Retirement strategies
25 plays in this category. Each one covers the mechanics, who it fits, and the estimated impact — then generates a deep dive against your own numbers.
- Retirement
Solo 401(k) + Loan Feature
Shelter $69K/yr and borrow up to $50K from yourself.
$25K+/yr in tax deferral - Retirement
Self-Directed IRA / Solo 401(k)
Invest retirement funds in real estate, private equity, notes.
Tax-deferred/free growth on alt assets - Retirement
ROBS (Rollovers as Business Startups)
Use 401(k)/IRA to fund a business — no tax, no loan.
Avoid 10% penalty + income tax on withdrawal - Retirement
Defined-Benefit / Cash-Balance Plan
Shelter $100K–$300K+/yr for high-earning owner-only businesses.
$60K–$120K+/yr federal tax reduction - Retirement
Backdoor + Mega Backdoor Roth
Get $46K+/yr into Roth despite income limits.
6-figure tax-free Roth balance in 5 yrs - Retirement
HSA Triple-Tax Stack
Pre-tax in, tax-free growth, tax-free out — the only triple-tax account.
$50K–$300K+ tax-free by retirement - Retirement
Solo 401(k) as Personal Bank
Borrow up to $50k against your own retirement — pay yourself interest.
$50k penalty-free liquidity, interest paid to yourself - Retirement
HSA as Stealth IRA
Triple tax-free vehicle — the best account in the code.
$500k+ tax-free medical fund by retirement - Retirement
§412(e)(3) Defined Benefit Plan
$300k+/year deductible contributions for older high-earners.
$100–200k/year in tax deductions - Retirement
Cash Balance Plan Stacking
Layer $150–300k/yr on top of Solo 401(k).
$100–200k/yr tax deduction on top of Solo 401(k) - Retirement
Nonqualified Deferred Comp (NQDC)
Defer S-Corp bonus income to future low-tax years via rabbi trust.
10–20% tax rate arbitrage between peak and retirement - Retirement
In-Plan Roth Conversions in Down Markets
Convert traditional to Roth when values crashed — pay tax on the low.
$60–150k lifetime tax savings per major conversion - Retirement
Net Unrealized Appreciation (NUA)
Company stock in 401(k) → LTCG rates instead of ordinary.
10–20% tax savings on unrealized appreciation - Retirement
Backdoor Roth IRA
High earners bypass Roth income limits legally.
$7K/yr Roth space unlocked - Retirement
Cash Balance / Defined Benefit Plan
Solo pros can shelter $200K–$400K/yr.
$60K–$150K/yr federal tax deferral - Retirement
529 → Roth IRA Rollover (SECURE 2.0)
Overfunded 529? Roll up to $35K into beneficiary's Roth IRA.
Convert $35K to lifetime tax-free growth vehicle - Retirement
QCD (Qualified Charitable Distribution)
Age 70½+: give directly from IRA — never taxed as income.
Save 15–37% federal + reduce Medicare IRMAA - Retirement
Rule 72(t) SEPP Early Withdrawals
Access IRA before 59½ — penalty-free via substantially equal payments.
Avoid 10% penalty on early IRA access - Retirement
Pension Lump-Sum vs Annuity Arbitrage
Rising rates = shrinking lump-sum offers. Time your exit.
Optimize $200K–$2M pension election - Retirement
Solo 401(k) + Defined Benefit Stack
One-person business — shelter $300K+/yr across combined plans.
Shelter $200K–$400K/yr of ordinary income - Retirement
Solo 401(k) with After-Tax + Roth Mega Backdoor
Solo entrepreneurs contribute up to $69K/yr to a 401(k), converting after-tax portion to Roth for tax-free growth.
$46K/yr additional Roth space vs Traditional 401(k) - Retirement
In-Service 401(k) Rollover to Self-Directed IRA
Roll 401(k) funds to a self-directed IRA WHILE STILL EMPLOYED — access RE, private lending, precious metals.
Access to 10–15% alt-asset returns vs 6–8% index funds - Retirement
Checkbook-Control IRA/LLC (Bank Account for Your IRA)
SDIRA owns 100% of a special-purpose LLC; you're the manager, write checks directly for investments — no custodian delays.
Speed + eliminates $150–$300 per-transaction custodian fees - Retirement
ROBS (Rollovers as Business Startups) — Fund Business With 401(k)
Roll existing 401(k)/IRA into a new C-corp 401(k), use funds to buy your own business — no tax, no penalty, no debt.
$50K–$500K debt-free business funding + no early-withdrawal penalty - Retirement
NUA (Net Unrealized Appreciation) on Employer Stock
Distribute employer stock from 401(k) — pay ordinary tax on basis only, capital gains on appreciation at sale.
17–22% tax rate reduction on appreciated portion (37% ordinary → 20% LTCG)