Smart Money Conversations

In this episode of Smart Money Conversations, Brett Croft and Chris Tabish chat with Allan Roth to explore why simplicity—not complexity—is the real edge for high-net-worth investors.Allan shares insights and stories from decades of advising affluent clients, including why many portfolios become unnecessarily complicated over time, and the challenges of simplifying without triggering taxes or behavioral mistakes. The conversation dives into:Why most investors focus on the wrong definition of riskHow to determine when you’ve “won the game” financiallyThe hidden dangers of over-diversification and legacy positionsWhy behavior—not optimization—is the biggest driver of outcomesHow advisors can use AI as a “co-worker” to enhance planningAllan also explains his unconventional approach to client conversations—including how he “negotiates with clients using their own money”—to test real-world risk tolerance.This episode is a deep dive into building portfolios—and mindsets—that prioritize clarity, discipline, and long-term success.website: daretobedull.comemail:[email protected]

What if most stocks are actually losers — and the entire gain of the U.S. stock market over the past 100 years comes down to just 4% of all listed companies? That's exactly what Professor Hendrik Bessembinder's landmark research found, and in this episode Brett Croft and co-host Chris Tabish break down what it means for everyday investors. From $100 turning into $2.5 million since 1925, to the shocking fact that the single best-performing stock over that century was a cigarette maker, the data makes a powerful case for broad diversification and staying invested for the long haul.Brett and Chris also look at the Nevada PERS pension fund — $70 billion managed largely through simple index funds, outperforming the majority of pension systems in the country — as a real-world proof point that you don't need complexity to win. Whether you're just starting out or wondering if your wealth level calls for something more sophisticated, this episode offers a grounding, data-driven reminder: boring works. Stop chasing, start compounding.email: [email protected]

Season 2 Episode 5In this episode, Samuel M. DiPietro, JD, CPA, LLM, MST joins us to discuss all things estate planning — from foundational strategies to advanced tax-efficient planning for high-net-worth families.We dive deep into one of today’s most important (and often overlooked) topics: successfully changing state residency. Learn what it really takes to establish domicile in a new state, avoid costly tax pitfalls, and align your estate plan with multi-state moves. Sam also shares his thoughts on why wealth can be like gasoline, and his own personal thoughts on the concept of enough.Whether you're building wealth, relocating, or protecting your legacy, this conversation delivers practical, actionable insights.Guest: Samuel DiPietro, Attorney at Spencer Fane LLP🔗 https://www.linkedin.com/in/samueldipietro/#EstatePlanning #TaxStrategy #StateResidencyemail us a question at [email protected]

Season 2, Episode 4: What Does It Really Mean to Be a Fiduciary?In this episode, Brett Croft and Chris break down what it truly means to be a fiduciary and how to tell if your advisor actually is one. They discuss compensation models, product sales vs. advice, willingness to put fiduciary duty in writing, full disclosure of conflicts, and the telltale “vibe” when fees come up. If you want to know whether someone is legally required to put your interests first, this episode delivers the practical framework and red flags you need.Tune in to get the questions that matter when choosing or evaluating a financial advisor.Send us an email at: [email protected]

Back by popular demand, I’m thrilled to have repeat guest Adam Cohen join me for a deep dive into private indirect real estate —how to properly evaluate deals and decide if they belong in your portfolio. We cover the exact metrics that matter (beyond just “yield”), common pitfalls, diversification plays, and the questions every serious investor should be asking before writing a check.Whether you’re already allocating to real estate or just starting to explore the space, this episode gives you a practical, no-fluff playbook you can use immediately.Find Adam here:Website: ⁠https://www.complementre.com/⁠Contact: [email protected] us a question to: [email protected]

In Episode 2 of season 2, we welcome Tim Borchers, accomplished estate planning attorney and co-author of the bestselling book Saving the Family Cottage: Creative Ways to Preserve Your Cottage, Cabin, Camp, or Vacation Home for Future Generations. This insightful episode dives into the challenges and strategies for passing down cherished family vacation properties without tearing families apart. Borchers shares expert advice on succession planning, avoiding common pitfalls like disputes among heirs, using LLC's, and trusts (spoiler alert: it's all about the operating agreement!) to maintain harmony, and help keep these beloved heirlooms, in the family for generations to come—perfect listening for anyone with a family cottage, cabin, or vacation home they want to protect.Website: https://www.borcherslaw.com/Email Tim:  [email protected]: www.brettcroft.com Email the show: [email protected]

In the Season 2 premiere of Smart Money Conversations, host Brett Croft sits down with Sara Grillo, CFA—financial advisor marketing consultant and founder of the Transparent Advisor Movement—to discuss her unconventional career path, her advocacy for advice-only and flat-fee financial planning, and how transparency and ethical alignment are reshaping the advisory industry. The conversation blends personal history, industry critique, and practical guidance for both advisors and clients navigating today’s evolving financial landscape.Find Sara here: www.saragrillo.comAsk us a question: [email protected]: www.brettcroft.com

To close out Season One of SMC, Brett and Chris sit down with a true legend in retirement planning — Bill Bengen, the creator of the original 4% rule and author of the new book A Richer Retirement. Bill’s research reshaped how advisors and retirees think about generating income from portfolios. But retirement planning has evolved, and so has his thinking. In this conversation, Brett and Bill go beyond the headline rule of thumb and explore what actually creates a secure, flexible, and meaningful retirement today. They discuss: How Bill’s latest research updates the traditional 4% rule Why asset allocation matters more than most withdrawal debates The role of small-cap stocks in historical retirement success How retirees can adjust spending without sacrificing peace of mind The difference between “not running out of money” and having a truly rich retirement Where advisors and DIY investors often misunderstand safe withdrawal strategies Bill also shares insights from A Richer Retirement about lifestyle design, spending flexibility, and why retirement success is about more than just portfolio math. This episode blends academic research, real-world planning, and practical takeaways — a fitting close to the first season. Contact Bill www.bengenfs.comSend us a question: [email protected]: www.brettcroft.com

In Episode 20, we welcome back Alexander M. Popovich, JD, LLM, Principal and Founder of Planning Advisory Services, LLC, and a seasoned expert in tax, trusts, and estate planning for high-net-worth families. Building on his previous appearance, Alex tackles our questions and dives into three essential topics: conducting effective wealth audits to identify gaps in your current plan, breaking down the ABC's of trusts (from revocable living trusts to advanced structures like A/B trusts), and critical considerations when changing residency to another state—including impacts on estate taxes, document validity, probate rules, and domicile planning. Packed with practical strategies and real-world insights, this episode helps you protect and optimize your legacy—no matter where life takes you!Website: www.https://www.planning-advisory-services.com/Contact Alex: [email protected] us a question: [email protected]: www.croftfinancialplanning.com

In this episode, co-host Chris Tabish opens up about his growing urge to pull money out of the stock market and adopt a more conservative approach. What starts as a discussion on potential market timing evolves into a deeper reflection on whether this is truly a tactical move or a fundamental strategic shift in his investment philosophy.We also dive into Warren Buffett's famous 10-year wager against hedge fund manager Ted Seides of Protégé Partners – the bet that a simple S&P 500 index fund would outperform a selection of elite hedge funds (after fees). Spoiler: Buffett won decisively, highlighting the power of low-cost, passive investing over high-fee active management. A timely lesson as we debate risk, patience, and staying the course.send us a question: [email protected]: www.croftfinancialplanning.comwww.berkshirehathaway.com

In this episode, co-host Chris Tabish—a Silicon Valley management consultant, author of Comediology: Be More Effective and Fulfilled in Business With Comedy, speaker, and stand-up comedian—steps into the spotlight to share his real-world process for acquiring his very first multifamily property in 2025. As a complete newcomer to the multifamily real estate space, Chris walks listeners through every step: spotting the opportunity, tackling financing, conducting due diligence, negotiating the deal, and closing.With his fresh perspective and honest reflections, Chris offers practical tips, key lessons learned, and insights on building a team, overcoming beginner hurdles, and what he’d do differently next time. Whether you're an experienced investor seeking new angles or just starting your multifamily journey, this episode delivers actionable advice from someone who's recently been exactly where you are.Tune in for an inspiring, no-BS look at breaking into multifamily in today’s market!Send us a question to: [email protected]: www.croftfinancialplanning.com

In Episode 17, we chat with recently retired tech executive Randy Von Feldt, who pulls no punches about what it really takes to walk away from a high-powered career. Randy breaks down the financial realities of retirement – running the numbers, stress-testing the plan, and making sure it all adds up before pulling the trigger.He also shares how open and ongoing communication with his wife was absolutely key to making the transition work for both of them. On top of that, Randy talks about amateur stand-up comedy as a retirement hobby and finding unexpected fulfillment in quietly supporting others in addiction recovery.Expect a straightforward, no-BS conversation about planning your exit, aligning with your partner, and building a purposeful next chapter – with a few laughs along the way. Perfect for anyone eyeing retirement or rethinking what comes after the corporate climb.For anyone struggling with addiction, start here: https://www.aa.org/Send us a question to: [email protected]: www.croftfinancialplanning.com

In this episode, we sit down with Dr. Jacob Liberman, a pioneering voice in the fields of light, vision, and consciousness, and recipient of the 2019 International Light Association’s Frances McManemin Award for Achievement in Light Medicine. Building on his lifelong exploration of light as the guiding intelligence of our lives, Dr. Liberman shares practical and profound wisdom on cultivating contentment, fulfillment, and a deeper sense of purpose.We explore what true wealth means—far beyond money—through the gifts we offer others: our love, time, help, and encouragement. As Dr. Liberman reminds us, “you don’t have to be wealthy to be generous; in fact, the generous are wealthy.” He also offers grounded guidance on quieting mental chatter, listening more closely to the intelligence that moves through us, and living with greater ease and presence.Dr. Liberman, author of Luminous Life, Light: Medicine of the Future, Take Off Your Glasses and See, and Wisdom From An Empty Mind, brings together science, spirit, and heartfelt practicality in a conversation that is both inspiring and deeply human.Find Dr. Liberman: Website: https://www.jacobliberman.org/Facebook: https://www.facebook.com/DrJacobLibermanInstagram: https://www.instagram.com/drjacobliberman/Contact: [email protected] us a question to: [email protected]: www.croftfinancialplanning.com

In this episode, we hear from Adam Cohen, CFA, founder of Complement Real Estate Advisors, LLC a firm specializing in real estate advising for high-net-worth families and businesses . We discuss the why, how, and when adding real estate to your portfolio makes sense. Adam touches on the appropriate use of leverage, why owning direct real estate can be a unique experience, and be sure and listen to the end where Adam tells us what advice he would give to his own kids about buying their first property. Find Adam here:Website: https://www.complementre.com/Contact: [email protected] us a question to: [email protected]: www.croftfinancialplanning.com

Listen to episode 14 where we answer a listener's question on annuities (the darker side), discuss the importance of healthcare advance directives (aka healthcare proxy or healthcare power of attorney) and where to access free forms for all 50 states. We also tell you how to think about asset allocation, what is the real risk investors face during a 30 + year retirement, and an effective inflation hedge for retirees to consider for their portfolio.Send us a questions at: [email protected]: www.croftfinancialplanning.com

In this episode we hear from Alexander M. Popovich, JD, LLM, Principal and Founder of Planning Advisory Services, LLC, a consulting firm specializing in tax, estate, and legal advisory planning for high-net-worth families and businesses.Alex leads an in depth discussion of good planning gone bad: , unfunded trusts, not documenting gifts correctly, unintentional gaps in insurance coverage, tax return mishaps, correct use and registration of LLC's , and more. Be sure to listen to the end where Alex handles how to talk to loved ones about your estate plan and when.Website: www.https://www.planning-advisory-services.com/Contact Alex: [email protected] us a question: [email protected]: www.croftfinancialplanning.com

Listen to episode 12 as we answer listener questions about stocks, CD's, risk, how to get started saving, and we discuss long term investment returns. We also recap our discussion of Medicare.

Maura Carley from Healthcare Navigation joins us for a very informative chat about signing up for Medicare. She also discusses the difference between traditional Medicare, Medicare Advantage, and Medigap Plans and t hings to watch out for and be aware of. Did you know that during initial Medicare enrollment, some of the choices you make could be for life? For instance, in 47 states, you are only guaranteed eligible for a Medicare Supplemental plan during the first 6 months of enrollment.

In episode 10, Brett Croft guides clients on managing portfolio risk, focusing on strategies for concentrated stock positions, such as exchange funds to diversify without triggering capital gains taxes. He discusses balancing risk and other diversification methods like charitable trusts. Tune in for actionable insights to optimize wealth and reduce single-stock exposure.Send us a question to: [email protected]: www.croftfinancialplanning.com

In episode 9, Brett Croft guides clients through essential estate planning tools to preserve wealth, including wills, revocable trusts, durable power of attorney, and healthcare proxies. He explains how these documents secure assets and minimize taxes. Tune in for clear strategies to ensure your legacy aligns with your goals.Send us a question to: [email protected]: www.croftfinancialplanning.com

In episode 8, Brett Croft shares expert strategies for UHNW clients to generate passive income through investments like passive etfs and real estate, while optimizing tax efficiency. He explores practical methods to minimize income taxes, such as tax-advantaged accounts and deductions, to maximize wealth. Tune in for actionable insights to build sustainable income with minimal tax burden.

In Episode 7, Brett Croft examines the Nevada pension system as a model for secure retirement income, offering UHNW clients strategies to create a reliable retirement paycheck using index funds for passive income. He also explores navigating equity compensation (e.g., stock options) to maximize wealth. Tune in for clear, actionable insights to build a robust financial future.

In Episode 6 : "Index vs. Active Scorecard, 3 DIY Portfolios, The Perfect Portfolio," Brett Croft compares index funds (e.g., S&P 500 ETF) to active management, unveiling three DIY portfolios for UHNW clients. He explores crafting the "perfect portfolio" by balancing risk, returns, and simplicity. Tune in for actionable strategies to optimize wealth with transparent, low-cost investing.

Thoughts on Debt, Withdrawal Rates, Mindfulness, and Net Worth," Brett Croft shares strategies for UHNW clients to manage debt, optimize safe withdrawal rates (e.g., 4% rule ), and align net worth with mindful financial goals. He blends practical insights with mindfulness to balance wealth and well-being. Tune in for clear, actionable advice to enhance financial freedom.

In Episode 4 Brett and Chris explore the concept of "enough" in financial planning, guiding UHNW clients to define sufficiency in wealth and lifestyle. He discusses balancing investments , income, and personal goals to achieve fulfillment without excess. This episode offers actionable insights for financial clarity and contentment.

Exit the forever fee matrix and learn to use low cost broadly diversified index funds for your long term savings.

In episode 2 we teach you how to keep emotions from overtaking your investment decision making. Use a UTMA to gift assets to minors, stay the course with a long-term investment perspective.Send us a question to: [email protected]

What is the real value of a financial advisor? How can I find an advisor that is aligned with my goals and interests? How do I find an advisor with (what Dave Ramsey calls) the "heart of a teacher" ? Find out about the advice-only model for financial advising and why it best and least conflicted of all advising models. Learn how to take control of your financial life and exit the "fee-matrix".Send us a question to: [email protected]