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.

Key takeaways:

Resources:

Connect with Michael Cy:

Connect with Robert Curtiss:

About Our Guest:

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.

Miles shares key insights:

Resources:

Educational videos (bottom of the page)

Connect with Miles Clark :

Connect with Robert Curtiss:

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.

Key takeaways:

Resources:

Connect with Chris Schelling:

Connect with Robert Curtiss:

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.

Key takeaways:

Resources:

Connect with Michael O’Shea:

Connect with Robert Curtiss:

About Our Guest:

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.

Key takeaways:

Resources:

Connect with Peter Repetto:

Connect with Robert Curtiss:

About Our Guest:

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.

Key points:

Resources:

Connect with Matt Kaufman:

Connect with Robert Curtiss:

About Our Guest:

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.

What to expect:

Resources:

Connect with Damian Gallagher:

Connect with Robert Curtiss:

This information is educational in nature and does not constitute a financial promotion, investment advice or an inducement or incitement to participate in any product, offering or investment. Bluerock is not adopting, making a recommendation for or endorsing any investment strategy or particular security or promoting the individuals or businesses referenced. All opinions are subject to change without notice, and you should always obtain current information and perform due diligence before participating in any investment. All investing is subject to risk, including the possible loss of principal. Bluerock cannot guarantee that the information herein is accurate, complete or timely. Past Performance does not guarantee future results. There are a number of significant risks that should be considered and reviewed when considering an investment in real estate or real estate securities. This is neither an offer to sell nor a solicitation of an offer to buy the securities. An offering is made only by the applicable offering documents and only in those jurisdictions where permitted by law. Our website must be read in conjunction with the applicable offering documents in order to understand fully all of the implications and risks of the offering of securities to which it relates and a copy of the offering documents must be available to you in connection with any offering. Securities offered through Bluerock Capital Markets, LLC | Member FINRA’s  BROKERCHECK® Affiliated with Bluerock Real Estate, LLC

It is not often that an economic moment feels this confusing for everyday people, and Robert Curtiss knows it. 

That is why he brings economist Bryce Gill, economist and national speaker with First Trust Advisors, into a conversation that puts words to the shifts everyone is sensing but few can explain clearly. Robert approaches the discussion the same way he approaches client conversations. He slows things down, asks the questions people are wrestling with, and pulls out insights that make a complicated world easier to understand.

Together, Robert and Bryce explore how global supply chains are being rebuilt, why inflation feels so different from what the data suggests, and how AI and automation are reshaping opportunities for younger workers. 

What to expect from this release:

Resources:

Connect with Bryce Gill:

Connect with Robert Curtiss:

About Our Guest:

A resident of Austin, Texas, Bryce graduated from Miami University of Ohio with a bachelors degree in economics and received an MBA from the University of Texas. An economist and designated national speaker with First Trust he works directly with his colleague Brian Wesbury in the creation of the firm’s widely read weekly “Monday Morning Outlook.” In 2022, First Trust’s work was recognized by its receiving the highly coveted Consensus Economics Award for most accurate economic forecasting.

With a highly energetic speaking style and a scholar’s understanding of current economic matters, Bryce is a frequent guest on financial related podcasts and other media platforms, as well as a speaker at numerous public forums with his listeners remarking upon his ability to make the often difficult to understand both understandable and interesting.

In his presentation on “The Dawn of the Era of Volatility” Bryce will be focusing in his talk on describing the coming changes in the global and US economy and how investment advisors can best prepare their investor’s portfolios for those changes in the years to come.

When most investors think about private credit, they picture direct lending. But as Tod Trabocco, Head of Private Debt Advisory at StepStone Group, makes clear, it’s much more nuanced than that. 

With over two decades in the space, Tod walks us through the four silos of private credit, including corporate, asset-based, asset-backed, and risk-sharing strategies, using unforgettable examples like leasing aircraft and monetizing Van Halen’s music catalog.

Listeners will learn:

Resources:

Connect with Tod Trabocco:

Connect with Robert Curtiss:

About Our Guest:

Mr. Trabocco is Head of Private Debt Advisory for StepStone Private Debt. He is responsible for helping public and private pension plans, endowments, and foundations build private credit portfolios and sits on the Private Debt Advisory Investment Committee.

Prior to joining StepStone Private Debt, Mr. Trabocco served as a consultant and product specialist at Aksia, where he sat on the firm’s credit fund investment committee. Prior to Aksia, he served as Head of Product for ITE Management, a leading transportation leasing fund. Prior to that, he was Cambridge Associate’s first Head of Private Credit, and chaired that firm’s Credit Investment Committee. He began his career in private credit in 2005 as Head of Research and Underwriting for LBC Credit Partners, now CIFC’s direct lending unit.

He holds an MBA from Columbia Business School and a MALD from the Fletcher School of Law and Diplomacy at Tufts University.

Why do 90% of heirs walk away from their parents’ advisor?

Robert Curtiss welcomes Natasha Kennedy, a former Wall Street professional turned mental health therapist, to explore why the Great Wealth Transfer is at risk of becoming the Great Disconnect. 

With $124 trillion poised to change hands in the next two decades, this episode tackles the emotional, behavioral, and generational blind spots advisors must navigate to retain relationships across family lines.

Expect insights on:

Resources:

Connect with Robert Curtiss:

Connect with Natasha Kennedy:

About Our Guest:

Natasha believes that growth is inevitable for those who patiently seek it. She also knows that change is usually messy, non-linear, and almost always uncomfortable. Said differently, she is profoundly aware of the vulnerability and trust required to explore the intricacies and contradictions of your inner world with another person. Natasha’s ultimate goal is to provide you with a warm and compassionate space to engage in this work together.

Natasha, perhaps unexpectedly, spent the first decade of her career working in finance. Along this journey, she received her MBA from Columbia Business School. Prior to this, she received her BA in English and Psychology from Georgetown University, where her interest in storytelling and the human condition truly began. She is now pursuing her Master’s in Counseling and Mental Health from Northwestern University.

Her therapeutic style draws from several theories, including Acceptance and Commitment Therapy (ACT), Cognitive Behavioral Therapy (CBT), and Narrative Therapy. It is extremely important to her that she tailors her therapeutic approach to best fit your individual needs, timeline, and desired outcome. It is her privilege to be entrusted with your story, and she commends you for courageously stepping toward the life you want for yourself.