Risk: All investments involve risk of loss, including potential total loss of principal. Past performance does not guarantee future results. Private investments typically involve higher risks than traditional investments including illiquidity, lack of diversification, and potential for total loss.
Alternative Investment Risks: Alternative investments including DSTs, Opportunity Zone funds, private syndications, and bonus depreciation strategies involve substantial risks including but not limited to: illiquidity and inability to access invested capital for extended periods; limited or no secondary markets; lack of daily pricing; concentration risk; development and operational risks; potential for total loss of principal; complex tax implications; limited regulatory oversight; high minimum investments; and dependence on sponsor/operator expertise and integrity.
Tax Considerations: Tax laws are complex and subject to change. Tax consequences depend on individual circumstances. This material is not intended as tax advice. Tax benefits discussed may be substantially limited or eliminated by future changes in tax laws. Consult qualified tax professionals before making decisions. Tax deferral strategies may result in higher future tax liabilities.
Suitability: Not all strategies are appropriate for all investors. Suitability depends on individual financial circumstances, objectives, risk tolerance, liquidity needs, and investment experience. Alternative investments are generally suitable only for sophisticated investors who can afford to lose their entire investment.
Liquidity: Alternative investments typically involve significant liquidity restrictions and are not suitable for investors requiring immediate access to invested capital. Some newer structures may offer enhanced liquidity features, but these remain limited and are not guaranteed.
Due Diligence: All investment opportunities require thorough due diligence. Past sponsor performance does not guarantee future results. Private investments involve additional risks including limited liquidity, lack of standardized pricing, potential conflicts of interest, and limited regulatory oversight compared to public investments.
Regulatory: Securities offered through IREXA Financial. Member FINRA/SIPC. Investment advisory services offered through IREXA Financial, a registered investment adviser.
Accredited Investor Status: Many strategies discussed are limited to accredited investors as defined by federal securities regulations. Some investments may be limited to qualified purchasers with even higher net worth requirements.
Forward-Looking Statements: This material contains forward-looking statements regarding potential legislative changes, market conditions, and investment outcomes. These statements involve risks and uncertainties that could cause actual results to differ materially from those expressed or implied.