7-14-26 Winning Less, Investing Better

7-14-26 Winning Less, Investing Better

July 14, 2026 · 51 min

About this episode

Lance Roberts and Jon Penn discuss the importance of knowing when to step back in investing and the challenges posed by today's speculative markets.

What if the biggest advantage in today's markets isn't making more trades or winning every debate—but knowing when to step back? Lance Roberts & Jon Penn examine two powerful ideas: why constantly trying to be "right" can actually hurt investment returns, and how today's financial markets increasingly resemble gambling platforms fueled by constant speculation, options trading, prediction markets, sports betting, and cryptocurrencies. 0:00 INTRO 0:54 - Mixed Market & Heightened VIX on Semi-conductors 4:41 - Markets Trying to Breakout of Wedge 9:18 - Candid Coffee Tease 10:01 - The Challenge of Investing in Current Market 12:18 - The Velocity of Information Makes us Worse Investors 18:15 - Being an Unemotional Investor - Be Like Spock 24:08 - Don't Benchmark Portfolio to High Water Mark 24:35 - We've Been Bred to Compete 26:07 - Gamification of Markets - 7 Rules of Poker 29:19 - When Enough is Enough 34:57 - Spotting Bubbles 36:12 - Using AI for Financial Advice 40:54 - AI is Not a Fiduciary 42:55 - Burt's Question on Solo 401k's & Roths Hosted by RIA Advisors Chief Investment Strategist, Lance Roberts, CIO, w Senior Investment Advisor, Jonathan Penn, CFP Produced by Brent Clanton…

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