This founder’s AI tool helps fund retirements

^{A week in AI is like a year in other industries. I hope these issues become your weekly source of AI information, inspiration, and ideas. If we haven’t met before, I’m Amanda Smith. I write about AI and the fascinating folks who are building in this brave new world.}

Good morning.

This week’s founder left big finance to help half a million hardworking individuals manage their financial futures. He’s calling it a financial wellness movement, akin to our exercise culture. 

Financial planning is still a niche activity, but with his new AI tooling, he hopes to change that. It’s a solid case study in how you can stand out against generic LLMs, especially if in a sensitive industry. 

Let’s dive in.

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Founded: 2015 

Team size: 50 

Funding to date: $20 million in Series A funding 

ARR: Not disclosed 

Growth metric: The Boldin community talks about their finances and their favorite tools (like Boldin) in Facebook groups and Reddit threads.

Steve Chen started his career as a founder, scaling one of the earliest SaaS businesses in the early days of the internet. He grew Embark, a higher education admission software, to 200+ employees and 130% year-on-year expansion. 

Chen went onto lead advising and investing at SEC Ventures and Charles Schwab, where he saw first-hand how the industry neglects the everyday investor. He returned to his builder roots to serve David instead of Goliath. 

In 2015, Chen launched Boldin, a personalized financial planning platform – with a mission to turn financial planning from a niche activity for the upper echelon into mainstream daily habit for all. With nearly half of Americans now using AI for financial advice, Chen was concerned about generic, inaccurate and potentially dangerous information, and knew he had to act. 

Last month, they launched BoldinAI, where users can ask any financial planning question and get personalized answers based on their fully modeled financial plan – including income, assets, insurance, tax assumptions, retirement timing, government benefits, and long-term projections. 

Chen explained BoldinAI is not an advisor, nor does it give advice. It surfaces opportunities and insights, monitored tool by the team of licensed advisors. They don’t sell data to third parties for AI modeling opportunities. 

BoldinAI was trained in Q4 2025 and introduced into limited Beta in January 2026, then full Beta in February. “We trained it on Boldin’s corpus of content, our help system, reputable third-party source and proprietary anonymized plan data,” he said. 

Certified financial planners on staff review the AI outputs to ensure accuracy and brevity. 

They’ve had over 35,000 individual users exchange 600,000+ messages during Beta testing, with an average of eight interactions per user, per day. who have exchanged hundreds of thousands of messages. The team constantly curates feedback from anonymized data and directly via Reddit and Facebook communities. 

BoldinAI is a retirement-specific planning tool, rather than a general financial planning platform. Users are supported by licensed financial advisors, and the platform allows for 250 variables from social security to taxes. 

A lot of customers simply want to understand the math behind their future, especially as they reach retirement age. 

“Boldin currently has over 500,000 planners, 75,000 paying subscribers on PlannerPlus at $144/year, and more than $300 billion in total assets on the platform. Our primary demographic is people aged 45+, with an average of roughly $1 million in total assets on the free tier,” Chen explained. 

“We also serve the FIRE community and younger planners. The average millennial on our platform with an advisor sought guidance at age 29 – nearly 20 years earlier than Baby Boomers did on average.” 

Chen stated they’re growing at 100% year-over-year. 

Most of their customers come through organic referrals. Users share with friends, family members, business partners, and colleagues. Organic is driven by high-intent channels like SEO, AI discovery, YouTube, social media, PR, and credibility-building content (classes and a podcast) when people are searching for answers. 

Chen said this multi-channel strategy is reinforced by partnerships with trusted creators and communities, which are critical in deeply personal spaces like finance. 

“Many of our customers are part of Facebook groups and Reddit threads where they share advice, ask questions, and even organize offline meet-ups,” he said. 

Boldin also has a B2B partnerships strategy, where they work with employers, plan providers and financial institutions to embed or co-brand the planning platform. This helps them connect with people in the moments they’re making important financial decisions, Chen concluded.  

If one of these stories stuck with you, I’d love to hear which one.

Speak soon,
Amanda

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