Case Studies
Real planning. Real results.
Three planning scenarios. Three different financial lives. Each illustrates how coordinated tax, investment, and life planning creates measurable value.
The Tech Founder
$4M net worth · Business Owners
$47K saved in Year 1
Situation
Founder of a B2B SaaS company, $4M net worth, $800K W-2-equivalent income, operating as a Delaware C-Corp with no employer-sponsored retirement plan. Paying 37% federal + 3.8% NIIT on nearly all income.
Challenge
Leaving $69K+ of annual tax-advantaged retirement contributions on the table. C-Corp structure creating double taxation on distributions. No quarterly tax planning cadence with CPA.
What We Did
- ✓Coordinated S-Corp election with CPA and set reasonable salary at $250K — reducing self-employment tax on remaining distributions
- ✓Established Solo 401(k) with $69,000 in combined employee/employer contributions (Year 1)
- ✓Built quarterly tax projection cadence with coordinated CPA
- ✓Rebalanced retirement allocation from 100% target-date fund to low-cost, tax-efficient index portfolio
Outcome
$47,000 in year-one tax savings between S-Corp election and retirement contributions. Ongoing annual tax advantage of ~$35,000. WIY annual fee: $17,000.
The RE Investor
$6M net worth · Real Estate Investors
$142K tax deferral
Situation
Real estate investor with 14 residential rental properties across three states. $6M net worth. Still working a W-2 day job at $180K. Self-managing most properties. No formal asset protection strategy.
Challenge
Zero cost segregation studies on any property. Missed a 1031 exchange on a recent $400K sale — triggering $80K in capital gains tax. Entity structure was a patchwork: some properties in LLCs, some held personally, no series LLC, no umbrella policy.
What We Did
- ✓Coordinated cost segregation studies on 4 highest-basis properties (combined basis: $2.1M)
- ✓Structured 1031 exchange for a pending $520K sale into two replacement properties
- ✓Coordinated with qualified legal counsel to establish series LLC structure with each property in its own series
- ✓Integrated accelerated depreciation into overall tax strategy to offset W-2 income via Real Estate Professional Status analysis
Outcome
$62,000 in Year 1 tax deferral through cost segregation. Additional $80,000 deferred via 1031 exchange. Working with qualified legal counsel, a series LLC structure was established — providing legal separation between properties. WIY annual fee: $21,000.
The FIRE Couple
$2.8M net worth · FIRE Followers
7 extra years of runway
Situation
Dual-income couple, both 48, combined $340K income. $2.8M net worth: $1.6M in traditional 401(k)s, $400K taxable brokerage, $200K Roth, $600K in home equity. Target: retire at 52.
Challenge
No withdrawal sequencing plan. $1.6M in pre-tax accounts with no Roth conversion strategy — meaning a massive tax bomb at RMD age. Healthcare costs for 13 years of pre-Medicare coverage completely unmodeled. Original plan ran out of money at age 81.
What We Did
- ✓Built a 40-year withdrawal sequencing model across all account types with Monte Carlo stress testing
- ✓Designed an 8-year Roth conversion ladder targeting $200K/year in conversions during the low-income window between retirement and Social Security
- ✓Modeled geographic arbitrage: keep Tahoe primary residence, spend 4 months/year in Portugal at ~40% lower cost of living
- ✓Built healthcare bridge plan: ACA eligibility by managing MAGI below 400% FPL during conversion years, with expat insurance as backup
Outcome
7 additional years of projected financial runway vs. their original plan (money lasts to 88, not 81), based on Monte Carlo analysis with historical return assumptions. $150K+ in projected lifetime tax savings from the Roth conversion ladder, dependent on future tax rates and conversion timing. Clear month-by-month retirement income plan they can actually follow. WIY annual fee: $13,500.
These case studies are hypothetical composites created for illustrative purposes only. They do not represent the experience of any actual client. The scenarios, strategies, and outcomes described are based on specific assumed circumstances and may not be applicable to your situation. Tax savings figures are estimates based on tax law in effect at the time of analysis; tax laws change and individual results depend on personal circumstances, implementation, and applicable law at the time of filing. Financial projections involve assumptions about future market conditions, tax rates, and spending patterns that may not materialize. No guarantee of similar outcomes is made or implied. Past results — whether actual or illustrative — do not guarantee future performance. Wealth In Yourself is a registered investment adviser. This content does not constitute personalized investment, tax, or legal advice. Consult qualified professionals regarding your specific situation.
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