CPA-Lens Review
Is it the right retirement planning tool for professionals building a second-act business?
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The Short Answer
If you want to start consulting or a side business after 55, Boldin shows whether the numbers truly work. It's the most comprehensive retirement planning platform I've found for modeling how entrepreneurial income integrates with Social Security, IRMAA, and long-term drawdown strategies — at a fraction of what a financial advisor charges.
Best For
Professionals 55+ modeling how business income fits retirement security
Our Recommendation
PlannerPlus at $144/year — start with the 14-day free trial
Rebranded from NewRetirement in early 2026, Boldin combines institutional-grade Monte Carlo simulations with plain-English guidance and AI-powered insights. The Mill Valley-based company now serves over 350,000 users managing more than $300 billion in assets.
For retirepreneurs, Boldin solves a critical challenge: understanding how business income, irregular cash flow, and evolving work arrangements fit into your retirement plan — without requiring a $2,000 financial advisor.
The platform helps you model exactly how your consulting income, side business, or phased retirement will impact your long-term financial security. That's the question you need answered before you build anything else.
Side-by-side "What-Ifs" Compare multiple business launch dates and income levels with Monte Carlo probabilities — not rosy single-point forecasts. Test scenarios before committing to a strategy. |
All income in one plan Social Security, pensions, annuities, rentals, investments, and business revenue — view the full picture at a glance. Retirement entrepreneurs often juggle 3–5 income streams simultaneously. Boldin handles all of them. |
Lifestyle clarity "Must Spend / Like to Spend" separates essentials from extras so you know the exact revenue target to maintain your lifestyle. You'll know precisely what your business needs to generate. |
Real-time account syncing Plaid integration (PlannerPlus) updates 250+ data points across investments and business banking automatically. Your plan stays current as your business generates revenue and your portfolio fluctuates. |
Tax-smart decisions Model Roth conversions, estimated taxes, IRMAA/Medicare impacts, and how self-employment affects benefits. This is where the CPA in me gets excited — most calculators ignore these interactions entirely. |
Guided expertise without advisory fees Live CFP Q&As and courses on taxes, Social Security, and RMDs through Boldin Classroom. Professional-level insights at a fraction of traditional advisory costs. |
2026 enhancements Financial Wellness Score tracks planning progress. Monthly date precision improves accuracy. AI-powered recommendations tailored to business transitions. Expanded Boldin Classroom content. |
Basic — Free
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Advisory — $1,500–$2,100/year
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CPA Perspective on Value
Avoiding a single 2% withdrawal error on a $400,000 portfolio is $8,000 — roughly 56× the PlannerPlus annual cost. At $12/month, this is less than one hour of consulting work for decades of financial clarity. Skip Basic if you're entrepreneurially-minded — the 100-input limit won't capture business complexity.
✅ Pros
Comprehensive scenario modeling — test multiple launch dates and income levels side-by-side |
Designed for non-technical users with step-by-step guidance and live CFP Q&A |
Outstanding value at $144/year vs. $1,500–$3,000 for traditional financial planning |
Real-time Plaid syncing keeps your plan current automatically |
Specific entrepreneur features — self-employment tax modeling, IRMAA cliff visualization, phased retirement scenarios |
❌ Cons
No prorated refunds if you cancel mid-year |
Annual prepay only — no monthly option for PlannerPlus |
Credit card likely required to start the free trial |
Free version too limited for retirement business planning |
Occasional Plaid reconnection issues (industry-wide, not unique to Boldin) |
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Feature |
Boldin |
MaxiFi |
Monarch |
Annual Cost | $144 | $109–$149 | $99–$120 |
Free Version | ✅ Yes | ❌ No | ✅ Yes |
Monte Carlo Simulations | ✅ Yes | ✅ Yes | Limited |
Business Income Modeling | ✅ Comprehensive | Basic | ❌ No |
AI-Powered Insights | ✅ Yes | ❌ No | ❌ No |
Live Q&A with CFPs | ✅ Weekly | ❌ No | ❌ No |
Courses & Education | ✅ Yes | ❌ No | ❌ No |
Bottom line: For retirepreneurs, Boldin offers the best mix of scenario depth, AI guidance, live CFP access, and business income modeling. MaxiFi excels at economics-based spending optimization but lacks educational resources. Monarch is primarily a budgeting app — not built for long-horizon retirement business planning.
"I was nervous about leaving a corporate job at 58 to start consulting, but Boldin let me model exactly what I needed to earn to maintain our lifestyle. We ran scenarios for three different income levels and Social Security claiming ages. Seeing the Monte Carlo results gave me confidence to make the leap. Two years in, we're right on track."
— Margaret R., Management Consultant
"As someone who avoided financial planning because it seemed overwhelming, Boldin's step-by-step approach made it manageable. The visual charts helped me understand immediately how my part-time business income would extend our savings. The weekly Q&A sessions answered questions I didn't even know to ask."
— James T., Part-Time Business Coach
Is Boldin worth the cost if I'm on a fixed retirement income? At $144/year ($12/month), Boldin costs less than a single hour with a financial advisor. If you're planning any retirement business, it pays for itself by helping you avoid one costly mistake. The 14-day free trial lets you test the full PlannerPlus features before committing. |
How difficult is it to learn for someone who isn't tech-savvy? If you can follow on-screen prompts, you can use Boldin. The platform is specifically designed for non-technical users with plain-English explanations at each stage. Most users complete initial setup in 30–45 minutes. Free weekly live Q&A with financial planners is included if you get stuck. |
Will my business income projections integrate with Social Security and Medicare planning? This is where Boldin excels for retirepreneurs. It calculates how business earnings affect Social Security benefits, models the earnings test, shows IRMAA Medicare surcharge impacts, and helps plan estimated tax payments on self-employment income — all in one integrated view. |
How does Boldin compare to working with a traditional financial advisor? Boldin gives you the planning tools advisors use, but you maintain control and save $1,500–$3,000 annually in advisory fees. The Monte Carlo simulations match institutional-grade software. Think of PlannerPlus as doing the planning yourself with excellent tools — versus hiring someone to do it for you. |
Can Boldin handle rental property income and multiple business streams? Yes. PlannerPlus includes modeling for rental real estate, multiple revenue streams, and complex tax situations including self-employment taxes and estimated payments. The 250+ input fields capture scenarios that basic retirement calculators miss entirely. |
Does Boldin support planning for couples? Yes. Model two earners, different Social Security claiming ages, and joint expenses — then test scenarios together. Particularly useful when one spouse is launching a business while the other continues traditional employment or retirement income. |
Final Verdict
Boldin delivers institutional-quality retirement planning at a fraction of traditional advisory costs, with specific features that make it ideal for retirepreneurs testing business scenarios. The platform's strength is comprehensive "what if" modeling combined with AI-powered insights that answer the question you need answered first: "Can I afford to start this business?"
✅ Best for: Self-directed retirees 55+ planning consulting, side businesses, or phased retirement who need to model how entrepreneurial income integrates with Social Security, pensions, and investment drawdown — with AI guidance and live CFP support.
❌ Not ideal for: Those wanting hands-on financial advice without using software, or anyone uncomfortable entering detailed financial data with guided prompts. If you need someone to do the planning for you, consider the Advisory tier or a traditional advisor.
Still Building.
Curt Roese, CPA | Founder, Retirepreneur | M.S. Entrepreneurship, University of Florida