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, Steve Chen sits down with Geoff Schmidt, the creator behind the wildly popular YouTube channel Holy Schmidt. Geoff shares his inspiring journey from Wall Street to YouTube, sparked by a mission to help his father and ultimately millions better understand retirement planning. With over 350 videos and 335K+ subscribers, Geoff offers powerful insights on financial literacy, Social Security, blind spots in retirement, and building wealth with clarity and intention. A must-listen for anyone navigating retirement planning or curious about becoming a trusted voice in personal finance.

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, host Steve Chen reconnects with Dr. Jim Dahle, founder of The White Coat Investor, to reflect on life, money, and purpose five years after their first conversation. Jim shares the impact of a serious 2024 climbing accident, how it shaped his perspective on aging, balance, and living with intention. They dive into investing philosophy, simplifying wealth, estate planning for kids, and the challenges of being a content creator in the age of AI. The episode blends financial wisdom with personal insight, showing how resilience and purpose evolve with experience.

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 welcomes Leisa Peterson, a financial coach, author of The Mindful Millionaire, and advocate for financial mindfulness. Leisa shares her personal journey from growing up in a financially unstable household to becoming a successful financial expert, entrepreneur, and coach. She discusses the impact of scarcity mindset, the importance of financial confidence, and how personal experiences—both triumphs and tragedies—shaped her path toward financial independence.

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.

In this episode of Boldin Your Money, Steve Chen sits down with Jackie Cummings Koski, co-host of Catching Up to FI, to talk about her inspiring journey to financial independence after overcoming poverty, divorce, and single motherhood. Jackie shares practical advice for late starters, those in their 40s, 50s, and beyond who feel behind on saving for retirement. They cover the importance of mindset, overcoming the fear of investing, and how to build wealth even if you’re starting late. Whether you’re looking for guidance, motivation, or just the reassurance that it’s not too late, this episode has something for you.

In this episode, we sit down with Mike Richardson, former SVP and CTO of Nationwide, who retired at 55 to embrace a fulfilling second act. Mike shares his inspiring journey of building a financial plan, navigating early retirement, and redefining purpose. Learn how he transitioned from leading large tech teams to mentoring others as a financial coach, volunteering, and pursuing personal passions. Whether you're planning your retirement or seeking insights on financial confidence, Mike’s story offers practical advice and inspiration. Tune in for strategies, reflections, and lessons for your own journey toward financial independence.