Month: January 2026

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 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:

  • How equity markets can be used to generate consistent monthly income instead of relying on bonds
  • Why auto callable strategies trade upside participation for predictable cash flow
  • How downside barriers work and when coupons may pause or resume
  • Tax treatment differences compared to traditional fixed income
  • Where auto-callable ETFs may fit alongside equities, munis, or covered call strategies
  • And more!

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.

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, 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:

  • How like-kind rules truly work
  • The 45-day and 180-day deadlines are explained in real terms
  • When DSTs may help simplify life for aging investors
  • The lesser-known 1033 disaster exchange option
  • And more!

Resources:

Connect with Damian Gallagher:

Connect with Robert Curtiss:

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