The Boldin Your Money Podcast

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/BoldinMoneyhttps://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/BoldinMoneyhttps://www.threads.com/@boldin.moneyhttps://bsky.app/profile/boldinmoney.bsky.social

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 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

In this episode of Boldin Your Money, Steve Chen chats with Scott Garrett, a retired software engineer and active member of the Boldin community. Scott talks about how he went from selling forklift parts to leading tech teams, and why he and his wife decided to retire earlier than planned. After dealing with job stress from a company buyout and feeling like his work no longer aligned with his values, Scott realized he had saved enough and had the confidence, thanks to the Boldin platform to call it quits. They talk about real-life retirement planning stuff: how to handle your spending, adjust when the market changes, deal with health insurance, do smart tax moves, and how weird it feels to go from saving to spending. Scott also shares how he formed a small support group of other Boldin users to swap tips and stay motivated. The episode is packed with honest advice on what it really takes to retire early and stay on track, both financially and emotionally.

In this episode of Boldin Your Money, Steve Chen talks with Barry Ritholtz about his journey from law to leading a $6B wealth management firm. They discuss Barry’s book How Not to Invest, focusing on avoiding common mistakes, tuning out media noise, and the value of humility and process in investing. The conversation covers tech's role in finance, behavioral biases, and how to build smarter, tax-efficient portfolios in a rapidly evolving market.

In this episode of Boldin Your Money, host Steve Chen welcomes back Sam Dogen, the Financial Samurai, to discuss his journey from Wall Street to financial independence, and his latest book, Millionaire Milestones. Sam shares hard-earned insights from his early career in finance, the emotional and financial toll of market downturns, and how he transformed a cathartic blog into a thriving income source and community. The conversation explores the power of compounding, the value of real estate in wealth-building, risk tolerance, money mindset, and why aligning financial goals with personal values is crucial. Sam also dives into how AI is shaping the future of content creation and wealth strategy, both as a tool and a hedge. Whether you're starting your financial journey or refining your path to early retirement, this episode offers rich takeaways on how to invest with intention, build passive income, and live a life of purpose and autonomy.

In this episode of Boldin Your Money, host Steve Chen sits down with financial advisor and YouTube creator Devin Carroll, the mind behind Social Security Intelligence and the book Social Security Basics. Devin shares his journey from tire salesman to financial planner, and how a curiosity about Social Security turned into a mission—and a media platform reaching millions. The conversation covers the evolution of financial advice, Social Security reform, building trust in a digital world, and why education is the foundation of confidence. Devin also opens up about how he uses content to grow his advisory firm and what the future of planning, media, and AI means for both advisors and everyday savers.

In this episode of Boldin Your Money, host Steve Chen and guest Mike Himmelfarb unpack the newly announced "Liberation Day" tariffs and their sweeping impact on global markets, economic strategy, and personal finance. Recorded just days after a sharp market correction, the discussion blends macroeconomic insight with practical, real-world investing perspectives. Mike shares his background in finance and tech, and how his conservative, index-focused investment approach helps him navigate market volatility. The conversation explores the rationale behind the tariffs—including revenue generation, trade imbalances, and national security—as well as the risks of stagflation, geopolitical tension with China, and broader economic uncertainty. Together, they emphasize the importance of long-term planning, emotional discipline, diversification, and critical thinking in times of change. With insights on everything from debt refinancing to the role of automation and immigration in America’s future, the episode offers a thoughtful, grounded take on a complex moment in economic history.