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 risk
• How to determine when you’ve “won the game” financially
• The hidden dangers of over-diversification and legacy positions
• Why behavior—not optimization—is the biggest driver of outcomes
• How advisors can use AI as a “co-worker” to enhance planning

Allan 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.com

email:[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 5

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 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 #StateResidency

email 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]

Send 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]

Website: 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.com

Ask us a question: [email protected]

Website: 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.com

Send us a question: [email protected]

Website: 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]

Send us a question: [email protected]

Website: 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]

website: www.croftfinancialplanning.com

www.berkshirehathaway.com