Boldin’s AI Planner Assistant: Advancing Mission to Make Financial Planning More Accessible, Affordable, and Understandable

AI is rapidly reshaping how decision-making power is distributed — moving the capability from institutions to individuals.

And that’s exactly what Boldin was built for. Boldin was founded on a simple belief: high-quality financial planning should be accessible, affordable, and understandable to everyone.

AI allows us to advance that mission faster than ever.

Introducing AI Planner Assistant (Beta)

The Boldin AI Planner Assistant is a new AI-powered experience (currently in beta) designed to help you understand, explore, and evolve your financial plans.

Unlike generic AI tools that respond to isolated prompts, Boldin’s AI Planner Assistant works in the context of your complete financial plan – including income, assets, taxes, retirement timing, and long-term projections – and operates alongside Boldin’s proven financial modeling engine.   

How Boldin’s AI Planner Assistant works: 

• Ask a question. 
• The AI engages with your plan inputs and Boldin’s financial model.
• Scenarios are run within Boldin’s powerful planning engine. 
• The AI interprets those outputs and explains options, tradeoffs, and potential outcomes in clear conversational language. 

The intent comes from you. The math comes from our planning engine. The AI explains what it means  — providing insights, education, and scenario-based exploration grounded in your data.

A Letter from Steve Chen, Our CEO and Founder, About AI

If you’ve been with Boldin for any length of time, you know we are constantly improving our tools. With the launch of the AI Planner Assistant in beta, we are accelerating that pace of innovation. It was first released in January of 2026, and we’ve been making continuous improvements to increase the relevance, clarity, and accuracy of responses — and we are only at the beginning of what’s possible. We will keep getting better faster. 

What will not change is our alignment with you. Boldin does not sell financial products. We do not earn commissions. We are not steering you toward proprietary investments or transactions that benefit us. Our platform is built to serve one interest: yours.

That independence matters. It means the insights you receive — whether through our planning tools or the AI Planner Assistant — are grounded in your data, your goals, and your long-term well-being. Not in a quota. Not in a product lineup. Not in a hidden incentive.

Our purpose is to strengthen your financial know-how and help you build clarity, control, and confidence in your future. The technology will continue to evolve, but our commitment remains steady: to give you the power to make informed decisions that are truly aligned with what matters most to you.

The tools will evolve. Our mission — and our alignment with you — will not.

Please reach out anytime!

Steve Chen

Frequently Asked Questions About Boldin’s AI Planner Assistant

Why would I want to use Boldin’s AI?

Boldin’s AI Planner Assistant helps you understand your financial plan more deeply and explore decisions in real time.

Instead of searching for general financial information, you can ask questions within the context of your own plan. The Assistant interprets projections from Boldin’s financial model and shows how choices — such as retiring earlier, adjusting savings, or changing spending — may affect your long-term outcomes.

It’s designed to make sophisticated financial planning more accessible, immediate, and understandable, so you can build confidence and make more informed decisions.

What makes Boldin’s use of AI different and unique? 

Boldin’s AI Planner Assistant is differentiated in three important ways.

First, it works inside your complete financial plan. The AI is built directly on top of your live financial plan. Responses are grounded in your real data — income, savings, taxes, Social Security timing, spending assumptions, and long-term projections — not generic financial assumptions. This allows users to explore tradeoffs, test scenarios, and see how decisions may affect their modeled outcomes.

Second, calculations are powered by Boldin’s proven financial modeling engine. The AI does not independently “guess” financial outcomes. Boldin’s proven and sophisticated planning model runs all projections. The AI interprets and explains those results in plain language. This separation between financial calculation and conversational explanation improves transparency and reduces the risk of hallucinated math.

Third, the platform is completely aligned with you and your goals. Boldin operates on a subscription-based business model. You are paying us, no one else. We do not sell financial products, earn commissions, or steer you toward proprietary investments.

This structure allows the AI to focus on helping you understand your plans rather than promoting transactions or strategies that are not fully aligned with your goals.

What questions can I ask Boldin’s AI Planner Assistant?

You can ask questions across the full spectrum of your financial life. Boldin’s AI Planner Assistant can engage with strategy-level topics, planning concepts, and broader financial decisions — and then connect those ideas back to your modeled financial profile when relevant.

The experience is designed to move fluidly between financial education and personalized modeling, helping you connect ideas to your own numbers.

NOTE: While Boldin’s AI Planner Assistant provides education insights and explorations, it does not provide personalized financial, tax, or legal advice.

What are the most asked questions of Boldin’s AI Planner Assistant?

While nothing is off limits, some commonly asked questions of the AI Planner Assistant include:

• When is the earliest I can securely retire?
• How can I do better financially?
• Would I benefit from Roth conversions?
• What scenarios should I run?
• Is my plan complete and up to date?
• What will healthcare cost me in retirement?
• What risks am I open to when I retire?
• Should I consider Roth vs. traditional savings contributions?
• How might changes in Social Security timing affect my modeled income?
• Am I prepared for a market crash?
• Can I afford private college? A lake house? A round-the-world cruise?

Can I trust answers from the AI Planner Assistant? 

The AI Planner Assistant is currently in beta, and like all AI systems, it can make mistakes. However, you can trust that the AI Planner Assistant is designed to ground its responses in your actual financial plan — not generic internet content. 

When you ask a question, the underlying calculations and projections come from Boldin’s established financial planning model, and the AI translates those results into clear, personalized explanations. That means the math is driven by your data — income, assets, timing, assumptions — and not generated by AI alone.

We encourage users to carefully review important decisions, including modeling them in the Boldin plan and consulting qualified professionals when appropriate. The AI Planner Assistant is intended to strengthen your understanding and help you explore scenarios — not replace professional financial, tax, or legal advice. 

Will AI replace advisors and other human financial guidance and support? 

We believe AI is a complement to human expertise — not a replacement.

Boldin’s AI Planner Assistant is designed to help users explore scenarios, understand tradeoffs, and engage more confidently with their financial plans. It does not provide definitive financial advice or replace professional judgment.

In fact, human support remains an essential part of the Boldin experience. We offer: 

• Live and recorded planning classes 
• Community discussion forums (Facebook and Reddit) to connect with peers
• Professional coaching to help assess if your plan is set up correctly
• Access to CFP® professionals through Boldin Advisors for advice, perspective, and reassurance  — especially when decisions become complex or emotionally charged.

What if I receive an incorrect response?

AI is not perfect, and responses may occasionally contain errors. If something seems inaccurate or unclear, we encourage you to double-check your plan details and assumptions.

You can provide feedback using the thumbs-up or thumbs-down feature included with each response. This helps us improve the AI Planner Assistant over time.

You can also ask follow-up questions or request clarification within the chat. The AI is designed to refine its responses based on additional context.

How long will Boldin’s AI Planner Assistant be in beta? 

“Beta” refers to software that is publicly available but still evolving. We use the term intentionally because AI systems continue to improve over time and require ongoing refinement.

Given the nature of AI technology, including the possibility of occasional inaccuracies, we expect the Planner Assistant to remain in beta as we continue enhancing reliability, clarity, and performance.

Boldin is committed to responsible AI deployment — with transparency about limitations, clear disclosures, and ongoing improvements to accuracy and user experience.

What is Boldin doing to try to ensure accuracy in AI responses? 

Accuracy in financial planning matters. Boldin’s AI is designed with multiple safeguards to reduce errors and improve reliability.

We approach AI accuracy as a systems problem — not just a language model problem.

1. First, financial calculations are generated by Boldin’s established financial planning engine. The AI does not independently create projections. Instead, it interprets and explains results produced by structured financial models, reducing the risk of hallucinated math.
2. Second, we use multiple AI models and validation techniques to review responses before they are delivered. This layered approach helps identify inconsistencies and improve reliability.
3. Third, we incorporate ongoing review by financial planning professionals, along with structured user feedback, to refine explanations and improve clarity over time.
4. Finally, we continuously update the system to reflect changes in tax rules, financial planning assumptions, and platform enhancements.

While no AI system can guarantee perfect accuracy, we are committed to responsible deployment — combining structured financial modeling, multi-model validation, and human oversight to improve reliability and usefulness.

How will the AI Planner Assistant evolve?

The AI Planner Assistant will continue to improve in three primary ways: model depth, domain expertise, and user experience.

1. First, it will evolve alongside Boldin’s financial planning engine. As we enhance our Planner functionality — incorporating additional goals, resources, tax rules, and regulatory updates — the AI will reflect those improvements in the scenarios and projections it interprets.
2. Second, we will continue refining its financial domain expertise. Ongoing review by CFP® professionals and coaches, combined with structured feedback from users, helps us improve clarity, accuracy, and the quality of explanations across areas such as retirement income, investments, and taxes.
3. Third, the conversational experience will improve over time. We will enhance prompts, context handling, and personalization so the AI can better understand users’ goals and priorities within their plans.

AI technology is advancing rapidly, and we expect meaningful progress. At the same time, we remain committed to responsible deployment — protecting user data, maintaining transparency about limitations, and continually working to improve accuracy and usefulness.

Long-term, we envision Boldin evolving to become a fully aligned, transparent, holistic financial co-pilot that helps you make good decisions, take action, and stay on track over the course of your whole life. We hope this leads to more families having better long-term outcomes and making the most of their money and time. 

Is Boldin’s AI secure? What privacy protections are in place?  

Our security and privacy posture are foundational to how Boldin operates.

Boldin maintains SOC 2 Type II compliance, which means our security controls are independently audited on an ongoing basis to ensure your data stays protected. We use encryption in transit and at rest, strict access controls, and secure infrastructure practices.

Conversation Handling: Conversations with the AI Planner Assistant are temporarily stored securely within the Boldin platform, so you can revisit prior conversations and get better results over time. Access to this data is limited to authorized personnel and governed by strict confidentiality and security controls, as described in our Confidentiality and Security section.

LLM and Data Access: When generating responses, AI models receive only the information necessary to process the request. We do not sell personal data, and user conversations are not used to train public AI models. Where we use third-party AI providers, they are bound by contractual data protection obligations and may only process your data to deliver the service.

We are committed to responsible AI deployment, transparency about limitations, and continuous strengthening of our privacy and security safeguards.

We apply rigorous controls and governance practices to protect user information.

Can I opt out of using AI in Boldin? 

Yes. The AI Planner Assistant is an optional feature.

Boldin’s core planning tools, projections, and modeling engine function independently of the AI. You can choose whether or not to use the AI Planner Assistant, and your financial plan will continue to operate normally without it.

If you prefer not to interact with the AI, simply use the Planner and other features directly. You remain in control of how you engage with the platform.

Is the Boldin AI Planner Assistant available to all Boldin users? 

Yes. The AI Planner Assistant is available to all Boldin users and does not require beta mode or a PlannerPlus subscription.

Access limits vary by subscription level:

• Basic users: Up to 5 questions per day. You’ll see an option to upgrade if you reach the limit.
• PlannerPlus users: Up to 10 questions per conversation, with the ability to start new conversations at any time.

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