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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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.

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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:

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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:

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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:

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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.

Is private equity still worth it, and can everyday investors finally get access without the complexity?

Robert Curtiss, CFP,® welcomes back Phil Huber, Managing Director and Head of Portfolio Solutions at Cliffwater, to unpack the rise of evergreen private equity funds, an innovation reshaping the private investing landscape.

Phil explains how Cliffwater’s newly launched Evergreen Private Equity Index is giving advisors better visibility into performance, while opening doors for accredited and even unaccredited investors to tap into long-term private market strategies.

Expect an honest look at tradeoffs, manager due diligence, and the evolution of access, with a side of market context as the AI boom and public market concentration unfold.

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About Our Guest:

Phil is a Managing Director and Head of Portfolio Solutions for Cliffwater, based in their Chicago office. In this role, Phil leverages his prior experience as a wealth management CIO to produce and curate investment research, advise on product strategy and positioning for the firm’s growing platform, and help establish and strengthen relationships with the nation’s leading wealth management firms.

Prior to joining Cliffwater, Phil was the Chief Investment Officer for Savant Wealth Management. He earned a bachelor’s degree in finance from the Kelley School of Business at Indiana University. He is a CERTIFIED FINANCIAL PLANNER professional, has attained his Chartered Financial Analyst® (CFA®) designation, and is a member of the CFA Society of Chicago.

Certified Financial Planner Board of Standards Inc. (CFP Board) owns the certification marks CFP® and CERTIFIED FINANCIAL PLANNER in the U.S., which it authorizes use of by individuals who successfully complete CFP Board’s initial and ongoing certification requirements.

As markets surge on the backs of the Magnificent Seven, are investors missing what’s happening off the radar?

Robert Curtiss, CFP®, is joined by Andrew Hull, CFA, Vice President and ETF Strategist at First Trust, to unpack overlooked investment opportunities that may hold stronger long-term value than today’s most-hyped tech names.

Andrew explains how today’s market is historically concentrated and why that creates risk and opportunity. From the reshoring of American industry to massive grid upgrades and the rise of water-cooled data centers, this conversation clarifies themes that may shape the future of returns.

What to expect in this episode:

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LinkedIn: Andrew Hull, CFA

About Our Guest:

Andrew Hull is a seasoned financial professional with a robust background in exchange-traded funds and commercial banking. Currently serving as Vice President and ETF Strategist at First Trust, he has cultivated a deep understanding of monetary authorities and central banking dynamics. With over a decade of experience at First Trust, including roles as an Economic Analyst, Andrew has demonstrated a strong commitment to financial strategy and analysis. Prior to this, he held a Vice President position at Columbia Bank, where he honed his skills in commercial banking. Andrew graduated from Wheaton College with a Bachelor’s Degree in Business Economics, which laid the foundation for his analytical expertise. His career reflects a blend of strategic leadership and technical financial acumen, positioning him as a valuable asset in the finance sector. He is particularly interested in the intersection of finance and emerging technologies, aiming to leverage innovative solutions in investment strategies. Andrew’s professional journey exemplifies adaptability and a dedication to continuous learning in a rapidly evolving industry.

When electricity demand in the U.S. hit a record-breaking high on July 28th, 2025, it wasn’t a blip; it was a signal. 

In this powerful follow-up to Episodes 69 and 78, Robert Curtiss welcomes back Michael Underhill, founder and CIO of Capital Innovations, to unpack the megatrends shaping the future of investing.

From surging AI-driven capital expenditures to the multi-trillion-dollar rebuild of America’s power grid, Michael outlines why infrastructure is no longer a “nice to have” but an essential portfolio diversifier. He explores how interest rate cycles, inflation, and the evolving definition of risk are impacting investor behavior and how private infrastructure may offer consistent returns, lower volatility, and true non-correlation in today’s concentrated markets.

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About Our Guest:

Michael Underhill is the Chief Investment Officer of Capital Innovations, a firm focused on infrastructure, energy, and ESG-aligned strategies. With decades of investment experience, Michael brings a deep understanding of macro trends and emerging opportunities in private and public markets. His team manages infrastructure-focused portfolios designed to align long-term capital with long-term value creation.

What happens when public markets no longer provide the diversification they once promised? In this episode, Robert Curtiss, CFP®, is joined by Tony Davidow, Senior Alternatives Investment Strategist at the Franklin Templeton Institute, to explore the tectonic shifts transforming private markets.

Tony shares insights from decades of experience working with institutional capital, family offices, and advisors. He breaks down the evolution of private equity, real estate debt, and evergreen structures and why today’s investors may be missing out on an illiquidity premium worth 3–5% per year. 

From secondaries to real estate, digital infrastructure to target-date funds, this conversation offers a masterclass in building smarter portfolios in an uncertain world.

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About Our Guest:

Tony Davidow is responsible for developing and delivering the Franklin Templeton Institute’s insights on the role and use of alternative investments through independent research, participating in industry conferences, webinars and engaging directly with key partners and clients. He also serves as the host of the Alternative Allocations podcast series. The Franklin Templeton Institute harnesses the depth and breadth of the firm’s global investment expertise and extensive in-house research capabilities to deliver unique investment insights to our clients.

Prior to his current role, Davidow was retained by Franklin Templeton to develop a comprehensive Alternative Investment educational program for financial advisors. He previously held senior leadership roles with Morgan Stanley, Guggenheim, and Schwab, among other firms. Davidow began his career working for a New York-based family office and has worked directly with many institutions and ultra-high-net-worth families over the years. He is a frequent writer and speaker with deep expertise in the use of alternative investments, asset allocation, and portfolio construction, as well as goals-based investing.

It’s the dog days of summer, but the market hasn’t gone to sleep.

Robert Curtiss welcomes back frequent guest Miles Clark from Dorsey Wright for a timely conversation on where we are and where we might be headed. 

From all-time market highs to yellow-flag participation levels, this episode dives into the realities behind performance, volatility, and how history favors the long view.

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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 indicators and research projects, and the creation of weekly media distributed to prospective clients.