Smart Money Conversations

Most trusts are great at protecting money and cutting taxes. They do almost nothing to get the person inheriting it ready. You've probably seen how this plays out. Heirs sit in meetings with advisors and can't follow what's being said. Grown kids still have to ask permission for money at 50. And a founder's "nobody touches this money" rule sticks around long after anyone...

Michael Warszawski built Citibank's family office in 1999, ran private banks in London and Zurich, and now chairs Tiger 21 New York while advising multi-generational families through CWM Partners. In this episode, he breaks down the VOICE framework he built to help families move past estate planning mechanics and into the harder conversations about values, decisions, and legacy. Brett Croft an...

What happens when an investment portfolio includes a little bit of everything, but lacks a clear strategy? Brett and Chris examine the “kitchen sink portfolio” , including overlapping mutual funds and ETFs, tiny positions, layered fees, and investments that may add complexity without adding meaningful diversification. They discuss the case for simplicity, the importance of understanding what you o...

Suma Nair has spent more than two decades helping families navigate the most important and most avoided conversations around wealth: what happens to it, who controls it, and who's left to carry it out. As a former practicing estate attorney, and now owner of SVN Solutions, and President of the Boston Bar Association,she's reviewed and drafted thousands of estate plans, served as trustee on...

Getting a non-renewal letter out of nowhere? You're not alone. Brett and Chris sit down with Madeline Matosian, Director of Personal Lines at Indaco Risk Advisors, to unpack why home and auto insurance have gotten so brutal, and what you can actually do about it. Madeline breaks down why carriers pulled out of California, what really happens when a neighborhood catches fire, and why she'd...

Most people don't think about estate planning until something goes wrong. As a professional trustee, Marguerite Lorenz has spent 20 years handling everything from complex situations involving special needs trusts, incapacitated clients, families at war over a rocking chair and what happens when families wait too long — she's seen it all. In this episode, the co-founder of Lorenz Private Tr...

Real estate gets a lot of credit for being tax efficient, but most investors don't fully understand the mechanics behind it. Matt Hamilton is a CPA and founder of Surefire Tax and Accounting, a boutique firm built exclusively for real estate operators and syndicators. In this episode he breaks down how depreciation really works — and why he calls it a loan, not a free pass, because the IRS col...

Dr. Meghaan Lurtz is one of the world's leading experts on the psychology of financial planning — and in this episode, she joins Brett Croft and Chris Tabish for a conversation that goes well beyond the numbers. Meg is a professor at Kansas State University and Columbia University, a partner at Shaping Wealth, a past president of the Financial Therapy Association, and the author of the Substac...

Mark Roth has been investing in real estate limited partnerships for over 20 years — across 10 different operators, through boom markets and rate shocks, through deals that 3x'd and one that came back at 50 cents on the dollar. He's also spent 39 years as a commercial broker advising institutional clients, which means he's seen these deals from both sides of the table. In this episode...

Most small business owners don't call a lawyer until something's already gone wrong. By then, it's expensive. Matthew Fornaro has spent 23 years in the trenches of business law in South Florida — one of the most litigious business environments in the country — and he's seen the same preventable mistakes play out over and over again. Wrong contracts, LLC's losing that coveted li...

What does a hospice doctor know about money, purpose, and living a life without regret? As it turns out — everything. Dr. Jordan Grumet spent decades at the bedside of dying patients, and what he heard changed the way he thinks about wealth, success, and time. In this episode of Smart Money Conversations, Brett Croft and Chris Tabish sit down with the physician-turned-podcaster and author of The P...

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 be...

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...

Episode 26 In 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 cos...

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...

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’...

In Episode 23 , 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 sh...

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...

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...

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 t...

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...

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 ev...

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 abs...

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 cont...

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...