Estate Planning Isn’t Done When You Sign the Papers with Brad Repinsky (Ep. 97)

Estate Planning Isn’t Done When You Sign the Papers with Brad Repinsky (Ep. 97)

Many people assume their estate planning is “done” once the documents are signed, but that’s actually only the beginning. This conversation explores what actually happens when financial, tax, and estate planning are all aligned. In this episode, Robert Curtiss sits down with Brad Repinsky to break down how integrating financial planning, estate planning, and tax …

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Private Credit, AI Concerns, and the Power of Diversification with Mark Gatto (Ep. 96)

Private Credit, AI Concerns, and the Power of Diversification with Mark Gatto (Ep. 96)

Markets shift, headlines create noise, and uncertainty rises, but what actually matters when building a resilient portfolio? How do you separate real risks from exaggerated fears and position yourself for long-term growth? In this episode, Robert Curtiss welcomes back Mark Gatto, Chief Executive Officer at CION Investments, to discuss the growing attention to private credit …

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When Success Feels Like a Trap: The Hidden Emotional Side of Wealth with Stacey Inal (Ep. 95)

When Success Feels Like a Trap: The Hidden Emotional Side of Wealth with Stacey Inal (Ep. 95)

You can have the career, the income, and the life that looks perfect on paper, yet still feel something is missing. Why do high achievers feel stuck, overwhelmed, or quietly unhappy despite their accomplishments? In this episode, Robert Curtiss speaks with Stacey Inal, MA, MBA, LMFT, Licensed Psychotherapist and Women’s Career Coach, about the intersection …

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AI and the Future of Financial Advice with Michael Cy (Ep. 94)

AI and the Future of Financial Advice with Michael Cy (Ep. 94)

Technology is moving fast, and it’s raising big questions about how decisions get made. Can tools replace human judgment, or do they simply change how we think, plan, and act? In this episode, Robert Curtiss welcomes back Michael Cy, advisor consultant, about how artificial intelligence is shaping financial services and what it means for clients. …

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Sector Rotation, AI Spending, and What Market Momentum Is Telling Us with Miles Clark (Ep. 93)

Sector Rotation, AI Spending, and What Market Momentum Is Telling Us with Miles Clark (Ep. 93)

Markets can feel calm on the surface while powerful shifts happen underneath. Are recent pullbacks a warning sign, or simply part of a broader rotation? In this episode, Robert Curtiss welcomes back Miles Clark of Nasdaq Dorsey Wright to break down sector rotation, weakening tech leadership, and renewed strength in international equities. They explore how …

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Private Markets and Long-Term Investing with Chris Schelling, CAIA (Ep. 92)

Private Markets and Long-Term Investing with Chris Schelling, CAIA (Ep. 92)

Long-term investing can feel more difficult when headlines are loud and markets seem unpredictable.  What happens when investors stop reacting to daily noise and start thinking like institutions that plan decades ahead? In this episode, Robert Curtiss welcomes Chris Schelling, CAIA, Managing Director at Aksia, to explore how private markets have shaped institutional portfolios and …

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Opportunity Zones Explained: What’s Changing in 2027 and Why It Matters with Michael O’Shea (Ep. 91)

Opportunity Zones Explained: What’s Changing in 2027 and Why It Matters with Michael O’Shea (Ep. 91)

For investors facing concentrated wealth or future liquidity events, understanding tax-aware planning options matters long before decisions are required. Opportunity Zones are one of the most talked-about and least understood tools in that conversation. In this episode of The Millionaire Next Door Podcast, Robert Curtiss sits down with Michael O’Shea, CFA, Head of Private Wealth …

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Balancing Markets, Policy, and AI Spending in the 2026 Outlook Peter Repetto (Ep. 90)

Balancing Markets, Policy, and AI Spending in the 2026 Outlook Peter Repetto (Ep. 90)

Markets are entering a year shaped by crosscurrents, shifting signals, and unresolved questions. Economic strength, policy decisions, and investment concentration all point to a period that demands close attention and thoughtful positioning. In this episode, Robert Curtiss speaks with Peter Repetto, Vice President and Investment Strategist at iCapital, about their 2026 economic and market outlook. …

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Turning Equity Exposure Into Monthly Income With Auto Callable ETFs with Matt Kaufman (Ep. 89)

Turning Equity Exposure Into Monthly Income With Auto Callable ETFs with Matt Kaufman (Ep. 89)

Reliable income is harder to find when markets shift, and traditional tools feel less predictable. Many investors are looking for new ways to generate cash flow without stepping away from equity exposure altogether. This week, Robert Curtiss welcomes Matt Kaufman, Head of ETFs at Calamos Investments, to explain how auto-callable strategies work and why they …

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The Real-World Guide to 1031 Exchanges with Damian Gallagher (Ep. 88)

The Real-World Guide to 1031 Exchanges with Damian Gallagher (Ep. 88)

If you own investment property in California, you may have wondered how to handle the built-up gain without losing a significant portion to taxes.  Robert sits down with Damian Gallagher, Senior Vice President at Blue Rock, for a grounded, practical walkthrough of 1031 exchanges and DSTs. The conversation opens with the history of 1031 rules, …

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