Today we're sharing the tax loss selling secrets you need to know before 2026! We also talk understanding personal strengths and psychological limits in investing. It's good to avoid shiny-object strategies like day trading and prioritize risk management through diversification. We explore how market structure, valuations, and historical data suggest future returns may be lower and more volatile, making stress-testing portfolios and aligning risk with temperament essential. Remember long-term success comes from discipline, education, adaptability, and thoughtful strategy rather than chasing returns in overheated markets. Today we discuss...
- Successful goal-setting focuses on small, repeatable actions over time rather than unrealistic short-term outcomes.
- Investors must design strategies that align with their psychological makeup, risk tolerance, and time availability rather than copying what appears profitable for others.
- Stop-loss orders can be dangerous in volatile or less-liquid markets due to slippage and market maker behavior, often leading to worse-than-expected exits.
- Markets can remain expensive longer than expected, making flexibility and balanced positioning more important than precise market timing.
- Concentration in high-performing assets like AI stocks or precious metals can lead to severe losses if momentum reverses sharply.
- Historical examples showed that long periods of weak or flat equity returns are normal following valuation extremes.
- Diversification across asset classes, regions, and styles was highlighted as essential for retirement sustainability and long-term wealth preservation.
- Static portfolios such as traditional 60/40 allocations were questioned, with an emphasis on active monitoring and adjustment as conditions change.
- Precious metals typically move in sequence, with gold leading, followed by silver and then platinum, often ending in unsustainable parabolic moves.
- Misuse of statistics, such as confusing average with median net worth, can distort perceptions of wealth and financial reality.
- Investment performance should be evaluated using geometric averages rather than arithmetic means to reflect true compounded returns.
- Emotional states like greed and fear often peak near market extremes and should signal the need for reevaluation rather than increased risk-taking.
- Political, macroeconomic, and election-cycle dynamics can temporarily suppress or amplify commodity prices, particularly in energy markets.
- Long-term success in investing depends less on prediction and more on preparation, adaptability, and disciplined execution of a well-structured plan.
"Cash is not trash... Cash is King" - Kirk Chisholm
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Today's Guest: Kirk Chisholm
Kirk Chisholm is a Wealth Manager and Principal at Innovative Advisory Group, an independent Registered Investment Advisor located in Lexington, MA. He has been providing wealth management services to individuals, executives, entrepreneurs, and their families since 1999. He is an outside the box thinker, risk manager, inflation expert, blogger, podcaster, and all-around interesting guy. Kirk is dedicated to developing lasting relationships with all of his clients and their families. One of the benefits of working with Kirk is his patience, empathy, and his ability to provide clear and easy-to-understand explanations to complex financial topics.
Kirk developed a unique philosophy for the wealth management industry called Risk Management First. The medical field has a similar way of thinking of âfirst do no harmâ. This philosophy focuses on risk management for clients in all aspects of their lives in ways the industry does not address. Risk management does not stop with investments. It also requires working closely with other professionals to address areas of their financial lives not currently being met.
In 2008, Kirk co-founded Innovative Advisory Group to address the needs not being addressed by the wealth management industry. It started with specializing in alternative assets held in retirement accounts (i.e. self directed IRAs/401ks). Then the company expanded into the specialization of college funding (i.e. planning, strategy, and paying the least possible for a high quality education), Risk Management First, exit planning for business owners, advanced planning (estate, tax, etc), and providing practice management and leadership training to other financial advisors, accountants and attorneys.
Kirk's Online Presence:
Today's Panelists
- Kirk Chisholm | Innovative Wealth
- Douglas Heagren | Mergent College Advisors