The Boldin Your Money Podcast

Jesse Cramer, a fee-only fiduciary planner and former aerospace engineer, explores the human and financial tradeoffs of retirement. They discuss Coast FIRE, preparing for identity and lifestyle changes, balancing safety with growth, and avoiding overly conservative assumptions. The conversation also covers competing retirement risks, income planning, and the tax and estate considerations behind Roth conversions.

Ed Williams, a Boldin financial advisor with Vanguard and Facet experience, joins Michael Byram, Boldin’s CTO and former Altruist engineering leader. They unpack Vanguard’s Altruist acquisition, the shift from AUM pricing to flat fees, and how AI can expand advisor capacity. They explore proactive financial agents, living plans, automated implementation, and why technology will augment rather than replace human judgment.

Subbiah Subramanian, a fintech and data executive with 30+ years in capital markets, explores AI’s rapidly evolving role in personal finance. They discuss smarter portfolio analysis, the advice gap, institutional investing, trusted digital agents, and the future partnership between technology and human advisors. Real estate, financial independence, and careful AI adoption round out this forward-looking conversation.

Nir Eyal, bestselling author and former Stanford lecturer who studies behavior and tech, explains why knowing is not enough. He talks about how beliefs shape what we notice, why limiting beliefs block action, and practical ways to swap them. Conversations touch on AI as a coaching tool, habit design ethics, and societal trends like falling birth rates.

Paul Merriman, a six-decade authority on index and evidence-based investing who left Wall Street to teach, shares practical investing ideas. He outlines why simple total-market and four-fund factor-aware mixes matter. He explains rebalancing, behavioral pitfalls, the case for small-cap value sleeves, and how automated, low-cost indexing can improve long-term results.

Mark Miller, journalist and retirement expert behind RetirementRevised and author of Retirement Reboot, dives into Social Security and Medicare policy. He discusses why claiming later often helps, real trust fund depletion risks, staffing and service shifts at the SSA, why original Medicare may beat Medicare Advantage, the new $2,000 Part D cap, and quiet rollbacks that affect low-income beneficiaries.

Erin Moriarity, creator of the Erin Talks Money YouTube channel and master’s in personal finance, shares the personal roots of her money mission. She talks DIY financial management into your 50s. She explores building retirement income floors like Social Security timing and annuities. She also explains using AI to run a business and even aid her health.

In this episode of Boldin Your Money, host Steve Chen sits down with California State Treasurer Fiona Ma and CalSavers Executive Director David Teykaerts to explore how California is tackling the retirement savings gap through the CalSavers program. Fiona shares her personal journey from the private sector into public service and explains the treasurer’s broader role as the state’s banker, overseeing investments, bonds, and multiple savings initiatives. Together, Fiona and David walk through why CalSavers was created, how automatic payroll savings can dramatically increase participation, and why default design, low fees, and simplicity matter most for workers who’ve historically lacked access to retirement plans. The conversation highlights the program’s scale and impact—hundreds of thousands of savers, billions saved, and growing along with lessons about behavioral finance, employer responsibility, and the power of “set it and forget it” systems to build long-term financial security for everyday Californians.

David Bach joins Steve Chen to discuss the evolution of The Automatic Millionaire and his newest idea, the IRA Flat Tax, which aims to rethink how Americans use their retirement savings. Bach explains that decades of automation have helped millions accumulate wealth, but most retirees now delay spending their money until required minimum distributions, leaving trillions of dollars idle. He proposes a limited window allowing early retirement withdrawals at a flat tax rate to encourage spending, improve retiree quality of life, and stimulate the economy. The conversation also explores the difficulty of shifting from saving to spending, the importance of enjoying wealth while health allows, and how AI is reshaping financial planning without replacing the need for human guidance, reinforcing Bach’s long-held belief that money is ultimately a tool to support a better life.

In this conversation, Paula Pant, the founder of Afford Anything, shares insights from her journey in personal finance. She emphasizes the rising importance of human soft skills in an AI-dominated world and discusses the challenges of economic uncertainty affecting housing choices. Paula introduces her 'Double-I FIRE' framework, advocating for financial psychology and real estate investments. She also highlights the effects of salary transparency and the balance between remote work and geo-arbitrage, all while urging listeners to prioritize healthy money conversations.