The Boldin Your Money Podcast

Latest Episodes:

Retirement Planning's Hidden Tradeoffs | With Jesse Cramer (Ep. 114) Oct 01, 2026

Show notes

Building a retirement plan means balancing financial security with the life you want to live. Steve Chen sits down with fee-only fiduciary financial planner Jesse Cramer, host of Personal Finance for Long-Term Investors and writer behind The Best Interest, to explore both the numbers and the human side of retirement.
They discuss how Coast FIRE can create flexibility, why retirement requires more than a portfolio adjustment, and how stacking conservative assumptions can keep you working longer than necessary. Along the way, Jesse shares ways to think about retirement income, competing risks, and the trade-offs behind Roth conversions.

To learn more about the Boldin Planner, visit boldin.com. You can also find full video episodes of Boldin Your Money on YouTube and subscribe wherever you get your podcasts.

Find Jesse on Social:
Best Interest Blog: https://bestinterest.blog/
LinkedIn: https://www.linkedin.com/in/jesse-cramer-11b58155/
Newsletter: https://bestinterest.kit.com/
Rialto Wealth Management: https://rialtowealth.com/

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The Future of Financial Advice Is Closer Than You Think | With Ed Williams & Michael Byram (Ep. 113) Sep 10, 2026

Show notes

Vanguard's $4.6 billion acquisition of Altruist made headlines across the financial industry, but the bigger story is what it says about the future of financial advice.

In this episode of Boldin Your Money, Steve Chen is joined by Ed Williams, Lead Financial Advisor at Boldin, and Michael Byram, Boldin's CTO and former engineering leader at Altruist, to discuss why this acquisition matters and how technology is reshaping the way people plan for retirement and manage their money.

Together, they explore why traditional financial advice can't scale to meet growing demand, how AI is making both advisors and consumers more capable, and why the next generation of financial planning will be more personalized, proactive, and accessible than ever before.

The conversation also covers the evolving role of financial advisors, flat-fee advice versus traditional AUM models, AI agents, automation, and why the future isn't about replacing human advisors—it's about combining human expertise with powerful technology to help more people make better financial decisions.

Whether you're working with an advisor, managing your own finances, or simply curious about where AI is taking personal finance, this episode offers an inside look at where the industry is headed.

To learn more about the Boldin Planner, visit boldin.com. You can also find full video episodes of Boldin Your Money on YouTube and subscribe wherever you get your podcasts.

How AI Is Changing Personal Finance | With AI & Data Expert Subbiah Subramanian (Ep. 112) Sep 01, 2026

Show notes

What does the future of financial advice look like when AI, automation, and modern technology reshape how people manage their money? In this episode of Boldin Your Money, Steve Chen sits down with Subbiah Subramanian, VP of Product Management at Clearwater Analytics, to explore how technology is transforming wealth management, financial planning, and the advisor-client relationship.

They discuss the recent Vanguard–Altruist acquisition, the growing advice gap, how AI can empower both advisors and consumers, and why the future of financial planning will likely combine intelligent technology with human expertise. Whether you're interested in retirement planning, fintech, or the future of AI in personal finance, this conversation offers valuable insights into where the industry is headed.

Connect with Boldin:

Build your retirement plan at Boldin.com
Watch more retirement education and expert conversations on the Boldin YouTube channel
Follow Boldin Your Money for weekly conversations on retirement, investing, financial planning, and the future of personal finance.

Nir Eyal: Beyond Belief - Why We Don’t Do What We Know We Should Jul 01, 2026

Show notes

Here's Where to Find Nir: ⬇️

Purchase Beyond Belief: geni.us/beyondbelief
Free belief change guide: www.nirandfar.com/beyond-belief-live
Bonus content and the 30-Day Belief Transformation Journal: nirandfar.com/beyond-belief
Website: http://nirandfar.com
LinkedIn - https://www.linkedin.com/in/nireyal/
Instagram - http://instagram.com/nireyal
Previous books: Hooked: geni.us/hooked I
ndistractable: geni.us/Indistractable

Paul Merriman: Evidence Based Investing May 28, 2026

Show notes

Paul Merriman — nationally recognized authority on index investing and one of the most trusted voices in evidence-based investing — joins Steve Chen to share what nearly six decades in financial services taught him about how the industry really works. Paul opens up about why he walked away from Wall Street in his 20s, how he accidentally built a $1.6 billion advisory firm, and why he gave it all up to focus on financial education. He breaks down the simple investing framework he's spent his career refining, makes the case for going beyond the S&P 500, and explains why the most powerful portfolio move most investors never make might also be the simplest.

Mark Miller: Social Security & Medicare, What’s Changing and What It Means for You May 07, 2026

Show notes

In this episode, host Steve Chen sits down with Mark Miller — journalist, author, and retirement expert behind RetirementRevised.com — to unpack the biggest changes hitting Social Security and Medicare right now. Mark shares his personal experience claiming both programs, explains why “later is better” for most Social Security claimants, and breaks down the trust fund depletion risk without the fear-mongering. The conversation covers the real-world impact of DOGE-driven SSA staffing cuts, why traditional Medicare beats Medicare Advantage for most people, the landmark $2,000 Part D out-of-pocket cap, and the quiet Medicare Savings Program rollback buried in the “One Big Beautiful Bill.” Mark’s no-nonsense take: understand the rules, claim strategically, and shop your Medicare coverage every single year.

Erin Talks Money: Personal Finance for Real People May 07, 2026

Show notes

Erin Moriarity, creator of the Erin Talks Money YouTube channel, joins Steve Chen to share the personal story behind her passion for financial independence — from investing at age eight alongside her Depression-era grandmother to watching her mother lose financial control through a difficult divorce. Now reaching over 340,000 subscribers, Erin breaks down her philosophy that most people should DIY their finances well into their 50s, how to build a retirement income plan anchored by guaranteed income floors, and why she's fiercely selective about partnerships. The episode wraps with a candid conversation on AI — how she's using it in her business, her content, and even to manage her own health.

Fiona Ma & David Teykaerts: What Happens Next for CalSavers? Feb 05, 2026

Show notes

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: The Automatic Millionaire in an Automated World Jan 22, 2026

Show notes

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.

Paula Pant: You Can Afford Anything, but Not Everything Dec 18, 2025

Show notes

In this episode of Boldin Your Money, Steve Chen catches up with Paula Pant, founder of Afford Anything to explore how her work and thinking have evolved. Paula shares how earning a graduate degree in economic journalism deepened her approach to personal finance, why her audience is juggling more competing priorities than ever, and how rising uncertainty is shaping financial behavior. She and Steve discuss housing lock-in, geo-arbitrage, and the growing value of human soft skills in an AI-driven world. Paula also breaks down her “Double-I FIRE” framework and explains why real estate, entrepreneurship, and empowered decision-making matter more than ever.

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