Boldin Review

Introduction

If you want to start consulting or a side business after 55, Boldin shows whether the numbers truly work. Built by the team behind NewRetirement (founded 2015), Boldin combines institutional-grade Monte Carlo simulations with plain-English guidance so you can launch with confidence—not guesswork. This Mill Valley-based company now serves over 155,000 users managing $168 billion in assets. The platform helps you model exactly how your consulting income, side business, or phased retirement will impact your long-term financial security.

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.

 

Key Features & Benefits

• 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, one plan: Social Security, pensions, annuities, rentals, investments, and business revenue—view the full picture at a glance. This matters because retirement entrepreneurs often juggle 3-5 income streams simultaneously.

• Lifestyle clarity: "Must Spend / Like to Spend" separates essentials from extras so you know the revenue target to keep your lifestyle. You'll understand exactly what your business needs to generate.

• Always up to date: Plaid syncing (PlannerPlus) updates 250+ data points across investments and business banking—no spreadsheets. Your plan stays current as your business generates revenue and investments fluctuate.

• Guided expertise: Live CFP Q&As + courses on taxes, Social Security, RMDs—education without advisory fees. Get professional insights through weekly sessions and self-paced learning.

• Tax-smart decisions: Model Roth conversions, estimated taxes, IRMAA/Medicare impacts, and how self-employment affects benefits. Optimize strategies specifically for business owners transitioning to retirement.

• Timing optimizer: Test phased retirement, delayed claiming, and launch dates to find your most resilient path. Identify your optimal transition strategy before making irreversible decisions.

Ready to see your odds? Try a quick Monte Carlo run with your business income assumptions.

 

Pricing

Plan	Monthly Cost	Annual Cost	Key Features	Best For
Basic	Free	Free	100+ inputs, simple reports, basic calculations	Testing the platform, very simple financial situations
PlannerPlus	N/A	$120/year	250+ inputs, Monte Carlo simulations, scenario comparisons, courses, live Q&A sessions	Recommended: Retirepreneurs modeling business income (best value)
Advisory	N/A	$1,500-2,100/year	Everything in PlannerPlus + 1:1 CFP consultations	Complex situations needing professional guidance

14-day free trial available for PlannerPlus—no credit card required.

Our recommendation: Start with the PlannerPlus annual plan at $120/year if you're planning a retirement business. The scenario modeling and Monte Carlo simulations are essential for understanding how irregular business income affects your retirement security. That's just $10 per month—less than one hour of consulting work—for financial clarity.

Skip Basic if you're entrepreneurially-minded; the 100-input limit won't capture business complexity. Upgrade to Advisory only if you need help interpreting results or have estate planning needs beyond the platform's scope.

ROI Snapshot: Avoiding a single 2% withdrawal error on a $400,000 portfolio is $8,000—~67× the PlannerPlus annual cost.

Security & Privacy: Bank-level encryption, read-only connections via Plaid, and no custody of your funds. You control what you connect and what you share.

Start PlannerPlus free for 14 days—build two scenarios and compare results side-by-side.

 

Pros & Cons

 

How It Works

1. Create your baseline financial profile
   by entering current income sources, assets, debts, and expenses—taking 20-30 minutes for comprehensive initial setup with guided prompts.

2. Add your business income projections
   including expected consulting revenue, startup costs, and phased work reduction timelines so Boldin can integrate entrepreneurial cash flow with your existing financial picture.

3. Run Monte Carlo simulations
   that test your plan against thousands of market scenarios, showing probability ranges for success rather than single-point projections, giving you confidence in various economic conditions.

4. Compare scenarios side-by-side
   by creating multiple versions testing different business launch dates, Social Security claiming strategies, and spending levels to identify your optimal approach.

5. Update and refine quarterly
   as your business generates actual revenue and your situation evolves, with real-time feedback showing how changes impact your long-term security and actionable recommendations from the AI coach.

 

Comparison with Competition

Feature	Boldin PlannerPlus	MaxiFi Planner	Monarch Money
Annual Cost	$120	$99	$99-120
Free Version	✅ Yes (limited)	❌ No	✅ Yes
Monte Carlo Simulations	✅ Yes	✅ Yes	✅ Yes
Business Income Modeling	✅ Comprehensive	✅ Basic	❌ Limited
AI Coaching	✅ Built-in	❌ No	❌ No
Live Q&A with CFPs	✅ Weekly sessions	❌ No	❌ No
Courses & Education	✅ Extensive library	❌ No	❌ Limited

Bottom line: For retirepreneurs, Boldin offers the best mix of scenario depth, guidance, and price. MaxiFi is great for spending optimization but lacks live education and community. Monarch excels at day-to-day budgeting—not long-horizon business-plus-retirement planning.

 

Testimonials

"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

 

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 lies in comprehensive "what if" modeling that answers the critical question: "Can I afford to start this business?" At $120 annually, you're paying less than one client meeting to gain clarity on decades of financial decisions.

✅ Best for: Self-directed retirees (55+) planning to launch consulting practices, side businesses, or phased retirement who need to model how business income integrates with Social Security, pensions, and investment drawdown strategies.

❌ Not ideal for: Those wanting hands-on financial advice without using software, or anyone uncomfortable entering detailed financial data even with guided prompts. If you need someone to do the planning for you rather than empowering you to do it yourself, consider their Advisory tier or a traditional advisor.

Why Retirepreneur Recommends Boldin: We recommend Boldin for retirepreneurs because it uniquely models business income alongside Social Security, IRMAA, and drawdowns—questions our audience asks every week.

💡 Ready to model your retirement business scenarios? Start your 14-day free trial of Boldin PlannerPlus and see exactly how your entrepreneurial plans affect your long-term financial security—no credit card required.

👉 Start Free with Boldin

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✅ Frequently Asked Questions

Is Boldin worth the cost if I'm on a fixed retirement income?

At $120 per year ($10/month), Boldin costs less than a single hour with a financial advisor who might charge $150-300 per session. If you're planning any retirement business or need to optimize Social Security timing, the platform pays for itself by helping you avoid one costly mistake. The 14-day free trial lets you test the full PlannerPlus features before committing, and many users find that modeling just their Social Security claiming strategy alone justifies the annual cost.

How difficult is Boldin 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 step-by-step guided entry and visual feedback at each stage. You don't need spreadsheet skills or financial expertise. The platform walks you through each section with plain-English explanations, and if you get stuck, you can attend free weekly live Q&A sessions with financial planners or access the extensive help center. Most users complete their initial setup in 30-45 minutes with the guided prompts.

How much time do I need to invest in setting up and maintaining my plan?

Initial setup takes 20-30 minutes if you have your financial documents handy (recent statements, Social Security estimates, current expenses). After that, you'll spend 10-15 minutes quarterly updating actual business income and investment values if you're using manual entry, or essentially zero time if you connect accounts through Plaid for automatic syncing. The real time investment comes when you want to model scenarios, which takes 5-10 minutes per "what if" test.

How does Boldin compare to working with a traditional financial advisor?

Boldin gives you the planning tools that advisors use, but you maintain control and save $1,500-3,000 annually in advisory fees. You'll get better results than advisors using simple calculators, and the Monte Carlo simulations match institutional-grade planning software. However, Boldin won't make decisions for you or provide personalized advice unless you upgrade to their Advisory tier. Think of PlannerPlus as DIY planning with excellent tools, versus hiring someone to do it for you.

Can Boldin handle complex situations like rental property income and multiple businesses?

Yes, PlannerPlus includes modeling for rental real estate income, multiple business revenue streams, and complex tax situations including self-employment taxes and estimated payments. The 250+ input fields capture scenarios that basic retirement calculators miss. If you have really complex estate planning or trust questions, you might eventually need the Advisory tier with 1:1 CFP access, but the software itself handles most entrepreneurial situations that retirees encounter.

What kind of customer support is available if I need help?

Most questions are answered same day via email, plus weekly live Q&A with CFPs. Boldin offers multiple support channels: live weekly Q&A Zoom sessions with certified financial planners (included in PlannerPlus), an extensive searchable help center, email support with typically same-day responses, and a community forum where users share strategies. Many reviewers specifically praise Boldin's patient, educational approach to customer service—they want you to understand the concepts, not just click buttons. This is particularly valuable for users new to financial planning concepts.

Will my business income projections integrate with Social Security and Medicare planning?

Absolutely—this is where Boldin excels for retirepreneurs. The platform calculates how your business earnings affect Social Security benefits if you claim before Full Retirement Age, models the earnings test, shows how consulting income impacts Medicare Part B and D premiums through IRMAA calculations, and helps you plan estimated tax payments on self-employment income. You can test scenarios like "What if I delay Social Security to 70 but generate $50K annually from consulting?" to see the complete financial picture.

Can I import data from other tools (e.g., Mint, Personal Capital, spreadsheets)?

Yes—connect accounts via Plaid for automatic syncing, and you can enter or adjust values manually for full control. This gives you flexibility whether you're migrating from another platform or prefer hands-on data management.

How accurate are Monte Carlo results?

They use historical volatility and correlations to test thousands of possible futures. Results are probabilities—not guarantees—so plan updates are key as your business and markets change. This approach gives you a realistic range of outcomes rather than false precision.

Does Boldin support planning for couples?

Yes. Model two earners, different claiming ages, and joint expenses—then test scenarios together. This is especially valuable when one spouse is launching a business while the other continues traditional employment or retirement.

What happens after the 14-day trial?

Your plan remains saved. Upgrade to keep advanced simulations and comparisons; otherwise you'll retain limited free features. This means you can always access your basic plan even if you decide not to subscribe immediately.