Smart Money Conversations: an advice-only podcast hosted by Brett Croft, CFP®, CFA®, CTFA®, and entrepreneur Chris Tabish CCO (Chief Comedic Officer) delivers expert financial strategies for families, covering taxes, investments, estate planning, and passive income. Tune in for clear, actionable insights to build and preserve wealth, inspired by a life of adventure and laughter.
This Podcast is for educational purposes only.
Episode #39 Most Trusts Are Built To Protect The Money, Not The Person Who Inherits It with Kristin Keffeler
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 remembers why it exists.
In this episode, we get into:
A three-step trust setup where the trustee starts as a mentor, becomes a partner, and then steps aside
Why making your spouse the trustee for your kids can leave everyone unsure who they're talking to, Mom or the trustee
Why kids who'll never need a paycheck still need meaningful work
Brett Croft, CFP®, CFA®, CTFA®, and Chris Tabish talk it through with Kristin Keffeler of JFG Family Office. Kristin wrote The Myth of the Silver Spoon and co-wrote Wealth 3.0. She knows this from both sides. Her dad took his company public and then sold it when she was in her early 20s. The wisdom she shares comes partly from lived experience.
17 Sept 2026
#38 Inside Tiger 21: What $20 Million Buys You (Hint: It's Not Investment Advice) With Michael Warszawski
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 and Chris Tabish dig into the tools Michael uses in real family meetings, including a card exercise that surfaces where family members actually agree, the Six Thinking Hats method for group decisions, and what really happens inside a Tiger 21 peer group. Michael also shares his own answer to a question every wealthy family eventually asks: how do you know when you have enough?
3 Sept 2026
#37 The Kitchen Sink Portfolio: a little bit of everything, but no strategy
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 own, and how a clear portfolio plan can help investors avoid emotional decisions during volatile markets.
They also recap estate-planning lessons, explore the psychology of money and “enough.”
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
3 ratings
Spotify
5.0 / 5
4 ratings
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