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 strategy can help create a more coordinated decision making for families over time.

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About Our Guest:

Brad Repinsky is the Director of Estate, Tax, and Financial Planning at Signature Estate and Investment Advisors. With over 20 years of experience, including roles at Goldman Sachs and Fidelity, Brad specializes in helping high-net-worth and ultra-high-net-worth families navigate complex planning decisions. As a former attorney, he brings a unique perspective to integrating estate planning, tax strategy, and wealth management to help clients create clarity, efficiency, and long-term alignment with their goals. 

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 and the role of diversification in uncertain markets. They explore how AI concerns are shaping investor sentiment, why fund structure and liquidity matter, and how infrastructure investing offers long-term opportunity. 

Mark also shares insights on manager selection, underwriting discipline, and how individual investors can access strategies once reserved for institutions.

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About Our Guest:

Mark Gatto is Co-Founder, Co-Chief Executive Officer, and Co-President of CION Investment Group, CION Investment Corporation (CIC), and CION Grosvenor Infrastructure Fund.

He is also a Director and Co-Chief Executive Officer of CION Ares Diversified Credit Fund (CADC). Mr. Gatto serves on the investment committee of CIC and the investment allocation committee of CADC.

Mr. Gatto joined CION in 1999. He served as Executive Vice President and Chief Acquisitions Officer from May 2007 through January 2008. He served as Executive Vice President of Business Development from May 2006 through May 2007 and Vice President of Marketing from August 2005 through February 2006. He was also Associate General Counsel from November 1999 until October 2000.

Previously, Mr. Gatto served as an executive at a leading international product development and marketing company from 2000 through 2003. Later, he co-founded a specialty business-consulting firm in New York City, where he served as its managing partner before re-joining CION in 2005. He was also an attorney in private practice prior to joining the firm.

Mr. Gatto received an M.B.A. from the W. Paul Stillman School of Business at Seton Hall University, a J.D. from Seton Hall University School of Law, and a B.S. from Montclair State University.

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 of financial decisions and emotional health. They explore how burnout shows up in high performers, why social media fuels anxiety, and how “golden handcuffs” keep people stuck. Stacey also shares practical ways to reset your nervous system, reconnect with yourself, and take the first step toward a more aligned life.

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About Our Guest:

Stacey Inal is a Licensed Psychotherapist, MBA, and Women’s Career Coach who works at the intersection of mental health, career transitions, and financial identity. With a background in corporate sales and business strategy, she brings both clinical insight and real-world experience to her work, helping high-achieving individuals, especially women, navigate moments when outward success no longer feels aligned internally. Stacey supports clients through burnout, life reinvention, and major transitions by helping them reconnect with what they truly want and build a path forward with clarity and purpose.

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. They explore how AI improves efficiency, speeds up research, and enhances communication, while emphasizing the lasting importance of personal advice. The conversation also covers market uncertainty, client anxiety, and how a structured process helps people stay grounded and focused on what they can control.

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Michael Cy works closely with financial advisors across the country, helping them refine their processes and strengthen how they serve clients. With years of experience supporting advisory firms, he focuses on improving efficiency, enhancing client communication, and integrating practical tools that elevate day-to-day operations. His perspective blends technology with a strong emphasis on relationships, helping advisors balance innovation with the human side of financial planning.

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 momentum strategies respond to shifting trends, why AI spending faces rising scrutiny, and what participation indicators reveal beneath flat index performance. 

The conversation also covers sentiment signals, precious metals, crypto volatility, and the importance of selecting the right benchmark.

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About Our Guest:

Miles currently works as a Research Analyst for Nasdaq Dorsey Wright (DWA), a boutique investment advisory and asset management division of Nasdaq focused on providing quantitative strategies to Wall Street and professional money managers globally. Since 1987, DWA has been a recognized expert in relative strength and momentum through the application of Point & Figure (XO) charting, as well as a thought leader in tactical portfolio construction.

Miles joined the DWA team as an intern in 2021 and now creates technical-based analysis and client-facing research in the firm’s Daily Market Analysis segment, with more focused coverage in the communication services, industrials and cryptocurrency spaces. Other areas of involvement to note include supplementing broad-based technical indicator and research projects and the creation of weekly media distributed to prospective clients.

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 why some individual investors may now gain access to approaches like those used by institutions, depending on account type, regulatory eligibility, and minimum investment requirements. They break down private equity, private credit, liquidity planning, diversification across vintages, and the importance of manager selection. 

The conversation also touches on volatility, long-term return expectations, and what advisors and investors should look for when evaluating alternative investments.

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About Our Guest:

Chris Schelling is an investor, advisor, and published author. With degrees in psychology, business, and finance, Chris is an expert at incorporating insights from behavioral finance into investment decision-making. During his 20+ year tenure in the investment industry, building portfolios, mostly focused on alternatives, Chris has met with over 4,000 managers and allocated roughly $7 billion, generating top quartile to top decile returns across hedge funds, real assets, private credit, and private equity.

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 at Origin Investments, to unpack one of the most misunderstood and potentially powerful tax planning tools available today: Qualified Opportunity Zones.

Together, they walk through how Opportunity Zones work, why the original structure created a temporary pause in interest, and why upcoming changes beginning in 2027 may reopen the door for investors facing large capital gains. The conversation focuses on real-world planning scenarios, including concentrated stock positions, private business exits, and highly appreciated real estate.

Michael explains how Opportunity Zones differ from 1031 exchanges, what the long-term benefits may look like when paired with professionally managed real estate development, and why advanced coordination with tax and legal advisors matters. This episode is designed as an evergreen educational resource for investors who want to understand their options well before a liquidity event occurs.

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Michael brings more than 18 years of real estate and capital markets expertise to Origin as Director and Head of Private Wealth Solutions. In this role, he leads the firm’s capital raising initiatives, oversees the sales strategy, and develops strategic partnerships with Registered Investment Advisors (RIAs) to expand Origin’s investment platform.

Previously, Michael served as the head of Origin Exchange, the firm’s 1031 Exchange Platform. During his career in the alternative investment sector, Michael has played key roles with various real estate sponsors, facilitating the syndication of more than $10 billion in commercial real estate investments, including over $500 million in 1031 tax-deferred exchanges.

Michael holds an MBA with dual concentrations in Finance and Real Estate Investment from DePaul University, where he graduated summa cum laude. He earned his bachelor’s degree from Purdue University and is a CFA® charterholder.

A resident of Elmhurst, Michael lives with his wife Lauren and their three children Declan, Alice, and Tristan. Outside of work, he enjoys golf, Chicago sports, and spending time with his family.

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. They explore slowing labor trends alongside strong GDP growth, the role of AI investment, and how fiscal and monetary policy may influence markets. 

The conversation also covers inflation risks, tariffs, and why selectivity across asset classes matters heading into a midterm election year.

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Peter is a Vice President and Investment Strategist at iCapital, focusing on developing and delivering research, investment ideas, and thought leadership content for external and internal audiences on behalf of iCapital’s Investment Strategy team. Prior to joining the firm, Peter spent over eight years at Franklin Templeton Investments, where he contributed to their asset allocation strategy and macroeconomic research. Peter holds a BA in Economics from Fairfield University.

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 are gaining attention. They break down how equity-linked income differs from bonds, how coupons are generated, and where these tools may fit inside a portfolio. The conversation also covers risk considerations, tax treatment, and how ETFs are changing access to structured strategies.

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Matt Kaufman serves as SVP, Head of ETFs at Calamos Investments, where he leads the firm’s ETF business.

Matt joined Calamos Investments in 2023 as an accomplished financial services executive with more than 20 years of experience serving the asset management and insurance industries across North America, Europe, and Asia. Matt has designed, led, and helped build hundreds of exchange-traded funds (ETFs), unit investment trusts (UITs), indexes, variable insurance trust funds, registered index-linked annuities, fixed annuities, and closed-end funds. He is also a sought-after source by leading financial publications and is a frequent speaker at industry conferences and events.

Prior to Calamos, Matt spent more than a decade at Milliman, Inc., where he served as President of the firm’s broker/dealer (Milliman Investment Management Services LLC) and as a principal of the firm’s $170b RIA (Milliman Financial Risk Management LLC). Matt also draws from his prior experience at PowerShares ETFs, where he helped the firm grow during the formative years of the ETF ecosystem.

Matt earned a B.A. in Public Administration and Economics from Cedarville University and maintains Certified ETF Advisor (CETF®) and Professional Certified Marketer® designations through The ETF Institute and American Marketing Association, respectively. He also holds FINRA Series 7, 63, and 24 and CFTC Series 3 licenses.

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, then moves into what actually happens when you sell, how timelines work, and why so many investors struggle with the 45-day identification window. 

Damian also explains DSTs in plain language, including when they might help reduce hands-on management and how they fit into long-term estate planning.

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