Options Strategies for Modern Investors with Lawrence Kriesmer

Larry Kriesmer shares how his career evolved from life insurance to options-driven wealth management, explaining that supervisory limitations at his former firm pushed him to launch his own RIA focused on option-based strategies. He and the host discuss the industry's longstanding discomfort with options, the differences among custodians, and the surge in option-centric ETFs driven by investor demand for income, downside buffers, and more predictable outcomes. Larry explains why he favors synthetic long exposure to the S&P 500, how options can create defined risk in ways traditional 60/40 portfolios cannot, and why repeated market shocks have increased interest in structures that limit drawdowns. He also stresses that while options can be powerful, they require real understanding—especially given the asymmetric risks—and that most investors are best served using simple strategies or working with experienced professionals.

• Larry Kriesmer shares his background transitioning from life insurance into wealth management and ultimately founding his own RIA due to options-related supervision limitations at his prior firm.
• We highlight how many insurance and brokerage firms restrict options usage because supervisors often lack the necessary licensing or comfort with the risks.
• Early-career experiences show how compliance departments often misunderstand options and overburden advisors executing client-driven trades.
• Larry explains that custodians also vary widely in their options competency, noting TD Ameritrade's historically advanced approach compared to more conservative platforms like Schwab and Fidelity.
• He describes how the growth of option-based ETFs and structured strategies reflects rising demand for income, risk buffers, and outcome-based portfolio design.
• Why options are resurging in popularity despite being decades old, tying it to investor frustration with unpredictable markets, multiple major drawdowns, and the need for more controlled outcomes.
• Larry outlines his discovery of options through studying indexed annuities, which showed him how options could define downside risk and reshape portfolio construction.
• He explains his core strategy of staying synthetically long the S&P 500 at all times, avoiding market timing, and focusing on capturing upside while limiting drawdowns.
• The conversation touches on potential expansion of his strategy into other sectors or international markets, though the S&P remains his primary exposure due to its self-healing nature.
• Larry critiques modern portfolio theory as outdated and insufficient for managing real downside risk, arguing that a bond-plus-options structure can outperform a traditional 60/40 on a risk-adjusted basis.
• You discuss how 2022 exposed the limitations of conventional diversification when both stocks and bonds fell simultaneously.
• Larry emphasizes that while options can be powerful tools, investors must deeply understand which side of the contract's risk they are assuming to avoid catastrophic losses.
• He concludes that most investors should pursue education but ultimately rely on professionals or ETF structures if they want to safely incorporate options into their portfolios.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Phil Weiss | Apprise Wealth Management

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For more information, visit the show notes at https://moneytreepodcast.com/strategies-for-modern-investors-lawrence-kriesmer-770