The Boldin Your Money Podcast

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

In this episode of Boldin Your Money, Steve Chen talks with Jillian Johnsrud, author of Retire Often, about how taking intentional career breaks, what she calls mini-retirements can lead to greater freedom, career clarity, and personal growth. Jillian shares her journey from debt at age 19 to financial independence by 32, and how sabbaticals became a core part of her life rhythm. They explore how mini-retirements can be used not just for rest, but for skill-building, career pivots, and even wealth creation. Jillian also introduces her four-step framework Dream, Career, Money, and Journey offering practical tools to help anyone take time off with purpose, not regret.

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.