Even after choosing contribution types, retirees and pre-retirees don't know how to optimally withdraw from multiple account types to minimize taxes, manage RMDs, and control bracket exposure.
Users link or manually enter their retirement account balances across Traditional, Roth, and taxable buckets. The tool models year-by-year withdrawal strategies, Roth conversion ladders, and RMD impacts to produce a tax-optimized drawdown plan through retirement.
Subscription $10-20/month or $99/year, with premium tier including Roth conversion optimization and annual plan refresh
The pain is real and high-stakes: a suboptimal withdrawal sequence can cost $50K-$200K+ in unnecessary taxes over a 30-year retirement. The Reddit pain signals show people actively wrestling with this. However, many retirees don't *know* they have this problem until educated—it's a 'known unknown' for the financially literate segment only.
~75M Baby Boomers, ~30% have multiple account types (Traditional + Roth + taxable). That's ~22M people. Addressable market is the self-directed segment who won't hire an advisor: maybe 5-8M. At $99/year, theoretical TAM is $500M-$800M. Realistic early TAM for a niche tool: $10-50M. Solid niche but not venture-scale without expansion.
Boldin at $120/year has tens of thousands of paying subscribers. Pralana sells at $109-$189 one-time. This audience (mass-affluent 50-65 year olds) has money and understands that saving $5K-$20K/year in taxes easily justifies $99/year. The challenge: free tools and brokerage calculators set a low anchor. You need to clearly quantify the tax savings to justify the subscription.
The UI and basic modeling are straightforward for a solo dev in 4-8 weeks. BUT the tax optimization engine is genuinely hard: federal bracket math, LTCG stacking on ordinary income, IRMAA cliffs, ACA subsidies, state taxes (50 jurisdictions), RMD calculations using IRS life expectancy tables, and Roth conversion optimization across 30+ years. This is a constrained optimization problem that requires real tax knowledge—not just coding skill. An MVP with simplified assumptions is doable; a credible optimizer takes longer.
Clear gap exists: Pralana has the math but terrible UX (Excel). Boldin has great UX but heuristic optimization. i-orp has true optimization but is abandoned. No product combines globally optimal tax-minimizing withdrawal sequencing with modern web UX at a consumer price point. This is the wedge.
Natural annual refresh cycle: tax laws change yearly, account balances change, life circumstances change. Roth conversion windows are time-sensitive. Annual plan refresh is a real value prop. Risk: some users may compute their plan once and churn—need to build in ongoing value (alerts, tax law updates, rebalancing triggers, annual re-optimization).
- +Clear market gap: no product combines Pralana-level optimization with modern web UX at consumer prices
- +High-stakes problem where users can quantify ROI ($X saved in taxes vs $99/year subscription)
- +Demographic tailwind: 10K Americans turn 65 daily, Roth conversions are trending, self-directed investing is growing
- +Natural content marketing angle: tax optimization is endlessly shareable and educational content practically writes itself
- +Low customer acquisition cost potential via personal finance communities (Reddit, Bogleheads, FIRE forums)
- !Tax engine accuracy is critical—one wrong recommendation and you lose trust or face liability. Need disclaimers and potentially CPA review
- !Boldin could add a true optimizer and close the gap with their existing user base and resources
- !Regulatory risk: could this be construed as tax advice? Need careful framing as 'educational tool' with disclaimers
- !Churn risk: users may run the optimizer once, get their plan, and cancel—the 'insight' is somewhat one-shot
- !Building a credible tax engine across 50 states with IRMAA, ACA, NIIT, and annual law changes is an ongoing maintenance burden
Full-lifecycle DIY retirement planning platform with scenario modeling, Monte Carlo simulations, Roth conversion explorer, and multi-account withdrawal projections.
Excel-based retirement planner built by a retired engineer. Deep withdrawal optimization engine that computes tax-optimal sequencing across account types, Roth conversion ladders, and RMD planning.
Newer web-based consumer financial planning tool gaining traction in the FIRE community. Multi-account drawdowns, Roth conversion modeling, and tax bracket visualization.
Economics-based lifetime planning tool using consumption smoothing methodology. Built by a Boston University economist. Models taxes, Social Security, and withdrawal strategies.
Free academic web tool that actually computes optimal withdrawal ordering and Roth conversions using linear programming. Solves a simplified version of the global tax minimization problem.
Web app where users manually enter balances for Traditional IRA/401k, Roth IRA, and taxable accounts plus basic info (age, filing status, expected expenses, Social Security estimate, state). Output a year-by-year withdrawal plan showing: which account to draw from each year, recommended Roth conversions to fill brackets, projected RMDs, and estimated lifetime tax savings vs naive withdrawal. Start with federal taxes only, single/MFJ only, simplified capital gains. Show a clear 'you save $X over 30 years' number. Skip account linking, skip state taxes, skip IRMAA/ACA for V1.
Free: basic calculator showing withdrawal order for current year only → Paid ($99/year): full 30-year optimization with Roth conversion ladder, RMD projections, scenario comparison, annual re-optimization → Premium ($199/year): state tax modeling, IRMAA optimization, ACA subsidy preservation, spousal coordination, PDF report export for CPA review → B2B: white-label for RIAs and fee-only advisors ($200-500/month) who want to show clients optimized plans without doing the math manually
8-12 weeks to MVP with simplified tax engine, 2-4 weeks of beta testing with r/personalfinance and Bogleheads users, first paying customers by month 4-5. Meaningful revenue ($5K+ MRR) likely 6-9 months given the niche audience and need to build credibility through content marketing and community trust.
- “look up the three bucket strategy and how you manipulate your income in retirement”
- “Do you want to be subject to RMD's”
- “every dollar you put into your 401k / IRA is locked in at 24%”