Episode 99: Should You Wait to Invest When the Market Feels Expensive?
Stuff About Money They Didn't Teach You In SchoolShow Notes
In this episode of Stuff About Money They Didn’t Teach You in School, Erik Garcia is joined by Miles Clark, Senior Analyst at Nasdaq Dorsey Wright, to explore a simple but important question: what’s better—time in the market or timing the market? The conversation opens with a long-term look at how markets have behaved over multi-decade periods and what that data can teach investors when they’re deciding what to do with new money, especially when markets are sitting at or near all-time highs.
From there, Erik and Miles walk through three common investor approaches: investing a lump sum right away, waiting for a pullback, or easing in over time. They discuss which experiences tend to lead to better long-term outcomes and why those results often surprise people. The conversation also touches on momentum, relative strength, and market breadth, including what it means when market leadership becomes narrow and valuations stretch. The episode wraps up with Miles’ thoughts on what matters most heading into 2026, what investors tend to worry about too much, and what deserves more attention moving forward. If you found this episode helpful, follow the show and share it with someone who’s still waiting for the “right” time to invest.
Episode Highlights:
Miles discusses a study showing "Average Joe," who invests $500 monthly regardless of market conditions, outperforms market timers by about $1 million. (07:25)
Miles breaks down market breadth through a football analogy: it tells investors whether the market is on offense or defense. (13:20)
Miles mentions that in core-dominated markets, the real risk isn't beating the benchmark but simply keeping up with it. (18:55)
Miles discusses how Dorsey Wright applies relative strength to identify which assets to hold, focusing on sustained trends rather than short-term news. (22:45)
Miles explains how momentum investing rotated out of tech in 2022 into energy and utilities, then back into tech for 2023-2024. (29:30)
Erik emphasizes that risk capacity matters more than risk tolerance, which is often driven by emotions about current market conditions. (36:25)
Key Quotes:
"We don't necessarily have to focus on protecting against the entire market washout. We really just need to protect ourselves against where we're over-concentrated in our portfolios." - Miles Clark
"In core-dominated markets, a lot of the risk is actually just not keeping up with the benchmark because it is so strong." - Miles Clark
"Finding and earning positive relative strength is just trying to pick those assets that are doing relatively better towards the up or downside than their benchmark." - Miles Clark
Resources Mentioned:
Miles Clark
Nasdaq Dorsey Wright
Erik Garcia, CFP®, BFA
Xavier Angel, CFP®, ChFC, CLTC
Plan Wisely Wealth Advisors
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