The Boldin Your Money Podcast

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 Andy Hill, creator of Marriage, Kids and Money, about Andy’s journey from having a negative net worth to achieving financial independence through intentional saving, living on one income, and aligning money decisions with family goals. Andy shares how reaching “Coast FI” allowed his family to work less and enjoy life more, the importance of early financial conversations with a partner, and his strategies for teaching kids about money by making it a regular, open topic. He also reflects on how purposeful time use can lead to a happier, healthier life and discusses his upcoming book Own Your Time, which helps parents build financial security while prioritizing family.

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.

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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.

In this episode of Boldin Your Money, Steve Chen connects with FinTech pioneer Mark Goines, the force behind TurboTax, Quicken, and Personal Capital. Mark reveals the keys to scaling innovations, mastering distribution, and how AI is transforming the future of financial services. Packed with insights on building impactful products, driving growth, and embracing change, this episode is a must-listen for anyone navigating money, technology, and the evolving financial world.

Steve Chen welcomes Christine Benz, Director of Personal Finance at Morningstar, to discuss her book How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement. Christine shares practical strategies for retirement planning, including tax-efficient decumulation, dynamic spending, and the bucket approach for managing cash flow and investments. They also explore the importance of relationships, purpose, and staying socially engaged in retirement, along with tackling challenges like long-term care and financial fraud. Packed with actionable insights, this episode is a must-listen for anyone planning a secure and fulfilling retirement.

In this episode of the Boldin (formerly NewRetirement) podcast, Steve Chen interviews Fritz Gilbert, a former corporate executive and author of Keys to a Successful Retirement, who has been retired for six years. Fritz discusses his journey to retirement, emphasizing the importance of physical fitness, financial planning, and finding purpose post-retirement. He shares insights on maintaining a healthy lifestyle through activities like trail running and strength training, while managing finances with strategies like the bucket approach and delaying Social Security. Fritz highlights how the transition to retirement requires more than just financial preparation—it also demands planning for purpose and fulfillment. He encourages retirees to focus on what brings them joy, embrace curiosity, and live intentionally, fostering both personal and community connections for a rewarding retirement experience.

Next Gen Personal Finance

In this podcast episode, Steve Chen interviews Ryan Van Gorder from Opto Investments, discussing the rise and role of alternative investments. Ryan shares his journey from an accounting background to working in finance and technology, including his time at BlackRock. He explains how Opto Investments helps advisors confidently invest in private markets by providing advisor-aligned, efficient, and top-tier investment opportunities. The conversation covers the increasing accessibility and efficiency of private markets, the importance of diversification, and the evolving nature of liquidity. Ryan highlights Opto’s benefits from being part of the HC ecosystem and stresses the enduring value of human relationships in financial advice, enhanced by technology. The episode concludes with resources for further learning about private markets and a reminder to explore financial planning tools on NewRetirement.com.

In this podcast episode from NewRetirement, Todd Taylor, the newly appointed head of Life Insurance Solutions at New York Life, shares his career journey from actuary to executive. He discusses his early interest in math and economics, leading to his role at New York Life, where he works on life insurance, annuities, and financial planning. Todd explains the role of actuaries in quantifying risks, particularly in life expectancy, and how actuarial science is evolving with new technologies like fitness trackers and data sharing. He touches on the implications of precise risk predictions on insurance and privacy concerns. The conversation also explores how insurance and annuities are integrated into retirement planning, the behavioral aspects of financial decisions in retirement, and the impact of technology on the insurance industry. Todd’s insights reveal the depth and complexity of financial planning and the critical role of insurance in managing long-term financial risks.

In this podcast episode, Andrew Biggs, an expert in retirement economics, discusses the perceived retirement crisis in America, challenging the notion by presenting data on Social Security and private retirement savings. He argues that Americans are generally better prepared for retirement than commonly believed, emphasizing the substantial wealth embodied in Social Security benefits and the improvement in retirement plan structures over time.

In this episode of the NewRetirement Podcast, Steve Chen interviews Robert Brokamp, a certified financial planner and key figure at the Motley Fool. They discuss Robert's journey in the financial sector, the valuable lessons he's learned about financial planning, and the story behind the Motley Fool. They also touch on topics such as the 4% rule, retirement planning, and the importance of purpose in retirement. Robert emphasizes the need to think about what you want to do with the rest of your life and develop your human capital, including your ability to earn a paycheck, intellectual curiosity, and physical health. He also suggests considering opportunities beyond traditional retirement, such as continuing to work in a different capacity or pursuing new interests and skills.