7-14-26 Winning Less, Investing Better

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, Executive Producer ------- Do you enjoy our content? Rate us on Google: https://bit.ly/4b9JtEo ------- Watch Today's Full Video on our YouTube Channel: https://youtube.com/live/K-mLdepNr6Y?feature=share ------- Watch today's "Before the Bell" premarket commentary, "Oil, Chips, and a Market at Support," https://youtu.be/rk3wl-CHUKs ------- Watch our previous show, "Why Spotting Bubbles Is So Hard" https://youtube.com/live/7bEwrd8UCHM ------- Articles mentioned in this report: "Poker (Gambling) Can Teach You To Be A Better Investor" https://realinvestmentadvice.com/resources/blog/poker-gambling-can-teach-you-to-be-a-better-investor/ 'Spock And The Logic Based Approach To Volatility" https://realinvestmentadvice.com/resources/blog/spock-and-the-logic-based-approach-to-volatility/ "Spotting Market Bubbles: Why History Says It’s Nearly Impossible" https://realinvestmentadvice.com/resources/blog/spotting-market-bubbles-why-history-says-its-nearly-impossible/ --- Get more info & commentary: https://realinvestmentadvice.com/insights/real-investment-daily/ ------- * REGISTER for our next Candid Coffee, "Narrative Busters: Market Stories Investors Should Approach With Caution," Saturday, July 18, 2026: https://streamyard.com/watch/RfJtCj2byfDr --- Visit our Site: https://www.realinvestmentadvice.com Contact Us: 1-855-RIA-PLAN --- Subscribe to SimpleVisor : https://www.simplevisor.com/register-new --- Connect with us on social: https://twitter.com/RealInvAdvice https://twitter.com/LanceRoberts https://www.facebook.com/RealInvestmentAdvice/ https://www.linkedin.com/in/realinvestmentadvice/

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