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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/ 🌐 Follow us on other social media channels: https://www.facebook.com/BoldinMoney https://www.instagram.com/boldin.money/ https://www.linkedin.com/company/boldinmoney/ https://www.reddit.com/r/Boldin/ https://www.pinterest.com/boldinmoney/ https://x.com/BoldinMoney https://www.threads.com/@boldin.money https://bsky.app/profile/boldinmoney.bsky.social

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. 🌐 Follow us on other social media channels: https://www.facebook.com/BoldinMoney https://www.instagram.com/boldin.money/ https://www.linkedin.com/company/boldinmoney/ https://www.reddit.com/r/Boldin/ https://www.pinterest.com/boldinmoney/ https://x.com/BoldinMoney https://www.threads.com/@boldin.money https://bsky.app/profile/boldinmoney.bsky.social

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.comWatch more retirement education and expert conversations on the Boldin YouTube channelFollow Boldin Your Money for weekly conversations on retirement, investing, financial planning, and the future of personal finance.

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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.

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 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.

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 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.

In this episode of Boldin Your Money, host Steve Chen sits down with Katy Song, a Certified Financial Planner based in Mill Valley, to explore how modern families can achieve financial confidence and “work optionality.” Katy shares her journey from investment banking to flat-fee financial planning, driven by a desire to help young families make smarter money decisions without needing large investable assets. The discussion spans real-life financial challenges in Bay Area cost of living, homeownership versus renting, intergenerational planning, and the psychology of money. Katy emphasizes holistic advice over asset management, revealing trends like women becoming the primary earners, the growing “sandwich generation,” and the emotional side of money stress. Her core message: true financial success comes from clarity, balance, and aligning money with personal values.

Leslie and Thomas Martin share how years of consistent saving and do-it-yourself planning helped them confidently retire early and enjoy life on their own terms. Starting with the classic “save 10%” rule, they eventually built detailed retirement models using Boldin, holding regular “family finance” meetings to test scenarios and understand when and how they could retire. Those tools gave them peace of mind and what they call a “license to spend”—freedom to enjoy their go-go years without fear of running out of money. They stay invested, manage taxes carefully, and keep a cash cushion for market swings. Now traveling the country in their Winnebago Revel, they focus on experiences, community, and helping their kids learn smart money habits. Their advice: plan several years before you retire, keep learning, use planning tools, and make your money work for you so you can spend confidently and live fully. Big lessons: have a plan (even if it changes), invest (not just save), stress-test worst cases, and use community and coaching for confidence.

Beth Pinsker CFP®, MarketWatch columnist, and author of My Mother’s Money explains how caring for her mom exposed the gap between “knowing” and “doing” estate/care plans. Only ~30% have wills; even fewer have POAs/health proxies, creating real cash-flow and authorization crises when care starts. She describes the emotional and ethical knots (siblings, guilt) and how illiquid assets/annuity rules and bank hurdles complicate paying caregivers. Takeaways: set POAs/health proxies, add phone legacy contacts, name beneficiaries on all accounts/titles to avoid probate, and use fee-only help when needed. Beth frames inheritances as “Bubby money” spending aligned with a loved one’s values and urges investing in health and lifestyle now.

In this episode of Boldin Your Money, host Steve Chen talks with Andrea Solarz, a Boldin community member from Arlington, Virginia, about her lifelong journey to financial independence. Andrea shares how early lessons from her parents about saving and budgeting set her on the right path, later reinforced through self-education and following experts like Rob Berger, Christine Benz, and Andy Panko. She discusses using Boldin’s financial planning platform to confirm she was ready to retire and shift from saving to spending confidently. Andrea now relies on Social Security and TIAA-CREF annuities for guaranteed income, giving her the freedom to travel and support friends and causes she cares about. A single woman with no children, Andrea highlights the importance of independent financial planning and encourages others, especially women, to start saving early, invest consistently, and plan intentionally for retirement.

In the 100th episode of Boldin Your Money, host Steve Chen chats with community member Mark Eakle about his real-life money journey. Mark shares how he went from relying on pensions to taking charge with 401(k)s, paying off his house, and helping his daughters graduate debt-free. He talks about the lessons he learned along the way—like starting early, sticking with it, and letting compounding work its magic. Mark also explains how being part of a small group of Boldin users keeps him motivated, accountable, and confident about his financial future